David sent out another application on a Tuesday morning, the same way he had been doing for months. Tailored resume, strong cover note, submitted through the portal, and then the familiar silence that follows. He was doing everything the job search playbook said to do, and the playbook was failing him.

In one of our sessions, I asked him a simple question. For every role on his list, who did he know inside that company?

Not a recruiter. Not a LinkedIn connection he had never spoken to. A real person who knew his work, trusted his judgment, and would pick up the phone if he called. The answer, more often than he expected, was someone. A former colleague who had moved there two years earlier. A contact from a previous role now sitting in a relevant function. Someone a mutual friend could bridge him to in a single message.

That question shifted how David ran his search entirely.

For every role worth pursuing, there is almost always someone inside that company who knows the culture, knows the work, or knows the hiring manager. That person is worth more than any application sent through a job portal, because they can do something a resume will never do. They can walk a name into the building before anyone has seen the credentials.

This is what a side door conversation is. Not a referral, not a favour, not a shortcut. A relationship activated with purpose.

The distinction matters because most executives approach it the wrong way. They reach out to a contact and ask for help getting considered for a role. The contact feels put on the spot, does what they can, and the relationship carries a quiet awkwardness it did not have before. When it does not work out, something has been spent that cannot easily be replaced.

Going in with a give is different. Reach out because there is something genuinely useful to offer. An insight about the industry, a relevant article, a real question about how they are finding the new company. When the ask comes naturally from there, it lands differently because the relationship has been warmed rather than spent.

What a side door conversation produces

David had a contact at one of his target companies, someone he had known for years and had been at a wedding with. He reached out on a Monday evening. By five the next morning she had responded. By noon they were on a call. That conversation gave him a level of intelligence about the company, the new CMO’s mandate, the internal politics, the unspoken challenges, that no job description would ever reveal. He walked into that opportunity knowing more about the real problem than any candidate who had applied through the front door.

Access is useful. Context is what makes the difference in a room.

How to run it

Start by identifying who is inside the target company. A first level connection is ideal. A second level connection through someone who trusts both parties works almost as well. Going straight to the decision maker with a cold message about the role is what most candidates do and what produces the least return.

Once the right person is identified, the outreach needs to lead with them, not the role. A message that opens with the job signals immediately that the contact is being used as a vehicle. A message that opens with genuine curiosity about what they are working on, or something specific and useful about the company, signals that this is a real relationship worth having.

From there, asking good questions and listening carefully surfaces the kind of intelligence that shifts how a conversation with a hiring manager goes. The ask, when it comes, feels natural rather than transactional, and the contact has something specific and honest to say on the candidate’s behalf when the right moment arrives.

The application still gets submitted. But by the time it lands on a hiring manager’s desk, there is already a name inside the building who knows who this person is and why they are worth a conversation.

One puts a resume in a pile. The other puts a person in a room.

If your search is producing activity but not movement, a Positioning Diagnosis is where to start. It gives you a clear picture of how to identify the right doors, build the right relationships, and make sure your name is traveling into the right rooms before any formal process begins.

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Nadia spent eleven years leading regulatory affairs at a pharmaceutical company that became one of the most talked-about industry failures of the decade. A series of clinical trial setbacks triggered a leadership overhaul, the stock collapsed, and the acquisition that followed was covered across every major industry publication. By the time she left, the company’s name meant one thing to everyone in the market.

Her work had nothing to do with what went wrong. The regulatory function she led delivered every approval it was responsible for, on time. The failure lived entirely on the clinical and commercial side. But that distinction was not traveling with her name, and she was about to find out how much that cost.

When she reached out to former contacts, the conversations felt less like networking and more like catching up on a scandal. People were warm, curious, but nobody was moving anything forward. And in the few interviews she did get, something strange kept happening. Hiring managers who had brought her in were spending more time asking about the company than asking about her. What really happened behind the scenes. Who was responsible. What the culture was like in the final months. She would leave those conversations having told a story about a company, not about herself, and never hear back.

She was not being evaluated. She was being used as a source.

Why staying quiet makes it worse

The instinct in that situation is to keep answers about the company short and move on quickly. The problem is that short answers to loaded questions read as defensiveness, and defensiveness makes people more curious, not less. Every time she let the conversation drift into an extended discussion about the collapse, she handed control of her own story to the other person, and that person was interested in the gossip, not the hire.

What Nadia needed to do was get ahead of it entirely. Walking into every conversation and acknowledging plainly that the company went through a well-documented commercial collapse, that the challenges lived on the clinical development side, and that the regulatory function she led delivered every approval it was responsible for, takes the topic off the table before it becomes the whole conversation. A senior executive who addresses a difficult chapter with clarity reads as someone with judgment. One who waits to be asked reads as someone with something to manage.

Building a story that stands on its own

Beyond getting ahead of the company narrative, leading with what she actually produced changes the frame entirely. The FDA approval she delivered belongs to her regardless of what happened to the company afterward. Stating it plainly, early, and with the right level of detail gives the other person something concrete to hold onto about her work, rather than leaving them to fill the gap with what they read in the press.

The longer term work is rebuilding a visible professional identity that exists outside the company’s name. Publishing a point of view on regulatory strategy, reconnecting with contacts around a specific idea, showing up in the conversations that matter in her field, all of it builds a current picture of who Nadia is that stands on its own, separate from what her last employer became.

The company’s story ended badly. Nadia’s did not. But in a market that moves on perception, that distinction is hers to make before anyone else makes it for her.

If you are carrying the weight of a difficult chapter in your career history and want a clear picture of how to reframe it, a Positioning Diagnosis is where to start.

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Caroline had never struggled to find work. Fifteen years as a marketing leader in Chicago meant that when a role opened at her level, someone in her network usually knew about it before it was posted. Hiring managers she had worked with years earlier reached out when they moved to new companies. Her reputation did its own outreach.

Then her husband accepted a role in Atlanta and things changed.

Six months into her Atlanta search, Caroline was doing everything she had done in Chicago. Reaching out to her network, applying to the right roles, taking recruiter calls, showing up prepared to every conversation. But, nothing was converting. First round interviews went well and led nowhere. Recruiters who seemed genuinely interested went quiet after the first call. The market was active but somehow she was invisible in it.

The problem was not her experience. It was that her experience was in Chicago.

Every relationship that had made her search effortless before was three states away. The hiring managers who would have vouched for her without hesitation werenow in a different market. The recruiters who knew her work had no reason to think of her for Atlanta roles. And the people she was meeting in Atlanta for the first time had no context for who she was beyond what her resume said, which told them where she had been but said very little about why they should trust her with a senior role in a market she had no visible track record in.

This is the part of relocation that nobody prepares for. A strong reputation is not a portable asset. It is built inside a specific market, through specific relationships, over a specific period of time. Moving to a new city does not transfer it.

Building credibility in a market that does not know you

It’s often better to approach relocation searches as a cold start rather than a continuation. That shift in thinking changes everything about how you approach the first six months.

Caroline’s instinct was to keep doing what had worked in Chicago. The problem was that what worked in Chicago worked because of fifteen years of accumulated trust that did not exist in Atlanta. Replicating the activity without the underlying relationships produced activity and nothing else.

The first move in a new market is visibility, not applications. Before a senior executive in a new city starts applying to roles, they need people in that market to know who they are. That means showing up at the right industry events, publishing a point of view on LinkedIn that speaks to the challenges their target companies are facing, and reaching out to people in their function in that city with a specific and useful reason to connect, not a job ask.

The second move is translating the track record for a new audience. A reputation built in Chicago means nothing to a hiring manager in Atlanta who has no way to verify it and no mutual contacts to call. The work that made Caroline exceptional needs to be told in a way that lands for someone hearing it for the first time, with specific results, recognisable company names, and a clear account of the problems she solved and what changed because of her.

The third move is patience with a plan. A cold market takes longer to warm than a familiar one. Six months of unfocused activity produces frustration. Six months of deliberate relationship building in the right corners of the new market produces the kind of warm pipeline that starts to feel like the one Caroline had built over fifteen years in Chicago.

Caroline eventually landed a CMO role in Atlanta. It took eleven months and a complete rethink of how she was running her search. The experience and the results were always there. What took time was building enough trust in a new market for those things to matter to the people evaluating her.

If you are running a search in a market that does not know you yet, a Positioning Diagnosis is where to start. It gives you a clear picture of how your profile is reading to a new audience, what is translating and what is not, and what needs to shift for the right people in the right market to see what you bring.

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“I know I was the best person for that role. I still do not understand why they picked someone else.”

Several senior executives have sat with that exact feeling. They do great work, but they end up watching a louder, more visible colleague get the promotion. In the workplace, visibility without substance will lead to disgrace, but substance without visibility is a well-kept secret. Unfortunately, at the senior level, secrets do not get promoted.

If the only people who know about your achievements are those already in your immediate circle, your work is not reaching the people who decide on promotions. Sharing the thinking behind a result, in a leadership meeting, on LinkedIn, or in a direct conversation with a senior stakeholder, puts it in front of the people who actually control what comes next in your career.

What visibility means

Promotion decisions are made by people who have never seen your work up close. They know you from a LinkedIn profile, a mention in a meeting, or a conversation someone else had about you. If that picture is vague or incomplete, it does not matter how strong your results are. You will be overlooked in favour of someone whose story is clearer, even if their work is weaker.

That is why understanding how senior stakeholders currently see you matters as much as the work itself. If a decision maker who has only heard your name in passing cannot describe what you do and why it matters, your positioning needs work.

How to get your work seen

Speaking up in leadership meetings with a clear point of view is the fastest way to change how senior people see you. Updates tell people what happened, but your point of view tells them how you think. Decision-makers promote people whose thinking they trust, and the only way to build that trust is to make your thinking visible in the rooms where they are present.

Beyond the meeting room, building a direct relationship with at least one senior leader above your manager changes your trajectory more than any single result ever will. Promotion conversations happen between senior people, and your name needs to be already familiar to them before your manager brings it up. A brief check-in, a relevant article shared with a short note, a question that shows you are thinking about the business at their level are the kind of moves that build familiarity with the right people.

Finally, your LinkedIn profile is the version of you that exists when you are not in the room. Some senior stakeholders look people up before they advocate for them. If your profile reads like a job description from three years ago, it is working against you in conversations you will never know happened.

None of this replaces great work. It makes great work visible to the people who have the power to reward it, and at the senior level, that visibility is not optional. It is the job.

If you want a clear picture of how senior stakeholders currently see you and what needs to shift, a Positioning Diagnosis is where to start.

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Every hiring manager has a type. A specific type of person they want before the search begins. The external process, the postings, the recruiter calls, the multiple rounds of interviews, exists around that decision, not before it.

Victor knew none of this when he applied.

He was SVP of Sales at a mid-size SaaS company with eight years in revenue leadership. When a retained search firm reached out about a Chief Revenue Officer role at a private equity-backed technology business, everything about the opportunity made sense.

He prepared harder than he had prepared for anything in years. He researched the business model and growth trajectory. He went into the first round, and it went well. The second round went better. By the time he reached the final stage, he was certain he was the frontrunner.

He did not get the role.

The feedback was the standard language. Strong candidate, very close decision, went with someone whose background was a slightly stronger fit. Victor sat with that for days trying to understand what he had missed and what he could have done differently.

Nothing had fallen short. The search was never designed to find him.

The company had promoted a VP of Sales internally eighteen months earlier. That person had not yet hit the metrics to justify the CRO title, but the CEO had already decided he was the answer. The board wanted an external search run for governance reasons, to demonstrate due diligence before making the internal appointment official. Victor and the other external candidates were never competing for the role. They were providing cover for a decision that had already been made.

This happens more than anyone in the hiring industry will say out loud.

How to know when you are in a real search

The signs of a genuine external search are specific. The hiring team goes deep on culture fit, leadership philosophy, and how the candidate thinks through problems, because they are genuinely trying to understand whether this person is right.

A search running as a formality feels different. The questions are thorough but somehow thin. The process moves fast in the early rounds and then slows dramatically before the final decision. The feedback after each round is warm but non-specific. Nobody is pushing hard enough on the hard questions because nobody needs the answers.

The most telling sign is what happens when a candidate pushes back or challenges an assumption in the room. A genuine search welcomes that. It is exactly the kind of thinking the hiring team is trying to evaluate. A formality search goes quiet when challenged, because the person asking the questions already knows who is getting the role and has no reason to engage deeply with anyone else.

What to do with that information

Identifying a process search early is not a reason to immediately withdraw. Sometimes an external candidate performs so well that they genuinely displace the internal preference. It happens. The question is whether to invest the time and energy required to become that candidate, knowing the odds are deliberately stacked.

The more useful move is to treat every senior search as an information-gathering exercise regardless of outcome. Every conversation with a hiring team reveals something about the organization, its challenges, culture, and the kind of problems it’s trying to solve.

Victor did not get the role. However, he walked away with a precise understanding of how that company thought about revenue leadership, the specific gaps in their current commercial function, and the name of the CFO who had asked him the most interesting questions in the final round.

Six months later, that CFO moved to a different company. The first person he called about building out the commercial team was Victor.

The room was never his to win. The relationship was.

If you have been in a search that felt like it was going somewhere and then went nowhere, the issue might not be your performance. A Positioning Diagnosis helps you understand how the market is reading your profile, which rooms are worth being in, and how to make sure the right people have the right picture of you before any process begins.

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Diana had done this before. Fifteen years in HR leadership and the last five as Chief People Officer at a mid-size financial services firm. She had sat on the other side of the table hundreds of times, evaluating candidates, deciding within the first ten minutes whether someone had what the role needed. When a retained search firm reached out about a Chief Human Resources Officer role at a larger organisation, she felt ready.

She prepared thoroughly. Metrics from her current role. A clear narrative about her leadership philosophy. Structured answers for every likely question. She walked into the room confident, delivered everything she had prepared, and left feeling like it had gone well.

She did not get a second interview.

The feedback from the search firm was that she was strong but not quite the right fit. That answer told her nothing useful. What was actually happening was that Diana had prepared a strong case for why she was a great HR leader. She had never prepared a case for why she was the right person for the new organisation at this specific moment.

The company was a high-growth healthcare business eighteen months into a major transformation. They had doubled headcount in two years, were struggling to retain senior talent, and had a people function that had never been built properly from the ground up. The CHRO they needed was someone who had navigated that exact kind of pressure before. Diana had, but her answers never revealed so.

Every example she gave was polished and credible. But, it was also generic. She talked about building high-performing teams without connecting this to the retention crisis the company was facing. She talked about navigating organisational change without referencing the specific transformation the company was in the middle of. She answered every question well and left the hiring team with no clear picture of whether she understood what they were dealing with.

The Difference Between a Strong Interview and the Right One

By the time a senior candidate walks into a first interview, the hiring team has spent weeks with the problem. They have talked about it internally, debated the profile, and arrived at a set of assumptions about what the right person looks like. The interview is where those assumptions get tested.

A candidate who walks in with a strong general case gives the room very little to anchor a decision on. While credentials are important, they’re not what the hiring team is evaluating at that stage. What they’re looking for is whether the candidate understands the problem deeply enough to be trusted with it. Every answer that speaks directly to the specific situation in front of them builds that trust. Every generic answer that could have been given in any interview, to any company, in any industry, erodes it.

Why Experience Alone Does Not Close the Gap

Most senior executives prepare for interviews by researching the company. Annual reports, recent news, leadership team backgrounds. That research produces general familiarity. It does not produce the kind of specific understanding that changes how a candidate shows up in the room.

The research that matters at the senior level goes deeper. What is the organisation struggling with right now? What has the people function looked like historically, and what does that say about what needs to change? What has the leadership team said publicly about their priorities and what does that reveal about the gaps they are carrying into this hire? What does the market say about this company as an employer and what does that tell a senior HR leader about the work waiting on the other side of the offer?

Diana had read the annual report. She had looked at the leadership team on LinkedIn. But she had not done the work that would have let her walk into that room and speak directly to the problem the organisation was dealing with. If she had, every example, answer, and question she gave would have been in service of the current predicament of the role she was interviewing for.

Positioning Is Not Personal Branding

Positioning is the story a candidate tells about who they are, what problem they solve, and why this specific organisation is the right place for them to solve it. It is built before the interview starts, tested inside it, and confirmed or contradicted by every answer given and every question asked.

Diana did not have a performance problem. She had a positioning problem. Her experience was strong, but the hiring team walked away unconvinced because nothing she said revealed that she understood what were actually trying to solve.

That gap, between what a candidate brings and what the hiring team understands them to bring, closes only when the positioning work happens before the first conversation starts. If Diana’s story sounds familiar, the experience is rarely the issue. A Positioning Diagnosis cuts through the noise and gives a clear picture of how the market is reading a profile, where the story is landing, and what needs to shift for the right rooms to start responding differently.

Book a free call to learn how to better position yourself for career success.

England had no business being in that position, and they knew it. Argentina were the defending champions, the tournament favourites, and had been getting favorable referee decisions throughout the competition. When Anthony Gordon put the ball in the net in the 55th minute, it was gearing to be one of the biggest upsets building in World Cup history.

Then Thomas Tuchel blinked.

He pulled the team back, packed the defensive line, and told his players to hold what they had. For thirty minutes, England sat deep while Argentina pressed. One shot, another one, and even one more, but the England keeper kept making incredible saves.

But no one is infallible, and eventually, Argentina equalized in the 85th minute, Argentina equalized. In the 92nd, they scored again. England lost the opportunity to win the World Cup because they stopped playing to win and started playing to survive.

Senior executives do this in job searches all the time. The moment a promising offer appears, most people stop reaching out, and conversations get paused. They forget about the pipeline that took weeks to build and go all-in for that opportunity. If that opportunity falls through, the search starts over from the beginning with nothing warm left in the pipeline.

It isn’t over until it is

The only moment a senior search is over is when the contract is signed, the start date is confirmed, and the first day has passed without incident. Everything before that is a conversation. Offers get extended and then quietly withdrawn when a business priority shifts.

This is where the psychology of the search works against the executive. A recruiter who says “You are the top candidate” feels like confirmation, and a verbal offer feels like a done deal. But it isn’t. They are stages in a process that can reverse at any point for a myriad of reasons.

The executive who treats a verbal offer as a signed one stops negotiating from a position of strength. They stop building relationships with other companies because it feels pointless now. And then, when something changes on the other side of the table, they are left exposed with nothing else in motion.

What Staying in the Search Looks Like

Keeping the search alive doesn’t mean treating every opportunity as equally likely. It means keeping the pipeline warm enough that a single outcome falling through does not send everything back to zero.

In practice, that means continuing to have conversations with other target companies even when one opportunity looks close. It means keeping networking contacts warm with a brief check-in rather than going silent. It means preparing for the next interview with the same focus applied to the last one.

It also means being honest about the timeline. Senior searches move slowly. A strong first interview can take six weeks to produce a second one. A verbal offer can take three weeks to become a written one. During that window, the executive who stays active is building options. The one who waits is losing them.

The Offer Is the Start, Not the Finish

Even a signed offer is not the end of the search mindset. Two weeks into a new role, a workforce reduction can be announced. Or the manager who hired you is fired. These things happen, and they happen at the senior level more than anyone admits during the hiring process.

Executives who handle those moments well are those who never fully closed the door on their network, never stopped being visible in their space, and never allowed a single outcome to become the only outcome they were building toward. The Missfit Mindset is a career strategy. It means understanding that the market for senior talent is always moving, and staying ready to move with it, whether or not a search is actively underway.

Argentina pressed for ninety-two minutes because they understood that a match is not won at the 55th minute. It is won at the final whistle. Executives who get the offer they came for are the ones who kept pressing until they heard it.

Not sure if your pipeline is warm enough to survive a fallen-through offer? Schedule a free 20-minute call for a second opinion on where your search stands.

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Sam had been in sales leadership for fifteen years. He knew how to build a pipeline, develop a team, and close deals fast. When a growing company came to him with a VP role, the fit seemed obvious. They needed someone who could bring structure to a chaotic sales function. He had done it three times before.

Six months in, he was miserable.

The president of the company ran every client meeting like a performance. Loud, aggressive, all pressure and no process. He wanted his sales leaders visible, reactive, and constantly in motion. Sam worked differently. He built systems, coached his team, and let the results speak. In this company, that approach read as passive. Every week, he left the president’s meeting feeling like he had failed an audition.

It took him time to understand that he had not failed at the job. He had been cast in the wrong movie.

Every organization has a culture, and every culture has a type. A specific kind of person who thrives in it. The way decisions are made, and success celebrated, all adds up to a casting brief that never appears in the job description.

Costs of the wrong cast

The first cost is energy. Adapting to a culture that runs against your grain is exhausting. It’s the difference between pushing through fatigue on a project you believe in and showing up every day with no will to work.

The second cost is positioning. Every month spent in the wrong culture is a month delivering less than your best. The results you produce in such an environment that does not fit are rarely the results that reflect what you are capable of. And those are the results that follow you into the next interview.

The third cost is time. Executives who stay in the wrong company long enough start to lose sight of what the right one looks like. The longer the stay, the harder it becomes to articulate what kind of environment brings out the best work, because the last environment has become their reference point.

How to know when you are in the wrong company

The clearest sign has nothing to do with how hard the work is. Hard work in the right environment produces energy. What to pay attention to is when the role requires a version of yourself that you have to consciously perform rather than naturally bring. When preparing for a meeting starts to feel more like getting into character than doing your job, it may be a sign that you might be in the wrong place.

The second sign is that your best work keeps going unrecognised. Your output can be solid, but the leaders around you have no interest in it. When that pattern repeats week after week, it is worth asking whether this company values what you do best, or whether it is looking for something else.

What to do next

Leaving is not always the answer, and it is rarely the first one. The more useful move is to get honest about what kind of environment produces the best version of your work, and then to measure the current one against that standard with clear eyes.

Some gaps are bridgeable. A culture that is imperfect but fundamentally compatible with how you work is worth staying in and shaping. An executive who understands the culture well enough to influence it from the inside is doing more valuable work than the one who leaves at the first sign of friction.

However, if the gap is between who you are and who the role needs you to be, that is a different conversation. No amount of effort closes that one. You need to find the right company that values what you do best

Sam eventually found such a company, but It took leaving the wrong one first.

We have all heard of similar stories. A VP leaves a stable role for what looks like a great offer with an exciting startup. Three months in, they’re running weekly status calls and managing vendor relationships. Nothing about that was in the conversation.

That is the bait and switch. And it comes in different sizes.

Sometimes, nobody lied. The people in the room during the interviews meant every word they said. What they did not account for was the difference between how the organization sees itself and how it actually runs day-to day. That difference exists in a lot of companies, and is only visible to the person walking in fresh.

By the time the picture is clear, your previous role is filled, and it’s risky to live without a plan. Your resume now shows a tenure too short to explain cleanly and too long to pretend it didn’t happen. That is the trap that keeps executives in the wrong seat far longer than they should stay.

For situations where the difference is fundamental, the instinct is to give it more time. The problem is that time is the one resource that cannot be recovered. Every stretch spent hoping the situation changes is time the search that should have started is sitting still.

What to do about it

The first move, regardless of how wide the gap is, is a direct conversation with your manager. What was agreed, what exists now, and what it would take to close the distance. Most managers respond better to that conversation than expected because they are often aware that things have changed.

When there are timely positive updates as a result of the conversation, stay and build. When it doesn’t, that’s your answer.

Schedule a free call with me, if you’re ready to build the career you deserve.

Sandra had been out of work for four months. She was a senior operations executive with two decades of experience.

She picked up the phone and called a former colleague, Judy.

“Sandra! It’s been forever. How are you?”

They caught up for twenty minutes before Sandra got to the point. She explained where she was, what she was looking for, and what kind of conversations would move the needle. Judy listened, then said what people who care about you say. “Leave it with me. I know a few people. I’ll put some feelers out this week.”

Sandra felt good about that. Judy meant it. Two weeks later, nothing had come through.

The message Sandra wanted to send was simple. “Hey Judy, I haven’t heard from anyone yet. Did you get a chance to reach out?” Honest, direct, reasonable. But what Judy would read underneath it was that she had dropped the ball. People who feel like they have let someone down go quieter, not louder. The last thing Sandra needed was for Judy to start avoiding her calls.

So Sandra sent something different. “Judy, I keep thinking about our conversation, and I’m really grateful you thought of me. Based on what you know about where I’m headed, is there anyone you think would have a sharp view on the market right now?”

Judy responded within the hour. “Actually, yes. There’s someone I should have already connected you with. Let me make that introduction today.”

One message. Handled well. The difference between a contact who feels guilty and a contact who feels good about helping you is usually one sentence.

The pressure behind the message

Sandra’s search had been running long enough that every unanswered conversation felt personal. That pressure shapes the language people reach for without them realising it. When you are months in and waiting on someone who said they would help, asking directly what happened feels reasonable. The problem is that it puts the weight of your outcome on someone else, and most people pull back when they feel that weight land on them.

Judy had not forgotten Sandra. She had just not found the right moment yet. Sandra’s message gave her a low-effort way back into the conversation that felt like sharing perspective rather than settling a debt.

When the timing and the language are right, the follow-up does not feel like chasing. It feels like two people picking up a conversation they were already in. That is the only version of a follow-up that actually moves a search forward.

There is a situation most executives can relate with. You get off a difficult call, close the laptop, and give yourself thirty seconds to feel annoyed. Then you move on. You have learned, somewhere along the way, to absorb a certain kind of bad leadership and keep going anyway.

That is a skill. And like most survival skills, it costs something.

At some point in a long career, you watch a colleague handle a difficult leader in a meeting. The leader gives the same directive he has given before, with the same edge in his voice. The colleague responds, notes that they had already tried that approach twice without results, and asks whether they should try it again. No anger. No frustration. A flat, even response from someone who has been in that room long enough to know what was coming and stopped expecting anything different.

That is what tolerance looks like from the outside. From the inside, it feels like survival.

You develop a tolerance for the aftertaste. The behavior becomes predictable. You build distance from it, file it away, and keep working. The difficult leader becomes background noise rather than a source of disruption.

Executives who handle this best draw a line between tolerance as a strategy and tolerance as an excuse not to take action.

How to make the tolerance work

The starting point is separating the person from the environment. A difficult leader is one variable in a larger situation. If the work itself is good, the manager below him is solid, the compensation is real, and the people around you are worth staying for, then the difficult person at the top becomes a cost rather than a reason to leave. That framing does not make his behavior acceptable. It makes it manageable.

The second step is making the tolerance internal and time-bound. A clear answer to the question of what you are staying to build and how long that takes. Executives who move through difficult cultures without that anchor tend to look up one day and realize they traded years of energy for a situation that was never going to change.

The aftertaste is bearable when you know what you are drinking toward. When you have lost track of that, the question worth asking is whether you are tolerating something with a purpose, or whether you have simply stopped noticing the taste

If you’ve ever been in a situation where you needed to endure or ignore at the workplace, share in the comments.

Eight months without a salary does something to a person.

Ezekiel had been sending applications into what felt like a void, watching his savings shrink, and feigning smiles through conversations with his wife about “how the search was going.” Then one morning, an email landed in his inbox that changed his situation.

A recruiter from his dream company had reached out to him. He closed his laptop, leaned back, and for the first time in months, exhaled. This was it. His big break.

Rather than continue wasting time on applications that hadn’t been working, he decided to focus all of his efforts on this interview. He stopped checking job boards. Stopped returning recruiter calls. Stopped the whole exhausting machinery of a search he was convinced was finally over.

Luckily, it paid off. Three weeks later, he was in the final round of interviews, and they loved him.

“We’ll get back to you with a decision before the end of the week.”

Week two, he was still waiting. Week three, he had sent two reminder emails. Week four, a short email arrived. They had gone with a different candidate.

Devastated, he opened his laptop and went back to the applications he had paused. Three roles had been filled, two had expired, and the recruiters who had shown interest had moved on.

Eight months of searching, and he was back at the beginning.

Nothing is set in stone until it’s set in stone. Don’t stop searching because a promising role is on the horizon. The moment you stop the job search process, you hand someone else the timeline.

Keep on applying until you’ve signed the offer letter.

If you’re tired of searching for months, schedule a free call.

Your most technically brilliant hire might be the reason your best people are leaving.

Companies spend significant money recruiting for skills, qualifications, and track records. The interview process checks competence, and references confirm capability. The offer goes out, the person starts, and within six months, the team is in disarray.

This is rarely a question of technical ability, but rather of behavior.

Organisations assume that adults who are good at their jobs will naturally work well together. That assumption gets expensive fast. One person who cannot regulate their behaviour in a team setting does more damage to morale than any skills gap.

The part that leaders miss is that communication intelligence is a skill, and it can be assessed, developed, and held to a standard just like any other. The problem is that many organisations treat it as a personality question rather than a performance one. So it gets ignored in hiring, underdeveloped in management, and only addressed when things are in a mess. But by then, it’s already cost the team’s output, culture, and the people.

Executives who get this right do two things differently. They screen for behavioral dynamics before the hire. And they build environments where people can raise concerns early. Problems that surface early can be addressed. Problems that fester become the reason your strongest performers update their CVs.

Technical skills get people through the door. How they communicate, collaborate, and conduct themselves determines whether the people around them stay.

Hire for both. Hold both to a standard.

There is a particular kind of busy that produces nothing. Reading career articles, saving job postings, watching LinkedIn thought leaders break down the market, organizing a spreadsheet of target companies. All of it feels like progress, but none moves the search forward.

The MissFit mindset draws a hard line between consuming and doing. Preparation has a ceiling. At some point, the next right move is action, and action in a job search is more specific than most people treat it.

What Profitable Action Looks Like

Profitable action has a direct output. It either creates something, surfaces something, or moves a relationship forward.

Actions like updating a resume bullet to reflect the actual scale of a project, writing down three specific problems solved in the last role, or researching a target company well enough to speak to their current operational challenges.

It also includes reaching out to a former colleague with a specific ask rather than a general check-in or practicing an answer to “tell me about yourself” out loud until it sounds like a conversation rather than a recitation. These are all actions that compound.

The Mindset Shift That Makes It Click

Reading about job search strategy and doing the job search are two different activities. One feels safer because it carries no risk of rejection. The other is where the real work is done.

The MissFit mindset starts from the belief that you have something valuable to offer. That belief makes action feel less like risk and more like motion. . With that as the foundation, updating a LinkedIn banner with recognizable brand names becomes a statement. Practicing a pitch becomes preparation for a conversation worth having. Following up with a contact becomes relationship management, not desperation.

The search moves when the candidate does.

Follow for more career insights.

Let’s say it plainly. Ageism in hiring exists, it is common, and pretending otherwise does not help anyone over 40 who is currently looking for work.

Companies will tell you they are unbiased. Some mean it. Many do not. Behind closed doors, age comes up in hiring conversations more than anyone wants to admit publicly, which is exactly why it became a protected class in the first place.

The Age Discrimination in Employment Act, enforced by the EEOC, protects workers 40 and older. Hair color is not a protected class. Shoe size is not a protected class. Age is, because the discrimination is so widespread and so well-documented. Recent high-profile lawsuits have made this harder to ignore, but 40% of senior executives still admit to factoring age into hiring decisions. The law exists, but the behavior persists anyway.

So what do you do with that?

Read the room

Job postings are the first signal. Language like “energetic,” “digital native,” or requirements that effectively describe a recent graduate are worth noticing. A heavy emphasis on “cultural fit” with no further definition is another one. These are not always intentional, but they are telling.

Before you apply anywhere, spend ten minutes on the company’s LinkedIn page and website. Look at who they feature, who leads the organization, and what their employee photos show. If everyone pictured is under 35, including the CEO, that is useful information. Glassdoor reviews also reveal culture concerns that the careers page will never mention.

For the search itself, job boards built specifically for experienced professionals exist and are underused. AARP’s job board, Workforce50, and YourEncore are worth bookmarking alongside the standard platforms.

Clean up your resume

Your resume does not need to be a complete career autobiography. The last ten to fifteen years is enough. Leave graduation years off entirely. The goal is a document that positions your experience as an asset, not a timeline that lets someone do the math before they have read a single bullet point.

Walk in prepared

The age concern rarely gets asked directly. It shows up sideways, as “don’t you think you might be overqualified?” or vague probing about adaptability to new environments. These are not innocent questions, and you do not have to treat them as such.

Chris Voss’s negotiation framework is genuinely useful here. When you sense the hesitation in the room, name it calmly and let them respond. Something like “it seems like there’s a certain age demographic here” followed by a deliberate pause puts the observation on the table without accusation and invites the other person to engage honestly. If the silence stretches, a label like “it sounds like you have some reservations about fit” opens the door further.

The same approach works when making the case for your experience. Rather than stating your value directly, invite them to arrive at it themselves. “Given my years in this field, how valuable might you find the relationships I have built, particularly for a role centered on sales or business development?” That framing lets them conclude on their own that your network is an asset, which lands differently than you telling them it is.

The challenge is real, and it’s not fair. It’s also not the whole story. Organizations that actively seek experienced professionals exist, and they tend to be the ones worth working for anyway. Targeting companies whose workforce already reflects diversity is a better use of your time than trying to convince a 26-year-old hiring manager that you can keep up.

You walked into this search carrying decades of hard-won judgment, relationships, and range that nobody in their twenties has yet. The right organization already knows what that is worth.

Find that organization

.

A Chief Operating Officer at a 10,000-person corporation has a team for everything. A Chief Operating Officer at a 10-person startup is sometimes that team.

This is one of the most common mistakes senior executives make in transition. Their focus goes to the title and compensation, and they pay less attention to what the jobs look like day-to-day. That difference has ended many promising tenures before they had a chance to begin.

The Job Before the Title

When evaluating a new role, the title tells you your position in the hierarchy, but it tells you very little about what you will be doing on day one.

The structure of the organization shapes the job more than the title does. A large corporation has established systems, dedicated teams, and clearly defined functions. Your job is to lead within that structure. A scaling company or an early-stage business often has none of that in place yet. Your job is to build it while delivering results at the same time.

Both can be the right environment depending on where you are in your career and what you are trying to accomplish. But walking into one while expecting the other is where things go wrong.

What to ask before you sign

Many executives skip the questions that would have told them what the job actually demands

Before you accept, you need to ask clarifying questions

1. What decisions are yours to make, and which require approval from above?

2. What did the outgoing person in the role spend most of their time on?

3. What is the organization trying to solve by creating or filling this position?

4. What resources are available?

5. What is the timeline for results?

These are some questions many executives skip in the excitement of a strong offer. The answer to each one tells you something specific about whether this role matches your strengths, your working style, and where you are trying to go next.

The terrain matters as much as the title

A strong offer from the right company at the wrong stage, or the right company with the wrong structure for how you work best, is still the wrong move. The executives who transition well are the ones who treat the interview process as a two-way evaluation. They are assessing the role with the same rigor the organization is assessing them.

Before you focus on the title, make sure you understand what the job requires. That is the conversation that determines whether you thrive or spend the first year wondering what you walked into.

Every week, there is another headline. AI is taking jobs. AI is changing everything. AI will make your role obsolete. Your board is asking about your AI strategy. Your peers are talking about it at dinner. Your inbox has three newsletters that you have not opened.

Most of what you’re reading about AI wasn’t written for you.

Common AI Assumptions

The AI conversation has been hijacked by two groups: technologists who want to explain how it works, and media outlets whose job is to make you feel everything has gone catastrophically wrong. Neither group is talking to you. Neither group knows what your day looks like, what your P&L responsibility looks like, or what your board is asking when they say “AI strategy.”

This leads to most senior executives carrying one of two false conclusions about AI.

The first: AI is too complicated and too technical for me to engage with seriously. I will leave it to the IT function.

The second: I use ChatGPT. I get it.

Both conclusions are costing you.

AI for Executives

Asking ChatGPT to rewrite your emails puts you at roughly the same level of AI engagement as a graduate intern.

The executive role has always been about decision quality and decision speed under conditions of imperfect information. Every system, team, or process you have ever built has been in service of that.

AI compresses the information gap, and changes how much information you can access before making decisions.

For a Chief Executive, that means faster pattern recognition across markets, competitors, and internal performance data with less dependency on analysts.

For a Chief Financial Officer, that means scenario modelling that used to take a finance team two weeks now takes an afternoon. You can walk into a board meeting with five stress-tested scenarios rather than two.

For a Chief People Officer, that means the ability to identify risk, skill gaps, and team performance patterns before they become a crisis on your desk.

These are some of the many ways in which AI extends the reach of executives who know how to use it.

What to do next

There are free certification courses specifically designed for executives. Claude’s AI certification and Google’s AI Essentials are two worth starting with. Both go into the strategic applications of AI for professionals, beyond how to get chatbots to write your LinkedIn posts.

They are designed for people who need to understand what this technology means for their decisions, their teams, and their industry position. The best part is that these courses can be completed over a weekend. Start this weekend.

You're in a crucial team meeting, a brilliant idea sparks in your mind, but then… a flicker of doubt. "What if I’m wrong? What if they think I’m dumb?” So, you bite your tongue, and the potential breakthrough remains unspoken.

This all-too-common scenario is the silent killer of innovation and true collaboration in workplaces everywhere. But what if there was a way to flip this script entirely?

What if making mistakes wasn't just tolerated, but actively celebrated as a launchpad for learning and growth?

That’s where Failure Fridays come in. What started as a niche engineering experiment has quietly become one of the most powerful ways to build stronger, more creative, more resilient teams.

Stop Fixing Fault—Start Mining Mistakes

At its core, Failure Friday is about creating a designated, blame-free space for teams to openly discuss what went wrong during the week. Engineers at PagerDuty first started experimenting with it. The idea was simple: intentionally introduce small system failures in a controlled way and see how the team responded.

It was a smart way to stress-test systems. But something else happened, too.

Teams began talking about real-life mistakes more openly. Someone would share a missed deadline. Another would describe a late-night scramble to fix broken code. Soon, even new hires felt comfortable speaking up, and senior staff shed the pretense of having all the answers. The entire team culture began to shift.

Failure Friday evolved from a technical test into a human one. Not just "What went wrong?" but "What did we learn?" And “How can we make this easier next time?”

That small shift, talking through failure without blame, made all the difference.

Setbacks: Your Untapped Superpower

The beauty of Failure Fridays isn't just in promoting a healthier work environment; it translates directly into tangible results. Companies that have embraced this practice consistently report significant boosts in innovation, creativity, and overall performance.

At a healthcare nonprofit known for red tape, one manager introduced a weekly failure share with her team. No slide decks. No formal reports. Just space to talk. Within months, her team became the most innovative in the department.

Similarly, Buffer reportedly saw a 30% increase in team creativity and collaboration after implementing their open discussion of failures. JetBlue also saw customer experience improve after teams started reviewing service slip-ups regularly.

These results didn’t come from one big win. They came from dozens of small conversations that built trust.

When failure becomes safe to talk about, learning gets faster. And when learning gets faster, performance follows.

Small Failures, Big Breakthroughs

Let’s bust the myth that only the big, dramatic failures count.

When we start noticing our tiny missteps—the missed details, the quick fixes, the little things that go wrong—we train ourselves to see failure differently. By getting comfortable with the small stuff, we build the courage to face bigger mistakes.

Zooming in on micro-moments provides incredible insights into the definition of “failure”.

• Hangry before dinner? My failure to make time for lunch.

• Forgot to order groceries? My failure to check my daily to-do list.

• Can’t find the phone again? My consistent failure to designate a spot.

Our days are full of micro-failures.

It’s in seeing the little stumbles that we find the strength to own the big ones.

Devaluing Failure Is the Real Failure

While implementing Failure Friday might raise concerns about "airing dirty laundry," the pros outweigh the cons. Start small. Talk about your micro-failures. Start by sharing a recent "miss" of your own. It doesn't have to be a catastrophic error; perhaps a project detail you overlooked, a miscommunication, or a time you felt you could have handled a situation better. Eventually, step up the scope.

Be open about what happened and, crucially, what you learned from it. You’d be surprised at how others pick up on your candor and follow your lead.

Chasing Perfection? You’re Missing the Point

Every mistake, no matter how small, tells a story. Every team, no matter how high-performing, experiences setbacks. The critical question is whether you're actively cultivating an environment where those stories can be openly shared and learned from.

Failure Fridays aren't just a catchy name; they're a deliberate decision to prioritize learning over appearances and progress over pride. It's a commitment to seeing setbacks not as shameful secrets, but as invaluable data points for growth.

Sometimes, the most productive thing a team can do isn’t to jump in with a “fix” but to acknowledge that something broke and uncover the opportunity to learn.

Hats off to the team at Pager Duty for daring to question the old rules, for choosing honesty over ego, and for leading the way so the rest of us could follow.

Warmly,

Dee DeRidder | MBA, SHRM-SPC, NRWA, ICF

Founder & Executive Career Coach

www.missfitcoaching.com

Connect on LinkedIn

Let’s be honest: Most of us never learned how to communicate at work—we just picked it up by watching others, copying what seemed safe, and learning (sometimes painfully what not to say.

Along the way, we internalized unwritten rule: “Be polite first, and everything else will follow.” But here’s the catch: Politeness can soften edges, but it can also blur meaning. A direct request comes out as a vague suggestion. We think we’re being considerate, but often, we’re just being unclear.

Let’s talk about how to move beyond “nice” and start communicating in a way that actually gets things done.

What We Get Wrong About Office Communication

A lot of what passes for office communication is only guessing:

• Guessing when it’s okay to push back.

• Guessing how to ask for help without sounding weak.

• Guessing if your boss’s message is a suggestion or a deadline.

Most people are just trying to be respectful, keep things light, and avoid stepping on toes. But when tone takes priority, the point gets lost.

In trying to be nice, we forget to be clear.

After years of coaching teams, I’ve seen how unclear communication rarely causes dramatic blow-ups—but it does create a slow and painful drain:
Missed cues. Unspoken tension. Tasks that circle back because no one knew what was expected in the first place.

Workplaces aren’t just one big group—they’re a web of relationships: your boss, your team, your peers, your clients. Each one needs a different approach. Here’s how to get it right.

When You’re the Boss

Leadership isn’t about perfect speeches—it’s about removing doubt.
If your team is unclear, they’ll second-guess, stall, or head in the wrong direction.

Great leaders provide structure:

• “Please have this done by Thursday at noon.” (Not: “Let’s try to wrap this up soon.”)

• Asking for updates before deadlines hit.

• Inviting feedback to make adjustments, yet, being decisive when it counts.

And when things go wrong? They address it—directly, calmly, and without blame.
People don’t need to be shielded from discomfort; they need to be guided through it.

When You Report to Someone Else

This is where things get tricky.
No one wants to look like they’re pushing back, so we say “I’m fine” when we’re not.
We start with, “Just wondering if…” and end with, “But totally fine either way!”

It feels polite, but it creates confusion and hides what you actually need.

There’s a way to express curiosity, and ask for clarity without seeming difficult. You don’t have to say, “This is wrong.” But you do need to make sure you’re aligned on priorities before you start.

Respectful? Yes. But also clear.

When You’re Working With Peers

You’d think peer-to-peer would be easiest. It’s often the hardest.

No one wants to create tension, so we joke, hint, or wait for someone else to speak up.
But teams don’t grow through avoidance. They grow through clarity.

That means saying, “There’s a gap here. How do we fix it together?”
That means telling the truth when something isn’t working—before resentment builds.
That means asking for what you need, and trusting your team can handle it.

When You’re Talking to Clients

This is where people switch into “performance mode.”
We want to sound polished and in control. But clients don’t need polish—they need honesty they can trust.

You don’t have to over-explain every detail. But you do need to be intentional:

• Tell them what your product can do—and what it can’t.

• Speak in plain language.

• Admit when something’s outside the scope.

Clients don’t want to be dazzled. They want to feel confident in you.
That confidence comes from clarity, not charisma.

Clear Communication is What Keeps Teams Moving

The best teams don’t run on charm or politeness—they run on clarity.

Clarity reduces confusion, prevents rework, and creates space for real collaboration.
Whether you’re giving instructions, asking for help, flagging an issue, or managing a relationship, your words only work if they’re understood. And to be understood, they need to be specific, focused, and unambiguous.

That doesn’t mean we stop being thoughtful. It just means we stop hiding behind soft language when direction is needed.

Most workplace stress comes from the gap between what was said and what was meant.
Close that gap, and you’ll change everything.

Warmly,

Dee DeRidder | MBA, SHRM-SPC, NRWA, ICF

Founder & Executive Career Coach

www.missfitcoaching.com

Connect on LinkedIn

How clear is your communication?

People come to me from all walks of life. Some are quietly considering a change, others are already preparing to leave. But no matter where they are in the process, one thing matters more than anything else: understanding why they want to move.

Back in those early, hazy days after the pandemic, the reasons felt pretty obvious. It was all about reprioritizing, redefining balance, and escaping those arbitrary return-to-office rules.

But things have shifted. Now, the reasons people are contemplating a change feel… deeper. More nuanced.

Sometimes, a life shift creates the need: the arrival of a child, an aging parent who now needs care, a desire to slow down. Then you have others who are being pulled by something new and exciting. A surprising opportunity pops up, and suddenly, they can see a completely different version of their future unfolding. These are the people running toward something.

But more often, people are running from something, and what they’re running from deserves more attention than it usually gets.

Running To or Running From?

This distinction is huge and matters way more than you might think.

When you're running to something, there's usually this buzz of excitement. You've got clarity, momentum, and a real sense of purpose driving you forward.

But running from something is a whole different ballgame. It often feels murky, clouded by frustration and that heavy weight of burnout. The energy behind it feels reactive, like you're just trying to escape the discomfort.

For so many people I talk to, the problem is not even the job itself. It's the experience of doing it. The company culture may feel completely off, or perhaps the team dynamic is draining all their energy.

If you feel like you're reacting to whatever comes your way instead of making conscious choices, chances are you're running from something. So, before you dive headfirst into those job boards again or start tweaking your resume for the umpteenth time, pause and ask yourself some really honest questions.

1. What was happening in your life the last time you decided to make a career change?

2. What has shifted in your current situation that's making you consider leaving now?

3. What was that specific moment, that tipping point, that moved you from just thinking about leaving to acting on it?

4. All situations are co-created. What are you contributing to this situation?

5. What are you really trying to get away from?

6. What are you hoping to find in your next role? Is it even possible?

Your Role in the Situation

You've probably heard the saying, "People don't quit companies; they quit managers." While there's definitely some truth to that, it's only one piece of the puzzle.

Every single work relationship, whether it's amazing or a struggle, is co-created. It takes two (or more!) to tango. Nothing exists in a vacuum, and no dynamic is ever entirely one-sided. You're not just a passive recipient of what's happening around you. You're actively shaping it, even in small ways.

So, if you want to create a different and more fulfilling experience in your next role, you've got to understand the part you played in your current one. What were your patterns? What did you bring to the table?

Could You Be the Issue?

This is one of those questions that can feel uncomfortable. But it's also one of the most crucial ones to wrestle with.

Is there a fundamental mismatch between what your current job actually demands of you and what you're currently bringing to the table? Do your core values truly align with the company culture? Or could the issue be the broader context you're operating in?

Context always matters. You could be absolutely brilliant and thrive in one environment, and then feel out of your depth in another. What one manager values and appreciates might be frowned upon by the next. Your inherent capabilities haven't suddenly vanished; the rules of the game have simply changed.

So whenever you feel discomfort at work, pay attention. Don’t just push past it. Take time to understand what it’s telling you.

Move with Intention, Not Impulse

You don't need to have every single answer perfectly mapped out before you make a move. That's rarely how life works anyway. But you need to take a breath before you leap into something new.

A new job won’t automatically fix what you haven’t unpacked. A new boss won’t erase a lack of clarity. A new title will not provide a sense of fulfillment if your goals are undefined.

Get honest with yourself, understand what’s pushing you to leave and clarify what you want to move toward.

Warmly,

Dee DeRidder | MBA, SHRM-SPC, NRWA, ICF

Founder & Executive Career Coach

www.missfitcoaching.com

Connect on LinkedIn

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