If those statistics hold true for younger generations in the workforce, that means, on average, we will recalibrate our work and our work relationships every 4 years.

So how do we do that well?

That question was on the mind of a mid-career leader, Daniel, who reached out to me a few weeks ago. Daniel is moving his family across Canada to become the lead pastor of a congregation in Ontario.

“I want to start by listening,” Daniel told me. Then he asked for help in finding good questions for uncovering the congregation’s realities—the sort of truths that, without intentional listening, would otherwise take leaders months or even years to understand.

Understanding as a starting place

There’s a newly built home just a block away from my own house in Chicago. It’s new construction, but that wasn’t the owners’ original plan. They purchased an older home, built in the late 1890s like the others on our street, and planned to renovate it themselves. Wanting a fresher look, they began to remove walls on the first floor to create an open concept living area.

Their intentions were good—but the house collapsed. Unknowingly, they had removed a support beam, and the home quickly fell on itself. (Thankfully, no one was hurt.)

I think of that story often when I hear of leaders who arrive at a new job with plans of impressing their new team on Day 1. They roll in with fresh ideas, new directions, and powerful insights. The make fast changes, at the risk of taking out a support beam.

A little research would have saved the home. A little research can also keep executives from making moves that have shortsighted implications.

Entering a new role means walking into an organization with an existing set of opportunities and challenges. The existing team has worries and hopes, superpowers and talent gaps. It’s your job to uncover them. This level of understanding is only reached through intentional listening.

Conducting a listening tour is an essential first activity of your first 90 days in a new role. Without focused listening, you run the risk of taking out a support beam. With focused listening, you might uncover hidden opportunity that helps you succeed faster.

Questions for your first 90-days listening tour

In our conversation, Daniel and I crafted a series of questions he could ask congregational stakeholders to help him understand their hopes for his leadership. We shaped the questions using the Appreciative Inquiry framework; Appreciative Inquiry is a collaborative and future-focused process of organizational change.

Below are three questions you can use as you enter a new role.

#1: High Point Experience

I’m sure you’ve had ups and downs throughout your time at our organization. I want to hear about one of your high point experiences—a time you felt you were really contributing to our mission. A time when the work was high quality, people were performing well, and progress was clear. Tell me the story of this high point experience.

What was it about you that made this experience possible? What was it about others? What was it about the organization (its culture, ways of working, processes, resources, values, or systems)?

Why this question works well: Starting here gives your team a subtle opportunity to share strengths and experiences, without feeling like they’re bragging. You can find out what is working well, and what people are proud of.

#2: Images of the Future

Now, imagine it’s two years from now, and this is the organization (or team) of your dreams. The work is energizing, you feel productive and valued, and we’re making incredible progress toward goals. As you look around, you can see others feel this way too—people are working with efficiency and ease, and the results ore impactful. Tell the story of this future.

What is new? What is different? What is the same? What does it mean for our products, our processes, and our teams? What does it mean for you? Tell me what’s happening.

Why this question works well: People can get stuck in the day-to-day; by looking a few years ahead, the growth that is needed often becomes clearer. This question also allows people to name changes they’d like to see happen without being seen as a complainer. Incredible new ideas often emerge as people realize they have permission to share ideas that compel them.

#3: Strategic Opportunities

Now, with that future in mind, what are the most important things for me to know or focus on right now? In six months? Tell me in order of priority.

Why this question works well: Blue sky thinking in the previous question can unlock a lot of organizational truths; with the third question, we ask people to make a choice—what is your highest priority to help us get to the future we desire? The ideas become more concrete and actionable, helping you find possible paths forward.

How to conduct your listening tour

For small teams, these questions are great to ask one-to-one. Listen carefully to the answers, repeat back what you’re hearing, and take good notes. Then, be sure to follow up as you implement ideas or move the team closer to the vision shared by a teammate.

With a larger group, you may need to bring sub-teams together for a listening session where colleagues can interview one another using these questions and then share their collective insights with you, their new executive.

Of course, the listening shouldn’t stop with these three questions. Follow up and continue to ask questions that deepen your understanding of the organization, which will mean going beyond simple facts to truly understand the relationships, assumptions, values, motives, and priorities that shape the work.

Follow listening with action

Eventually, it is time for your insights to be shared. At the end of your listening tour, you’ll have the benefit of connecting your fresh ideas to the hopes, needs, and opportunities that your team identified in their responses.

People support what they help to create. Your team will receive your ideas with more enthusiasm if they can see their fingerprints on the plans.

If you’re about to join a new organization or move into a new role, conducting your listening tour will signal that you hear and appreciate the ideas of your team. It will create psychological safety and earn respect, especially if you follow listening with action.

You’ll also have created a personal connection with your team members, helping fast track the familiarity that makes work easier and creates understanding between team members.

The three questions outlined above are a great place to start; if you want to better understand how to adapt these questions, which draw on the Appreciative Inquiry framework, revisit the free e-book you received when you subscribed to this newsletter (or subscribe below) and then join me for a free one-hour workshop on October 1. Registration is free but required.

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This article appeared first in SmartBrief Leadership newsletter.

More questions for when you’re new

The day after I submitted the article above to my editor at SmartBrief, my friend and colleague David Schreiner posted on LinkedIn about this same topic. I love his questions and feel like they’re good corollaries to the ones I share above - especially the first one about identifying what is “load bearing.”

With David’s permission, I share his questions here.

• "What's working here that I should protect?" — Before you change anything, find out what's load-bearing.

• "What have you given up trying to tell leadership?" — The most important information is usually the thing people stopped raising.

• "Whose job is harder than it looks?" — It surfaces the invisible work holding the place together.

• "What would you fix if it were your call?" — Ownership hides in that sentence.

• "How will I know if I'm losing your trust?" — Ask it early, out loud, and mean it.

Photo by Vitaly Gariev at Pexels.

“What if we could give the kids the experience of living in another country for a while?”

At first, it was just an idea. Our kids were learning Spanish at school, and we thought spending time in a Spanish-speaking country could deepen their learning. But Cliff and I both had jobs in the States. We couldn’t simply pack up and move.

So we kept talking.

What if we couldn’t relocate, but could work remotely for a few weeks? What if we found a language school that could double as childcare while we worked from a coworking space? What if we found a place where all of that was possible?

A friend suggested Antigua, Guatemala. It didn’t take long to find a reputable language school with an attached Airbnb and a coworking office down the block. We made the reservations.

The simple words “What if…” had created a whole new world.

Not literally, of course. Talking about Guatemala didn’t magically make the trip happen. But the conversation made a possibility visible. Once we could see it and talk about it, we could begin figuring out how to make it real.

This is one of the foundational ideas of Appreciative Inquiry:

Words create worlds.

And if that’s true—and I fundamentally believe it is—then our words and questions carry more power than we might realize. As leaders, we have a responsibility to pay attention to the possibilities we’re making visible through the conversations we create.

Imagining the future we want

Because Appreciative Inquiry practitioners know that words create worlds, they intentionally ask questions that invite people to imagine the world they want.

You may recall from last week’s newsletter that Appreciative Inquiry has three questions you can adapt to fit your topic. The second question, Images of the Future, asks people to imagine a preferred future.

In its generic form, the question sounds something like this:

Imagine it’s X years (or months) in the future, and we’re excelling at [our topic]. What is happening? What is new or different? Tell me the story of the future, as if you’re already there.

Try it yourself for a moment.

Imagine it’s two years from now and your team is functioning exactly as you’d hoped. The results are remarkable, and the team feels energized and engaged. What is happening? What has changed? What are people doing differently? What would you see, hear, or feel?

That’s the power of the question.

Instead of starting with what’s broken, we’re giving ourselves permission to describe what’s possible.

And when I share my vision for the future, and you share yours, and we weave those ideas together with others, something interesting happens. We’re no longer just talking about our current state—often a state that involves a problem or the feeling of being stuck. We’re beginning to map a different reality.

Our words have created a new possibility.

Flipping complaints

But don’t we need to ask about problems?

That’s the most common question we hear when introducing Appreciative Inquiry.

Of course we need to acknowledge the risks and challenges that are present. Appreciative Inquiry isn’t about pretending problems don’t exist.

But instead of dwelling on the problems, we can listen for the future hidden inside it.

As the leader of one organization told us when we explained this concept to him:

“Every complaint is an unexpressed wish for the future.”

Imagine someone tells you, “This organization has too much red tape.” They’re identifying a real problem. But they’re probably also expressing a wish: “I wish we could get work done more efficiently.”

That gives you a different conversation to have. Instead of spending the next 30 minutes talking about everything that’s wrong with the bureaucracy, you can ask, “If we were getting work done efficiently, what would be different?” Or, “What would it look like if we had significantly less red tape?”

The problem hasn’t been ignored. You’ve simply turned your attention toward the future you want to create.

If you’ve been reading this newsletter for long, you might remember the “find it, flip it, elevate it” process for giving feedback. That process operates on the same principle.

Instead of, “Anna, you’re always late,” you can say, “Anna, I need you to be on time.”

We move from describing what we don’t want to describing what we do want.

Using this to ask better questions

Remembering that words create worlds reminds me to ask better questions. The “how to” is surprisingly simple. Spend more time asking about the world you want rather than the world that is disappointing you.

For example, imagine you have a colleague who frequently responds to ideas with, “That won’t work because…” Don’t ignore the obstacles he’s raising. Listen to them. There may be important information in them. But once you’ve heard the concerns, you might shift the conversation:

“I hear you saying there are some real challenges. Imagine it’s a year from now and we’ve solved those problems. What does that look like?”

You’ve changed the question without dismissing the problem.

Or consider a more personal example. It’s back-to-school season, and your daughter is lamenting that none of her friends are in her new classroom. You might first listen. She may simply need you to understand that this feels awful or even scary right now.

But if she’s ready to move beyond the frustration, you could ask:

“I know it’s frustrating that none of your current friends are in your class. Imagine it’s a month from now and you have a lot of new friends. What would that feel like? What might have made that possible?”

Again, you’re flipping the question from what we don’t want to what we do want. You’re using words to make a different future visible.

When NOT to use this

This is one of the most helpful and hopeful tools I have as a leader—and as a parent, partner, and friend. But it isn’t a one-size-fits-all tool for asking better questions. There are times when flipping toward the desired future isn’t the right choice.

1. When the other person wants you to listen.

Sometimes our colleagues, friends, or family just want us to listen, not problem-solve. They need to rant. They want to process their emotions. They’re looking for empathy, not a solution.

You have to assess whether this is the right time for a question that helps map the future. It might not be. It might be time to, as a friend of mine says, “sit in the suck” with someone else.

2. When quick corrective action is needed.

If I discover my CFO is embezzling funds, I’m not going to flip to a question about what he or she wants. “Imagine a future where you were managing our finances ethically…”

No. I’m going to lock them out of their accounts and call my lawyer.

3. When you don’t yet understand the problem.

Sometimes we need to investigate before we imagine. If a team is struggling with a serious performance problem, for example, jumping immediately to “What would great look like?” could cause us to miss important information about what’s actually happening.

Understanding the problem and imagining the desired future aren’t mutually exclusive. Sometimes we simply need to do them in that order.

In many other cases, however, flipping the conversation from what we don’t want to what we do want can open up a more productive conversation. Because words create worlds. And sometimes the first step toward creating a different world is simply finding the words to describe it.

More on the principles of Appreciative Inquiry

I hope these ideas help you think a little more carefully about the worlds you’re building with the questions you ask.

To learn more about the principles of Appreciative Inquiry, join me for a free one-hour workshop on October 1. Registration is free but required.

And don’t forget to check out my free e-book, co-written with Dr. Jim Ludema, on Appreciative Inquiry’s three questions. Subscribers received a link in an email last week.

BONUS CONTENT

If someone you love has gone back to school recently, you might find these questions useful. The article also has questions for anyone needing a mid-year reset button.

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There are obvious life changing moments, of course, like when you stand in front of your closest friends and family, and say “I do,” or when a nurse puts a tiny, blanket-wrapped bundle in your arms.

Other life changing moments don’t show their true qualities until years later.

With the benefits of hindsight, that was my experience in the early 2000s. I was working for the Chicago offices of World Vision, the global humanitarian organization. Our team was trying to build a volunteer force from the external leaders who normally just donated to our organization. Yes, we needed their money and resources. But, we thought, it would be a win-win for us and the donors if we could get their brainpower too.

My boss brought in a specialist in Appreciative Inquiry, which is a positive and collaborative approach to organizational change. I witnessed the Appreciative Inquiry process bring a hotel ballroom full of very different people (with strong personalities and sometimes conflicting ideas and approaches) together to shape a shared vision and then design a path to get there.

The process was transformative.

And the process centered around (drum roll) … asking questions. Really powerful, really carefully crafted questions.

Between me and Appreciative Inquiry, it was love at first sight.

Fast forward over 20 years, and I still use the questions of Appreciative Inquiry, and its process, multiple times every week. The process was formative for me—this newsletter and much of my work would not exist without it.

Life changing. I just didn’t know it yet.

That consultant my boss brought in was Jim Ludema, one of the early doctoral students of the methodology’s founders, Suresh Srivastva and David Coopperrider. Eventually, I trained with Jim and other Appreciative Inquiry pioneers, and later began consulting with Jim. He is a colleague of mine to this day—you’ll hear more about Jim at the end of this post.

The most productive (and flexible) questions you’ll ever find

Appreciative Inquiry has a standard set of questions that can be applied to a remarkable number of circumstances.

Want to grow sales? These questions will help you find opportunities.

Want to plan a great family vacation? These questions will help you find the common ground between what you want, and what your 8 year-old does.

Want to simplify a complex process between multiple teams in your organization? These questions will get everyone on the same page.

I know that sounds too good to be true, and of course the questions aren’t enough on their own. You have to know how to ask them, and how to bring the insights to a series of exercises that help you go from questions to answers to action plans.

I introduce you to the questions below. But if you want a fuller introduction to Appreciative Inquiry, I have a gift for you.

Earlier this year, Jim and I wrote an e-book, The Three Most Valuable Questions You’ll Ever Ask, on how to use the questions of Appreciative Inquiry. The resource will help you find opportunities to use Appreciative Inquiry in your personal and professional life; and you’ll have the details you need to write great questions using the Appreciative Inquiry approach.

Our ebook is available for subscribers to this newsletter—tomorrow you’ll get an email with a link to the download.

If you’re reading this but you don’t receive Better Than Fine in your inbox, subscribe today. The welcome email will give you access to the ebook as a thank you for subscribing.

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The three questions of Appreciative Inquiry

In their generic form, the three questions are:

#1: High Point Experience (HPE)

Think of a time when we’ve been at our best around [our topic]. Tell me the story. What was it about you that made this possible? About others? About the organization?

#2: Images of the Future

Now imagine it’s X years (or months) in the future, and we’re excelling at [our topic]. What is happening? What is new or different? Tell me the story of the future, as if you’re already there.

#3: Strategic Opportunities

With that future in mind, what are the 2-3 more important opportunities for us to pursue, in the coming weeks/months to succeed at [our topic]?

The trick is, you don’t leave these questions in the generic form. You adapt them for your circumstances—what you or your team really desires.

If your organization was trying to become more innovative, you might gather a group and ask these questions:

#1: High Point Experience

We all have days where we feel inspired, and days where we don’t. Think about a time when you were part of a truly creative or innovative process or project that made an important difference and you felt inspired, engaged, and fulfilled. Tell me the story—what was the situation, what happened, and what were the results?

What was it about you that made this possible? What was it about others that made this possible? What was it about the organization (its processes, ways of working, culture, tools) that made this possible?

#2: Images of the Future

Imagine that tonight you fall into a deep, relaxing sleep, and you don’t wake up for three years. When you awake, you see that a miracle has occurred. Major changes have taken place, and our company has grown and is thriving. You can truly say that we are the organization you dreamed it could be—better, smarter, faster than ever before, with a sustainable culture of industry-leading innovation driving its products, processes, solutions, and more.

What does the organization look like? What’s happening that is new and different? What does the culture look like, feel like, and sound like? How is the engineering department showing creativity in all they do? What do you see in terms of new products? New processes? New ways of working?

#3: Strategic Opportunities

Think about the vision you just described – your vision for creating a sustainable culture of industry-leading innovation within the next few years. With that in mind, what are the 3-5 most important actionable strategies we must implement over the next 3 years to launch us toward your vision?

If your topic were something else, like becoming a better public speaker, the structure of the questions would stay the same, but you’d change the focus to explore your goal.

Using Appreciative Inquiry

You’ve got enough information already to start using the questions of Appreciative Inquiry (especially if you read the e-book!). Just pick a topic that matters to you, and adapt the questions to fit your context.

But if you prefer to learn new ideas live, join me for a 1-hour virtual workshop on the Appreciative Inquiry process on October 1. We’ll focus on using Appreciative Inquiry’s questions to:

• Lead change without starting from what’s broken

• Help your team (or yourself) imagine what’s possible

• Develop people in a more strengths-based, energizing way

Learning and using the Appreciative Inquiry process truly has been transformative for me. I hope you’ll check out the e-book and join us at the workshop (registration required) to see how it might benefit you.

BONUS CONTENT

This week, I listened to an episode of The Curiosity Shop podcast, hosted by Brené Brown and Adam Grant, featuring author John Green.

John (I like to imagine we’re on a first name basis) made the point that “friendships need a project.” By project, he meant a shared area of interest or activity that gives you a regular reason to be in contact.

Examples:

• A sports team can be a project—my husband knows he’ll hear from certain friends during Bears game time on fall Sundays.

• John mentioned he and his mother work in the same community garden, a shared project that brings them together on a regular basis.

• A high school friend and I planned a trip to Alaska with our families, earlier this summer. The planning kept us in regular contact, helping us deepen the friendship.

Here’s your bonus question:

Which of your relationships need a project?

“Any fun plans this summer?”

We spent the first five minutes of the call sharing about our summer travels—my recent trip to Alaska, the rustic family cabin (with questionable plumbing) where she was planning to spend a long weekend.

Was this small talk at the start of the call a good use of our precious, limited time together? I’m a firm believer that it is.

Casual conversation, when contained to a reasonable amount of time, serves an important function in your meetings with clients and colleagues. It reminds you to breathe, to exhale; it reminds you that we’re all human. And the bonds that are created as we share small aspects of our lives make future work together easier.

These little exchanges that start meetings may seem simple, perhaps they even feel like a diversion from the important work at hand. But skipping over the small talk can have an outsize, negative impact on your meeting and your day.

Those chit-chat conversations are doing more work than you think.

The science behind the chit-chat

Small talk has a reputation problem. In a culture obsessed with productivity, efficiency, and “deep work,” casual conversation at the office or at the start of a Zoom meeting can feel like a time-waster. But research suggests we’ve been dramatically underestimating the positive impact of small talk.

A study published in the Academy of Management Journal found that on days when employees engaged in more small talk than usual, they experienced a measurable boost in mood and positive energy. That uplift didn’t stay contained—it spilled over into their behavior. People were more willing to help colleagues, more collaborative, and reported higher levels of well-being.

Reread that sentence before you move on: people who invest in casual conversation with their colleagues are more collaborative and helpful. The small talk actually creates conditions for important work to take place.

The researchers propose that small talk eases transitions, making it easier to move from one topic to the next. The brief exchanges also make work life feel more relational, less transactional. Over time, these micro-exchanges build something more durable: trust, and even friendship. Those factors enable meaningful collaboration over the long term.

High-quality connections: The bigger picture

Organizational theorist Jane Dutton, of the University of Michigan, researches High Quality Connections (HQCs). Dutton’s work shows that even brief, positive interactions between people at work (not deep friendships or long conversations, just moments of genuine human contact) can have profound effects on energy, resilience, and performance.

HQCs are characterized by a sense of vitality, being seen, and positive regard. Importantly, Dutton’s research demonstrates that these connections don’t require intimacy or history. A two-minute conversation in the elevator, a warm check-in as a team call begins, or a genuine “how are you holding up?” in a corridor: these are the building blocks of meaningful engagement.

What small talk does, in Dutton’s framework, is open the door to HQCs. You don’t build trust through grand gestures; you build it through accumulated small ones.

For leaders especially, this matters enormously. Research consistently shows that employees who feel seen and valued by their managers are more engaged, more loyal, and more likely to go the extra mile.

What good small talk actually looks like

If you’re someone who finds small talk awkward or forced, the good news is that the bar is lower than you think. You don’t need to be witty, charming, or naturally gregarious. You just need to be attentive and genuinely curious.

Here are three practical tips for using small talk to its full advantage:

1. Ask about something specific, not generic. “How was your weekend?” is fine. “Didn’t you say you were going to that art exhibit—how was it?” is better because it signals you were listening last time.

2. Be genuinely curious, not performatively friendly. People can tell the difference. Small talk works when it’s rooted in actual interest in the other person.

3. Notice and acknowledge. If a colleague looks tired, or mentions they’ve had a tough week, a simple “that sounds like a lot—are you doing okay?” is small talk that shows attentiveness and genuine concern.

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A word of caution and of encouragement

The study mentioned earlier did find a downside to small talk: too much can be a distraction. (We’ve all had that colleague.) If someone is deep in concentration and you pull them out of it for a 20-minute chat, you’ve done them no favors.

The goal isn’t to become the office social butterfly. Instead, the goal is to be intentional—to use the natural transition points in your day (before meetings, as you pass one another in the hallway, in the moments between tasks) to invest briefly but genuinely in the people around you. They will notice, and you’ll feel better for doing it.

So here’s the gentle push: small talk more. Not endlessly, not at the expense of focus or productivity, but more than you probably do right now.

Small talk isn’t the opposite of serious work. It’s what makes serious work possible.

Bonus resources for easier small talk

One way to get started is to build “ice breaker” time into the start of team meetings by asking everyone to briefly respond to a question. (The secret—make the questions bite-sized and safe for work.) Here’s a list of questions that go beyond “How was your weekend?’ while still staying safely contained:

1. What’s giving you energy this week?

2. What is one work-related thing you’re nerdy about?

3. What is one thing that this team should know about how you like to work?

4. Name three values you try to live by at work. From whom did you learn these values?

5. Tell me a story about the best leader you’ve known personally. What made their leadership great?

6. What’s the best piece of professional advice you’ve ever received?

7. What is one work habit that has served you well?

8. What’s one thing you’re curious to learn more about this year?

9. What do you do when you need a short break? (For example, what websites do you visit?)

10. What was your first job? What was something you learned from it that sticks with you today?

(Note: I originally shared these questions, plus 10 more, in a newsletter on the value of ice breakers.)

This article appeared first on the Ad Lucem Group blog.

Photo by RDNE Stock Project at Pexels.

I want to start with a story. This story isn’t mine; it comes from Susan Scott’s book Fierce Conversations, and she borrows from the poet David Whyte.

There once was a newly married couple, a woman and man. Each week, the wife wanted to talk about the relationship. She asked questions like, Are we happy with how things are going? How are we, really? Is there anything you need from me?

Exasperated with the weekly conversations, the husband complained, “I wish we could just talk about the relationship once and be done with it.”

But you can’t, Scott writes, because “The conversation is the relationship.”

The Venn diagram of the communication you have and the relationship you have is a circle; the overlap is complete.

At work this is true too; we might say, “The conversation is the culture.”

The strength of the relationship (or the culture) is directly related to the conversations we can have, and the tone with which we have them. When there are things we think we can’t bring to the conversation, or we avoid bringing, we lay a brick. Too many bricks make a wall; and while walls can be busted, it requires tremendous effort.

Questions matter

This is why I value questions. When asked authentically, they keep bricks from the wall by allowing us to understand the people who matter most to us at work and at home. (Lori Gotlieb writes that “’I understand you’ are the three most romantic words in the English language.)

Questions also matter because they’re something we can control. We can’t control the other person’s responses or where the conversation goes after the opening question or two. But we can ensure we start with authentic curiosity and positive regard.

That questions matter is our starting place. From there, we must improve our question quality.

Asking better questions

This newsletter is full of other ideas that can help you improve your question quality—but it really boils down to this: two essential steps for improving our questions. (These are the same two steps I covered in my TEDx Talk—and if you only click one link in today’s link-heavy message, make this the one.)

#1: Ask unpredictable questions, questions that don’t have scripted answers.
When we ask predictable questions, we get predictable answers.

How are you?
Good.

How was work?
Fine.

Did you like the movie?
Yes.

This isn’t about asking open questions; this is about asking wide open questions with answers that tell you something new. The wider open, the more opportunity to really know the other person.

#2: Ask about feelings, not just facts.
We understand each other better and strengthen relationships more when we ask not only about facts (“What’s new at work?”) but about feelings (“How are you feeling about your new role?”).

Feelings are a great starting place for deepening questions, but you don’t have to stop there. The REVAMP acronymreminds us to also ask relationships, emotions, values and vulnerabilities, attitudes or assumptions, meaning or motives, and priorities.

One more thing to note: asking better questions is a practice, the sort of thing you get better at over time.

Asking better questions is just the starting place

Questions can start conversations, but they can’t carry it the full way. If the conversation really is the relationship, we have to be attentive to the full conversation and not just its opening lines.

Some skills for this include active listening, good follow up questions, and answering with handles. Handles are responses or ideas someone else could grab on to, to carry the conversation along. These are especially useful in small talk:

Any vacation plans this summer?

We just got back from a trip to Alaska, which was incredible. We have one more long weekend planned, a camping trip, with our kids. And then we take our oldest back to college late in the month.

See the three handles in that response? We could go deeper on Alaska, camping, or the return to college.

Difficult conversations need to be had

You can find conversations that deserve special attention in your life by looking for the RUTS: conversations that are routine, uncertain, tense, or super significant. Those conversations take extra intention.

There are a lot of reasons we avoid difficult conversations, and most of those reasons end up costing us in the end. Remember how any conversation we can’t have lays a brick in our relationship? That means, at work and at home, we need to build the skill of having difficult conversations well.

Especially when we’re feeling hurt or angry, the attitude with which we start a conversation predicts its success more than the questions we use. A generous interpretation is often a good place to start.

Getting these tough conversations started can be easier with a few key phrases. I like “would you let me stumble through this?” There are also some questions we can always ask authentically, even when we strongly disagree.

Leadership is about the conversations you have

This newsletter’s focus bounces between communication and leadership topics. That may seem like two separate topics, but to me, they are trees whose root systems are so closely entwined, they cannot be separated. Leadership is a process of influence, and people are most influenced by our words and our behaviors.

Because of this symbiotic relationship, we also cover topics like growing your self-awareness at work, learning to speak up even when you’re intimidated, building connection on virtual teams, running effective meetings, and prepping for mid-year reviews.

Thanks for being here

If you’re a new reader—welcome. I hope you find this newsletter lives up to its promise of helping you be a better leader, partner, and parent.

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BONUS CONTENT

Today’s newsletter was meaty, a 1000-word summary of the foundational ideas that help us be Better Than Fine. So let’s keep the bonus section light, shall we?

You’re probably familiar with the game “Would you rather?” The idea is to offer two impossible choices and ask the other person to choose between them. For example, on a recent episode of Amy Poehler’s podcast Good Hang, she asked Anne Lamott (one of my favorite authors) this question:

Would you rather eat only buttered noodles for the rest of your life, OR eat anything you want but you can only have it on a moving bus?

Here are three “would you rather” questions raised recently by teenagers in my life:

• Would you rather eat a s’more every day OR never eat a s’more again?

• Would you rather always pee in a sink OR need to pee after every sip of water?

• Would you rather call everyone “dude” OR call everyone “Mister” followed by their middle name?

These aren’t high brow questions. And I’ll be honest, they’re unlikely to deepen your understanding of the other person. But ask them, laugh, and enjoy each other’s company. That’s meaningful too!

Photo by Tiger Lily at Pexels.

After years of working in large organizations, he’d grown frustrated with the fast pace. A job search led him to a non-profit role on a smaller team, where he hoped for an easier pace and that the organization’s mission would make his work feel purposeful.

In some ways, it did. But in important other ways, the leader struggled to fit with his team and in this new context.

His efforts to engage with his colleagues left him feeling as if he were speaking a different language. They talked about stewardship and impact, while he was wondering about strategy and innovation. The director’s boss encouraged him to move his innovative ideas forward, but without the support of a big team, he struggled to make deadlines and manage details. Disappointed, the director’s boss had little positive feedback to offer.

After two years of feeling like a misfit, the director left the organization.

What does it mean to belong as a member of the team?

The director never felt he belonged or that his uniqueness was valued. His story is a cautionary tale — not just about culture fit, but about what happens when belonging and uniqueness are never established.

Belonging is the experience of being accepted, valued and included as a genuine member of a group — not despite who you are, but because of it. It’s not simply being present in a group, but feeling that your presence matters to the people around you.

To truly feel we fit in, belonging must be paired with uniqueness — that your distinctiveness is appreciated and your contributions are valued.

To understand this, it’s often helpful to reflect on your experiences in junior high or high school. No doubt you longed to be part of the group and made efforts to conform to the group’s expectations.

But back in junior high or high school, you also probably relished your identity as a distinct individual. Perhaps you wanted to be the smart friend, the funny one, or the sporty one. When your group appreciated the uniqueness you contributed, it felt good.

As adults, our desire for belonging and uniqueness hasn’t gone away. Imagine a marketing team member named Tammy is placed on a cross-functional team tasked with designing an employee engagement program. At the team’s first meeting, Tammy can’t help but notice something: she’s the lowest-ranking team member present.

At first, Tammy feels insecure. “Maybe I’m just here to listen and learn,” she wonders. “Or take notes?”

Then, the project’s advisor introduces her to the team. “Many of you may not have met Tammy yet, but she’s a rising star. We wanted her on this team to build relationships with you all, and to get her perspective as a Gen Z team member, since we need a solution that engages all generations in the workforce.”

Throughout the meeting, senior colleagues invited Tammy to speak. When Tammy offered an observation, team members nodded in appreciation; one leader asked a follow-up question, and Tammy was able to clarify her thinking. Later, when the team broke into smaller committees, the leader sitting next to Tammy asked her to join his committee.

These small gestures — the thoughtful introduction that explained her role, the invitation to speak, the appreciation for her contribution and being selected to join a working group — all gave Tammy the sense of belonging and uniqueness she needed to feel at ease.

Imagine if the experience had been different—if she weren’t introduced and instead spent the whole meeting suspecting her teammates wondered why she was at the table. Tammy would have stayed silent rather than risk saying the wrong thing. No one would have recognized her insights. Her insecurity would have grown, and her contribution would have shrunk. Like the director who eventually left the non-profit, the sense of being a misfit might have thwarted her career trajectory.

4 ways to create belonging on your team

Helping each team member feel both a sense of belonging and uniqueness is part of creating psychological safety. Research shows psychological safety impacts learning, performance, engagement, and even physical safety. When team members feel safe, like they belong and that they are distinctly valued, it can have an out-sized impact on their career path, as we see with Tammy, and it can prevent damaging interpersonal conflict that arises when people feel they’re not part of the in-group.

Here are four ways you can create belonging on your team, all while helping team members feel uniquely seen and appreciated for their distinct contributions.

1. Onboarding that introduces the person, not just the role

So often we introduce people by their titles. (“Meet Marcus, our data analyst.”) That’s a great start, but it doesn’t recognize Marcus as a whole person or clarify what unique contributions he might offer.

An alternative introduction might be, “Meet Marcus, our data analyst. I’ve asked him to create our shared files for this team, because he’s one of the most organized people I know, while still managing to keep his eye on the bigger picture.”

That intro takes 10 seconds longer but helps clarify his contribution to the team (belonging) and the unique capacities he brings (organized, big picture thinker).

2. Inviting in quiet voices

People stay silent in meetings for a variety of reasons. While team members like Tammy build their confidence for speaking up, you can make it easier by inviting them into the conversation.

When possible, give quieter folks time to prepare their thinking. “In a minute, I’m going to ask Tammy and Lyle for their thoughts, as they represent important perspectives we don’t want to miss. Before I turn it over to them, I do want to revisit the point Beth made earlier …”

3. Appreciation that names strengths, not just completed tasks.

Hearing “good job” is always nice, but it’s not instructive. What made your contribution valuable?

To help build a team member’s sense of belonging and uniqueness, name their specific strengths.

Instead of this: “Thanks for finishing the report.”

Say this: “Thanks for finishing the report, and especially for the insightful work you did to tighten the language and make sure it aligned to our KPIs. You have an eye for detail and unified messaging. That was a significant contribution to our team.”

See how that helps build a sense of belonging while recognizing uniqueness?

4. Feedback that acknowledges the future

When corrective feedback is needed, be direct and clear, and reassure the person that they still belong. A good way to do this is by framing the feedback as information they need for the future.

Here’s an example: “The event felt disorganized at points, which I know wasn’t your goal. I want to share some feedback so that as you plan future events here, you can keep these ideas in mind.”

Can you see the subtle message there? You’re still a valued part of the team; that’s why we care enough to share feedback.

What does your team need?

The director who left the non-profit, and Tammy, who found her footing — both stories hinge on the same variable: whether a leader took the time to make someone feel they mattered.

Belonging and uniqueness aren’t soft extras; they are the conditions under which people do their best work and stay committed to the team.

The good news is that the gestures required are small. A thoughtful introduction. An invitation to speak. Feedback that names a strength or points toward the future. These moments cost almost nothing — but for the person on the receiving end, they can change everything.

Before your next team meeting, take a moment to consider: who on your team might be waiting for one of those moments?

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This article was first shared at SmartBrief Leadership.

Bonus Content

Let’s connect the ideas above to questions you can ask. Here are 4 questions a leader can use to assess if an individual feels belonging and uniqueness.

Ask these one at a time, spaced across regular 1:1s.

• Do you feel comfortable with the team, and like your presence matters?

• When you’ve raised a concern or disagreed with the group, how did that feel afterward?

• What’s something you bring to this team that you don’t think anyone else quite brings in the same way? (Many people may struggle to answer this. Be ready with your own ideas, and reflect them back to your team member.)

• Can you be fully yourself here?

Photo by DS Stories at Pexels.

The participants were council leaders for Never Search Alone, an organization that helps people ready for a career change find community and insight for their search. (More on this remarkable organization in the “bonus” section below.)

Our conversation centered around a theme that you may remember from my TEDx Talk: We can’t just ask questions for facts; we have to ask questions for understanding.

Understanding questions go deeper than the facts to engage with feelings and motivations—the “why” of who we are and what we’re really thinking.

Getting to that deeper layer of what is happening beyond just the facts is essential. Without it, we miss truly understanding the people we care about most. And in our professional lives, such as with the leaders of these job search councils, when we don’t ask questions for understanding we risk focusing on the small stuff instead of the problems or worries or possibilities that lie at the deeper level.

Here are some examples I offered for the job search context:

Imagine a council member, who has been laid off and is searching for work, says, “This week I wrote my favorite old boss to see if we could have lunch, and she said she was too busy this month.”

As the group leader, you could focus on the facts and move back to the next steps in your process. “So who will you reach out to next?”

But that response will leave the council member’s feelings unresolved and likely ignores the concerns that lay beneath the surface. A more powerful, understanding-seeking next question might be, “What is the meaning you’re making of her response?”

See the difference in that question? By asking about the meaning of the experience, we can surface the emotional layer that reflects what is really going on inside the council member’s head. You’ll see these same layers again in the REVAMP framework below.

Or another example—Imagine Tom, who is fed up with his current job, reports that he feels tempted to apply to every job he sees, but he knows that isn’t a strategic choice. A good facilitator might ask something like, “What’s motivating that desire?” Or, “What do you want to prioritize right now?”

REVAMPING your questions

Those alternative questions above have been revamped. We revamp a question when we move beyond facts to focus on what’s happening beneath the surface. REVAMP is an acronym to help you remember to deepen your questions by asking about these things:

R – Relationships

E – Emotions

V – Values or Vulnerabilities

A – Attitudes or Assumptions

M – Meaning or Motives

P — Priorities

The examples above asked about meaning, motivation, and priorities. Here, let’s look at a question that digs into relationship: Imagine your partner is sharing about a tense work meeting where he observed two colleagues in conflict. Instead of asking, “Then what did Megan say?,” you might go a layer deeper by asking about the relationship between Megan and the colleague she was in conflict with. “What’s the dynamic between Megan and Paul, and how do you fit into it?”

You could also ask, “Does their dynamic threaten your team?”—a question about vulnerabilities.

Or if your aunt is giving you a movie recommendation, you could ask, “Who is in that movie?,” but a Google search would answer that. You’ll understand your aunt better if you ask, “What was it about the movie that spoke to you?” That question gets at values and attitudes, maybe evening meaning or priorities.

None of this takes much extra time or training—you know everything you need to put REVAMPed questions into practice right now. What you do need is intention—the intentional commitment to seek understanding in conversations that matter.

How can you REVAMP your questions?

I love a good multi-step process, but there isn’t one needed here. To REVAMP your questions, all you have to do is try.

Not long ago, I was at lunch with a friend of mine. We don’t get to talk regularly, so we caught up on our families and work lives. We could have kept it at the surface level—how’s the new grandbaby? But I think we both value our conversations because they go deeper. So after we shared the general status updates, we discussed how these things make us feel and what they make us think. Our questions were in the territory of relationships and emotions and priorities; in other words, they were REVAMPed.

All you have to do is remember to ask a deeper question.

REVAMPing your questions offers the gift of understanding; we know each other better. We feel seen and heard in meaningful ways, when others ask these questions of us. And these kind of questions give us the opportunity to really process our own experience, and support others as they do the same.

BONUS CONTENT

Let me share a little more about Never Search Alone, the organization I mentioned at the start of this article. This is a movement of 5,000 volunteers that has helped over 50,000 job seekers through 6,200 job search councils (JSC)..

Through the organization, you can join a free JSC, which are peer support groups for people who are seeking work. Council members work through tools to help seekers find the right fit for the market (“candidate-market fit”) and improve their search process.

I’ve been on the sidelines of Never Search Alone for a few years now, and have just started volunteering as a trainer for the council moderators. Some things in life are too good to be true—this isn’t one of them. Take my word for it … this is a truly free opportunity to offer support for people in the job search process. The only related cost is if you decide to purchase the corresponding book, also called Never Search Alone; every dollar from the sales is donated to run the community.

If you’ve been laid off, let go, or are looking for your next job, take some time to see if it might be a good community for you: https://www.neversearchalone.org/about.

BONUS NOTE

When I originally sought a memory device to help recall the ways we could deepen questions, the first acronym I tried was VAMPIRE. Some trusted advisors wisely cautioned me to find a different option. I think they were right, but I still laugh when I think my tagline could have been “VAMPIRE: draw blood with your questions.”

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I’ve written before about powerful questions coaches use. These are the kind of “have it in my back pocket” questions that good coaches and leaders know when to use, to great effect.

The great thing about a powerful question is that it’s simple, and it’s clarifying.

Simple: These questions are short and to the point. No big words, no complex concepts. Rarely do you have to research in order to answer it.

Clarifying: You know the answer instinctively. Your gut responds as much as your mind does. Often, the instinctiveness of the response points at a greater truth.

I was reminded of another favorite coaching question recently—one that I didn’t include on the original list. I want to share it here, along with three stories about when I’ve used this question in my life.

The question is this: what is the work that only you can do?

Story 1: Prioritizing and Delegating

If you’re familiar with the CliftonStrengths profile, you can probably make some guesses about my personality by knowing this: I’m high in Strategic, Arranger, Achiever, and Responsibility.

What this means: I’m absolutely ready to take on a big task, break it down into smaller pieces, and execute with excellence, almost never missing a step.

What this also means is I tend to hold on to work, even when volume and logic says I need to hand things off. Delegating is not a strength, even when I’m overwhelmed.

This became evident a few months ago, when a large project’s administrative requirements had me drowning. I didn’t have the bandwidth to do it this time around.

“What is the work only you can do?” I asked myself.

As I considered the overall project, I knew I was the team member best suited for designing the project and directing its overall content. That was the work only I was in a position to do for this project. Thankfully, another team member was ready and able to manage the administration. By focusing on my unique contribution, I was able to see the need for handing other responsibilities to trusted colleagues.

Here’s the TLDR for busy leaders: stop doing work that others can do, and focus on what requires your unique strengths.

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Story 2: Making Space for My Family’s Needs

The question was useful again about 18 months ago, when my grandmother (who was 94 at the time) tripped and broke her wrist. She needed physical care for the short term that was beyond what my mother could provide.

“What is the work only you can do?” I asked myself. I was the only family member with the physical capacity and work and family flexibility to meet the needs. So I made temporary plans to care for her as long as I could.

The arrangement didn’t last long; Grandma’s needs became overwhelming and she moved into a rehab center. She passed away a few months later. I’m so glad I was able to make myself available for the work that I was uniquely capable of; it gave us precious time together in the last months of her life.

(Side note: It was during those weeks together that my grandmother told me a story of my mother’s childhood—a rare story I hadn’t heard before. I shared it in the “bonus” section of a previous post. The lesson it offers comes to mind often.)

Story 3: Determining Career Direction

For the final story, let me jump back to professional life. As many of you know, I’ve worked over the last few years to define more clearly the work I do, as part of launching my company Bright Threads Leadership Group. Refining our purpose and offerings has benefitted from asking the same question:

What is the work that only we can do?

Believing I have something unique to offer the world is what inspires me to do this work. I’m grateful for the colleagues and collaborators who helped me define that offering.

If you’re in a job search process, angling for a promotion, or thinking about how to shift the direction of your career, asking this question might provide greater clarity on your distinct contributions.

Using this question in your own life

The question tends to be most useful at decision points—when you’re overwhelmed, when someone needs something from you, or when you’re trying to figure out where to focus your energy.

If you’re at one of these points, or you’re supporting someone who is, asking “What is the work only you can do?” may be helpful.

Where in your life might this question be useful right now?

BONUS CONTENT

Drum roll please …. I’m proud to share that as of late last month, I’m a Gallup Certified Global Strengths Coach. I’ve found CliftonStrengths (formerly known as StrengthsFinder) to be an incredible tool for understanding and growing your leadership, and helping teams improve productivity and joy in working together.

Drop me a note if you’d like more information about coaching and team retreats designed around leveraging your strengths.

“What do you do when a team member doesn’t want to grow?” the manager asked. Heads nodded in her direction—she wasn’t the only one with this question.

In fact, the question of how to talk with an employee who has no interest in growing or developing is so common that it’s been asked in almost every workshop I’ve ever led on developing people and teams.

Some people are happy with who they are and don’t want to change.

As leaders, can we live with that?

The growth vs promotion myth

There are good, thoughtful reasons to avoid some growth. A promotion, for example, can often come with new responsibilities that disrupt the balance you’ve achieved in your life.

One vice president I know recognized that moving up the next rung in the ladder would come with strings attached. He wasn’t willing to make those kinds of sacrifices of his time, if it meant spending more hours at work and less hours with his family and on hobbies he enjoyed. Avoiding the promotion made good sense.

Others have turned down promotions that would have required more travel, relocation, less enjoyable work, or more late nights on Zooms with global colleagues. Fair enough.

Growing to the next level in the organization is not everyone’s objective. We can choose to be ambitious about something other than work if we have an employee who doesn’t want advancement or promotions. That’s not a bad sign. They may just be happy with the balance they have right now.

But promotions are different than growth. Promotions are avoidable. Growth is not. When a team member insists they are not interested in growth, leaders need to understand what is really being communicated.

4 types of growth in the workplace

No matter the role, there are four types of growth beyond advancement up the ladder that need to be considered.

#1: Willingness to change

Change is the first type of growth. Change is inevitable, whether we like it or not. Colleagues come and go, business models shift, the market rises and falls and technology evolves. Lack of willingness to change is career-limiting. Adjustment will always be required.

Is it mandatory? Yes. Change is inevitable.

#2: Growth in capacity

The next type of growth is building capacity, either by handling more complex work or a higher volume. Most work requires individuals to become more productive over time, or more advanced.

Is it mandatory? Usually.

#3: Growth in skill

A third type of growth is the development of new skills or knowledge. An accounting team member might be asked to learn to process payroll as a backup to another colleague. Or a graphic designer might learn how to use AI tools to stay on top of their industry. This kind of growth includes process improvements or innovations that help a team member get better over time.

Is it mandatory? Usually, but often with some flexibility.

#4: Growth in leadership

The fourth and final type of growth is to develop leadership capacity. Informally, senior team members should be leaders among their colleagues, role-modeling good behavior, mentoring new teammates and providing guidance on complex work.

Is it mandatory? It should be.

Focus on measurable indicators of growth

When you have a direct report who says they don’t want to grow, your first job is to assess what they mean by “grow.”

Are they willing to change when necessary? Good.

Are they open to growing in leadership, capacity, or skill, even if they aren’t ready to climb the ladder? Even better.

Contentment in a current position isn’t the same as stagnation. If you can see visible signs of growth—including measurable indicators in their productivity, skills or leadership—then you can most likely be satisfied that their trajectory is healthy.

But if you can’t see any signs of growth or willingness to change, then you have a problem.

Knowing what growth looks like makes it easier to recognize when it’s missing. The four types of growth are useful because they give you something concrete to look for and something concrete to notice when absent. From there, you can offer compelling feedback.

Red flags that indicate a problem with growth

If any growth is difficult to see, then watch for other red flags, such as:

• Resistance to change.

• Declining productivity.

• Skipping learning opportunities.

• Lack of respect from other team members.

• No self-identified growth areas in their annual review.

Performance plateaus are to be expected on occasion: sales numbers sometimes dip because of market factors, for example. But sustained plateaus and truly static employees may require difficult conversations and ultimately difficult decisions. Work with your team member to improve performance, but if they aren’t willing to grow, your best move may be to find a new team member who is.

Questions to gauge genuine growth vs. stagnation

Truly assessing a team member’s willingness to develop takes observation and conversation. The following questions can help you gauge stagnation versus a willingness to grow:

For willingness to change:

• “When we’ve had to adjust our processes recently, how did you adapt?”

• “What changes in our industry do you think will affect how we work?”

• “How do you typically respond when priorities shift unexpectedly?”

For capacity growth:

• “What aspects of your work feel more challenging now than they did a year ago?”

• “How has your ability to handle complex projects evolved over the past year?”

• “What is more sophisticated about the work you’re doing now compared to when you started?”

For skill development:

• “What new skills or knowledge have you developed in the past 12 months?”

• “Where do you see gaps in your current skill set that would help you be more effective?”

• “What industry changes or trends are you staying current with?”

• “What process improvements or innovations have you brought to the team?”

For leadership growth:

• “How do newer team members typically come to you for guidance?”

• “What role do you play in helping colleagues solve problems?”

• “How do you contribute to team decisions or process improvements?”

These conversations are rarely easy. But the leaders who avoid them aren’t protecting their team members. They’re failing them.

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Growth, in its many forms, is what keeps people relevant, engaged and valuable. Your job is to create the conditions for growth, name it when it’s missing and make clear that standing completely still is not a sustainable option for anyone on your team.

This article was first published in my column at SmartBrief Leadership.

BONUS QUESTION

As with individuals, teams need to be committed to their growth and development. Here are my three favorite questions for assessing how your team is doing:

1. Did we meet expectations? That’s the metrics measurement, or to put it in project management terms: were we on time, on spec, on budget?

   But Hackman doesn’t stop there. He says real success has two additional evaluation questions.

2. Are we improving so we can work better together next time? To get better over time requires improving technical skills, developing capacity to work cross-functionally, and learning to give and receive feedback often and well. Successful teams are teams that improve with age.

3. Are the individuals growing? Teams are containers for the development of people (so say other top team dynamics scholars)—so if your people aren’t growing, your team is failing. There’s trouble coming if individuals on your team find more friction than fulfillment and learning in their work.

Find more in this article I wrote a few years ago.

Photo by Vitaly Gariev for Pexels.

There are times when our family goes out for dinner or a long drive and we chat happily the whole time. But I’ll be honest, there are also times we’ve sat across a restaurant table and struggled to put full sentences together.

After we encountered a few awkwardly silent meals, we developed a game: we take turns asking questions.

The questions we ask can be fanciful or realistic. They can be outrageous or practical. They can be on any topic that comes to mind. The two requirements are that both of us must answer every question, and it can’t be a question we know the answer to. (So no asking, “Who was your first celebrity crush?,” because the answers are known—Alyssa Milano and Ricky Schroeder, respectively.)

Saturday is a national holiday, for folks in the U.S. Here are some questions you can keep in your pocket if your day involves a long drive, a dinner with family, or a few hours at the pool or beach.

Bonus points to anyone who hits reply and shares their answer to #16.

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Fun questions for long car rides

1. For each niece and nephew, predict who they’ll be at 30.

2. If you had a round-the-world trip, where would you want to stop?

3. If you had to start a business, what would it be?

4. If you were making a movie of our family (or friend group), what actors would you cast?

5. If your house were on fire but the family and pets were safe, what three things would you grab?

6. What nightmares did you have as a kid? Have you had any nightmares recently?

7. When you think back to high school, what is the soundtrack you hear in your head?

8. How is your career like your grandparents’ work? How is it different?

9. Fill in the blanks - I’m cheap about ____ but spendy about ____.

10. Name one character from literature, TV, or movies that you related to as a child. One character you relate to now. And one you hope you are like in your future.

11. Make one prediction about the future.

12. What’s one story you want your grandchildren to know about you?

13. What do you want to remember about this stage of life?

14. What’s the best piece of advice you ever received?

15. What are three things you recommend? (Podcasts, books, products, music, etc.)

16. What do you believe that is unseen? Or, what’s the weirdest unexplainable thing that’s ever happened to you? (True story, I swear I saw a kangaroo running freely in Naperville, Illinois. My family doesn’t believe me, but I know what I saw!)

17. Who in the family do I look the most like? Who did I get my attitude from?

18. If you had to bury a body, who in the family would you call for help?

19. What rivalries could start a fight in our family? (Example: Cubs vs. Cardinals. Crunchy vs. Creamy.)

20. Tell me 3 things on your bucket list.

If you still need more inspiration for your holiday gatherings, be sure to check out these question games for kids, which I shared last year.

Photo by Michael Li at Pexels.

What happens next is ours to influence. Read further to find questions that can help you reframe the conversation.

“I started spiraling immediately,” my friend Carrie (name changed) told me, as she described a comment from her father that sent her off.

Like many in our generation, Carrie is managing a busy career and full life while also trying to care for her aging parents. She was at their home one Saturday, delivering flowers and doing some light cleaning when her father made an abrupt statement.

“You should be better about money,” he told her.

It was a gut punch comment—the kind that felt designed to hurt while also being misguided. Not only had Carrie been exceptionally responsible in her finances and she’d recently taken a less demanding job to have more time for her parents.

“My mind went off on its own mission,” Carrie told me. She felt judged, as if her contributions were invisible.

Misinterpreting the moment

It’s so easy to read intentions into others’ comments—even people we know well—and get them entirely wrong. I saw this recently at work, when a retiring president told me about receiving letters of support from people he considered nemeses. He wondered: had he been misreading their attitudes all along?

This kind of misreading is common. As a leadership coach, I hear clients describe “nasty” emails from colleagues they consider enemies. They’ll read the messages aloud, infusing venom into the tone—but the words themselves are neutral.

A question you can ask yourself to diffuse

A friend once asked me a question that changed how I approached a tense work situation:

“What’s the most generous interpretation of this?”

I had been frustrated by a team member who seemed obstructive. Her question forced me to consider their perspective: what values or logic were they working from? Could their objections be valid?

It turned out they were. The question helped me extend more positive regard, reframe my approach, and work collaboratively with the team member to move our project forward.

My therapist offers a similar approach. After hearing my complaints, she’ll say:

“That’s one way to interpret this. What’s another meaning you could make?”

On my best days, I’m able to see that the world is not against me—most of the time, neither are your parents or colleagues.

Our minds often cast us as the main character in a drama, spinning stories that confirm hidden fears rather than reality. These questions let us explore alternative plotlines and extend positive regard.

Carrie could have used these questions as she processed her father’s comment. Fortunately, she paused and sought clarification instead of storming out.

“I want you to retire well,” her father explained. “And to do that, you should be good with money where you can.” I like to imagine he gestured to the fresh flowers on the table, the clean space, and the daughter who was caring for his needs.

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BONUS QUESTION

Here’s another useful question for seeing situations like these in a different context:

“What might be going on for this person that I can’t see?”

Carrie’s dad was obviously thinking about retirement; but because Carrie couldn’t see that, his out-of-context statement felt like judgment rather than advice.

Photo by SHVETS production on Pexels.

Convinced, I started adding a few bicep curls and weighted squats to my workout routine. I started at 6 pounds in each hand.

Eventually I became bored with the same two exercises, so I started using exercise videos. My 6 pounds graduated to 10. I bumped the practice from two days a week to three, and increased my reps.

(This story really does have to do with asking better questions—stick with me.)

Earlier this year I worked with a trainer, knowing I needed to push myself and improve my form. I started reaching for the 15 lbs weight; I learned to go until I felt tired, then do a few more reps.

Finally, a few months ago, I joined a gym and started strength training in public. Working out in front of other (younger, fitter) people takes courage—but I feel proud every time I come home.

I tell you this to illustrate how we can go from a total beginner to a competent practitioner with dedication and effort. I won’t be slinging 50 lb weights around any time soon, but I’m getting past my nerves and doing something new, with dedication.

Dedicating ourselves to a practice

That dedication is what I really want to write about today. Most good things in life take dedication. They take starting as a beginner and putting in the work to build competence, sticking with it over the long term.

We sometimes use the word “practice” to describe these sorts of pursuits. This type of practice is a noun, as in “My meditation practice is teaching me to be more present.” When we engage in practices, we invest our time and energy not because we are experts, but because the effort and the outcomes are meaningful—worthy of our dedication over time.

Today, I invite you to develop an intentional practice of inquiry. Make question-asking a practice you pursue with dedication and intentional effort—knowing that over time, that practice will build your expertise and deliver a meaningful outcome.

Where do you start a practice of inquiry?

The beginnings of any practice can be modest. I started weight training with 6 lbs. Others I know have started their meditation practices with 1 minute of silence. Start small so you can’t fail, and build from there.

Here’s how I believe a practice of inquiry might progress over time:

• Begin by asking more questions. Specifically, always ask a question before sharing your opinion. Create reminders for yourself, so you don’t forget as you get busy—a sticky note on your computer monitor or refrigerator, a pop up reminder on your phone.

• From there, work to grow your curiosity. Walk around wondering. Ask yourself why things work the way they do, what you’re assuming, and what you might be missing.

• Next, notice what you don’t understand, and ask more in those moments. If you’re surprised by a colleague’s reaction, don’t react to their reaction. Ask.

• Now, begin to improve the quality of your questions. Specifically, focus on asking questions that are unpredictable, and that seek understanding rather than just facts. (Watch my TEDx Talk for more on this.)

• Once you’ve committed yourself to this practice for a while, begin to consider your impact. “Where did I live in alignment with my intention to ask better questions today? Where might I extend my practice tomorrow?”

• Finally, advance your practice by building the skills that can help you in complex situations. (I’ll include some links to guide you in the “bonus content” section.)

Considering what makes a practice successful

If you decide to make your practice of inquiry more intentional, I want to invite you to consider one question:

How have you developed committed practices in the past?

Let me use my husband Cliff as an example. Like many people, during the pandemic, Cliff began baking sourdough bread. His practice started with curiosity—I wonder how that works? Then he researched the process and followed a recipe to create a sourdough starter. (We named it Flossie.) For five years now, he’s fed Flossie consistently because he made it a routine. Saturday morning is Flossie’s time to shine.

Cliff also follows sourdough bakers on social media, saves their recipes, and tests them at home. When we go to a family gathering, he brings delicious baked goods and shares the recipes with others. “The spawn of Flossie” (as we call it) has been gifted to friends and family, who now have their own sourdough practice.

Like the sourdough example illustrates, building a habit or practice, takes these kinds of consistent behaviors as we incorporate the practice into our daily lives.

What will help you make the practice of inquiry a habit that sticks for you?

Take time to think about your previous experience in building new habits. What motivated you? What made it too obvious, or important, to overlook? Often creating routines, engaging our community, and building accountability plans are part of what makes our practices and habits stick.

BONUS CONTENT

To help you deepen your practice, you can find tools, resources, and ideas in these articles.

• Using questions to shift thinking when you’re stuck

• Asking questions that get beneath the surface

• Finding a generous interpretation when in conflict

• Practicing self-reflection at home and at work

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Whether you’re the person being reviewed, or the reviewer, these meetings serve as a great check point for progress toward established goals. Even better, mid-year reviews are a natural opportunity to focus on growth.

Quite often, I’ll ask a manager or executive how one of their team members wants to grow … and they have no idea. “How do I find out?”

This feels like the set up to a joke, with a very simple punchline:

Q: How do you know how someone wants to grow?

A: You ask them.

Of course, sometimes you ask, and the team member has no idea how they should grow. Or they offer a vague response, like “I want to grow my leadership skills.” The questions below give you a simple framework for identifying specific ways someone wants to grow.

Asking these questions of your team members is worth doing—it’s difficult to reach a destination you haven’t identified. Uncovering specific growth areas gives you a clear destination; and when that identification process happens between a supervisor and employee, it creates interest (“I really want this!”) and accountability (“My boss knows!”).

This is a great retention strategy, too. Team members who do not feel like they are growing in their role are 2.5x more likely to quit in the next 12 months, according to Deloitte.

A framework for identifying growth areas in mid-year reviews

This framework uses questions (big surprise) to probe in three areas: 1) future vision, 2) skills gaps or acquisition, and 3) building on strengths.

While there are nine questions here, you shouldn’t ask all of these. Instead, pick the ones that feel right for the moment. Or, give your team member the list in advance and ask them to come to the mid-year review prepared to speak to two or three questions that most resonated.

1. Envisioning the future

• What do you want to feel more confident doing 6 months from now?

• Tell me how you imagine your career 3-5 years from now.

• What’s a project or challenge on the horizon that you’d like to take on?

2. Identifying growth areas for skills development

• What skills or knowledge do you wish you had more of?

• What’s one thing you’ve seen someone else do well that you’d like to learn?

• Where do you feel out of your depth—but excited to learn?

3. Building on strengths and creating support

• Where do you feel you’re already growing and want to keep growing?

• Where do you see opportunities to contribute more to the team’s success?

• What kind of support or resources would help you grow right now?

How to use these questions and what to do with the answers

After you’ve selected the questions that are most relevant for the team member, ask them one at a time and really listen. Focus on understanding rather than just the facts of their response. Listen for themes and help your team member align to the organization’s highest priorities, when possible.

Then work together to create a plan. (Find some free development ideas in this article.) Add the topic to your regular check-in document, so you can ask about progress or offer support.

How to use these questions to talk to your boss

You don’t have to wait for your boss to ask how you want to grow. Come to your mid-year review prepared to share your responses to a few questions above, and with a clear request for their support. Here are a few examples:

• I’d like to work on more cross-functional projects, so I broaden my understanding of the business. In the next few months, would you help me find projects with other departments where I could meaningfully contribute?
  

• I know I can be quiet in meetings, and I’d like to speak up with more confidence. I’m going to start by being more vocal in our departmental meeting. It might help me if you called on me to share my opinion—would you consider that?
  

• I’m really interested in cyber-security and our team could benefit from more in-house expertise on the topic. There’s a conference I could attend next month—could I start there, and then shape a plan for what the next steps might be?

Be intentional about growth

Growth conversations don’t have to be complicated, but they do need to be intentional. When you invest time in understanding how someone wants to develop, you’re not just checking a box on your management to-do list—you’re building trust, demonstrating that you see them as more than their current role, and creating a foundation for meaningful progress.

The best part? These questions work just as well for your own growth conversations with your boss. After all, the most effective leaders are those who never stop growing themselves.

More to help you prepare

• Four types of feedback to ask for and give

• A three-step process for giving feedback that gets heard

BONUS QUESTION

Mid-year is a great time for reviewing your full life, and not just work.

Here are 3 questions for a personal mid-year life review:

1. What do you want to feel more confident doing in your personal life 6 months from now?

2. What’s one thing you’ve seen someone else do well in their life that you’d like to learn or incorporate into yours?

3. Where do you see opportunities to contribute more meaningfully to the people and communities that matter to you?

Thank you!

Last week I asked you to forward this newsletter to someone who might like its content, and recommend that they subscribe. Many of you did—thank you! I’m currently sitting at 1001 subscribers.

To say thank you, I’m plotting a special offering for sometime in July. Subscribers will be the first to hear about it, so watch your inbox.

And of course: it’s not too late to share this newsletter—please forward to a friend!

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Photo by Yan Krukau at Pexels.

The topics of these many meetings are often in our professional wheelhouses: we know how to discuss sales strategies, share revenue numbers, or plot a change effort.

What we don’t know is how to run a meeting.

This lack of training shows in the complaints that are all too familiar:

• This meeting could have been an email.

• The discussion devolved, and we never got past the first item on the agenda.

• What agenda?

• Was anyone taking notes? We’re going to need another meeting to remember what we decided in the last one.

• This was a waste of my time.

About a year ago, my colleagues and I began sharing our best meeting facilitation tips with participants in the leadership development programs we facilitate. At first, we worried these ideas were too basic — but we’ve watched senior leaders, with “chief” in their titles, scribble notes as we walk through these principles.

We’ve also watched early career and emerging leaders breathe a sigh of relief as we share these ideas. “Finally,” they seem to be saying, “someone is naming what we need to make our meetings more productive.”

The need for meeting hygiene

Ensuring that your teams are as productive, efficient and meaningful as possible requires strong meeting hygiene.

I use the word ‘hygiene’ intentionally. Good hygiene is a daily practice — we don’t brush our teeth once and then assume we’re done for the year. We must be consistent in our efforts. At the same time, once those efforts become routine, they don’t require much of our mental bandwidth to make them happen. The habit is formed.

Meeting hygiene operates in the same way. We must follow the essential meeting hygiene practices daily to see results. But once we build the habit, little mental effort is required. The processes happen naturally, with minimal perceived effort.

7 tips for getting the most out of your meetings

There are seven essential practices for running a meaningful meeting.

#1: Clarify the purpose of the meeting: update, discuss and align, or decide

First, you must know why you’re meeting. Are you there to update team members? Discuss possibilities and align on next steps, or make a decision?

In longer meetings, such as a bi-weekly team meeting, the purpose may shift from segment to segment. But the intent should always be clear. When the intent isn’t clear, info updates turn into debates.

The following chart can help you determine the meeting type and avoid some of the common pitfalls of each.

#2: Default to fewer, shorter meetings

Meetings are necessary — they are often the most efficient way to ensure everyone is informed, ideas are carefully evaluated, and decisions are shared and executed. But meetings shouldn’t take up so much time that we have no space for executing the work.

To minimize meetings, default to shorter, fewer time blocks.

• Consider 10-minute daily huddles instead of longer meetings (or a slew of emails).

• Schedule meetings for 25, 50 or 75 minutes rather than 30, 60 or 90. This allows time for bio breaks and (importantly) information sharing with those who were not in the meeting.

• Evaluate the right frequency — could that weekly meeting be bi-weekly? Could the monthly meeting be quarterly?

• Honor the time you have reserved. Show up on time and end on time.

• Review your recurring meetings quarterly: Do you still need them? Can they be shorter or less frequent?

#3: Have a clear agenda, shared in advance

A coaching client recently complained she never knew what to say in meetings. As we explored her concern, the challenge became clear: the agenda wasn’t shared in advance, so she didn’t have time to gather her thoughts. This client requested that her colleagues share topics in advance, and they did. The very next meeting, she felt better prepared and able to speak up.

This is why we want clear agendas: to give people time to prepare so they can bring their best ideas rather than needing to respond “off the cuff.”

Clear agendas also offer an opportunity to consider priorities: what really requires the group’s consideration, and what could be an email?

#4: Limit attendees and improve info sharing before and after the meeting

In many organizations, being in a meeting is a status symbol. But this status comes at a cost: team productivity. When possible, let one individual represent the team or department, and then improve pre- and post-meeting communication so that the representative shows up prepared to advocate as needed, and can also share updates from the meeting afterward.

In general, if you’re not leading, representing, or learning in a meeting, you should be leaving it.

#5: Have a clear closing

Never end a meeting without reviewing who should do what by when. These five questions will help your team close well:

• Let’s review our decisions.

• Who is responsible for each next step?

• When is it due?

• What needs to happen before we meet again?

• How should we prepare for our next meeting?

Make sure communicating decisions and updates is part of your “what needs to happen” plan.

#6: Make it safe to speak up

Meetings, especially discussion and decision meetings, are only effective if people feel free to share concerns, raise ideas and ask questions. If the energy of your meetings is falling flat, the problem may be a lack of psychological safety.

Running a red session, where someone plays devil’s advocate, can help others feel free to speak up. (Find other tips here.)

One thing participants should always feel free to speak up about — the meeting itself. Give the team permission: “If this meeting ever feels like a waste of time, let me know.”

#7: Be a model team member

Finally, as the meeting leader, you must model exceptional team behaviors.

• Know that if you don’t come prepared, no one else will.

• If one person starts multi-tasking, everyone will start multi-tasking.

• Be aware of power dynamics and tone. What the person with the most power says carries disproportionate weight in the room. Be mindful of the adage, “A cat is a lion to a mouse,” and model thoughtful dialogue.

Audit your meeting management

If almost a third of your time is going to be spent in meetings, get the most out of those minutes as you can. These best practices work. I’ve seen team productivity be transformed as the habits became part of the way the team functions.

Take time to assess your regular meetings today.

For the meetings you lead, take action ASAP. Share this article with the other meeting participants and invite feedback in your next meeting. Together, create a “stop, start, continue” list for the meeting, and put it into practice immediately.

For the meetings you don’t lead, consider the single change that would most impact the meeting’s productivity and functioning. Politely suggest the idea to the meeting leader, and volunteer to help implement the new approach.

If you do this for every regular meeting on your schedule, your meeting hygiene will improve, and over time, the new approaches will require little effort to sustain.

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This article first appeared in SmartBrief Leadership.

BONUS QUESTION

Are there poorly managed meetings in your life? If so, what is keeping you from saying something?

Bear with me as I tell a little story.

We moved into our house almost 21 years ago. The day we moved in, I unpacked bathroom items, putting less frequently used items in a cabinet drawer, and tossing my daily use lotion and makeup into a basket in the nearby closet.

A decade passed.

A decade where I, every day, went to the closet for the items I constantly needed while infrequently-used items sat in an easily accessible drawer.

Finally, I realized my foolishness and moved the basket of daily-use items to the more convenient location.

Duh.

Living with sub-optimal meeting structures is just as silly. How could you suggest something—gently, respectfully—that makes the meetings more productive and efficient?

Before you go, one more thing:

I’m SO CLOSE to my summer goal of 1000 subscribers, and technically we haven’t even hit the solstice yet. If you read this far, this newsletter must deliver a few insights each week that make it worth your time.

Would you forward it to a friend or colleague and encourage them to subscribe (it’s free!) as well?

I’ve got a public thank you gift planned for when I finally hit 1000. Watch for it!

In the same way, positive regard is necessary for a good conversation to advance. Positive regard is table stakes for a good conversation. Thankfully, most of the time it happens naturally, especially when communicating with people we value, like trusted colleagues or family members.

This isn’t the first time we’ve spoken about positive regard. Previously, I’ve said that:

• Positive regard transforms the quality of your questions—When you approach conversations with genuine care and respect for the other person, your questions become more effective and less threatening.

• Questions can carry hidden poison without positive regard —The same question can feel supportive or judgmental depending on the underlying attitude and intention behind it.

• Positive regard is the antidote to harmful questioning—By maintaining genuine care and respect for others, you can ask difficult questions in ways that strengthen rather than damage relationships.

• It enables meaningful conversations—Positive regard creates the foundation for moving beyond surface-level talk to deeper, more meaningful exchanges.

There are many, many benefits to positive regard. But sometimes showing this kind of regard is more complicated, for example when addressing a failure, a difference of opinion, or a person you find difficult. In those circumstances, positive regard is so essential you should likely postpone a conversation until you’re certain you can approach it with the right attitude.

Demonstrating positive regard

There are three primary ways we demonstrate positive regard: our tone, our word choice, and our track record.

Tone:

Much of our communication is nonverbal. The way a message is delivered is just as important as the words. I call this aspect of communication tone, which includes the inflection in your voice and the body language with which you delivered it.

Our hearing is more sensitive than our eyesight. We’ve all experienced the subtlety of this: have you ever had a conversation with someone where the words seemed fine, but you got a clear vibe something was off? If you follow up afterward, it’s likely you were right. Your gut picked up on the difference in tone even if your brain was still processing the words as “fine.”

We can show positive regard with our tone by filtering out our sarcasm or scoffing. Softer or enthusiastic tones and an uplift in your inflection are often signals of positive regard. We can also show positive regard with appropriately warm nonverbals. That means no eye rolling or finger pointing, and uncross those arms. Instead, make eye contact, lean in, keep your stance open.

One note: you don’t have to adopt the overly chipper “cheerleader” tone to communicate positive regard. Most of the time, your normal speaking voice will do.

Word choice:

The second way we demonstrate positive regard and orientation is with our word choice.

Imagine you’re part of a team that is debriefing an event that didn’t go well. Attendance was low, as was the energy. It felt disorganized. Even the food was disappointing—soggy eggrolls and warm white wine. You could start your debrief conversation by asking, “What went wrong?” It’s a valid question—this event was not a success. But that question is likely to lead to finger pointing and defensiveness.

“Who picked out that speaker?” Marcus might ask. “He was terrible.”

“Well, you were in charge of catering!” Tammy, who booked the speaker, might push back.

Instead of beginning with “what went wrong?” and starting the blame game, you could try asking a question with positive regard. “If we did this event in the future, what would you do differently?”

(Find more on this very example, in this article on debriefing events.)

Asking about the future is one of my favorite ways to stay positive. Reframing the question to address the future, rather than criticize the past, creates positive regard and positive orientation. It subtly communicates, “I’m sure we can do better,” rather than, “We really messed up.” While both statements may be true, only one helps people figure out how to improve.

Naming assumptions or explanations is another way I create positive regard through word choices. If I assume I know the answer, then why ask the question at all?

Imagine work has been busy, and you just spent all Saturday at the office. You come home to find the laundry undone, supper not started, and your partner playing video games with your daughter. A huffy “What have you been doing all day?” might be a natural first question, but it’s easy to let your tone shift negative with that. Instead, you could show positive regard by assuming there is a reasonable explanation and stating the assumptions you had. That might sound like, “Hey! I don’t want to fix supper tonight. Is there a plan for dinner or should we order out?”

Track record:

Finally, our track record with our conversation partner plays an outsize role in how our questions are received. I have a few, cherished colleagues I’ve worked with for years. Because I know them so well and trust they have a high positive regard for me, I know they’re asking to understand my decision making, and not criticizing, when one of them asks, “What were you thinking here?” I may still bristle a bit at the sentence construction, but I can quickly move past that because I know the intent.

Likewise, when Cliff, my husband, texts me “How are you?” in the middle of the workday, his track record of interest in my life says he’s not looking for just “busy” or “fine.” He genuinely wants to know how my last meeting went, or if I’m feeling restless or energized by my work that day.

On the other hand, there are people I’ve worked with that don’t have a supportive track record. I instinctively brace myself when their hand goes up at a forum or when they corner me in the hallway. Why? Because they have a history of negative tones and word choices. As a leader, most of the time I try to rise above this—returning positive regard even when it isn’t offered. But as a human, it can hurt. Their track record influences how I hear their questions. If we want deeper knowing, better outcomes, and more good relational energy, we each have to play our part in creating track records of showing positive regard.

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Showing positive intent matters

Positive intent matters. This week, as I was putting the finishing touches on this newsletter, I was also leading a multi-day training. As we began the training, my colleagues and I asked the group to identify the norms they wanted to establish as expectations for the participants. “Assume positive intent” showed up early on the list, and the call for positive regard was echoed in other norms as well.

Give the people what they want.

Show positive regard through your tone, your word choice, and your track record. Edit out those inauthentic questions or the hints of sarcasm. This week, pay attention to the attitude behind your questions. Your relationships—and the quality of your conversations—depend on it.

BONUS QUESTION

Another way we can show positive regard is by our authenticity. When we stop trying to be seen as impressive, we make space for the equally imperfect others in our lives. What shows more positive regard than welcoming someone as they are, rather than as they want to be?

With that in mind, today’s bonus question is for self-reflection: Where am I posturing instead of relating?

Photo by Vitaly Gariev at Pexels.

Meredith was at an event for her child’s school when she ran into another mother, whom she’d not seen in a while. The woman had an obvious bump—it seemed apparent to Meredith that this woman was expecting another child.

“When are you due?” Meredith asked.

And you can probably predict what happened from here. The woman wasn’t expecting at all.

Who among us hasn’t made that mistake, or a similar one?

Normally, I’m a proponent of asking a lot of questions. We need questions to truly know and understand the people who matter to us, and we also need questions to expand our social circles and build new relationships.

Some questions should come with hazard signs.

Need to figure out what can and can’t be asked? The guidelines below will help.

Then, I share a beautiful example of these insights in action. With permission, my former colleague Lindsey Branson, a current foster parent, shares her tips for what questions NOT to ask foster parents.

5 Guidelines for Knowing What NOT to Ask

1. Don’t ask questions that make assumptions about someone’s body or life choices

• “When are you due?” (assumes pregnancy)

• “When are you having kids?” (assumes they want children)

• “Are you trying to lose weight?” (assumes dissatisfaction with their body)

2. Avoid questions that otherize based on appearance

• “Where are you really from?” (to people who don’t look “typically American”)

• “What are you?” (referring to ethnicity/race)

• “Can I touch your hair?” (often asked to Black individuals)

3. Avoid questions that judge life circumstances

• “Why aren’t you married yet?”

• “Don’t you want kids?”

• “Why did you get divorced?”

• “When are you going to settle down?”

4. Don’t ask questions that highlight differences as deficits

• “What’s wrong with you?” (to someone acting differently)

• “Why are you so quiet?” (to introverts)

• “Are you okay?” (when someone simply looks different than usual)

5. Avoid questions that force disclosure of private information

• “Can you afford that?”

• “What medications are you on?”

• “How much do you weigh?”

• “Why don’t you drink?”

This list isn’t comprehensive. What is appropriate to ask varies by context and relationship, and also by law. (If you’re involved in hiring interviews, be sure to follow your company’s guidelines!) But in general, avoiding questions like these will keep you out of hot water.

To state the obvious, there are times when these questions are acceptable, of course. Are you a health care provider? By all means, ask about medications. You can talk with your dearest friends about the reasons for their divorce, or their plans (or lack thereof) to have children. You can ask a close colleague if they’re feeling okay. Feel free to ask your partner how much they spent on that new purchase, if that’s the kind of relationship you have.

Depth of relationship is what makes the exceptions possible. Otherwise, seek to get to know the person with questions that show more thoughtfulness.

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What Not to Ask Foster Parents

Most of us are well-meaning. We’re curious and caring. And we can still put a foot in our mouth without intending to. That’s why I loved this LinkedIn essay written by my former colleague Lindsey Branson, and reposted with her permission. Lindsey’s writing illustrates the guidelines shared above, and more.

What Not to Say When You Meet Me (and Find Out I’m a Foster Parent)

I get it. You don’t meet a lot of foster parents “in the wild.” We’re a strange family unit.

As a single foster mom for over seven years, I’ve become pretty accustomed to the confusion—and frankly, the lack of awareness—around foster care. Most people respond in one of four ways:

• curiosity (most common)

• pity (“I could never love a child who might go home”)

• admiration (“You’re a saint!”)

• confusion (“WHY???”)

I genuinely love talking about foster care and sharing my experiences. Mostly because it’s a system housing thousands of children in need—and a system that often lacks the support those kids (and families) deserve. Most people have no idea how great the need is, or that there are ways to help.

So, in the spirit of education and awareness, here’s what NOT to say to a foster parent—and what to ask instead:

“Do you get to adopt them?”

The goal of foster care is always reunification with a child’s birth family. Foster parents know this going in. If adoption happens, it’s usually after a long, complex process.

👉 Instead ask: What have been some highlights of your journey?

“Why were they taken?”

Honestly, most of the time I don’t even know. And it’s not important. What matters is that these kids have experienced trauma and need safety, love, and consistency.

👉 Instead ask: Are there any ways you or your family could use support right now?

“Won’t you be so sad when they go back?”

Yes. Of course. Heartbroken. I entered foster care fully aware that heartbreak was part of the deal.

👉 Instead ask: What’s your favorite thing about your kids? (Like any parent, I love bragging.)

And finally—please feel free to ask about the needs of the system and how you can help. You’d be surprised how much a meal, a listening ear, or some hand-me-downs can mean. Those small things can be a lifeline for a foster parent—and a huge gift to a child.

BONUS CONTENT

Not long ago, Terry Willis learned some difficult news—his granddaughter felt unsupported by some of her family. Terry wanted to change this for his family, but also for others. So he began a podcast designed to help families rebuild trust and communication across generations.

That’s a noble mission.

I appeared on Terry’s podcast recently, and the episode is now live. We talked about how to spark conversation with teens. Take a listen!

BONUS QUESTION

Are there questions you have to dodge or reframe, like Lindsey’s questions about being a foster parent? Leave a comment and share the questions that make you cringe, even when people mean well.

Photo by Ann H. at Pexels.

I remember that feeling myself. Even if you were leaving school with a job already secured, the question still seemed to apply pressure.

At lunch that day, I back pedaled. “That’s a big question,” I said. “Let me try again. What are you doing this summer?”

They visibly relaxed.

Making the decision of what to do after graduation, whether from high school or college, is momentous of course. Future plans deserve to be asked about and discussed. But questions can feel like pressure, and moving too quickly to future plans jumps over the milestone moment that your graduates also deserve to celebrate.

Also, the “what’s next?” question is a little predictable—and by now you probably know that predictable, scripted questions are definitely not my thing. (Though clearly, I make the mistake sometimes!)

So, inspired by a 2025 post from Jenny Rosenstrach, the author of Dinner: A Love Story, I’m sharing a few out-of-the-box questions you can ask the grad in your life.

Here are the excellent questions Rosenstrach shared in her newsletter:

• What would Freshman You be most surprised to know about Senior You?

• What are you most proud of from the past four years?

• Did you change your mind about anything while you were in college [or high school]?

• In the future, when you picture your quintessential college day, what will you describe?

• What are you looking forward to?!

Reflection questions for graduates

If you need a few more questions to get you through the long ride to the graduation ceremony, or the family dinner after, here are additional questions I wrote:

• What advice would you offer to an incoming freshman?

• What did you learn that you think you’ll still be using in 10 or 20 years?

• When you’ve been away long enough to feel nostalgic for your experiences here, what memories will make you feel that way?

• How has this school shaped who you are?

• How do you think your classmates perceived you, and what do you want to change about that image as you move on?

• What support do you wish you had in school? What support do you need now from me?

• What are you glad to leave behind?

For all who are celebrating in this season—congratulations!

An earlier version of this article was published in my newsletter last year.

Photo by Gonzalo Ba at Pexels.

BONUS CONTENT

Author Anne Lamott has been a continual source of inspiration to me for over two decades. If you like to write, or even just appreciate the idea of writing, you should definitely read her book Bird by Bird.

Not long ago, Lamott appeared on the “How I Write” podcast (find it here at Apple Podcasts, or on Spotify) and offered an observation that had me scrambling to open my notes app so I could write it down.

“We stop grading for curiosity in first grade.” —Anne Lamott

That is a succinct and articulate summation of what you’ve heard me say before. Research shows the number of questions kids ask begins to decline about the time they go to school. This may be because they’ve figured out some of how the world works; but the decline may also be because we start to believe that answers are better than questions.

Anne and I both think that’s ridiculous.

I’m trying to increase my curiosity—join me in asking more questions.

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Karl stared at his screen in disbelief. He can see the problem immediately, but knows leadership doesn’t. While the new system promises better collaboration, Karl knows his team is already overwhelmed with three major client deliverables due this month.

In theory, the new software program would offer benefits. In practice, it created several more problems. The transition will require training, data migration, and will likely cause delays that could jeopardize client relationships.

Karl’s challenge: how to tell his executive team that their timing won’t work when they’d already announced it to the organization.

Karl’s situation is fictional but not far-fetched. Those of us who have been in the workforce for more than a year or two have accumulated similar stories:

• Decisions made without consulting all the relevant stakeholders.
• Trade-offs that left your team with a mess to clean up.
• Good-intentioned but misguided ideas.
• Difficult choices that didn’t go your way.

All examples of feedback that needs to be shared, that the executive team won’t really want to hear.

Raising our concerns is essential—necessary for improving plans, minimizing risks, and ensuring the final decision has the impact you want. But how do you say “I have concerns!” without sounding defensive, obstructionist, or needlessly negative?

Your two-item checklist for giving constructive feedback

When you’re in Karl’s position, how you raise your concerns will determine if your message gets heard or ignored. Before you speak up, take your feedback through this two-item checklist to ensure the message has the impact you want.

1. Shift your language from judgment to specificity.
2. Shift your language from blame to problem-solving.

“Leadership’s announcement was totally thoughtless,” might be what Karl is thinking. But that’s judging and blaming. The executive team will hear Karl’s complaints and write them off as an insult that can be ignored.

Instead, Karl can be more specific about his concerns, and raise his fears with a problem solving step attached.

“We’re in a crucial timeframe for three projects with major clients, and I’m concerned we can’t make the software transition without disrupting service. (specific concern) Would it be possible to wrap up these projects in the old system while onboarding new projects in the new system?” (problem solving)

Here’s how this plays out in practice. Imagine your company announces a mandatory return-to-office policy starting immediately. Instead of saying “This is ridiculous—people will quit!” (judgment and blame), you could say: “I’m concerned about retention risk, especially for our remote hires who relocated during the pandemic. Could we phase this in over 90 days and survey the team about their specific challenges?” (specific concern + problem-solving approach).

Here are more examples of what it sounds like to be stuck in judge and blame mode versus taking a more constructive approach:

Don’t stay stuck

When we don’t like a decision made by others, our tendency is to complain in broad terms. But the broadness of our complaints disguises the root of our concerns, making them easy to dismiss. This makes us feel even more like the victim—”I’m being ignored!”—and doesn’t help us affect change.

By instead raising specific concerns and offering steps toward solutions, we demonstrate our leadership more clearly and help the organization progress toward better decision-making.

Next time you feel that familiar frustration rising, pause and ask yourself: “What specific concern can I raise, and what solution can I suggest?” Your feedback will be heard more clearly.

This post first appeared on the Ad Lucem Group blog.

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Bonus Question

While it’s technically been spring for weeks now, we’re only just getting to the point in the season that I’m certain my winter coat can move to the back of the closet. Perhaps that’s why this question from author James Clear appeals to me.

What is your purpose for this season?

Clear writes that:

“It’s rare to find your purpose for life, so instead look for your purpose for this season.

What lights you up right now? What’s a good thing to dedicate this season of your life to? Perhaps more importantly, what purpose served you well in your previous season, but you have outgrown?

Life is always changing. It’s okay to pick a new North Star.”

I have a long car ride with my husband this weekend. Perhaps we’ll discuss this question!

“Which question would be the most helpful to really know the truth about?” I asked. To my surprise, consensus built around a single question from the list: When have you seen me get in my own way?

When we get in our own way, we’re sabotaging our success. We’re seeing obstacles when an overpass has already been created. Often, it’s our thinking that is actively creating the obstacles.

The challenge with our sabotaging mindsets is that the way of thinking is so ingrained that we don’t even stop to question it. That ingrained thinking was to blame for one executive’s experience at a recent day of strategic planning. As the day ended, I could tell she was feeling disgruntled.

“I’ve spent the whole day hearing how I’m not doing enough,” the executive said when I asked about her concerns.

In reality, we’d spent the day planning for the future. But for this leader, each potential idea or initiative felt to her like an indictment of things she’d not yet accomplished. She was making it about her, rather than seeing the exercise as an exploration of the future. As a result, she felt defensive and was diminishing the overall energy in the room.

After years of leadership coaching, I see a pattern emerging in these sabotaging thoughts. Our contexts are different, but there are only a few ways we get in our own way.

I’ve identified 10 common traps and included reflection questions to help you recognize when you’ve fallen into each one.

10 traps in our thinking that get in our way

1. Avoidance

Putting off difficult conversations, decisions or tasks until they become bigger problems or missed opportunities.

Reflection question: What important conversation or task have I been putting off, and what story am I telling myself about why “now isn’t the right time”?

2. Making everything about us

Taking other people’s moods, decisions or feedback personally when it often has nothing to do with us at all.

Reflection question: Did I immediately assume I’d done something wrong? How else might I see this situation?

3. Perfectionism paralysis

Waiting for the “perfect” moment, plan or conditions instead of taking imperfect action that could lead to progress; endlessly tweaking something to make it perfect rather than risking criticism or a mistake.

Reflection question: What am I not starting because I’m waiting for the perfect moment? What do I keep tweaking instead of seeking feedback?

4. Catastrophic thinking

Imagining worst-case scenarios and letting fear of what might happen prevent us from trying things that could work out well.

Reflection question: What risks feel safe? What degree of uncertainty can I accept? What might go right?

5. Comparison trap

Measuring our behind-the-scenes reality against others’ highlight reels leads to unnecessary self-doubt and discouragement.

Reflection question: What is the fuller picture here?

6. All-or-nothing mindset

Believing that if we can’t do something completely, it’s not worth doing at all.

Reflection question: What partial solutions would still be beneficial? What’s worth trying because we’ll learn along the way?

7. Ruminating on past mistakes

Replaying failures or embarrassing moments instead of learning from them and moving forward.

Reflection question: What past mistake or embarrassing moment keeps replaying in my mind, and how is dwelling on it preventing me from taking action today?

8. Assuming we know what others think

Mind-reading and making decisions based on what we imagine others are thinking about us, often incorrectly.

Reflection question: What assumptions am I making here? How can I test these assumptions?

9. Staying in our comfort zone

Choosing familiar discomfort over the uncertainty that comes with growth and new opportunities; sticking with the devil you know.

Reflection question: What am I tolerating rather than leveraging? Where have I gotten so used to the rock in my shoe that I don’t even realize I can remove it?

10. “The way we’ve always done it” thinking

Relying on familiar patterns, even when the patterns no longer serve you well. Maintaining the status quo rather than working toward growth.

Reflection question: Where are we complacent? Where are we relying on old ideas?

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Get out of your own way

Our patterns of self-sabotage often stem from our brain’s attempt to protect us, but they end up limiting our potential and keeping us stuck in cycles that don’t serve us well. They leave us tending our wounds and storing up worries, rather than inching toward progress or finding new ways to view a situation.

Don’t sabotage yourself. Instead, use the reflection questions and seek the support of trusted colleagues to get out of your own way.

Through reflection and listening to others, I’ve learned “assuming I know what others think” is a common trap that gets in my way. When I fall into it, I withhold ideas I fear a client will think are too much or guess how my husband will respond and edit my own approach before I even bother to ask. Now that I’ve grown aware of my tendencies toward this pattern, I’m pausing myself more often to question my assumptions.

Your traps will look a little different than mine. But discovering and addressing your traps will open a door to possibilities you couldn’t see before.

If you’re feeling bold, share this list with a trusted colleague or mentor and ask them which trap they’ve observed in you. How are you getting in your own way? Sometimes others can see our patterns more clearly than we can.

Or ease into self-awareness by picking your top three traps and setting a phone reminder to ask yourself the reflection questions weekly. Small, consistent check-ins prevent these patterns from becoming obstacles in your life.

This article first appeared in my SmartBrief Leadership column.

BONUS QUESTION

A few weeks back, the Culture Study newsletter asked this question:

What is your favorite memory of being bored?

I love that question—so many memories flooded my brain. Childhood vacation days that seemed too slow but also went by super fast. Sunday afternoons as a kid, with the comics pages of the newspaper and some Silly Putty. Long road trips where eventually the endless miles gave way to play lists and good conversation.

But more recently, a clear memory emerges from February 2021: peak COVID. Our family had been isolating, and during the long winter months the walls of our house started to close in. Then there was a huge snowstorm followed by a day of sunny, mild weather. My daughter and I played outside in the snow for hours, building an igloo and eventually packing snow into the shape of a slide, which the neighbor kids tried scooting down. We laughed and played until we were numb.

This day is also the answer I would offer to another question, Tell me about a time you experienced real joy or play. And that day would never have happened if it weren’t for the boredom that preceded it.

What’s your favorite memory of being bored? Hit reply and tell me, or (better yet) ask this of a work colleague or friend.

Photo by Mizuno K at Pexels.

(I share one of my stories in the “bonus content” section below.)

The stories had us laughing and empathizing with one another from the very first second. We heard stories of wardrobe malfunctions, messages intended for one person but sent to many, and getting your facts wrong (really, comically wrong).

One group member, Rajesh, told the story of his fiftieth birthday party. He invited work colleagues, his extended family, friends from the neighborhood, and even his college buddies. What Rajesh didn’t know was that his wife had planned a roast, inviting guests to give speeches poking fun at Rajesh and sharing their best stories of him. The college buddies had some really great stories—stories that Rajesh might not have intended his work colleagues and extended family to hear.

“It was mortifying,” Rajesh told our group. I’m sure it did feel embarrassing, but it was also clear, from the laughter in his voice, that the memory carried no sting. Rather than mortification, what Rajesh felt now was delight at the enduring relationships and memorable moments he’d shared with friends.

Research-backed benefits of strong relationships

I hope we all have those stories. Why? Because strong, meaningful, enduring relationships have an incredible, positive impact in our relationships, and even on our health. I want to talk about that positive impact today and share a little research about the importance of strong relationships. Most of the time I write about leadership and communication and better questions—but we focus on improving those things because they matter for the relationships in our lives.

When we have strong, functioning relationships we experience more positive emotions. In his book Positively Energizing Leadership, University of Michigan researcher Kim Cameron summarizes the impact of positive emotions. Research shows people who experience more positive emotions have a range of benefits including:

• Living longer,

• Having fewer illnesses,

• Staying married longer,

• Tolerating pain better,

• Working harder,

• Performing better on the job,

• Making more money over a lifetime,

• Having better sex,

• Making better decisions, and

• Adapting faster when facing challenges.

With benefits like that, relationships that bring us more positive emotions are a worthwhile investment.

Longitudinal research agrees. In 1948, 5209 people in the town of Framingham, Massachusetts, enrolled in a study. Eventually, their children and grandchildren enrolled as well, giving researchers a remarkable opportunity to study how relationships impact health and happiness over generations and within the networks of a community. What they found is stunning.

They discovered that if you live within a mile of a friend who is feeling happier, your chance of feeling happier goes up by 25%. In other words, happiness is contagious, and not just for a few seconds but it can spread over weeks. If you’re in the center of a network that is happy, you are likely to be the happiest of all. (Interestingly, your same-sex friendships are more likely to increase your happiness more than your spouse. Developing these genuine, deep, and lasting relationships means you get to feel their happiness as your own.

Health benefits of friendship

But strong relationships don’t just make you happier; they may make you healthier. Even when you factor out socioeconomic status and health behaviors, men and women with fewer social ties showed a risk of death that was twice as high as more connected adults. One study even suggests that having a lack of friends is the equivalent of smoking 15 cigarettes a day.

Research also shows ambivalent relationships, especially in marriage, actually increase your risk of poor cardiovascular health. “If a relationship is worth maintaining, it’s worth improving,” says researcher and author Adam Grant. “And that’s not a job for you to do alone. It requires a conversation about what’s working and what’s not.” For our health, if for nothing else, we need to focus on improving our relationships through good questions and good conversation.

Strong relationships make us healthier, happier, and more productive. But strong relationships don’t happen by chance. We must invest in making our relationships more meaningful to see the benefits. If you want the incredible benefits of strong relationships, put more effort into your questions, your conversation, and even your leadership. Our predictable questions, lingering wounds, and lack of positive regard may be doing damage to our health, as well as our relationships.

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BONUS CONTENT

I shared Rajesh’s most embarrassing moment, so it’s only fair that I share one of my own. In February of 2020, a colleague gave me a lovely little plant. I kept it in my office at work, watering it occasionally. Then, a month later, COVID sent us out of the office. I forgot to take the plant. For months, I fretted over the plant’s fate—surely my neglect had killed the plant, with no access to water or much sunlight.

Months later, I returned to the office to get some supplies and decided to check on the plant. To my surprise, it looked perfect—exactly as I remembered it, with no signs of water deprivation.

And that was the moment I realized: the plant was plastic.

Now that I’ve shared one of my embarrassing stories, I want to hear yours. Hit reply and share your story. Better yet, share your stories around a table with friends, or at the start of a long work meeting. A little vulnerability and laughter can go a long way to deepening relationships.

Photo by the Centre for Ageing Better.