This person is sharp. That one’s political. This one I can trust with ambiguity. That one needs everything spelled out.

You don’t decide to make these reads. They happen, fast, in the margins of everything else you’re handling. And here’s the part that should worry you: under the pressure you’re under, you will almost never go back and check them.

That’s the real subject here. Not how to size people up. How your own judgment behaves when you don’t have time to doubt it.

The reads you’re already making

The first move someone makes is genuinely good data. It happens before they’ve learned to perform for you, before they’ve formed a theory of what you want and started supplying it. By the second or third interaction, the edges are managed and the reflexes are smoothed over. The first move is reflex, not strategy, and reflex is where the real operating system shows.

So your instinct to read it isn’t wrong. The instinct is sound.

The problem is when you make the read.

You’re reading people fastest at the exact moment you’re least equipped to read them well: in a transition, under load, with no exhale, when everything is new and everyone is a first move. The urgency that surrounds a new chapter doesn’t just rush your decisions. It rushes your conclusions about people, and then it never gives you the quiet to revisit them.

That’s the trap. Not that you read people. That you read them under conditions that make a snap judgment feel like a settled fact.

What you’re actually reading

It helps to know what the signal even is, so you can hold it more precisely. Six things the first move tends to reveal:

Speed: their relationship with risk. Not whether they’re fast or slow, but the gap between trigger and action. Moving before the picture is complete is comfort with uncertainty. Waiting may be deliberation, or bandwidth, or avoidance.

The first question they ask: where their mind goes under no pressure. Outcomes, process, risk, control. That first question is their dominant lens, and it’s rarely random.

Who they bring: how their team actually operates. Alone or surrounded? Inclusion or insecurity? You’re seeing the real org chart, not the drawn one.

Comfort with an open, undefined start: their tolerance for ambiguity. Do they fill the space, or reach for structure to make the open-endedness stop? It will show up again in every uncertain moment to come.

What they do with the first disagreement: how decisions really get made around them. Push back gently and watch: engage, defend, get curious, or quietly comply.

Follow-through on the first small commitment: the gap between word and behavior. They said Friday. Friday tells you more than the room did.

All six are worth seeing. None of them is worth deciding on yet. And that distinction is the whole game.

Why urgency is the enemy here

Here’s what Ambient Urgency does to a read.

It removes the pause between observation and conclusion. In a calm season, you notice someone moved fast and you file it as interesting, let’s see. Under pressure, you notice they moved fast and you file it as decisive: done, closed, acted upon. The urgency collapses the gap between noticing and knowing.

And then it does something worse. It makes the premature certainty feel like a strength. Reopening a read feels like waffling. Re-examining a person feels like inefficiency you can’t afford. So the snap judgment hardens, not because it was right, but because going back would cost time you don’t have.

This is how capable leaders end up running entire relationships off a story they wrote in five minutes and never updated. Not through bad judgment. Through good judgment, made too fast, under conditions that punished revisiting it.

Holding the read loosely on purpose

The skill isn’t reading the first move better. It’s refusing to let urgency turn a read into a verdict before you’ve earned one. A few ways that actually works, even when you’re moving fast:

Name the read as a story. “I’m telling myself this person avoids hard conversations.” The phrase telling myself converts a verdict back into a hypothesis. It costs you three seconds.

Write the competing story with equal conviction. If fast means decisive, fast also means anxious. Hold both. Whichever one you’re more reluctant to write is usually the one your bias is protecting.

Decide, in advance, what would prove you wrong. Not “I’ll keep an eye on it,” which is how the bias hides. Specifically: “If this is real decisiveness, they’ll also be comfortable not acting when waiting is right. I’ll watch whether they can sit still.” Now the story can actually fail a test.

Then watch your own effort. The tell isn’t in the data, it’s in your reaction to it. If a confirming signal gets a nod and a contradicting one gets three reasons it doesn’t count, that’s the bias, caught in the act.

None of this slows you down in any way that matters. It just keeps the read from setting like concrete while you’re not looking.

The point

You will keep reading first moves. You should. It’s good data and you’re right to gather it.

But the season when you most need to read people well, the transition, the build, the stretch when everything is new, is the exact season when your urgency is most likely to freeze a first impression into a fact. The danger was never that you’d misjudge someone. It’s that you’d judge them fast, under pressure, and never get the quiet to find out you were wrong.

Read the first move. Then hold it loosely enough that the person can still surprise you, before you’ve quietly decided they can’t.

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A piece published this week in The New York Times by David Epstein, author of Range, introduced me to Herbert Simon’s work in a new light. I have not stopped thinking about it since.

Simon won the Nobel Prize in Economics in 1978. He coined the term satisficing (a portmanteau of satisfy and suffice) to describe the only rational approach to decision-making when information is incomplete and options are overwhelming.

He solved the prioritization problem sixty years ago.

We have spent the decades since building a world that makes his solution nearly impossible to apply. And the AI transition has made it harder still, not because the problem changed, but because the conditions did.

What Simon Actually Said

The search for the best is itself a cost. Most people forget to account for it. The optimal strategy is not optimizing. It is setting a good enough standard, stopping when it is met, and saving your cognitive resources for what actually matters.

Simon lived this. One brand of socks. One black beret. The same breakfast every day: oatmeal, half a grapefruit, black coffee. The same house for 46 years. Not because he lacked imagination. Because he understood that small decisions are a tax on the decisions that matter.

He was not alone. Steve Jobs wore one black turtleneck. Obama limited himself to gray or blue suits. Zuckerberg wears the same gray t-shirt. Einstein owned several versions of the same outfit. All of them cited the same reason: decision fatigue is real and trivial choices are a tax on important ones.

Simon was not being eccentric. He was being rational. These people just had the platform to make it famous.

Where are you spending decision-making energy on choices that any reasonable person in your role could make? That is the first place to apply Simon’s insight.

Our Ancestors Did Not Have This Problem

Here is what is easy to miss: Simon was not rediscovering ancient wisdom. He was describing a workaround for a historically recent problem.

Preindustrial decisions were constrained by geography, availability, and social structure. You married someone from your village. You ate what the season produced. You wore what you could make or afford. The constraint was the decision. There was no maximizing because there was no menu.

Epstein cites an economist who calculated that the consumer options available to people in modern economies exceed those of preindustrial societies by a factor of roughly 100 million. Our brains were not built for this menu. They were built for the village. Simon was not recovering something our ancestors knew intuitively. He was solving a problem they never had.

Why It Is Nearly Impossible in 2026

Because the entire infrastructure of modern life is optimized to make you maximize.

Every app, every platform, every recommendation engine is designed to show you one more option. The algorithm’s job is to keep you searching. Amazon shows you what other people bought. Netflix shows you what else you might like. Dating apps show you who else is out there. Social media functions as an infinite comparison engine — a curated highlight reel of everyone else’s career, relationship, home, and vacation that makes the very concept of good enough feel like settling.

The attention economy is built on the premise that the best is always one more scroll away. Simon’s solution requires opting out of a system that is actively, profitably working against it.

And now AI promises to help you optimize everything: your schedule, your diet, your wardrobe, your creative output. Epstein notes that if Simon was right, the hidden danger of these tools is that they will expand the menu of options and comparisons even further — making the search for the best feel not just possible but obligatory.

The Layer Simon Did Not Address

This is where I want to add something to Simon’s framework, because his solution assumes you can set the good enough standard and stop. That requires one thing: the cognitive space to make a conscious choice.

Ambient urgency makes that nearly impossible.

Ambient urgency is the chronic, low-grade sense that everything is urgent and nothing can wait, even when the calendar is clear. It is not burnout. It is the permanent background state that most leaders are operating inside right now. And it is self-replicating: leaders caught in it inadvertently push it downstream to their teams.

When everything feels existential - and for leaders navigating the AI transition, much of it genuinely is - every decision feels like it requires maximizing. The stakes seem too high for good enough. Good enough begins to feel like negligence.

Epstein cites research showing that maximizers are less satisfied with their decisions and their lives, more prone to regret, and more likely to compare themselves endlessly with others. Under normal conditions, that is a tendency. Under sustained ambient urgency, it is what the system produces in otherwise healthy, capable leaders.

Simon’s insight was correct. The condition we have created makes it nearly impossible to act on. Nearly impossible, not actually impossible. The leaders who find their way through are the ones who recognize the condition for what it is, create the space to make a conscious choice, and commit to what is good enough to move.

Where is the search for the best costing you more than the best is worth? That is the question ambient urgency makes it hardest to ask, and most necessary.

The Murakami Proof

Leaders face this exact trap in high-stakes decisions every day. The right choice is in front of them. The information is sufficient. But the search for certainty keeps them from committing. Epstein tells the story of a Haruki Murakami short story that captures what happens when that search goes too far.

A lonely boy and girl recognize they are perfect for each other. They talk for hours. Then a sliver of doubt creeps in. They decide to part and trust that if they are truly meant to be together, they will inevitably meet again.

They were perfect for each other. Years later, they pass in the street. Their memories have faded. They never meet again.

That is the Fear Test in literary form. The Fear Test is a question I use with leaders facing hard decisions under pressure: am I avoiding this choice because it is actually wrong, or because committing to it is hard? The boy and girl failed the Fear Test. The decision in front of them was right. The difficulty was not the decision. It was the commitment. The refusal to commit to the directionally correct choice in front of you, in search of certainty that never comes, is not wisdom. It is the maximizer’s tragedy.

Simon would not have been surprised. Whether you are searching for a dishwasher or a life partner or a strategic direction, set a good enough standard. Stop when it is met. Save your cognitive resources for what actually matters.

Three Questions Worth Asking This Week

Where are you maximizing when satisficing would serve you better?

Where is the search for the best costing you more than the best is worth?

Where is good enough not settling, but the most strategic choice available?

Simon died in 2001. The world he left behind has made his insight harder to apply with every passing year. More options, more comparisons, more tools promising to help you find the best of everything.

He would not have been surprised by any of it. And he would have worn the same socks anyway.

The path to better decisions does not run through more information. It runs through the willingness to stop searching before you have exhausted the options, and commit fully to what is good enough to move.

That is not a compromise. That is the strategy.

🟥

I have been away from home for fourteen of the last thirty days.

I am tired. I am also grateful. And I have been sitting with the tension between those two things.

Some of those days I did not choose. A client onboarding that required in-person presence. A makeup trip rescheduled from March when weather cancelled the original. A home transition that happens every spring whether I am ready or not. These are good problems. They are also problems that compound when they cluster.

But one of those trips I chose deliberately. And it produced more return than I expected.

I had not been to Atlanta in six months. For a decade I was there every six weeks, sometimes more. People and relationships that matter. When I saw the Southbound conference on the calendar, I made a decision: two days, targeted, front row instead of FOMO.

What I got: a conversation with a CEO whose thinking on the AI transition confirmed something I had been sensing for months. A reconnection with a CMO I had not seen in too long. Dinner and reconnecting with friends. A reminder that the best ROI at any conference is never on the agenda.

That is what bundled travel looks like. One trip, multiple compounding returns. Not just attending, but arriving with intention about who I wanted to see and what I wanted to learn.

Here is what I know about travel and presence that I keep having to relearn:

The trips you choose deliberately compound. The trips you take reactively consume.

Both feel like work. Both show up on the calendar. But one builds something and the other just moves you through space.

My general rule these days is two trips per month, never back to back. This month broke that rule for reasons I could not fully control. Not because any single trip was wrong, but because they clustered. Fourteen days away in thirty. Each commitment worthwhile. The combination unsustainable.

And I felt it.

What the calendar does not show is what did not happen. The thinking time that got crowded out. The conversations I did not have. The ideas that did not surface because there was no space for them to form. That is the cost that never appears on a dashboard, and it is the one that compounds most quietly.

Here is the part I have to say out loud, because I teach this:

I work with CEOs on conscious prioritization. On the difference between reactive scheduling and deliberate choices. On Fewer. Better. Clearer. as a practice, not just a principle.

And I just lived through a month where my own calendar got away from me.

Not because I did not know better. Because client schedules do not wait for convenient timing. Because a weather cancellation in March becomes a makeup trip in May. Because a new client relationship is 100% worth the full-day travel it requires. Because the seasonal home transition happens whether I am ready or not.

Every single commitment had a good reason. That is exactly how it happens.

This is not a failure of discipline. It is the condition I write about. The urgency is real. The reasons are legitimate. And the cumulative effect is the same regardless of how good the individual reasons are.

Fewer does not always mean less. Sometimes it just means not all at once.

June is intentionally clear. No travel planned, the possibility of one trip. That is not an accident. It is the oscillation, the recovery that makes the next period of performance possible. Jim Loehr called it the corporate athlete principle. You cannot perform at peak without the recovery built in. I know this. I teach this. And I still have to plan for it deliberately or it does not happen.

But I would not have missed Southbound.

That is the test I use now. Not: can I fit this in? But: how much would I regret missing it?

The answer has to be significant. Not just “it would be nice to go.” Not just “I should probably be there.” The kind of regret that would still be sitting with you six months later.

The trips that pass that test are the ones worth taking. The rest are just motion.

What would you not have missed this month, and what are you scheduling now to recover?

🟥

He’d noticed it, wanted it to change, and couldn’t understand why it wasn’t happening.

My first question: Have you asked them - individually - to do more of that?

He had, actually. One person. And it worked. He could see exactly how much more impact that person had when they started showing up differently. He just assumed the others would notice, absorb it, and reach for the same thing on their own.

This is the mistake good leaders make. Not the rookie mistake of never developing their people, but the more subtle one: they ask one person, notice it works, and then stop asking. The behavior they want stays locked inside one relationship when it could be spreading across the whole team.

There’s a principle I come back to constantly in my work with senior leaders: ask for what you want, notice what you get. It sounds simple. It’s surprisingly rare.

Most leaders are good at the second half. They notice. They observe patterns, read the room, track who’s performing and who isn’t. What they skip, especially the higher they rise, is the first half. The direct, individual ask.

Here’s where I learned the difference between the two. A teacher of mine showed me the difference this way. I offered her something and she didn’t take it. I tried again, still nothing. I’ll be honest, I wasn’t sure what was happening. Finally, uncertain and a little awkward, I just held it out steadily and waited. She reached for it.

Only then did I understand what she’d been doing. She wasn’t refusing. She was waiting for me to actually offer - to hold it out with full presence and no agenda, and let her decide whether to take it. The moment I stopped pushing and simply made it available, everything changed.

That’s the difference between handing and offering. Handing has an agenda. Offering has patience. Handing needs the other person to receive. Offering lets them choose.

I want more of this from you is about the leader.

You will be more effective if you do more of this is about them.

One is a preference. The other is an offering — a map to their own greater impact, held out and waiting for them to reach for it.

Your team can’t reach for something you haven’t clearly held out to them.

So here’s the Fewer. Better. Clearer. version of this:

Pick one person on your team who’s capable of more than they’re currently doing. Have the conversation this week — not a hint, not a general team message, a direct individual ask. Tell them what you’ve observed, tell them specifically how they’ll be more effective if they lean into it, and then hold it out and wait.

Notice what you get.

Do that for each person, one at a time, and you won’t recognize your team in six months.

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I heard this from a client recently: “We just finished planning, and we have this brief moment before everything changes.”

Most people hear that and think: We need to execute faster. Lock down the plan. Get it done before things shift.

Wrong.

Your boss doesn’t need you to execute the plan perfectly. They need you to achieve the outcome even when the plan falls apart.

And it will fall apart. And you know why. Markets shift, crises emerge, priorities change. The work you mapped out with such precision last month? Half of it won’t matter by Q3.

So here’s the counterintuitive truth: The people who add the most value aren’t the ones who execute plans flawlessly. They’re the ones who understand what their boss is actually trying to accomplish and protect the capacity to respond when everything changes.

The Problem

Most people treat their boss’s goals like a to-do list. They see the quarterly priorities, the project assignments, the stated objectives. They fill their calendar executing against those commitments.

Then reality hits. A competitor launches something unexpected or a key person leaves. The market shift everyone saw coming finally arrives. Your boss wakes up with a better idea. (They do that.)

And suddenly half the work you’ve been grinding on doesn’t matter anymore.

But you have no capacity to pivot. You’re 100% allocated to the original plan. So you either:

• Keep executing work that no longer serves the real goal (busy but not valuable)

• Drop balls and disappoint people (career limiting)

• Work nights and weekends to handle what’s emerged (This is what most people do. They’re genuinely committed. They want to deliver on everything. So they just work harder.)
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The exhausted high-performer pattern: Say yes to everything because it all matters, absorb every change by working longer hours, wonder why you can’t sustain the pace.

That path is unsustainable. And it’s certainly not scalable.

The problem isn’t commitment. It’s that you don’t know how to push back successfully - because you’re treating the plan as the goal instead of understanding what the plan is meant to achieve.

The Solution

So what’s the alternative?

Understand your boss’s real goals - not just the plan, but what the plan is meant to accomplish and why it matters.

When you know what they’re actually trying to achieve, three things become possible:

First, you can be selective. You can say no to work that doesn’t serve the real goal, even if it was in the original plan. That’s not pushback, that’s strategic thinking.

Second, you can protect capacity. You can treat the plan as a foundation, not a finished product, and build in space to respond to what emerges. That’s not slacking, that’s leadership.

Third, you can pivot intelligently. When your boss wakes up with a better idea (and they will), you can adjust without starting from zero because you understand what success actually looks like.

This is how you practice ‘fewer, better, clearer’ in real time:

• Fewer commitments (only what serves the real goal)

• Better choices (aligned with what actually matters)

• Clearer impact (visible results even when circumstances change)

You become undeniable not by executing the plan perfectly, but by achieving the outcome regardless of how much the plan changes.

How to Actually Do This

Here’s how you learn your boss’s real goals. Not the sanitized version in the quarterly deck, but what they’re actually trying to accomplish:

Have this conversation when you’re not in crisis. Don’t wait until priorities are shifting and you’re scrambling. Schedule time specifically to understand context. “I want to make sure I’m focused on what matters most to you. Can we spend 30 minutes talking through your real goals for the year?”

Frame it as seeking understanding, not pushback. You’re not questioning their judgment or disagreeing with the plan. You’re working to understand the context so you can make better decisions when they’re not in the room. That’s what good leaders do.

Tell them what you’re doing and why. “I’m going to start asking you different questions - not because I’m disagreeing, but because I want to understand the why behind our work so I can be more strategic about where I focus.” Changes in behavior can be misunderstood without that context. Don’t surprise them.

Ask better questions. Don’t ask “What are your priorities?” (You’ll get the official list.) Ask:

• “What does success look like for you this year? Not just for the team, but for you personally?”

• “What are you worried about that might derail our plan?”

• “If we could only accomplish three things this quarter, what would they be?”

• “What would make you feel like we nailed it, even if everything else shifted?”
  ​

Listen for the why, not just the what. When they describe a priority, ask “Why does this matter?” Keep asking until you understand what it unlocks, what it protects, or what it proves. (Remember, you told them you’d be asking these questions - this is you following through on becoming more strategic.)

Notice what they pay attention to. In meetings, what do they ask about first? What derails their thinking? What makes them lean forward? That tells you more than any strategic planning document.

Test your understanding. Say it back: “So if I understand correctly, the real goal here is X, and the project is just one path to get there. If circumstances change, we might adjust the approach but we’re still aiming for X. Is that right?”

If they correct you, you’ve learned something valuable. If they confirm it, you now have clarity most people don’t have.

What This Clarity Gives You

Once you understand your boss’s real goals, everything changes.

You can say no strategically. When a new request comes in, you can evaluate it against what actually matters. “I can take that on, but it means deprioritizing X. Given your goal of Y, I feel like I should focus on X. Does that make sense?” That’s not pushback - that’s strategic thinking. You’re making the tradeoff visible and asking them to confirm or change your reasoning.

You can protect capacity for what’s unknowable. You don’t fill your calendar to 100% because you know things will change. You build in space to respond - not as slack, but as strategic capacity. Your boss doesn’t need you executing a perfect plan. They need you able to pivot when reality shifts.

You can make better decisions independently. When your boss isn’t in the room and you have to choose between three competing priorities, you know which one serves the real goal. You don’t need to check in constantly. You can move fast because you understand what success actually looks like.

You become undeniable. Not because you work the hardest or execute the plan most perfectly. Because you achieve the outcome even when circumstances change - and you do it without burning out.

Fewer commitments. Better choices. Clearer impact.

That’s what understanding your boss’s real goals makes possible.

Here’s the Truth

I know saying no feels impossible, especially to your boss. But here’s the truth: You’re already saying no.

When you’re working nights and weekends just to keep up, you’re saying no to sustainable performance. When you’re spread so thin you can’t think strategically, you’re saying no to your best work. When you have no capacity to respond to what emerges, you’re saying no to being truly valuable.

The question isn’t whether you’ll say no. It’s whether you’ll say it consciously and strategically or unconsciously through exhaustion and diminishing returns.

And here’s what most people miss: You don’t have to say no to your boss. You give them the information and let them prioritize. “I can do A or B well, or both poorly. Given your goal of X, which matters more?”

That’s not refusing work. That’s strategic partnership.

Your boss doesn’t need you to execute the plan perfectly. They need you to achieve the outcome even when everything changes.

That’s how you create impact without burning out.

Fewer commitments. Better choices. Clearer impact.

Take good care,

Karen

If you’re navigating what actually matters versus what just seems urgent, let’s talk. I work with senior leaders to create clarity where it counts most.

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P.S. This piece is longer than my usual newsletter. I wanted to give you the full tactical how-to, not just the concept. Does this format work for you? Hit reply and let me know if you prefer shorter, more frequent pieces or deeper dives like this one. I’m listening.

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You’re still behind.

Growth is outpacing your capability and it’s not getting better. You can’t hire fast enough. You can’t train fast enough. You can’t build systems fast enough. The gap between where you are and where you need to be never closes - it just changes shape.

Most leaders think their job is to close the gap. It’s not.

Your job is to lead through it.

The Trap Most Leaders Fall Into

When things start breaking, the instinct is to do more. Build more systems. Hire more people. Add more process. Work longer hours. Move faster.

You’re exhausted trying to keep up.

Here’s what most coaches won’t tell you: you can’t keep up. The gap is permanent. That’s the nature of scaling.

The question isn’t how to close the gap. The question is: what do you do differently when you can’t?

Scaling Doesn’t Mean Doing More

It means doing different.

Yes, you need systems that scale. Processes. Frameworks. Delegation. Clear decision rights. All of that matters.

But if you don’t change what you’re doing, you just become a well-systematized bottleneck.

I learned this early in my career at Compaq. I was doing work I enjoyed with people I genuinely wanted to work with. And I hit my limit.

I could do anything that I could do. But I couldn’t do more than that. I had to pay attention to that limit and find other resources to let me be scalable along with the rest of the business.

I watched people around me top out. Great operators. Smart leaders. They built systems. They worked hard. But they didn’t change what they were doing. They kept trying to do more of the same, just faster.

Eventually, they failed. Not because they weren’t capable. Because they weren’t scalable.

Systems Scale, People Don’t. Wrong.

People ARE scalable. But only if they’re willing to change what they do.

What got you here - your ability to execute, to solve problems, to be in the details - won’t get you there. At some point, doing what you’ve always done becomes the problem.

The leader who scales isn’t the one doing everything. It’s the one who knows what NOT to do anymore.

The Balls You’re Juggling

Here’s the reality: you have too many balls in the air. You can’t keep them all going.

Your job isn’t to juggle faster.

Your job is to not drop the important ones. And to know which balls you’ve dropped.

This requires a different skill set than execution. It requires you to:

• Let go of work you’re good at

• Trust other people to do it differently than you would

• Know what’s breaking without trying to fix all of it

• Make peace with things being messier than you’d like

Most leaders can’t do this. They keep trying to catch every ball. They burn out. Or they become the constraint their company has to work around.

What It Means to Become Scalable

• Stop doing work other people can do. Even if you’re better at it. Even if it’s faster when you do it. If someone else can do it at 70% of your level, let them. You’re not scalable if you’re still the one doing it.

• Change what “leadership” means. Early stage, leadership is doing. Mid-stage, leadership is deciding. Late stage, leadership is seeing. What worked two years ago doesn’t work now.

• Know what you’ve dropped. You can’t keep track of everything. But you’d better know which balls are on the ground and whether that’s okay. Ignorance isn’t an excuse.

• Enjoy it. This moment is rare. You might only get to experience hypergrowth once in your career. Most people never get to experience it at all. Pay attention. This is the game.

What To Do This Week

Make a list of everything you’re currently doing. Not your responsibilities. Your actual work.

For each item, ask: am I the only person who can do this?

If the answer is no, that’s work you need to stop doing. Not delegate better. Stop doing.

Then ask: what do I need to start doing that I’m not doing now?

That’s the work of scaling yourself.

The Mindset Shift

From: “How do I close the gap?” To: “How do I lead through the gap?”

From: “How do I do more?” To: “What do I need to do differently?”

You can’t scale fast enough. No one can.

But you can become scalable. And that’s what actually matters.

Fewer priorities. Better decisions. Clear leadership.

Not because it sounds good. Because it’s the only way to lead through chaos without becoming it.

What do you need to stop doing that someone else could do at 70% of your level?

Fewer. Better. Clearer.

You asked your top three people what to kill. They told you.

Now you’re staring at a list of 12 “strategic priorities” and wondering which ones actually matter. The board deck says they all do. Your leadership team defends every single one. And somewhere in the back of your mind, you know half of them are noise.

The Problem

Most scaling companies don’t have a priority problem. They have a disguised metrics problem.

Every department has KPIs. Every initiative has a business case. Everything looks important when you’re inside it. Marketing needs to hit pipeline targets. Product needs to ship the roadmap. Customer success needs to improve NPS. Sales needs to close deals. Engineering needs to reduce tech debt.

All true. All important. All competing for the same finite resources.

The Framework

The best framework I’ve seen came from a client. We were drowning in metrics - CAC, NRR, pipeline velocity, product adoption scores. He stopped me mid-sentence: “These all answer three questions, don’t they? Are they buying? Are they staying? Are we doing the work profitably?”

Are they buying? Everything about acquisition, conversion, pipeline, CAC - it all ladders back to this.

Are they staying? Retention, churn, NRR, product engagement - different metrics, same question.

Are we doing the work profitably? Gross margin, unit economics, burn rate, operational efficiency - can you sustain this?

Every metric you’re tracking should clearly connect to one of these three questions. If it doesn’t, it’s either noise or it’s so far downstream that it’s not a priority - it’s a tactic.

The Trap Most Leaders Fall Into

The problem isn’t that teams are tracking the wrong things. It’s that they’re treating everything they CAN measure as something they SHOULD prioritize.

Yes, improving onboarding completion rates might help retention. But if you’re optimizing onboarding while your product has a core value delivery problem, you’re solving the wrong problem.

Yes, reducing time-to-first-value matters. But if your sales team is closing deals with customers who aren’t your ICP, you’re going to churn them anyway.

This is about highest and best use of your resources. Including time.

Stress-Test Your Three Questions

What could derail this? Market shifts. Competitive moves. Internal gaps. List everything that could matter. Then decide: are you monitoring it, or acting on it? Most things are worth monitoring. Few are worth acting on.

Can your team actually handle this? A great strategy that overwhelms capacity isn’t strategy - it’s a burnout plan.

What does your history tell you? Look at the last two years. When did you lose focus mid-year? When did you stay disciplined? The pattern shows you what to protect.

The WIFM Test

Here’s how you know if your priorities are real: can everyone in your organization answer “what’s in it for me?”

Can your engineers see how their work connects to one of those three questions? Can your customer success team? Can the person managing your LinkedIn ads?

If the answer is no, you haven’t communicated priorities. You’ve communicated noise.

Clear priorities are measurable. Simple. And everyone can see how their work supports them.

What To Do This Week

Take your list of priorities. For each one, ask: which question does this answer? Are they buying? Are they staying? Are we doing the work profitably?

If you can’t answer clearly, it’s not a priority. It might be important work. It might even be necessary work. But it’s not a priority.

Then ask your leadership team: if we could only focus on three things this quarter, what would they be? Listen for what doesn’t make the cut.

That’s your signal.

What Happens When You Actually Do This

You’ll have fewer things on the roadmap. Fewer initiatives in flight. Fewer metrics on the dashboard.

Your team will be able to tell you what matters without checking their notes.

And the work that does get done? It’ll actually move the needle on one of those three questions.

Fewer priorities. Better decisions. Clear leadership.

Not because it sounds good. Because it’s the only way to scale without chaos.

If you had to explain your strategy in three questions, what would they be?

Fewer. Better. Clearer.

“What makes you undeniable as a business?”

Not good. Not competitive. Not differentiated. Undeniable.

The clearest possible proposition. The kind of clarity that makes decisions easy , both for you and for the people you serve.

I’ve been thinking about that question ever since. Not just for businesses, but for everything. What makes a commitment undeniable? A choice undeniable? A priority undeniable?

I know undeniable when I see it. When a client is right. Not ‘could work’ or ‘seems promising’ but right. I know within twenty minutes. I see how we’ll work together. Not push and pull, but partnership. We’re aligned around purpose, values, what we’re actually trying to create.

I know when it’s not undeniable too. When I’m working to convince myself. When I’m listing reasons it makes sense. When it’s a perfectly good opportunity that leaves me cold.

The difference isn’t rational. It’s clarity.

The Problem with Optimization

Most businesses are good at optimization. They run the numbers, adjust the strategy, improve the processes. Projects make strategic sense. Commitments look good on paper. The work is solid.

But here’s the harder question: What makes you undeniable?

Not your quarterly plan. Not your project list. Your core proposition. Why you exist. What you’re here to do that no one else can do quite the way you do it.

You can’t optimize your way to that answer. You have to discover what’s undeniable to you, then build everything else around it.

The same is true for your leadership, your career, your choices. You can optimize tactics all day. But if the foundation isn’t undeniable, you’re just making ‘pretty good’ slightly better.

How to Find What’s Undeniable

So how do you find what’s undeniable?

Not through addition and not by saying yes to more things hoping clarity emerges.

You find it through practice: Fewer. Better. Clearer.

Fewer commitments. Better choices. Clearer impact.

When you strip away what’s merely reasonable, what’s just strategic, what you’re doing out of habit or obligation, then what’s left is what’s undeniable.

Here’s how you test for it:

The Replacement Test: If this disappeared tomorrow - this client, this project, this commitment - what would you actually miss? Not what you think you should miss. What would genuinely change?

I wrote recently about how you feel when a meeting cancels. Relief or disappointment? That feeling tells you everything. If you’re relieved, that commitment isn’t undeniable, you’re just maintaining it out of momentum or obligation.

The Compounding Test: Does this create growing capacity over time, or does it just consume resources? Undeniable work compounds. It makes future decisions easier, not harder. It builds relationships, reputation, and results that grow.

The right clients make me better at my work. Each engagement deepens my thinking, expands my reputation, creates new opportunities. The wrong clients just drain time. Same hours invested, completely different trajectories.

The Fear Test: Are you doing this because it’s right, or because you’re afraid of what happens if you don’t? Fear masquerades as strategy all the time. We resist change because we fear uncertainty - even when staying costs us more than leaving would.

When I left Compaq without a “what’s next” plan, people were genuinely scared for me. “What?? You can’t do that...” Of course what they meant was they couldn’t conceive of doing it themselves. I would have had a good career if I’d stayed. I’ve had a great one because I had the courage to leave. The change curve teaches us this: we cling to what’s familiar even when it’s no longer undeniable. And yet so many of the good things in life wouldn’t have happened without the change.

Your Work

So here’s your work:

What’s undeniable in your life right now? Not what should be. Not what looks good. What actually is.

And what are you holding onto that isn’t? What commitment, client, project, or priority are you maintaining out of fear, momentum, or obligation rather than conviction?

What’s important (genuinely important, will-matter-at-80 important) that you’re not protecting because you’re too busy optimizing what’s merely reasonable?

You can’t build something undeniable on a foundation of ‘good enough.’

Fewer commitments. Better choices. Clearer impact.

Start with what’s undeniable. Build from there.

Take good care,

Karen

If you’re navigating what actually matters versus what just seems important, let’s talk. I work with senior leaders to create clarity where it counts most.

→ Learn more: www.karenwalker.us

The VP who “found a better opportunity.” The director who’s “pursuing a passion project.” The manager who’s “ready for a change.”

They’re not leaving for more money. They’re leaving because the chaos is unsustainable.

What Most CEOs Miss

When your best people leave, everyone notices. But here’s what most leaders get wrong: they’re not leaving because of the workload.

They’re leaving because the workload feels pointless.

That brilliant operator you hired to scale systems? They’re drowning in whack-a-mole. You brought them in to build leverage, to create processes that would make the company run smoother. Instead, they’re fighting fires, managing crises, and watching their strategic work get derailed by whatever emergency landed in Slack five minutes ago.

High performers can handle hard. They can’t handle meaningless.

Sometimes, it’s simpler than that.

Sometimes they leave because they realize they’re burning out. Because their kid’s elementary school years are slipping by. Because they’ve got maybe five good years left before their parents need full-time care, and they’re spending 60 hours a week in a chaos machine.

The work doesn’t have to feel pointless for someone to decide it’s not worth the cost.

But here’s what’s true either way: sustainable pace isn’t optional anymore. The operators who can tolerate chaos indefinitely, who’ll sacrifice everything for the mission - they’re not walking through your door. That generation is done.

The people you’re hiring now? They’ll give you excellence. They’ll give you results. But they won’t give you their entire lives for a company that can’t figure out what actually matters.

The Real Problem

Too many priorities means no real priorities.

When everything is important, nothing is. And your best operators are smart enough to see it. They know that “just get through Q1” has been the strategy for three quarters running. They know the roadmap changes every board meeting. They know leadership can’t decide what actually matters.

So they decide for themselves: this job doesn’t matter.

What This Costs You

The obvious cost: you lose your best person. Recruiting takes months. Training takes longer. You’re back to square one.

The hidden cost: everyone else is watching.

When your top performer leaves, your second-best operator starts updating their LinkedIn. Your third-best starts taking recruiter calls. The people you can’t afford to lose start asking themselves the same question your VP asked six months ago: “Is this worth it?”

Chaos doesn’t just burn out one person. It metastasizes.

What It Looks Like in Real Time

I’m watching a team right now. Seven days a week. Meetings all day, every day. I’m watching to see who drops out first.

Because someone will.

And when they do, replacing them won’t just be hard - it’ll be nearly impossible. This isn’t a team you can backfill with a job posting. These are people who know the business, who built the systems, who can hold ten competing priorities in their heads at once.

A C-suite exec already left. Experienced. Successful through multiple hypergrowth cycles. Their reason? “More than I signed up for.”

This team wants to win. They’re not afraid of hard work. They’re also human. We can’t give 200% all the time. Otherwise it wouldn’t be 200%.

If someone who’s been through this before can’t sustain the pace, what does that tell you about the pace?

The Diagnostic

This week, do this: ask your top three operators one question.

“If you could kill three things we’re doing right now, what would they be?”

Don’t defend. Don’t explain. Just listen.

Listen for the overlap. That’s your signal. If all three name the same initiative, the same meeting structure, the same “strategic priority” that everyone knows isn’t moving the needle - that’s not a coincidence. That’s your diagnosis.

Your best people already know what doesn’t matter. They’re just waiting for you to acknowledge it.

What To Do About It

You can’t eliminate chaos. Scaling always creates it. But you can stop pretending you can do everything.

Here’s what I see from the outside. You’re optimizing what looks best from your perspective - hitting the board metrics, shipping the roadmap, proving you can execute. But you’re not optimizing for what actually scales: keeping the people who know how to build.

The leaders who keep their best operators aren’t the ones who figure out how to work faster. They’re the ones who figure out what to stop doing.

Fewer priorities. Better decisions. Calm leadership.

Not because it sounds good. Because it’s the only thing that actually works.

What would your business look like if you did half as much, twice as well?

Fewer. Better. Calmer.

Not because something’s wrong, but because he doesn’t know what’s coming.

The market is shifting. Customer needs are evolving faster than his product roadmap. His board wants a three-year plan, but there’s a lot of uncertainty out there and he’s not sure what next quarter will look like. Every decision feels like placing a bet with incomplete information.

“When does it get clearer?” he asked.

I paused. Then said what I knew he didn’t want to hear: “It doesn’t.”

The clarity isn’t coming. The fog isn’t lifting. This is the weather.

The Illusion of Clarity

We’re conditioned to believe that good leadership requires perfect vision. Know where you’re going. Set the destination. Rally the troops.

There’s truth in that - direction matters. But here’s what we don’t talk about enough: the best leaders I work with aren’t the ones with crystal-clear answers. They’re the ones who’ve gotten comfortable moving forward when the path is foggy.

Because in a world that’s constantly shifting, certainty is mostly an illusion anyway. The leaders who insist on total clarity before they act end up paralyzed. Meanwhile, the leaders who’ve made peace with ambiguity? They’re already three moves ahead.

What Changes When You Reframe It

I’m not talking about recklessness—making big bets on gut feeling alone or ignoring data because “everything’s uncertain anyway.”

I’m talking about something more nuanced: the ability to act decisively even when you don’t have all the answers. To move forward with what you know, stay curious about what you don’t, and adjust as you learn.

Here’s what I’ve noticed about leaders who do this well:

They ask better questions. Instead of “What’s the right answer?” they ask “What can we learn quickly?” or “What’s reversible?” They’re comfortable testing and iterating rather than needing to be right the first time.

They get precise about uncertainty. “Here’s what we know for sure. Here’s what we think is true. Here’s what we’re betting on.” That clarity about what you don’t know is paradoxically stabilizing.

They act anyway. They take the next right step with the information they have, knowing they’ll course-correct as they go. Bias for action, even in the fog.

They stay curious. When something doesn’t go as expected, they get interested. What did we just learn? What does this tell us? Curiosity keeps them nimble and it keeps them from spiraling.

A Small Practice

One of my clients started asking his team before major decisions: “What would we need to believe for this to be the right move?”

Not “Is this right?” but “What assumptions are we making?”

It surfaces their bets. Makes the ambiguity explicit. And gives them permission to move forward even when they’re not 100% certain because they’ve named what they’re testing.

Another leader keeps a running document of “things we don’t know yet.” Not as a source of anxiety, but as a map of where to pay attention. It reminds her that ambiguity isn’t a planning failure, it’s the source of information she’ll gather as she goes.

These aren’t dramatic practices. But they shift the relationship with uncertainty from something to white-knuckle through to something you can actually work with.

The Real Advantage

Here’s what I’ve come to believe: in a world where no one has perfect information, the leaders who can act confidently in ambiguity have a genuine edge.

While others are stuck waiting for clarity, they’re learning. Experimenting and gathering data by moving, not by sitting still.

They’re not less thoughtful, they’re just less paralyzed.

And in a world that’s constantly changing, that agility is worth more than certainty ever was.

So maybe the question isn’t “When will things get clearer?”

Maybe it’s “What becomes possible when I stop needing them to?”

✨ What helps you move forward when you don’t have all the answers? I’m genuinely curious what keeps you from getting stuck. Leave me a comment and share—I’d love to hear how you navigate the fog.

Take good care,

Karen

It feels like chaos is everywhere—headlines blaring, inboxes overflowing, the pace of change unrelenting. Our instinct is to wait it out, telling ourselves: “Just get through this, and then things will calm down.”

But what if the calm never comes?

The truth is: what we often label as chaos is simply the natural condition of modern life and leadership. Complexity. Ambiguity. Disruption. They’re not temporary storms to endure until the skies clear - they are the weather.

So, how do you find calm in the middle of it all?

For me, it starts with small certainties:

• Sitting meditation, even for ten minutes, before opening my laptop. At a minimum, just finding my breath for a minute.

• Stress-testing big goals instead of clinging to rigid plans.

• Pausing before making a decision, and asking: Do I really need to decide this right now?

• Remembering that calm isn’t passive - it’s active clarity.

Calm doesn’t erase the chaos. It reframes it. It reminds us that while we may not control the storm, we can choose how we steer the ship.

As Lao Tzu wrote: “If you think the universe is agitated, go into the desert at night and look at the stars.”

Sometimes life and leadership require the same kind of stargazing—a moment to reconnect with what is vast, steady, and enduring. From there, the noise feels less like chaos and more like life simply unfolding.

✨ PS: I’m curious - what’s your favorite way to create calm when things feel noisy? Hit reply and share, I’ll include some of your ideas in a future newsletter.

Leadership advice is everywhere—books, podcasts, inboxes, LinkedIn feeds. It’s easy to feel like you need a new framework every quarter. But the best leadership lessons aren’t always found in long-form playbooks. Sometimes, a single word is enough to shift your thinking.

So I challenged myself to boil leadership down to 26 essentials. Anchors, provocations, and reminders—one for every letter of the alphabet.

This isn’t exhaustive. It’s not meant to be. But I hope something here helps you pause, recalibrate, or even lead differently today.

A to Z: A Leadership Alphabet

Clarity in the chaos, one letter at a time.

A — Ambiguity.

Get used to it. The higher you go, the fuzzier it gets. Great leaders don’t wait for perfect clarity—they move with conviction in the gray. (Shoutout to Herminia Ibarra, who writes beautifully on leading through liminality.)

B — Boundaries.

Not barriers. Boundaries help you lead with intention, not depletion. As Nedra Glover Tawwab reminds us, “Boundaries are the distance at which I can love you and me simultaneously.”

C — Curiosity.

The antidote to certainty. Satya Nadella says, “Don’t be a know-it-all. Be a learn-it-all.” In complexity, curiosity is your competitive edge.

D — Decisiveness.

Ambiguity doesn’t absolve you from choosing. Delay can be more damaging than the wrong call. Jeff Bezos calls these “Type 1 vs. Type 2” decisions—know the difference.

E — Empathy.

It’s not soft. It’s strategic. Empathy builds trust—and trust builds performance. Harvard’s Frances Frei shows how empathy, logic, and authenticity create lasting influence.

F — Feedback.

Give it early. Receive it openly. Kim Scott’s Radical Candor is a good reminder: challenge directly, care personally.

G — Grit.

Not the hustle-porn kind. The resilient, long-game kind. Angela Duckworth’s work on grit shows it’s less about talent, more about sustained effort over time.

H — Humility.

Leaders don’t need to have all the answers. They need to ask better questions. Adam Grant often reminds us: confidence and humility are not opposites—they’re a team.

I — Influence.

Forget authority. Influence is your true currency—and it’s earned, not granted. Think of Liz Wiseman’s Multipliers approach: amplify others, and your influence grows.

J — Judgement.

AI can give you data. It can’t give you discernment. That’s your job. (Daniel Kahneman showed us how easy it is to get judgment wrong—so stay humble.)

K — Kindness.

Not niceness. Kindness tells the truth with care. It challenges with respect. As Glennon Doyle says, “Be kind. Not nice. Nice gets you ice cream. Kind gets you through the fire.”

L — Listening.

The best leaders speak last—and rarely the most. Nancy Kline’s Time to Think reminds us that giving someone space to think is one of the deepest forms of respect.

M — Middle Managers.

Overlooked, overburdened—and absolutely essential. As Tomas Chamorro-Premuzic told me recently, “Invest in the middle.” They translate strategy into action.

N — No.

You can’t scale without it. Every yes has an opportunity cost. Greg McKeown’s Essentialism is a masterclass in the power of selective focus.

O — Ownership.

No blame, no finger-pointing. Take the wheel, especially when the road gets rough. Jocko Willink calls it “Extreme Ownership”—and it’s exactly that.

P — Presence.

Not perfection. Just presence. The ability to show up fully, even in chaos, changes everything. As Amy Cuddy taught us, presence isn’t posture—it’s power under pressure.

Q — Questions.

Ask better ones. “What’s possible here?” is often more useful than “Who’s responsible?” Michael Bungay Stanier’s The Coaching Habit reminds us: stay curious a little longer.

R — Reflection.

Action without reflection is motion without meaning. Herminia Ibarra again: “Act like a leader, think like a leader”—but don’t skip the thinking.

S — Strategy.

Not a plan on a slide. A real-time set of choices, anchored in values and aimed at impact. Roger Martin’s writing on strategy is a goldmine here.

T — Trust.

Not a buzzword. A business lever. No trust, no team. Stephen M.R. Covey’s Speed of Trust shows how trust accelerates everything.

U — Unlearning.

What got you here won’t get you there. Let go of the old playbook. Marshall Goldsmith’s famous line still holds.

V — Vision.

Not just a statement. A way of seeing. And helping others see it too. Think of Simon Sinek’s Start with Why—but don’t stop there.

W — Work.

The inner work, not just the job description. As Brené Brown reminds us, “You can’t get to courage without walking through vulnerability.”

X — X-Factor.

It’s not charisma. It’s credibility + consistency + calm in the chaos. That’s your X-factor.

Y — Yes, and…

Borrowed from improv, but powerful in leadership. Hold paradox. Make space for more than one truth. Priya Parker would say: how you hold the room matters more than who speaks in it.

Z — Zen.

Not the absence of action. The presence of intention. Stillness in motion. Calm under pressure. Or, as I like to say: clarity in the chaos.

What’s your go-to leadership word?

Drop your favorite letter (and what it stands for) in the comments or share this with a colleague who leads with intention. And if you’re navigating ambiguity, team challenges, or just trying to stay human at the top—let’s talk.

I work with senior leaders to find calm in the chaos and clarity where it counts most.

→ Learn more: www.karenwalker.us

→ Subscribe to my newsletter:

→ Or just hit reply and say hi.

As a leadership coach, I’m often asked what separates good leaders from great ones. People expect me to say strategic vision, sharp decision-making, or data fluency.

And while all of those matter, here’s the truth I’ve seen play out again and again: It’s the soft skills that set people apart.

The ability to communicate with clarity.
To listen without ego.
To influence without dominating.
To coach instead of command.
To stay steady in conflict—and lead with both confidence and humility.

Let’s be honest: soft skills are anything but soft. They’re nuanced, hard to teach, and take years to develop. And they’re often what determines who gets promoted, trusted, and followed.

I recently came across a Fast Company article that captured this tension beautifully. The author, an educator, noticed the discomfort people have with the term “soft skills”—not because they’re unimportant, but because we haven’t found the right language to describe them.

Some suggest “human skills” or “power skills,” but nothing has stuck. What did stick for me was a framework they shared:

• Character traits (like curiosity and integrity)

• Behavioral habits (like follow-through and listening)

• Teachable skills (like negotiation and conflict resolution)

• Contextual competencies (like executive presence or cross-cultural fluency)

It’s a more precise, actionable way to approach leadership development. Because technical skill might get you in the door—but soft skills are what keep you in the room.

As AI handles more of the technical, our human capabilities become the real differentiator. Influence. Emotional intelligence. Adaptability. These aren’t extras—they’re essentials.

So maybe we stop calling them soft. Or maybe, as the article suggests, we reclaim the word—letting it stand for something subtle, sophisticated, and distinctly human.

Because today’s most valuable leaders aren’t just the smartest in the room. They’re the ones who know how to bring out the best in others.

And that takes real skill.

​
Take good care,

Karen

P.S. Want more? Here’s an article I wrote for Forbes, “Soft Skills are Too Hard for Too Many People.” Or contact me directly karen@karenwalker.us to schedule time to talk.

I’m sitting in the Boston airport, four hours into what was supposed to be an early morning flight home. Here’s how it’s gone so far:

• We boarded the plane.

• We deplaned after a maintenance issue was discovered.

• Since then, we’ve had the same vague announcement—“waiting on updates”—every hour or so.

• The departure time has slipped four times.

And then something changed.

We were told exactly what was going on:

A replacement part is on its way from another airport. Here’s the flight number. It’s landing at the gate right next to us. Want to track it? Go ahead.

I immediately felt better—not because we were leaving soon, but because I finally understood the situation.

It was a reminder: in moments of uncertainty, information is power. But more than that, it’s comfort. It’s trust. It’s leadership.

We don’t need every detail. But we do need to know that someone is thinking clearly, tracking the issues, and willing to let us in on what’s real.

And thanks, Delta gate agents!

🟥 For leaders, this moment at Gate A7 felt familiar.

How often do we wait to communicate until we have a solution—rather than sharing where we are in the process?

In my work with executives, I see this all the time. Teams can handle delays. They can handle ambiguity. What they can’t handle is being left in the dark.

Transparency doesn’t have to mean certainty.

It means: Here’s what we know. Here’s what we don’t. Here’s what we’re doing next.

That’s what builds alignment. That’s what builds trust.

The next time your “flight” is delayed…

What will you tell your team?

👉 I’d love to hear how you’re communicating progress and uncertainty inside your org. Drop a comment or forward this to a leader who needs to hear it.

Welcome! I’m Karen Walker, and I’ve spent my career helping leaders navigate and apply the lessons of hyper-growth. If you’re scaling a company, leading a team, or just trying to keep up with the pace of change, you’re in the right place.

Here, I’ll share hard-won insights, real-world strategies, and stories from the front lines of leadership—things I’ve learned advising top executives and growing companies, and writing for places like Harvard Business Review, Fast Company, and Forbes. . No fluff, just practical guidance to help you build, align, and lead with confidence. Let’s figure this out together.

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