In the classical trivium, grammar comes first, before logic and rhetoric, because clear expression is the precondition for clear reasoning. What follows are five lessons from teaching and using grammar that transfer directly to program leadership.

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Precision

Grammar is not just a set of rules. It is how we structure our thinking. A well-formed sentence requires a clear subject, a precise verb, and defined conditions. “She will complete the assessment” names an owner and a deliverable. “The assessment will be completed” removes the owner and creates accountability ambiguity. That difference is not stylistic. It determines whether someone acts or waits.

Ambiguous charters, vague action items, and passive risk statements are all examples of where project failure starts. Do a grammar pass when reviewing a charter, decision log, or risk register. Is there a clear subject? Is the verb precise? Are conditions stated as clauses rather than assumptions? If the sentence cannot be written cleanly, the thinking is not ready.

Vocabulary

Burns connected vocabulary directly to comprehension: “If you don’t know what words mean, how can you comprehend what you’re reading? Not understanding directions, steps to follow, processes, that is a big problem.” She taught roots, prefixes, and suffixes so students could work out unfamiliar words independently, rather than stopping every time language outpaced them. The goal was not a larger vocabulary. It was the ability to keep moving through complex material without losing the thread.

In program contexts, the vocabulary problem is constant. Words like “benefit,” “done,” “aligned,” and “risk” mean different things to different stakeholders. Defining key terms is the mechanism by which a steering committee, a delivery team, and a sponsor can actually agree. If a stakeholder uses a loaded word repeatedly, paraphrase it back with a more precise synonym and confirm the meaning. Build a project glossary and use it as a living document in governance decks and onboarding.

Reading Between the Lines

Literature taught Burns’s students to detect what was not said. “It’s not just what’s said,” she noted. “Sometimes what’s implied, what isn’t said, is just as important.” Program leaders operate in exactly that environment. Stakeholders hedge. Executives soften objections. Sponsors signal concern through omission.

Grammar trains the ear for this. Hedging verbs such as try, hope to, and aim to are different from will. Passive voice (”it was decided”) removes accountability. Conditional overload (”if everything goes well”) is a risk dressed as optimism. After key discussions, write a two-sentence inference summary. It should be what they said, and what that implies about their real constraints.

Form Shapes Credibility

Burns was direct: “How you write and how you speak is the first impression that people have of you. Especially in business, people judge whether you can do the job.” Your decks, emails, and one-pagers are often your proxy in rooms you are not in. Leaders infer competence, reliability, and attention to detail from grammatical clarity.

Before any senior review, do a ten-minute edit. Shorten sentences. Make subjects and verbs obvious. Replace abstractions (”things,” “issues,” “stuff”) with concrete nouns (data quality gaps, testing delays, pending approvals). One idea per bullet. No vague pronouns without a clear referent.

Teaching is building

Burns never did the work for her students. When a student could not spell a word, she asked how they thought it was spelled. “How do you think you spell it?” she would say, and wait. When students wanted to type assignments so spell-check could carry them, she had them write by hand so she could see what they actually knew. The discipline was structural, not punitive. She designed tasks that forced students to internalize the standard rather than borrow the answer.

Program managers face the same challenge. A team that cannot write a clean user story, a crisp risk statement, or a clear benefits case has failed a process check. The fix is not to rewrite their artifacts. It is to teach the form. Ask before telling. The gap between what someone meant and what they wrote is the coaching moment.

The classical study of grammar was always preparation for governance. Who holds the subject? Who owns the verb? Under what conditions? For program leaders who move quickly, that discipline is not overhead. It is the foundation everything else is built on.

Pat Burns is a retired educator. She taught for 40 years in Catholic High Schools, including 28 years of English, primarily English III and AP English Language and Composition. In addition she advised the school’s yearbook.

Something to Read

Stylish Academic Writing by Helen Sword [240 pages or 6.5 hours]

Talking from 9 to 5 by Deborah Tannen [368 pages]

Sin and Syntax by Constance Hale [322 pages or 9.5 hours]

Something to Watch

Beware of nominalizations (AKA zombie nouns) with Helen Sword [5 minutes]

Five people send you their piece of the monthly status report, and you stitch them into one document before the client meeting. One entry is precise. Another is two sentences vague enough to describe any month of any project. You could send it back. Most months you don’t, because the deadline is an hour out and the four sharp entries make the vague one look fine sitting next to them. So it rides along, dressed in the same formatting as the rest, and nobody downstream invests enough time or energy to notice.

The opportunity for automation here is high, but so are the risks of cognitive offloading. Let something check the inputs before they reach you, the way a manufacturing line stops a bad part before it moves to the next station. Give the contributor real-time feedback at that seam, before a vague input ever becomes part of the deliverable.

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The first draft earns its messiness

In fiction, the messy first draft is doctrine. Its purpose is completion, not quality. “The first draft of your novel is not meant to be good,” Johnson said. “It’s meant to get what is in your brain out on the page and get it finished.” Most people who set out to write a novel never finish because they cannot move forward when the work in front of them is bad. The fix is giving yourself permission; allow the draft to be rough, get to the end, and only then discover what you were actually building.

The desire to produce polished work at every stage is understandable. It is also the instinct most likely to produce work that is neat, but wrong. A rough, documented hypothesis, circulated and tested, creates more value than a clean framework delivered after the moment has passed.

What stays off the page

Johnson described an aspect of the craft that surprises people outside of it. The author must know what happened to every character before page one, even though most of that history never appears in the book. She points to Tess Gunty, whose novel The Rabbit Hutch took seven years to write. Gunty produced nearly two hundred pages that did not make the final cut. That invisible work is why the book lands as hard as it does.

Programs invest heavily in requirements and almost nothing in context. Who are the people this program is built for, and what shaped their expectations before the initiative was conceived? The stakeholder conversation that surfaces this rarely appears in a status report. It is also frequently what determines whether a delivered program gets used.

Structure makes the detour navigable

Johnson described herself mostly as a plotter, “There are certain story arcs. This is what happens at this time.” But between those points, the work is genuinely chaotic. “It’s like throwing spaghetti at the wall,” she stated. “What can I do? How can I get to this big thing?” Her characters will take her in a different direction than planned and she follows. The structure is not there to prevent that. It is what allows her to leave the plan without losing the thread.

The same dynamic applies when a team first comes together. Priorities conflict. Language differs. People challenge each other’s assumptions. Leaders who rush past this stage in search of harmony tend to get compliance instead, with the real disagreements intact and unresolved. The mess is not a problem to eliminate. It is where alignment is created. Clear decision rights, escalation paths, and reporting cadence do not remove the friction. However, they make it productive, and they ensure that once the team has worked through it, the routine decisions no longer require renegotiation.

Range is unplanned

Johnson is a visual artist, a former choral singer, a marketing writer, and now a novelist. Her second book features a visual artist protagonist and song lyrics she wrote herself. She did not develop those capabilities in order to write better fiction. They simply became the material the work was made from. “It’s all one big pile of creativity,” she said. “Different mediums, and I really enjoy how they mix with each other and intersect.”

The program manager who develops outside the delivery lane is not preparing for a specific future use. Depth in one domain teaches you to recognize depth elsewhere. That recognition is what separates someone who follows a process from someone who knows when the process is wrong.

The thinking is the work

Before Johnson wrote her first novel, she spent three weeks walking, mapping characters, and building what she described as a slide deck of who each person was and what would happen to them. She had not yet written a single word of the book. Most organizations treat this kind of preparation as delay.

Getting clear on what a program must change, for whom, and what will be true when it succeeds is not preliminary to the work. It is the hardest part of the work. Teams that skip it do not save time. They spend it later, under pressure, making decisions that should have been made at the beginning.

Kelly Johnson is a novelist, essayist, and Substack writer based in Minneapolis, Minnesota. She holds a master’s degree in marketing from USC.

Little Freak

A 2x weekly newsletter about pop music and mental health for anyone who has ever been genuinely moved to tears by Taylor Swift :)

By kelly johnson

Kelly’s Something to Read

Story Genius by Lisa Cron

Motherhood by Sheila Heti

Everything I Know About Love by Dolly Alderton

Bye, Baby by Carola Lovering

The Rabbit Hutch by Tess Gunty

I have seen something interesting inside corporate document libraries. They are intended to be a standard, a source of best-in-class examples and templates, but the best employees with the most experience are not contributing to or using it. Nothing in it is technically wrong. It is also not right. Written to apply everywhere, updated by people with the least experience running the work it described, the result is the lowest common denominator. Segments of the company keep maintaining their own resources instead, resources the organization was already paying someone else to produce.

For most of my career, that left every program manager with a binary choice: follow the standard as written, or build something better and quietly absorb the cost of duplication. Neither option scaled well, and most organizations ended up with both problems at once, an unused library and a shadow one. What changes that binary is not a faster way to draft standards. It is the ability to match a new project against a knowledge base of past ones, with full knowledge of how those projects performed, show what it has in common with the closest cases, and flag what has no precedent in the base at all. That is a different kind of help than speed, and it comes with a different kind of risk.

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Eight years after buying a condo with an ugly kitchen, I was ready. I had done the legwork, solicited bids, selected a contractor, and was genuinely excited. I thought I knew what good looked like. My dad spent my childhood renovating our home, building furniture, and acting as a general contractor for family and neighbors. My brother-in-law is a general contractor. I had watched enough episodes of This Old House to be dangerous.

What I did not anticipate was how much that background would shape the outcome, but not in the way I expected. This was not just a renovation. It was a case study in how trust fails in delivery.

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Three Strikes

The project unraveled in stages.

The floor came first. I knew exactly what I wanted and had receipts from the original flooring it was meant to match. I shared the documentation. The contractor raised questions about the material more than once. I noted it, but did not worry. They had provided the evidence. Then the wrong floor went in. The contractor pushed to move ahead, first insisting that it was right, then focused on fixing it later, prioritizing schedule over agreed upon requirements. I pushed back. We lost time, but the issue was corrected before the next phase began.

The insulation came second. With the walls open, a co-owner of the business walked me through a plan to install spray foam to protect the pipes, an upgrade from what had been there since the 1970s. It wasn’t a requirement I knew to ask for, but I appreciated that they set a high standard for something so fundamental. I just happened to be present when drywall went up over a completely uninsulated wall. I engaged the project manager immediately. He explained why the original plan had not worked, but could not explain why the alternative was to do nothing. If I had not been standing there, I would not have found out about this until there was a water leak.

The definition of “done” came last, and it nearly broke me. The floor was damaged. The walls were unfinished in places. The refrigerator was wedged so tightly into its space that the door did not open correctly. Custom cabinet doors were wrong. Paint touch-ups were high gloss on a matte wall. The final straw came when the contractor sent an invoice for “completed” work.

After months of living in less than a third of my condo, breathing dust, I had a meltdown. Rational thought left the building. My dad and brother-in-law* bore the brunt of it. They talked me off the ledge, then reminded me that I still had a valuable tool available; withholding payment. It took six more weeks, more than a total of four months for a kitchen just over 40 square feet, to reach a result I could accept.

What the Contractor Did Not Know

People say projects are not personal. That is almost never true. Assuming otherwise is risky. In this case, the reason was obvious. It is where I live. But project managers should not assume they understand the sources of attachment stakeholders bring to their work. Those sources are rarely visible and almost never fully articulated.

What the contractor also did not know was that I was never evaluating their explanations alone. Every conversation I had with the project manager was one I could replay with two people who had the expertise to tell me whether it made sense. That changed the dynamic, whether the contractor was aware of it or not.

Project professionals can be, but should not assume they are, the most informed person in the room. Stakeholders frequently have access to outside expertise and perspective that never appears in a stakeholder register. In effect, every project has an invisible advisory layer. Your assurances are being tested against sources you cannot see.

The final invoice was not just a billing event. It was a signal. It told me what the contractor believed the completed work was worth and it arrived before I agreed that the work was complete. The gap between their definition of done and mine was the most expensive failure of the project. Not expensive in dollars, though the rework had a real cost. Expensive in trust, which by that point was nearly gone.

Knowing the right moves is the first step. Then you need the right support to make them. If your program is navigating a critical transition or growth inflection point, I can help you cut through the noise to turn strategic ambition into disciplined execution. Let’s talk.

Book a Discovery Call

The Game You Are Always Playing

I eventually found a useful frame for what had happened. Game theory describes repeated interactions as games where today’s behavior is shaped by tomorrow’s response. In repeated games, cooperation becomes rational because future payoffs matter. Trust is the currency.

Brené Brown’s marble jar analogy captures the same idea from a different angle. Trust is built over time in small, consistent deposits, and withdrawals empty the jar faster than deposits fill it. In project terms, trust is not a sentiment. It is an accumulating balance that affects decision speed, tolerance for risk, and willingness to continue the relationship.

Every status update, every explanation, every decision either builds or spends that account. The contractor made three withdrawals before the project was halfway done and never made a deposit large enough to recover the balance.

This is why context matters. PMI’s definition of a project, a temporary endeavor undertaken to create a unique product, service, or result, is precise and contractually useful. When the work is finished, the file can be closed.

But not all scorecards reset. For a business built on referrals, repeat clients, and reputation within a community, the game is not temporary. A project can be technically closed and strategically lost at the same time.

I would not recommend this contractor. I will never know whether they know that, or whether it matters to them. What I do know is that the kitchen is finished, and it is exactly what I wanted. I also know that I cannot look at it without remembering what it cost to get there.

The output is right. The experience is not something I would repeat. For delivery professionals, that gap is the real measure. Sponsors and stakeholders are keeping score in ways that do not show up in your project register. They are talking to people you do not know. They are carrying experiences you did not plan for. And they are deciding, long after the invoice is paid, whether the next opportunity goes to you.

Consistency and transparency add up slowly. Their opposites spiral exponentially faster.

*Quick reflection on sexism: The general consensus is that the contractor took this approach because I was a women. One option available to me was to bring in a pinch hitter, to invite my dad or brother-in-law to visit and read the contractor (and their subcontractors) the riot act on my behalf. There is a good chance I could have avoided some of the headaches if I used this option. Getting through the days, weeks, and months would have been easier. I chose not to because it made me deeply angry. They weren’t the customer, I was. Why should a successful project depend on them? Good program and project management is about using all the tools available to you, so I don’t know that it was the correct choice. I have no opinion on what you should do if you are in a similar situation, except on any given day, make the choice that leaves you standing to fight another day.

Something to Read

The Pivot Point: Success in Organizational Change by Dr. Victoria Grady [137 pages]

Who Can You Trust? How Technology Brought Us Together and Why It Might Drive Us Apart by Rachel Botsman [336 pages or 10.5 hours]

No Hard Feelings: The Secret Power of Embracing Emotions at Work by Liz Fosslien and Mollie West Duffy [304 pages or 4.75 minutes]

Governing the Commons: The Evolution of Institutions for Collective Action by Elinor Ostrom [298 pages or 10.5 hours]

Something to Watch

Staplers & Volleyballs: Why Strength May Not Be What You Think with Dr. Victoria Grady [11 minutes]

We’ve stopped trusting institutions and started trusting strangers with Rachel Botsman [16 minutes]

The signal was never missing, the escalation was. Everyone had the information. Nobody wanted to put their name on it to those with the authority to act. AI can accelerate how fast a risk gets routed and flagged. It cannot replace the will required to move a known problem to the person who can actually do something about it, and on this task that will is almost the entire difficulty.

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Programs do not deliver benefits. People do. Staffing decisions, incentive design, role clarity, and subcontractor accountability are the mechanisms through which strategy becomes execution. When those systems are misaligned or unmonitored, the evidence does not appear on a dashboard. It appears later, in attrition numbers, lost recompetes, and teams that stopped asking whether their work mattered.

Verna Staggers, a human resources executive and author with over 25 years of experience in professional services and government contracting, plainly identified the root cause: “The people work, the people systems, the hiring are foundational. It can determine the success or failure of the program.” The problem is not that leaders disagree. It is that the evidence never appears where they look. “It doesn’t show up cleanly on a dashboard,” Staggers said. “It tends to get undervalued until it becomes too expensive to fix.”

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Three forces drive avoidance. Program managers often lack formal authority over compensation, staffing, and vendor terms — functions fragmented across HR, Procurement, and Legal — so they stop monitoring what they cannot directly control. Delivery crowds out anything without a milestone date and measurement culture does the rest. Funding favors what can be measured and understood quickly, and motivation, role clarity, and incentive alignment resist easy quantification.

The consequences are specific. Staggers recounted an example about a program manager whose sole performance incentive was winning new business. After the award, a market analysis revealed that it required human capital that did not exist in the program location. Talent had to be imported. Delays followed. Cost overruns followed. Two years later, at the recompete, the work went to a competitor. A single misaligned incentive had unraveled a long-standing client relationship and future business potential. No one was willing to discuss it until it was too late.

Turnover adds to the issue. At two to three times the cost of hiring and onboarding, employee turnover is one of the most underestimated financial risks in program delivery. And beyond what a program costs to run, there is the harder question of what it failed to achieve. When teams lack the right people, programs hit their contractual minimum and stop there. The ceiling, including the innovation, the follow-on opportunity, the organizational capability that could have been built, quietly disappears.

Knowing the right moves is the first step. Then you need the right support to make them. If your program is navigating a critical transition or growth inflection point, I can help you cut through the noise to turn strategic ambition into disciplined execution. Let’s talk.

Book a Discovery Call

The Alignment Audit

Ultimately, people-to-benefits alignment is cultural, found in a persistent willingness to focus attention in this way. The practical entry point is a review before execution ramps up. Take the three most important program benefits and map each to the roles, teams, and external partners most responsible for enabling them. For each, ask four questions:

• Do they understand the benefit?

• Do they have the capability?

• Are they motivated?

• Do their incentives and contractual terms reinforce the right behavior?

That single exercise surfaces the highest-leverage interventions: a retention risk on a critical role, a vendor KPI measuring activity instead of outcomes, and a subcontractor clause that rewards delivery volume over adoption quality.

Incentive design requires more than adjusting pay. Staggers recommended building accountability around four dimensions: attracting the right talent, retaining it, developing it, and meeting client expectations. Each can anchor a measurable target. More importantly, she argued that program managers should be evaluated on team morale and retention, alongside revenue and delivery, because it “helps a program manager become well rounded, versus just over-indexing on one thing.” One organization she worked in built cross-functional collaboration directly into performance reviews, creating an explicit incentive to partner rather than compete. When she moved to a firm without that structure, the difference was immediate. Not only is this a best practice for people leaders, but it also trains program managers to understand trade-offs and the complexities of balancing business drivers and strategic objectives.

Intangible incentives are equally powerful and more frequently mismanaged. People assess what a role will do for their career, whether their contributions are visible to decision-makers, and whether their manager genuinely believes they can exceed the standard. Staggers affirmed the Pygmalion dynamic, belief has a measurable effect on performance, independent of ability. Conversely, misalignment does not require bad intent. Staggers described a recurring pattern where people are hired for one thing and rewarded for something else, with expectations that match neither. Programs that inherit that confusion spend years resolving conflicts that were baked in at the start.

Incentive design also cannot be one-size-fits-all. A 30-year specialist approaching retirement has a different motivational profile than a mid-career high-performer building a portfolio. Both deserve attention; neither benefits from the same intervention. Meeting people where they are is a prerequisite for getting the performance the program needs.

An achievable action: within the first 30 days of a new program, schedule individual 20-minute conversations with the five roles most critical to the program’s value proposition. Ask each person: What does success look like for you personally on this program? What would make you want to stay for the full duration? What would make you leave? The answers will tell you more than any engagement survey, and they immediately signal that this program manager treats people as a strategic asset, not a staffing input.

The Cost of Inaction

Aligned people systems protect revenue, reduce rework, lower attrition costs, and defend future work. The business driver is operational efficiency but the downstream effects extend to customer impact and strategic alignment. As Staggers’s recompete example illustrated, people failures do not stay contained to one program.

The cost of upfront investment is real: leadership time for alignment conversations, possible adjustments to compensation structures or contract terms, coordination across HR, Procurement, and Legal, and the organizational discomfort of surfacing hidden incentive conflicts. These costs are predictable and controllable, which is the point. Unlike the crises they will prevent, they can be planned for.

Tools help, and their limits matter. Staggers has seen pulse surveys and exit interviews return no signal until a critical, trusted one-on-one conversation brought up the right questions. Staggers has seen it first-hand. These insights “would not have come up on a survey,” she said. “It takes context. It takes a level of trust.” AI can aggregate trends, flag attrition risk, and reduce administrative load. The instinct to replace human judgment with algorithmic monitoring such as tracking keystrokes, scoring facial expressions, and optimizing every interaction produces teams that manage appearances rather than build capability. “There’s no opt-out,” Staggers observed of the most aggressive monitoring cultures. “That just means there’s no trust.”

Reduce the risks of acting by keeping scope narrow. Focus on the roles and subcontractors with the greatest influence on strategic outcomes. Use existing governance forums rather than building a parallel people-review process. Establish a limited number of leading indicators like retention risk for critical roles or subcontractor performance, and track them with the same cadence applied to schedule and cost. The goal is not a people program. It is a feedback loop honest enough to tell you whether the human system is working before the program is too far gone to fix.

Verna Staggers is a human resources executive and talent strategist with over 25 years of experience in professional services and government contracting. She is the author of What Companies Don’t Want You to Know: 39 Insider Secrets. Connect with her on LinkedIn and Instagram. Get more information on her workshops and programming here.

Something to Read

What Companies Don’t Want You to Know: 39 Insider Secrets by Verna Staggers [178 pages]

The Power of Project Leadership by Suzanne Madsen [336 pages]

Something to Watch

Building a Motivational Workplace Culture: Reinventing Compensation with Rebecca Ahmed [13 minutes]

Why the best hire might not have the perfect resume with Regina Hartley [10.5 minutes]

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In a conversation with tech leader Monica Arias, the game of Chutes and Ladders became the working metaphor; there is a clear end state, but progress is uneven, with both accelerations and setbacks. The path you want is almost never the one you finish on. A roadmap that cannot deal with change, exploit opportunities, or manage shifts in the business environment is useless to a program manager.

This is not a methodological debate. Whether operating in agile, hybrid, or traditional environments, the underlying problem is the same. How does a sponsor and a program manager translate strategic intent into a sequence of decisions that produces value? Roadmaps are often dismissed as relics of linear thinking or are deprioritized under delivery pressure. “Sometimes people get carried away,” Arias noted. “Let’s just do this, let’s try this. You don’t take a step back and say: what is our end goal? What are the midterm and short-term milestones you really have to think through?” The result is momentum without sequencing, activity without value.

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When the Strategy Is the Problem

The deeper failure often starts upstream. Strategies handed to program teams can be directionally sound, but operationally thin. Often strategies include high-level goals without enough definition to guide order, tradeoffs, or decision points. “A forceful personality who has a title makes it really hard to provide input, to redirect the strategy to make it even better,” Arias observed. When strategy is built in an echo chamber, the roadmap inherits its blind spots. Done early and with diverse input, a roadmap is how those gaps are surfaced and tested before they compound.

Without that translation layer, a familiar pattern emerges. Teams begin work, but lack clarity on what must happen first or what progress should look like along the way. Dependencies remain implicit. Then executives return looking for evidence of movement against outcomes. Without a shared view of how value is expected to materialize over time, teams are caught reconstructing logic under scrutiny rather than demonstrating it. Delivery slows not because of capability, but because sequencing was never well understood.

The downstream effects are predictable: cross-functional dependencies surface late, governance bodies make reactive decisions, and benefits erode. Status can remain green while value slips, because the program is tracking activity, not outcomes.

Stakeholder resistance reinforces the problem. Leaders stretched across priorities treat roadmap development as optional. Members of your team are attached to their individual projects because they don’t share a vision for what’s next. Others resist because transparency exposes misaligned commitments across functions. Some apply a harder veto: “We’re not going to make any changes to our roadmap unless there’s an ROI right there. It’s set in stone,” Arias remarked. That stance converts a decision tool into a static promise and closes off the very options the program was funded to explore.

Knowing the right moves is the first step. Then you need the right support to make them. If your program is navigating a critical transition or growth inflection point, I can help you cut through the noise to turn strategic ambition into disciplined execution. Let’s talk.

Book a Discovery Call

Work Backward

Start with the end state, not the timeline. Establish what must demonstrably change for this program to have been worth doing. Then work backward through the benefits realization plan to determine which outcomes must land in which order, the capabilities required to produce them, and the decision points where scope, funding, or direction may need to change. Near-term phases carry detail while longer horizons stay directional. Historical information from prior programs, including lessons learned about sequencing failures and dependency risks, should inform both the structure and the assumptions embedded in each phase.

“I’m very okay with going in different directions,” Arias said of programs that changed shape mid-execution. “I still need to get to the end and perform.” That is the Chutes and Ladders logic applied to execution. There is a winning square, but the route is variable. The roadmap acknowledges redirects as features of complex work, not failures of planning. Program leaders who internalize this stop defending original timelines and start managing toward outcomes.

Even as a draft, this surfaces assumptions early. Co-create it. “You can’t just think of these things in a vacuum. You need other ideas,” Arias said. And prepare: “Don’t go in with something half baked. Bounce those ideas off of mentors and peers.” Early involvement converts resistors into co-owners and gives program leaders standing to defend sequencing decisions when pressure mounts.

A Decision Instrument That Pays for Itself

The business case is straightforward: alignment, sequencing, and risk reduction. A roadmap makes a program’s contribution to enterprise goals visible and testable; it concentrates investment in the right order; it reduces the cost of late-stage dependency failures; and it gives governance bodies something to decide against, not react to. At the portfolio level, programs that cannot show sequenced value delivery are the first to lose funding when priorities shift.

The real cost is not time. It is the discomfort of embracing uncertainty in front of sponsors who prefer confidence. The corresponding risk is that an early roadmap is treated as a commitment rather than a planning tool.

Mitigate that explicitly from the first review: use phases and windows where certainty is low; distinguish commitments from assumptions; and set a review cadence tied to governance cycles, not crises. This holds regardless of methodology; the artifact adapts, but the function does not. Leadership sets the conditions. “They set the culture, they set the expectations, they set the tone, and then that filters down,” Arias said. That includes trusting program leaders to bring client and mission insight into sequencing decisions and making room for options that do not resemble what has worked before.

A roadmap only functions when leaders use it to make decisions. Invest in it early, and the program does not just move faster. It avoids accelerating in the wrong direction.

Monica Arias is a sales and partnerships leader specializing in dark web intelligence and cyber threat exploitation, with a career spanning cryptocurrency analytics, national security consulting, and defense intelligence. She has led federal business development and go-to-market strategy for leading platforms, building on nearly a decade of experience in DoD program management. Her expertise sits at the intersection of emerging technology, tradecraft, and strategic growth. Connect with her on LinkedIn.

Something to Read

The Little Black Book of Project Management Advice by Asya Watkins [300 pages or 6 hours]

Manage Your Project Portfolio: Increase Your Capacity and Finish More Projects by Johanna Rothman [240 pages]

Designing for Growth: A Design Thinking Tool Kit for Managers by Jeanne Liedtka and Tim Ogilvie [248 pages]

Something to Watch

How to make hard choices with Ruth Chang [15 minutes]

The power of paradox with Dr. Wendy Smith [16 minutes]

The contracting structure that had won the work made integration a condition of the deal, not a discussion point. What I learned only later is that the friction was never about whether integration made operational sense. It was about how being folded in against his will changed how he and his team saw themselves, and how they thought they were managing their own client relationship. That is a perception problem, not a data problem, and the truth of the matter was never written down.

AI can find integration opportunities faster than any manual review. It cannot tell you whether the people losing something will let you keep it.

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Melissa Reeder is a senior project management executive at a large technology firm, where she oversees governance and standards across a portfolio of client projects. She has spent years watching teams skip this task, they function for a while on collective memory, and fracture when someone asks who owns a decision and nobody knows.

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Not choosing is a choice

The most persistent barrier is a claim disguised as a method. Reeder remarked, “We have a lot of projects that don’t have a project management plan because they’re under the concept; well, everybody knows what to do, so why document?” Agile, invoked loosely, has given that position professional cover, and it may hold up as long as the original team remains intact. It collapses under audit, turnover, or a yellow status report. “As soon as a project goes yellow or red, everybody points fingers. ‘Well, I didn’t know.’ If you had it documented, you would know,” she added,

A newer version of the same problem has arrived. Teams have AI-produced plans that sit on the shelf. They passed initial review but are never operationalized. Reeder shared a common conversation she has with teams. “I’ll go to look at it, and I’m like, is this really what you’re doing? And the answer is, ‘it’s close enough.’” The plan specifies one risk classification system. The tool uses a different one. The plan requires daily risk reviews. There is no evidence that they occur. The document has been created. The thinking has not.

Both failures share a root cause. The delivery approach was never matched to the work. A project with regulatory constraints, fixed deliverables, and an external audit timeline needs predictive controls. A project that builds a new capability in an uncertain technical environment requires iteration and adaptive governance. Most projects need both, applied differently across workstreams. When no one explicitly makes that choice, teams default to the most familiar method, apply it uniformly, and manage the gaps through individual judgment. It is a glorified workaround.

The consequence is not dramatic. Roles get assumed rather than assigned. Cross-unit agreements are handshakes. Risk does not roll up. “You have the project risks, you have the project, the portfolio, and then you have other risk elements: data, privacy, security, travel, AI, cloud,” Reeder emphasized. “When you add all of those other layers, risks are very, very prominent.” And without documentation, improvement is impossible. “If you don’t document it, I don’t know how you can make improvements. How can people be consistent if nobody knows what they’re supposed to be doing?” She continued.

Knowing the right moves is the first step. Then you need the right support to make them. If your program is navigating a critical transition or growth inflection point, I can help you cut through the noise to turn strategic ambition into disciplined execution. Let’s talk.

Book a Discovery Call

Three Moves

The first move is to make the delivery approach explicit. Assess each major workstream against three variables: how well-defined the requirements are, how sensitive the task is to regulatory scrutiny, and how likely the environment is to change. Requirements that are clear, stable, and clearly bounded favor predictive planning. Requirements that are emergent or technically uncertain favor adaptive management. Most enterprise projects have both. The integrated plan should explicitly say so, specify where the modes interface, and describe how governance will reconcile them when they create conflicting signals.

The second move is to close the decision-rights gap. Reeder clarified, “How do people know if you can make a decision, if they can make a decision? That’s the whole part of your project management plan. How do you know how to escalate?” Especially In hybrid environments, the absence of an explicit decision model produces a recurring pattern: the team believes the product owner decides, the contract says the project manager decides, yet (sometimes) the actual decision is made by whomever is in the room. The plan must specify who holds authority, at what threshold, and what happens when authority is unclear.

The third move is to tailor by reference rather than reinvent. Most organizations already govern financial management, risk classification, and reporting through corporate standards. The integrated plan does not recreate those; it references them, which confirms the team knows where to find them, and adds only what the standard does not cover for this project. “If your corporate process says you’re going to use SharePoint and you’re going to use the risk list in SharePoint, then just say, refer to the corporate policy,” Reeder said. That discipline alone removes the most common cause of over-engineered, shelf-bound plans.

For any project manager starting now, create a one-page operating model that documents delivery mode by workstream, decision rights and escalation thresholds, cross-unit agreements, and the information leaders will review on what cadence. It will not substitute for a full plan. It will prevent the most common failures before they get out of control.

Where to Start

I subscribe to Richard Rumelt’s argument that good strategy is mutually reinforcing, and the same principles apply to the integrated project management plan. The components of the plan (risk, schedule, stakeholder management) amplify one another rather than operate in isolation. Articulating them separately creates clarity, but they are not independent variables.

Just as the program charter establishes the baseline against which benefits are measured and strategic decisions are defended, the integrated plan operationalizes that argument. When two workstreams lead to a dispute scope, the plan is the reference. When a sponsor asks why a decision was made three months ago, the plan is the record. It is also where conflict gets resolved, not by revisiting positions, but by negotiating a solution from a shared understanding.

We can also learn from the principles of Lean Six Sigma. Nothing can be improved without a clear understanding of the current state. The integrated plan should reflect the current state. If it does not reflect how the program actually works, it is fiction, and fiction cannot be improved. “If you don’t document it, I don’t know how you can make improvements. How can people be consistent if nobody knows what they’re supposed to be doing?” Reeder asked.

The process is disruptive for teams running on unspoken assumptions. A team that has worked together for years and is doing fine will experience this as friction. The resistance is rational. So is the investment. A team that has articulated its delivery model, decision rights, and risk logic is more resilient when a key person leaves, a client resets priorities, or a budget cycle forces hard trade-offs. The team knows why, what, and how, and that understanding allows adaptation rather than rebuilding from scratch.

Melissa Reeder is a transformational executive with 30+ years of global leadership in information technology, enterprise delivery, governance, and business transformation. She leads global transformation by aligning strategy, operations, and people leadership across complex enterprises. Reeder is a trusted advisor to senior executives and boards, recognized for executive presence, clear communication, emotional intelligence, and strong client and stakeholder relationships. Find her on LinkedIn.

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Be Hopeful, Be Strong, Be Brave, Be Curious: How Coaching Can Help You Get out of Your Own Way and Create a Meaningful Life by Ruth Pearce [256 pages or 8 hours]

Be a Project Motivator: Unlock the Secrets of Strength-Based Project Management by Ruth Pearce [248 pages or 5.75 hours]

Making Work Visible by Dominica DeGrandis [240 pages or 5.25 hours]

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Making Work Visible: How to Unmask Capacity Killing WIP with Dominica DeGrandis [30 minutes]

Not quite, or at least not entirely. Team leadership is one of the few program management tasks where the output is not a document, a forecast, or a plan. It is whether the people on your team believe you will act in their interest. That belief is earned, tested, and occasionally lost with a single bad call. AI can support the routines that surround leading a team. It cannot substitute for the judgment and accountability that make your authority legitimate to the people who report to you.

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Exploiting strategic opportunities for change is the discipline of continuously testing whether a program’s current path still represents the best route to its intended outcomes, and adapting when it does not. It separates programs that maximize benefits from programs that complete scope. For more than two decades inside a federal research agency, Marcia Pincus did this work directly: justifying new programs to leadership, redesigning existing ones mid-execution, and documenting pivots that kept her programs credible through audits and budget cycles.

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When the Plan Outlives Its Purpose

The task gets skipped for reasons that feel rational in the moment. Under delivery pressure, continuous strategic sensing takes a back seat to more urgent tasks. Governance systems protect approved plans. Re-baselining triggers scrutiny. Changing course after a hard-won business case approval is politically expensive.

There is also the problem of expertise mistaken for certainty. Senior specialists can reach a point where experience substitutes for inquiry. Assumptions age out quietly. Budgets get defended with activity rather than evidence. By the time a sponsor asks for proof of value, the program has little to offer except a completed work breakdown structure.

The deeper cost is systemic. When programs fail to document what worked and why, those lessons disappear. “If you are not incredibly honest,” Pincus said, “you mess it up for everyone.” De-risking the investment for others is part of the job.

Knowing the right moves is the first step. Then you need the right support to make them. If your program is navigating a critical transition or growth inflection point, I can help you cut through the noise to turn strategic ambition into disciplined execution. Let’s talk.

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The Outcome Narrative

Pincus starts with a single question, asked before execution begins: “At the end of this program, what is the story you want to tell about how you spent this money?” Not a goal statement. Not a deliverable list. The story is who benefited, in what way, verified by what evidence.

That question does two things. It forces clarity on outcomes rather than outputs. And it creates a navigational anchor for the program’s entire lifecycle. “You engineer go/no-go points,” she explained. “You engineer check-ins. Are we still on track to tell the story that we want to tell?” When conditions shift, the program manager has a reference point for judging whether adaptation increases value or just adds activity.

Reading what stakeholders actually object to, rather than what they say they object to, is equally important. Pincus spent months building a rigorous business case for a Center of Excellence in an organization where the term had become overused. The analysis was sound, the need for the work was proven. The appetite for a new “Center of Excellence,” however, was not. “The ideas were good,” she said. “It’s the organizational construct that was being objected to. My team had to separate one from the other.” She lost the proposal for the Center of Excellence, but nearly every idea in it was eventually implemented through other channels.

When a program does pivot, she documents it formally. For one program, her team produced an “autopsy report”, a structured post-mortem on what was working, what was not, and the reasoning behind the change. It proved its value when a GAO auditor asked what justified a change in methodology mid-program. She handed over the report. Pincus commented, “the documentation made that change credible, and it will also serve as a resource to the next leader long after I retire.”

Organizational Learning

All of this rests on the fact that programs are made up of projects. Each project is a hypothesis, a bet that this investment, executed well, will contribute to the program’s intended outcomes. A project can be managed rigorously and still be wrong. It’s not because the team failed, but because it was the wrong project for the program at that moment. Recognizing that distinction, and stopping work that no longer serves the program’s outcomes, is the discipline working as designed. Sponsors and steering committees share that responsibility. Selecting projects and closing them are governance decisions, not just delivery ones.

Because the story was established before spending began, it also structures the return on investment case. Financial benefits are defensible when connected to that narrative. Non-financial benefits, customer impact, organizational capability, and institutional knowledge, are harder to quantify but equally real. The program manager who can tell the full story of what changed, for whom, and what was learned, can make both cases.

The governance, political, and human costs are real. The question is not whether to absorb them but which changes are worth the cost. Prioritizing the most strategically significant opportunities, and letting smaller ones go, is how program managers protect capacity while maximizing value.

“Your job is not necessarily to be 100% successful 100% of the time,” Pincus said. “Your job is to learn about what worked and what didn’t work and then communicate those results to the world at large.” That learning, documented and shared, de-risks the next program for this organization and every one watching.

Marcia Pincus, Principal & Founder of Lucid Perch Consulting, is a senior transportation strategist with 20+ years executing complex transportation technology RD&D programs. She has deep practical understanding of transportation technology, policy, regulation, deployment, and market development and a proven ability to lead cross-sector coalitions and engage with key policy influencers/industry partners through partnership and collaboration. Find her on LinkedIn and check out The Perch Perspective on Substack.

The Perch Perspective

The Perch Perspective is where clarity meets strategy - above the noise.

By Lucid Perch Consulting LLC

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The story and the storyteller: Strategic storytelling that gets human attention for entrepreneurs by Srivasta Smita and team

Wired for Story by Lisa Cron

Storytelling in Business

Resonate by Nancy Duarte

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How your brain responds to stories -- and why they’re crucial for leaders with Karen Eber [14 minutes]

They are not and it is not a subtle distinction. It is the difference between a business problem and a bullshit one, and too many programs are currently funding the bullshit version at scale. Cathy O’Neil spent a book’s worth of evidence on what happens when a number that looks objective replaces human judgment. The people scored by that number tend to get worse outcomes. They also tend to never find out why, because the score looks like math and math doesn’t explain itself. Run that experiment on a customer segment and you have a business risk. Run it on the sponsor who controls your funding, and you have a program walking calmly off a cliff it built for itself.

If your plan is to let an AI agent manage your stakeholder relationships for you, this article is not for you, and no dashboard will fix what that plan is actually about. If instead you are drowning in stakeholder best practices and looking for where automation can genuinely make room for real attention, read on.

Executives want a dashboard that shows stakeholder health the way a P&L shows revenue, and vendors will sell it to you. AI can accelerate how you track, prepare for, and communicate with stakeholders. Barry O’Reilly covered this brilliantly in his book Artificial Organizations. O’Reilly and I agree on an essential limit; AI cannot replace the trust that makes a specific person spend political capital on your behalf when your program is in trouble and helping you costs her something.

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Sara Milne Rowe is a leadership coach and author whose practice draws on thirteen years of teaching drama in some of London’s most challenging schools. The students she worked with told her exactly why they worked harder for some teachers than others. Passion for the subject. Relevance to their lives. Consistent, fair leadership. “All of us, on some fundamental human level, want to be able to trust the person that is leading something,” she observed. “So that person needs to show up consistently.” The language of adulthood is different, but the principles are not.

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Working Together

Programs do not just need technically competent individuals. They need people who understand what they are collectively trying to achieve, have negotiated how they will work together, and trust each other enough to raise problems early. Coaching, mentoring, training, and recognition are the mechanisms that build and sustain that capacity. Without them, the program defaults to assumptions.

In conversation, I shared my previous experience working with a leader who adapted every message to each individual. After months of recurring conflict, the team pieced together that we each had different expectations and understanding of our program environment. The program manager may have been prioritizing buy-in over explicit clarity. “It dilutes the capacity, the collective force of the group,” Milne Rowe said, “to be able to talk with one another and ask for what they want and what they need.” The problem, she clarified, was not managing different personalities. It was leaving behavioral assumptions unspoken. “I’m often picking up a mess that’s made from an assumption versus an agreement,” she said. Scope assumptions are documented and visible. Behavioral ones, how decisions get made, how people ask for help, what each person expects from their manager, are rarely named until there is a problem.

In matrixed organizations, this work has no natural owner. Functional managers handle performance management. Program managers handle delivery. Development and recognition fall between them. The cost is real but delayed, which is precisely why the investment gets deferred. Disengagement slowly spreads, knowledge stays siloed, and the program quietly delivers below its potential.

Sponsors often resist these methods because the benefits are intangible, downstream, and harder to forecast. Coaching time, facilitated alignment sessions, and structured recognition are easy to cut when the budget is tight. What rarely appears in the forecast is the mediator brought in at month nine, or the technical lead who quietly exits.

Knowing the right moves is the first step. Then you need the right support to make them. If your program is navigating a critical transition or growth inflection point, I can help you cut through the noise to turn strategic ambition into disciplined execution. Let’s talk.

Book a Discovery Call

Build the Collective

When a program is already underway, Milne Rowe’s first recommendation is not a development plan. It is a reset. “Gather everyone together and re-articulate the main cause and aim of what we’re trying to do together, and get some excitement, some energy, into the collective,” she commented. From there, convert behavioral assumptions into explicit agreements. “Each project, depending on the leader and the people in the group, is going to be very different,” Milne Rowe remarked.

Two practices are immediately deployable without budget or approval. The first is a rapid review, just five minutes at the end of every recurring meeting, asking one question: “Against the intent, how useful has this been?” The language is deliberate. Not good or bad, right or wrong. Useful, or more useful. “What would be more useful in service to the shared intent protects the emotional triggering of ‘I’m being attacked.,’” she stated. Over time, the team learns what makes it effective. Recognition becomes embedded in the cadence rather than reserved for milestone celebrations that arrive too late to reinforce anything.

The second concept Milne Rowe introduces is the trophy cabinet. Ask the team what it has achieved this sprint, this month, this quarter. Identify future trophies and, when the landmark arrives, move them ceremonially from future to past. This creates a recognition cadence that keeps accomplishments visible and reinforces the collective progress the team is making. She stated “You can start to feel the progress you’re making together.” This is not morale management. It is the mechanism by which people understand that their work is registering and that someone is paying attention. Recognition also reinforces the behaviors and standards that helped the team get there.

The Return on Investment

Leading this way requires range. “Sometimes I’m a teacher, sometimes I’m a trusted advisor, sometimes I’m a coach,” Milne Rowe said. “Sometimes I say nothing, sometimes I’m a nudger. The skill of any leader is knowing what to apply to help somebody make faster progress.” For program managers accustomed to directing work through formal authority, that shift is the real development challenge. The practices above are the entry point.

Milne Rowe described a useful diagnostic, “Is the team playing at home or away?” Teams playing at home bring familiarity, trust, and the confidence to speak up. Teams playing away are guarded, expend energy on self-protection, and surface problems late. “When they’re playing away, you don’t get the trust to be able to speak up,” she explained. Over time the rapid review and trophy cabinet build home conditions. But the leader has to decide to build them.

The business value connects directly to execution quality, adaptability, and retention. Coached, mentored, and recognized teams make fewer avoidable errors, adapt more reliably as conditions change, and sustain the discretionary effort that complex programs require. The risk of starting this is low. Both practices require no budget and no mandate. Even when a team invests in outside help, Milne Rowe shares that “it works best when the team collectively says, ‘we could do with some external energy here.’” That conversation rarely happens unless someone first builds the conditions for it.

Sara Milne Rowe is the founder of Coaching Impact (2008), Legacy Moves (2023), a trusted Leadership Impact Coach, host of the Better Under Pressure Podcast, and author of The SHED Method®. She is a patron of The Bates Foundation and serves on the Advisory Board of Empathy Week, a global program that uses film to foster empathy among students in 40+ countries.

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The SHED Method by Sara Milne Rowe [368 pages or 6 hours]

Being the Boss: The 3 Imperatives for Becoming a Great Leader by Linda A. Hill [304 pages or 8.25 hours]

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Better Under Pressure Podcast with Sara Milne Rowe

Leadership Shouldn’t Be a Position with Dr. Rachel Kohman [11.5 minutes]

As I have said before, the artifact is not the part that mattered most. Governance is not just a documentation problem. It is an authority problem and the documents are supposed to make that authority visible so that the team has a shared baseline when they face disagreement. The charter is evidence that people formally agreed who decides what. It is not proof that the agreement is complete, or that it will hold once a decision gets expensive. Get real agreement, though, and something changes. The rule can be built into the workflow itself, so a decision that skips its named owner, or an escalation that misses its threshold, cannot move forward unnoticed. AI can carry more of that enforcement than you think, in narrowly defined, rule-bound gates, provided the authority question was settled by people first, not configured by the tool that enforces it.

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Jocelyn Lewis has spent her career managing federal programs, where technical delivery is non-negotiable, but the real work is navigating the human dynamics underneath it. As both a PMP and PgMP, she is precise about where the two disciplines diverge. At the project level, stakeholder analysis surfaces what individuals need and how to communicate with them. At the program level, the job expands in scale and consequence. The program manager’s task is not just understanding what each stakeholder wants. They also need to negotiate and balance competing perceptions without losing strategic coherence.

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The Evidence Gap

Lewis remembered a warehouse management system that went live and went unused. “We didn’t do training, we didn’t do change management, we didn’t do comms,” she said. The facility held supplies critical to federal agencies. Health and safety implications followed. Employees found workarounds. The program delivered as promised, but value was left unrealized.

The stakeholders were known. The failure was analysis. No one had mapped what each group actually needed, how they would encounter the system, or what would drive adoption versus avoidance. Formal agreements, prior program data, and structured interviews with the people doing the actual work would have surfaced those gaps early. Instead, the program learned them after go-live.

This is what distinguishes analysis from identification. Identification produces the list. Analysis produces a diagnosis that can be acted on. Who holds decision rights? Who absorbs the risk of failure? What incentives are actually in play? Where is the gap between formal authority and real influence? Without that diagnosis, the engagement plan is generic. With it, the program manager knows which conversations to have, in what sequence, with what framing, and where escalation or tradeoffs are inevitable.

The barriers are specific to analysis. Mining contracts, RFPs, and lessons-learned repositories take time and require someone who knows what to look for. Structured interviews expose misaligned expectations that many leaders would rather not surface early. The political cost of documenting what is actually true about influence and resistance is real.

“It’s the whole struggle with calculating ROI,” Lewis stated. “It’s difficult to quantify upfront how much it will cost if you don’t do these things.” Programs rarely go back to measure the cost of skipping analysis, which means the case for doing it gets rebuilt from scratch on every initiative.

Over-engineered stakeholder matrices are a related trap. Lewis has seen them built with care and never opened. “It doesn’t have to be beautiful,” she said. “It’s more important that it’s used.” Stakeholders themselves resist for a parallel reason. An analysis that honestly documents influence levels, decision rights, and resistance is sensitive material. Lewis drew a practical line: “You’re not going to write ‘this person is going to challenge the team.’ Instead we document things like ‘this person prefers a phone call to an email.’” Honesty makes engagement plans usable, but risky. The PM needs to balance sanitized uselessness with political exposure.

Knowing the right moves is the first step. Then you need the right support to make them. If your program is navigating a critical transition or growth inflection point, I can help you cut through the noise to turn strategic ambition into disciplined execution. Let’s talk.

Book a Discovery Call

The Discipline That Works

Lewis recommends a clear sequence. Start with documents before people. Pull the program charter, business case, major contracts, and prior lessons learned before conducting a single interview. That foundation surfaces obligations and constraints that informal conversations may miss, and it signals that the analysis is grounded in evidence, not opinion.

Then, define the segmentation that makes sense for the scope of the program. Lewis has watched teams fragment into fifty or sixty stakeholder groups and abandon the analysis because maintenance becomes impossible. “What are the categories that are manageable but still differentiated?” she asked. In federal programs, that typically meant broad groups at the program level and granular detail only for internal governance audiences. The test is simple. Can you maintain it? Does it actually change how you engage with people?

Then translate the analysis into action. “The core principle of program management,” Lewis stated, “is being able to describe the intended value in a way that resonates with your core stakeholder groups.” An executive cares about cost savings. An end user does not. Analysis tells you which argument to make to whom, when, and with what tradeoffs. A system that saves money but that nobody uses does not, in the end, save anything.

The business value is direct. Effective stakeholder analysis shortens decision cycles, reduces rework, and protects benefits realization. The political cost, naming what is actually true about influence and resistance, is higher and often avoided. But the program manager who builds that diagnosis early is the one with enough context to navigate competing demands before they become an embedded conflict. That is the job.

Jocelyn Lewis is a problem solver who helps teams bridge strategy and operations. She has over 20 years of experience working with federal clients to implement new technologies and process improvements that deliver real impact. Find her on LinkedIn.

Something to Read

Her Place at the Table: A Woman’s Guide to Negotiating Five Key Challenges to Leadership Success by Deborah M. Kolb, Judith Williams, Carol Frohlinger [256 pages]

Stakeholder Engagement Essentials You Always Wanted To Know by Michelle Bartonico [228 pages]

Something to Watch

How businesses can serve everyone, not just shareholders with Dame Vivian Hunt [14 minutes]

The Power of Organizing with Betsy Hoover [17.5 minutes]

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Could it?

Break the question in two.

Could AI write a book? Of course. Length is the easy part. Foundation models never tire, never experience writer’s block, never miss a deadline. Split the work across enough prompts and free tools and you could have a fluent, book-length manuscript by morning.

Could AI write that book? No. And the reason deserves your attention, because it is the same reason your hardest decisions resist automation.

Ferrer is a historian of Latin America, now at Princeton after many years at New York University. Cuba: An American History is her third book on the island, built on more than thirty years of research and travel. She was born in Havana and has been returning since 1990, archive by archive, family visit by family visit. She writes that the slogans about Cuba, on the right and the left alike, are insufficient to the thing itself.

That sentence is the whole book. History is not a string of facts or a tidy chain of cause and effect. It is the work of placing facts in context, and context is not universal. Ferrer shows the same event meaning opposite things to different people with different motivations, and she holds those meanings at once without collapsing them into a verdict. A model can imitate her cadences. It can manufacture the lived voice, the scholarly authority, the balanced sympathy. It can possess none of them. It has asked no question it was not prompted to ask.

If a tree falls in the forest…

There is a second part to that question that was unspoken over dinner. Does a book matter before you read it? AI can “read” all the books it has access to. It can summarize them, extract the passages, and compress the arguments into a brief you could skim before your next meeting. That is not reading. To read Ferrer is to spend time with a contested past until your own certainties loosen. The summary hands back the facts and discards the experience that changes you. A model cannot assign value to a book. Then again, neither can the Pulitzer board or the bestseller list. AI cannot write a book at that level, and no book, however decorated, matters at all if you do not read it.

Practicing Uncertainty

This is where the historians earn their keep, and where leaders should pay attention. Barbara Tuchman, who received the Pulitzer twice for general nonfiction, described writing as though she did not know what waited on the next page, placing herself inside the mind of a decision-maker facing an unknown outcome. Joseph Ellis, who won the prize in 2001 for Founding Brothers: The Revolutionary Generation, builds history from character: the private struggle, the road not taken, the choice that looked reasonable and proved ruinous. Both reconstruct judgment under uncertainty, which is precisely what a summary throws away.

You make those decisions every quarter. You commit before the outcome is known. AI can model your options and surface your patterns. It cannot remove the uncertainty, and pretending otherwise is the real hazard. Written history is the longest record we have of how decisions go right and wrong, how consequences arrive unbidden, how the intended and the unintended tangle. Reading it, questioning it, and understanding it contributes to developing judgment and teaches us how to question and understand our own best practices and lessons learned.

Watch what happens when that record is ignored. I was halfway through Ferrer’s book when this administration began treating Cuba as a binary. A blockade. Threats of a “friendly takeover.” A demand to “make a deal before it’s too late,” as the fuel ran out and the hospitals dimmed. Officials around the President carry their own readings of the same history toward different ends. Five hundred years of entangled empire, slavery, revolution, and intimacy with the United States, and the public posture is a coin flip with a known result. Ferrer shows why it never is.

So for America’s 250th, reach for the whole history, not the abridged one. Read the long books. Read the ones you will argue with. The leaders who can sit with a contested past are the ones equipped to govern a contested present. Speed without context, scale without judgment, and a clean answer where none exists will fail you when the consequences land.

A model can write you a book by morning. Whether it is any good is one question. The one that matters is that it cannot read a book for you, and it cannot tell you why it matters. That part is still yours.

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At the start, it feels risky. Managers who surface the full picture also surface a complex history and context they did not create and cannot control. The manager who opens her project data to cross-functional scrutiny invites interpretation from colleagues who may not understand the constraints, the context, or what a reasonable outcome looks like in a city carrying decades of disinvestment.

Data does not speak for itself. It gets read by people with different incentives and different definitions of success. Shared data can improve accountability when the group has agreed on the outcome it is trying to produce, the measures that matter, and the decision rights attached to those measures. Without that foundation, transparency can feel less like alignment and more like handing someone a tool they are not equipped to use responsibly. The result is a familiar workaround. Programs run on informal updates and bilateral conversations. Risks travel by relationship rather than through governance. Benefits get assumed rather than tracked. The program stays active while strategic intent quietly erodes, and no one is quite sure when it happened.

So why push past that resistance? And how does a leader bring fragmented systems together in a way that actually changes something for the people on the receiving end?

Start With the Future State

Crowe’s department is the connective tissue for every city service. “If we don’t work, you don’t work,” she told her cabinet. “Every one of them needs a system in them, and then we need those systems to talk to each other appropriately.” She is not describing a reporting problem. She is describing a translation problem, and the first step is not building the infrastructure. It is defining what you are trying to produce with that infrastructure.

Crowe continued, “Step zero is to sit down and think a little bit and dream a little bit about what success looks like.” Until a program has a settled picture of the outcome it is managing toward, there is nothing for the data to measure against. Once that future state is defined, the question becomes, “what dataset is needed to know whether the program is on track?” That question produces a sharper, more defensible reporting model than starting with available tools and working forward. It also changes the political conversation. Data tied to a shared definition of success is easier to defend and less easy to misuse than data floating free of any agreed standard.

From that foundation, the design follows the decisions. Map what each governance body needs to decide, not what they are used to receiving. Keep the model lean; a handful of measures with explicit definitions, named owners, and escalation thresholds. A one-page integrated performance model, maintained consistently, can often outperform a more sophisticated dashboard built on contested inputs.

Cleveland’s 311 launch is the proof. Ownership was explicit, and the system connected service requests to field crews in near real time. “When you hit submit on the website, it’s about like a one second connection out to the team who’s doing the work,” Crowe commented. The immediate result was not a surge in volume. It was a more organized approach to work already happening. Field crews had a queue. Residents felt the difference. Over time, as trust built, requests increased.

That credibility made something larger visible. When Crowe’s team mapped service delivery data against crime statistics, a pattern emerged that no single department could have produced alone. “We have seen over the last couple years, we’ve literally shifted crime maps, just by shifting the attention, how the city services are there, and underpinning all of that is technology and data systems,” she remarked. The data did not create the outcome, but it helped turn a shared problem into shared accountability.

Knowing the right moves is the first step. Then you need the right support to make them. If your program is navigating a critical transition or growth inflection point, I can help you cut through the noise to turn strategic ambition into disciplined execution. Let’s talk.

Book a Discovery Call

The Price and the Payoff

Jennifer Pahlka’s Recoding America amplifies many of Crowe’s key arguments. Pahlka argues that government technology fails not for lack of data, but because the systems that generate it were never designed to inform decisions. Data sits in silos owned by agencies with different mandates and no shared incentive to integrate, while the people closest to the problem rarely have access to the picture that exists two floors up. Pahlka’s diagnosis is structural and political before it is technical.

The business case for change is real but genuinely difficult to close. A streets project that reduces blight may shift crime patterns, reduce emergency response calls, and improve property values. Each of those is a second- or third-order budgetary effect, distributed across departments that were not party to the original investment and have no mechanism to report back. The resident does not experience a streets project. They experience their neighborhood, the same way they do not call 311 and think about IT infrastructure. They think about whether anyone responded. Assigning discrete ROI in that environment is not a failure of rigor. It is an honest acknowledgment that the value flows in directions the budget process was not built to track.

Understanding costs is more straightforward. Tools, architecture, and change enablement require financial investment. Aligning standards across teams with different incentives takes time and political capital. The vendor landscape adds its own friction. Crowe is direct: “The vendors come in and they sprinkle the AI pixie dust over everything.” Cleveland’s advantage was partial immunity to that pressure. Because prior administrations had not invested heavily in legacy data infrastructure, the city could move more directly into a modern cloud data warehouse without first dismantling an old one. That is not available to every organization. For those with inherited technical debt, the cost of consolidation includes the cost of exit, and vendors who benefit from that complexity are rarely motivated to simplify it.

To reduce that risk, keep the design decision-centered and the vendor relationship skeptical. Audit data quality before it reaches any reporting layer. Review which measures are influencing decisions at each cycle and retire the ones that are not. The fear that data will be misread is legitimate, but the answer is not less transparency. The real answer is better framing, clearer ownership, and a shared future state that gives everyone in the room the same reference point before the numbers appear on screen.

Elizabeth Crowe, PhD, is the Chief Information and Technology Officer for the City of Cleveland, where she leads the integration of data systems and technology infrastructure across city services to improve outcomes for residents. An economist and researcher by training, she brings experience spanning the Urban Institute, the Congressional Research Service, and JumpStart Inc. She holds a PhD in Public Administration and Policy and a Master of Arts in Economics from American University. Find her on LinkedIn.

Something to Read

Recoding America by Jennifer Pahlka [336 pages or 9.5 hours]

What if Women Designed the City? by May East [184 pages]

Something to Watch

How Government Can Get Sh*t Done with Jennifer Pahlka [40 minutes]

Governing in the Age of AI: Lessons from Recoding America [1.5 hours]

This is a problem of pricing risk, and organizations are bad at it in a specific way. In How Markets Fail, John Cassidy describes how rational actors, each behaving sensibly, can price systemic risk near zero right up until it arrives. AI adoption invites the same mistake. Each decision looks prudent in isolation. The aggregate exposure goes unpriced. A leader who does not understand the full cost of operating their program is still responsible for delivering value within those constraints.

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