“How do women approach leadership differently?”

A few days later I saw a consultant give a presentation on “Generational Differences” in the workplace. In other words, what does Gen Z care about compared to Boomers, what do Millennials want compared to Gen X.

The question and topics are understandably appealing. In business we spend most of our time thinking about people, and particularly hiring, leading, and motivating. There’s no shortage of headlines about the “generational divide”…

And talking about the differences between men and women is as old as time…

And while of course there are differences…

You’re either Gen Z or you’re not. Ditto any other arbitrary generation bucket you fall into.

The average height for men in the U.S. is 5’-9”—with most all standing between 5’-3”
and 6’-3”, while women average 5’-3” and are rarely shorter than 4’-11” or taller than 5’-11”.

When it comes to the differences in traits that actually impact workplace performance, they are not near as stark as many headlines and some gurus would have us believe.

So my answer to “How do women approach leadership differently?”…what specific person are we talking about?

In the world of business advice there is a big market for reducing the complexity of certain decisions. By presenting sex and age brackets as uniform monoliths we can be sold secret decoder rings. Adjust the dials to the correct sex and age, and suddenly we can unlock all the details of their tendencies and motivations.

Unfortunately, and as we know, the real world and real people are more nuanced. And if we’re wanting to make good decisions as leaders we best not sacrifice important nuance for (false) convenience.

To be clear, there is some truth to common generalizations about men, women, and different generations.

• Women do tend to be more collaborative and relationship-oriented in team settings.1

• Men are more likely to take risks or compete for status in work environments.2

• Younger employees do tend to place more emphasis on flexibility and work-life balance.3

• While older employees to place more emphasis on stability and long term job security. 4

And so while I can’t argue many of the headlines in the media or claims from gurus are wrong, that doesn’t mean they’re right for the decision you’re trying to make.

Here’s the catch:

Just because something may be true at a population level doesn’t mean it’s useful for making decisions at an individual level.

I don’t care about the preference of the “average” Millennial, or personality traits of the prototypical man. I care about Ryan, the 38-year old project manager that applied for an open role. (Substitute your “Ryan” and decision to be made here).

And zooming in on the decision to be made is one of three good practices when it comes to dealing with new information:

1. What is this information actually telling me? (What’s the split — 60/40? 55/45? What does “statistically significant” mean here in plain numbers?)

2. What kind of decision am I making? (One bet across many people, or one decision about one person in front of me?)

3. What other information can I access? (Is this baseline all I have, or can I zoom in — ask, observe, probe?)

If you’re running for political office or designing a marketing or recruitment program targeted at thousands of people then by all means, population differences (even if small) can be very valuable. But for the typical business decision—#2 is about individual decisions, while #3 offers the opportunity for resumes, interviews, and conversations. And it turns out, #1 was never that useful to start with.

And to avoid the idea that I’m cherry-picking data points, below is a more thorough analysis of the overlap between sex and age brackets in regard to personality and work preferences. Again, the key takeaway: people are far more alike than different.

So, in general we’d be wise to avoid the “Siren Song” of reducing people to their sex and age.

While it’s easy to cook-up a story about why life experience, cultural shifts, and different expectations placed on individuals would lead them to be predictably different, the data just doesn’t support the intuition.

Because if we revisit our checklist from earlier:

1. What is this information actually telling me? (What’s the split — 60/40? 55/45? What does “statistically significant” mean here in plain numbers?)

2. What kind of decision am I making? (One bet across many people, or one decision about one person in front of me?)

3. What other information can I access? (Is this baseline all I have, or can I zoom in — ask, observe, probe?

We often find we’re making individual decisions against a backdrop of headlines and claims that really aren’t “telling” us all that much. And we’d be better off focusing on #3….What other information can I access.

We’ll cover that next time—how collecting the right information about individual people massively outperforms predictions based on general trends around sex and age.

In other words, how to be generally wrong, but specifically right in your next decision about people.

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Learn more about my latest book “Craft: The Expedition of Business” at:

https://TheExpeditionofBusiness.com

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The whiteboard filled up fast. Revenue targets. Employee retention. Customer satisfaction. Market expansion. Profit margins. New product launches. Hiring plans.

All worthy objectives. I wouldn’t call any of them wrong. But were they all goals? Or were some of them strategies? Were a few actually tactics?

Nobody could agree. And in my experience working with business leaders, that’s more common than most teams want to admit. Without a shared language for categorizing decisions, every planning conversation risks becoming a debate over semantics rather than a conversation about direction. Teams stay busy making decisions all day but can’t point to which ones actually moved the business forward.

Goal, Strategy, Tactics, Execution

In Craft: The Expedition of Business, I introduce a framework called the Pyramids of Decisions — a structure where most business decisions find a home across four levels, stacked like a pyramid, each level supporting the one above it. The same structure works whether you’re mapping out a five-year plan or figuring out why leftovers are piling up in the break room fridge.

A goal is what you’re trying to accomplish — the outcome, the destination. A goal is the target — it doesn’t support anything else; everything else supports it. It’s the answer to “Where are we going?”

A strategy is the core bet you’re making about how to reach the goal. My favorite definition comes from Seth Godin: “Strategy is our philosophy of becoming.” It reflects what you believe matters most and what you’re willing to trade off. Will you compete on price or quality? Grow through new customers or deeper relationships with existing ones? Build expertise in-house or partner with specialists?

A good strategy reflects a clear point of view about what matters most and what we’re willing to trade off. It’s the bets that we’re willing to place.

Tactics are the specific actions that make the strategy real. And execution is how well you actually do what you said you’d do.

Execution is where most businesses win or lose — not in having the perfect strategy or clever tactics, but in doing the work that reinforces the base of our Pyramids of Decisions.

In my business, the goal was running a successful professional services company. A core strategy was leveraging more junior and less expensive staff to do work on par with their more senior counterparts. One tactic to support that strategy was a series of checklists that created a scaffold for people to climb as they completed a project. Decisions around execution included making those checklists easy to find and requiring a signed version to be turned in with each project.

Many decisions. Varying degrees of importance. But each had a clear place in the pyramid, and each either supported or undermined what sat above it.

What Happens When the Levels Get Confused

A town manager is proud of their city parks. They’re ornate and manicured, but one park keeps having trouble with kids trampling the flower beds. It’s working against the department’s goal of keeping the parks beautiful.

Their instruction to the maintenance crew — their strategy: “Keep the kids out of the flower beds.”

I saw the result when I visited the park. The flower beds were full of blossoms, a kaleidoscope of colors. But also there were the biggest, tackiest signs you can imagine: “STAY OUT OF FLOWER BEDS.”

The tactic (the signs) supported the strategy (keep kids out). But it sabotaged the goal (keeping the park beautiful). If the goal had been communicated alongside the strategy, would the tactic have been different? Almost certainly.

This pattern shows up in business constantly. A sales team told to “grow revenue” says yes to every lead — including terrible-fit customers who churn quickly and consume disproportionate support resources. The tactic supports the stated strategy. But it undermines the actual goal of building a profitable, sustainable company.

The problem isn’t bad people making bad choices. It’s a missing structure connecting daily decisions to the destination they’re supposed to serve.

The Weight Matters Too

My wife recently interviewed for a leadership role managing a team of twelve. During the process, she was asked: “What would you do if you made a decision, and all 12 people on your team disagreed with you?”

It sounds like a reasonable question until you realize it assumes all decisions carry equal weight — when one of a leader’s chief responsibilities is knowing they don’t.

If it’s on the tactics or execution level, then my job is to explain — hopefully with a first-principles understanding of why — how it supports the relevant goal or strategy. If it’s a decision about our goal or a key strategy, then I’m on a fool’s errand trying to accomplish either with a full mutiny brewing.

People getting bent out of shape about granola bars replacing potato chips in the break room is a different situation than someone redefining the ideal customer. How you respond to disagreement should depend entirely on where the decision sits in the pyramid.

Why This Changes How You Lead

When a leadership team can look at any decision and place it in the pyramid, the way they work together shifts. Delegation gets easier because you know which decisions require your involvement and which ones don’t. Alignment improves because everyone understands how their daily work connects to the bigger picture. Disagreements become more productive because the conversation moves from “I think we should do X” to “where does X sit, and does it support what’s above it?”

And maybe most importantly, it changes how you communicate with your team. Instead of issuing instructions and hoping people fill in the gaps correctly, you’re giving them a map — one that connects their daily execution to the strategy it serves and the goal it’s all pointed toward. People stop guessing what matters and start knowing.

It all starts with the leadership team being honest about one question: can we all agree on what our goal actually is? If the sticky notes don’t match, nothing beneath them will either.

The Pyramids of Decisions is one of several interconnected frameworks in Craft: The Expedition of Business — a guide for leaders of small and mid-sized businesses who want to make better decisions, build stronger teams, and lead with more clarity.

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Most business owners hit this wall eventually. The company grows to a point where the leader’s personal bandwidth becomes the constraint. Every decision runs through them. Every fire gets put out by them personally. Every new employee learns how things work by asking them directly.

The business doesn’t scale past what one person can touch. And the leader — who probably got here by being good at doing the work — can’t figure out why doing more of it isn’t fixing the problem.

The Perspective Gap

Part of what makes this so hard is that the leader and the team are operating with very different views of the same organization.

The leader has the full picture — the strategy, the relationships, the history of how things got to where they are. They can see the route from here to the destination. Their team often can’t. They’re navigating with limited visibility, incomplete information, and confusing signals. So they do the rational thing: they ask the boss.

Every question that lands on your desk is a symptom of this gap. And the instinct to just answer it — to jump in, solve the problem, and move on — is what keeps the cycle going. You’re not scaling yourself. You’re becoming the system.

Many business leaders are great at activity — the doing, the jumping in, the explaining (and re-explaining). However, it doesn’t scale. The results we get are symmetric to the time we invest, but that time is a limited resource.

Activity vs. Assets

I loved fishing when I was a kid. Baiting the hook, casting, waiting, retrieving, walking to the next spot — fish or no fish, there was always lots to do. Then someone gave me a fish trap. Add some bait, tie it to a tree, toss it in the river, come back the next day and collect your catch. Far less time, much less activity, many more fish.

Traditional fishing was an activity. Without my time and energy, there would be no fish. The trap was an asset — and with it, I could decouple the results from my constant involvement.

Most business owners are still fishing with a rod. Personally onboarding every new hire, attending every client meeting, manually checking the quality of every deliverable, answering the same questions week after week. These tasks feel productive, but if you stop doing them, nothing gets done. Your results are symmetric to your input — one hour in, one hour of output.

The alternative is building assets that produce results disproportionate to the effort required. An operations manual that answers questions without anyone asking you. An onboarding process that trains new hires without consuming your calendar. Templates, checklists, reference guides, automated workflows — things you build once that keep working whether you’re in the room or not.

To make the waters of our organizations more navigable, to create the conditions where more of our team can operate more often without our specific direction, we need the benefit to be asymmetric.

Making Your Organization Navigable

In Craft: The Expedition of Business, I use the story of the Lighthouse Board — the organization that transformed North Carolina’s “Graveyard of the Atlantic” from a ship-killing stretch of coastline into navigable waters. They didn’t do it by putting more captains on every ship. They did it by building the infrastructure that allowed competent sailors to navigate safely on their own: standardized buoys, distinctive lighthouses, comprehensive charts, and a published “Light List” that put every reference point in one accessible place.

The parallel to business is direct. Your team isn’t incompetent. They’re navigating without the infrastructure they need. And every time you step in to answer a question or make a decision they could have made themselves, you’re being the captain on their ship instead of building the lighthouse.

The Lighthouse Board’s approach rested on principles that apply to any organization trying to become more self-sufficient:

Define what qualifies as a “good” decision. The default benchmark in most organizations is “what would the leader have done?” That’s the wrong measuring stick. A good decision is one where the person used reasonable judgment and sought out the tools and information available to them. If they did that and the result was still wrong, the problem isn’t the person — it’s the system.

Reduce the number of decisions to be made. Every decision that can be eliminated by a template, a default setting, a checklist, or an automated workflow is one less opportunity for things to go wrong — and one less question on your desk. The Lighthouse Board’s first act was standardizing the buoy system. One simple rule — “red right returning” — eliminated thousands of judgment calls for ship captains approaching unfamiliar harbors.

Make ownership clear. When everyone is responsible for everything, no one is responsible for anything. The Lighthouse Board assigned one person at every level — one district inspector per region, one keeper per lighthouse, one station keeper per stretch of beach. No ambiguity about who owned which decisions.

Provide clear reference points. The Lighthouse Board created the “Light List” — one published source containing everything a captain needed to navigate the coast. Not six documents scattered across different drawers. One book, regularly updated, available at every port. In my company, we had the same: an Operations Manual that served as the single trunk from which every other document branched. If someone needed information, they knew where to look.

The Communication Trap

There’s a related problem that keeps leaders stuck as the bottleneck, and it’s counterintuitive.

While good communication is undoubtedly an asset, the need for good communication is a liability.

Every conversation required, every message that must be sent, every meeting that wouldn’t be needed if the system was designed differently — these are all points of failure. And every one of them tends to flow through the leader.

The answer isn’t “communicate better.” It’s to reduce the need for communication in the first place. When your organization has clear reference points, documented processes, and defined ownership, entire categories of communication become unnecessary. People stop asking because the answer is already available. Updates stop requiring meetings because dashboards show the status. New hires stop needing weeks of hand-holding because the onboarding system does the heavy lifting.

Every asset you build eliminates conversations that would otherwise require your involvement. And the time you save goes into building the next asset. It becomes a flywheel — more infrastructure leads to more independent decisions, which frees up more of your time to build better infrastructure.

The Ecosystem, Not the Machine

This is where the bottleneck conversation connects to something deeper. Most business owners think about scaling as adding capacity — more people, more hours, more resources. That’s the mechanical approach, and it works up to a point. But machines require constant input. They run down. They need someone to keep cranking.

The alternative is building an ecosystem. When the right systems are in place and people have what they need to navigate independently, something shifts. The business stops requiring your constant input and starts generating its own momentum. People don’t just complete tasks — they find better ways to do them. They solve problems you didn’t know existed. One person’s improvement becomes the team’s new standard.

That’s asymmetric output. An hour spent building a reference guide doesn’t just save you one future conversation — it saves hundreds. A clear ownership structure doesn’t just prevent one dropped ball — it prevents a pattern of confusion that would have consumed your attention for months.

The leader who builds these systems isn’t less involved. They’re involved differently — at a higher level, on higher-value problems, with a team that’s capable of handling everything else. That’s what scaling actually looks like. Not doing more, but building the conditions where your organization does more without you having to push.

The business may not become a true perpetual motion machine. But it can become what most business leaders want: an organization that is more self-managing. And one that makes the efforts and inputs of its leaders more discretionary than mandatory.

The principles of building navigable waters for your team — along with the systems for navigation, communication, supply lines, and strategic pauses that keep an organization on course — are covered in Part 4 of Craft: The Expedition of Business.

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Culture is the stories we tell ourselves about ourselves.

That reframe changes everything. Culture isn’t a poster on the wall, a list of perks, or a set of values workshopped at a leadership retreat. It’s the narrative running through an organization — who we are, what we’re trying to do, what we’re up against, and how we plan to overcome it. When that story is clear and compelling, culture takes care of itself. When it’s absent or hollow, no amount of free snacks or ping pong tables will fill the gap.

Most businesses have some version of a culture statement. And most of the time, employees couldn’t recite it if you asked. Not because they don’t care — but because the words don’t connect to anything they experience at work.

Why Most Culture Efforts Fall Flat

The problem usually starts with how organizations try to build culture in the first place. They break it into pieces — a mission statement here, a set of core values there, a vision exercise over here — and treat each one as a standalone project. It’s the organizational equivalent of assembling furniture one piece at a time without looking at the picture on the box.

Consider a fictional company, ThreeDucks Technology. Here’s a version of their story that’s typical of what most businesses produce:

We’re ThreeDucks Technology, a mid-sized software company founded in 2015. Our mission is to provide innovative cloud-based solutions that empower businesses to achieve digital transformation and operational excellence.

Who’s the hero here? It’s not the employees. It’s not even the customers. The hero is “innovative cloud-based solutions” — an abstraction nobody can see themselves in.

Now consider a different version of the same company:

Every day, millions of hardworking people show up to their jobs ready to do their best. They’re nurses, schoolteachers, and firefighters. They’re our neighbors, friends, and family members. And none of them sits down at their desk hoping their software will crash or their file system is down. But too often, that’s the frustrating reality.

Technology changes at an overwhelming pace, hackers are always up to something new, and companies face limited IT budgets. At ThreeDucks, our work may focus on technology, but our results focus on people. By ensuring that any solution starts with empathy for our users and ends with a deliverable they can both understand and afford, we let them focus on the important work they do.

Responding with “I fight against computer hackers” is a much better answer at a party than “I work at a mid-sized software company.” The second version has real people, a real challenge, and a real character — and it gives every employee a role in a story worth being part of.

Writing a story isn’t hard. Writing a good story is the challenge — and it’s the work most businesses skip.

The Four Parts of a Good Story

A compelling organizational story has the same elements as any good narrative: a character worth rooting for, a goal worth pursuing, a challenge worth overcoming, and a plausible path to resolution.

The goal is where the organization is headed — and it has to work for everyone. Leaders may privately want revenue growth or a comfortable exit, but employees don’t wake up determined to fund the boss’s beach house. The public-facing version of the goal needs to speak to the whole team.

The challenge is the structural force the business is up against — not the daily fires, but the real enemies. For ThreeDucks, it was the pace of technology change, the threat of hackers, and limited budgets. Those are enemies the whole team can rally against.

As a leader, I had to control the narrative and frame the bigger picture. Yes, clients were often slow to respond, but they were no villains. Once it was made clear that complexity was the real enemy, attitudes shifted. Clients moved from being seen as headwinds to being viewed as our partners.

The resolution is your plan — and it has to reflect real strategic choices. “We’ll focus on customer service” has no tension. “We’ll choose reliability over novelty in an industry obsessed with the latest and greatest” — that’s a real bet with real tradeoffs that tells your team what to do when the next decision isn’t obvious.

The character ties it all together. This is where core values actually belong — not as ingredients mixed into a recipe, but as the impression made by what already is.

We err with character traits and “core values” when we treat them as ingredients in a recipe. They should be the impression that is made by what already is, and the fruit by which you know the tree.

Roald Amundsen and Fridtjof Nansen both led successful expeditions through some of the harshest terrain on Earth. Amundsen was patient, observant, adaptive — he lived with indigenous communities to learn their survival techniques and chose a small crew with a slow, methodical approach. Nansen was bold, driven, decisive — he intentionally started from a point of no return because eliminating the option of retreat was the only way to guarantee forward progress.

Both succeeded. Both had clearly defined character. But the values that described each were demonstrated before they were ever named.

Making the Story Real

A story that sits on a shelf breeds exactly the cynicism that makes employees roll their eyes at the next retreat or the next poster.

We can weave our stories throughout our organizations, recognize people and examples that demonstrate living out the character and acting on the resolutions, celebrate steps taken toward our goals, and remind people often of the real enemy and the challenges they’re working against.

But the real test isn’t whether leadership can recite the story. It’s whether the people three levels down are telling it to each other — in their own words, in the hallway, to the new hire on their first day.

When that happens, culture isn’t something you manage. It’s something your organization lives. When it doesn’t — when nobody knows the story or nobody believes it — then every person in the organization is writing their own version. And none of them match. You don’t end up with a bad culture. You end up with no culture at all — just a collection of people who happen to share a building and a paycheck.

Getting the story right is the work that makes everything else possible. It changes how people decide whether to join, how they make decisions once they’re part of it, and how long they choose to stay. It gives your team a reason to say “yes” that goes beyond compensation — and that’s an advantage no list of values on a wall can replicate.

This article draws from Part 4 of Craft: The Expedition of Business, which covers how to build the narrative of your organization, select the right people, and create the systems that make culture sustainable — not just inspirational.

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But anyone who’s actually managed people knows that’s not how it works. You can offer bonuses, throw pizza parties, hand out gift cards, and plaster “Employee of the Month” plaques on the wall. Some people respond. Most shrug. And the ones you really want to keep — the ones with options — are rarely motivated by any of it.

The problem isn’t that leaders aren’t trying hard enough. It’s that the entire framing is wrong.

In Craft: The Expedition of Business, I build the case around a principle that changed how I lead:

People are very good at doing what they want to do, and not so good at doing what they don’t want to do.

That’s not a complaint about work ethic. It’s a fact about human nature. And once you accept it, the question shifts from “how do I motivate my team?” to something far more useful: “how do I build an environment where what people naturally want to do aligns with what the business needs?”

What People Actually Want

If you ask employees what they want, most will say more money. It’s not that they’re wrong — more money is always welcome. But as Susan Fowler writes in Why Motivating People Doesn’t Work... and What Does:

People don’t understand the nature of their own motivation, so when they are unhappy at work, they ask for more money. They yearn for something different — but they don’t know what it is — so they ask for the most obvious incentive: money.

Money doesn’t solve the real issue. It’s their best guess at what will. They know something is off. They feel dissatisfied. But naming the actual source is harder than pointing at their paycheck.

The opportunity for leaders isn’t in asking people what they want. It’s in understanding what drives them — even when they can’t articulate it themselves. A plant doesn’t know it needs phosphorus-rich soil and twelve hours of sunlight. It just grows or it doesn’t. Our job as leaders is to architect the conditions where people grow.

So what are those conditions?

For most of human history, surviving meant being part of a group. Our distant ancestors didn’t have agriculture, running water, or grocery stores. Survival meant being part of a tribe — and being valuable enough to that tribe to stay in it.

Evolutionary psychologist David Buss makes the case in Evolutionary Psychology: The New Science of the Mind that many of our workplace desires — certainty, belonging, competence — trace back to mechanisms that kept our ancestors alive. That wiring hasn’t changed. We’re still looking for the same things at work that our ancestors looked for in their bands of 30 to 50 people. In the book, I call them the five poles of the Tent of Comfort:

Certainty — Do I know what’s expected of me? Do I understand how decisions are made and what success looks like? Uncertainty causes our brains to work overtime. Employees who don’t know spend energy worrying instead of working.

Competence — Can I do good work here? Am I recognized for it? We all want to feel capable, and we get uncomfortable when we feel like we’re falling behind — possibly becoming a liability rather than an asset to the group.

Autonomy — Do I have control over how I do my work? I’ve looked for years, but I have yet to find an employee who likes to be micromanaged. We want the freedom to take on challenges our own way.

Relatedness — Am I part of something? Who has my back? More than anything, relatedness is about the question: “What is my safety net?” We are ridiculously social creatures — so social that even for the most antisocial among us, isolation borders on punishment.

Engagement — Am I challenged? Am I growing? No one wants to be bored. Our ancestors faced constant problems requiring creativity and adaptation. Those with a bias toward action and improvement had an advantage. Today, that same wiring makes us miserable when our work feels stale.

These aren’t soft concepts. In First, Break All the Rules, Marcus Buckingham and Curt Coffman used Gallup survey data from 80,000 managers across 400 companies to identify the conditions that best predicted employee engagement and high performance. Their findings pointed to the same five conditions — clear expectations, opportunity to use strengths, meaningful connections, regular feedback, and autonomy. Two completely different paths, one from evolutionary first principles and one from massive empirical data, leading to the same destination.

Why Most Engagement Strategies Miss

Most employee engagement strategies target one or two of these conditions and ignore the rest. A company invests in team-building events (relatedness) but leaves expectations unclear (certainty). Another offers professional development (competence, engagement) but micromanages every project (autonomy). A third pays well above market rate but has no clear mission and a revolving door of leadership priorities — leaving people well-compensated but adrift.

The conditions work as a system. Strengthening one while neglecting another doesn’t produce engagement — it produces confusion.

I learned this the hard way. I once hired a director of operations. Great credentials, incredibly smart, true team player. He took directions and ran with them. Appreciation was shown publicly, privately, and financially. Eighteen months in, he was ready to quit.

What was missing wasn’t money or recognition. It was relatedness and certainty. His role had him working alone most of the time, and without clear metrics, he had no way of knowing if he was succeeding. Some people would manage fine in those circumstances. For him, the isolation and ambiguity were draining.

The fix didn’t require more compensation or a new title. We restructured his role to include projects involving a team. Together we built a dashboard that tracked the metrics he was responsible for. His environment changed. Within six months, he was happier and more productive than ever — and he stayed for years.

It was a small adjustment to the conditions. But it made the difference between losing a key employee and having one who thrived.

Machines vs. Ecosystems

There’s a deeper problem with how most businesses approach motivation. The default metaphor for an organization is a machine — hire the right parts, assemble them correctly, fuel the system, and it produces output. When something breaks, replace the part. When output drops, add more fuel.

But machines require constant input. They run down. They need someone to keep cranking. And that’s exactly what many business leaders experience — the never-ending feeling of pushing, fueling, and pleading with an organization that won’t run under its own power.

The problem begins when we set out to build a “well-oiled machine,” believing that we only need “more horsepower” and to “fine-tune the operation,” because then, once we “grease the rails” and “streamline the process,” we’ll finally be “firing on all cylinders.” But again — the metaphors are wrong.

People aren’t mechanical parts. They’re living organisms. And like any living thing, they don’t need to be fueled — they need the right conditions to grow.

I grew up in North Carolina where summer gardens were the norm. A handful of tomato plants would have my family with more than we knew what to do with by late summer. The question wasn’t “are we going to have enough tomatoes?” It was “what are we going to do with all these tomatoes?”

That’s the difference between a machine and an ecosystem. One requires constant input. The other produces abundance — when the conditions are right.

The Real Job

The question was never “how do I motivate my employees?” It was always “what conditions am I creating — and are they the right ones?”

That means understanding each person on your team — not just their skills and experience, but what drives them, where they struggle, and what conditions bring out their best work. It means accepting that the same role, the same office, the same compensation can produce completely different results depending on who’s in it and what they need.

When we see people as living organisms in need of the right conditions to thrive, our teams can become the lifeblood of an organization. People no longer just complete tasks; they create ways to improve processes; they solve not only their problems but help others with theirs.

That’s not motivation. That’s what happens when you stop fighting human nature and start designing for it.

The Tent of Comfort and the broader model of what drives human behavior — genetics, personality, adopted narratives, and real-time constraints — are covered in Part 2 of Craft: The Expedition of Business. The book explores how leaders can use these forces to build teams that are aligned, engaged, and self-sustaining.

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Confidence in service of what? Resilience toward what end? Without a clear understanding of what leadership is actually for in a business, these traits become a checklist with no destination — a list of things to “be” with no connection to what you’re trying to accomplish.

It’s like cobbling together bricks, rope, and fan blades and expecting an elephant. You end up with parts that don’t add up to a whole.

In Craft: The Expedition of Business, I make an argument that reframes the entire conversation:

Business leadership is a means, not an end. It is a strategic choice in the service of business goals.

We can have a business without leadership. I don’t recommend it, but some current and many more failed businesses have unknowingly given it a try. The decision to instill effective leadership is a choice — a good one — but it’s an option in service of something larger. Once we see leadership that way, the question shifts from “what traits should I display?” to “what does my organization need me to provide?”

Business Leadership Is Its Own Thing

Most of what we think we know about leadership comes from contexts that don’t match the one we’re actually in. We mimic sports coaches, military commanders, historical figures — and then wonder why it doesn’t translate.

The reason is that business leadership operates in a specific quadrant defined by two variables: the complexity of the situation and the agency of the people being led.

A sports coach works in a world of defined rules, set playing fields, and clear win conditions — lower complexity. But they need their players to think and act independently — high agency.

A cult leader navigates high complexity — making sense of life’s biggest questions — but suppresses agency entirely. Obedience is the point.

Business leadership sits in the upper right: high complexity and high agency. The world is messy and uncertain, and you need your team making good decisions without you in the room.

Business leadership is specifically about leading individuals of high agency in a situation of high complexity.

That combination is what makes business leadership its own craft. And it tells us exactly what leadership needs to provide.

Clarity and Order

If leadership is a means in service of business goals, then the question becomes: what does it produce? The answer is two things.

Leadership provides clarity in the face of external confusion and order in the face of internal chaos.

Clarity means standing in the gap between your team and the uncertain world outside. Where are we going? Why? What’s the plan? A warehouse manager gathering their team during COVID-era supply chain chaos and saying “We can’t control the delays — here’s what we CAN control” is providing clarity. It doesn’t require a stage or a famous company. It requires a leader who knows what their organization needs to hear.

Order means creating the structure that allows people to do their work with confidence. Clear expectations, consistent standards, accessible information, and accountability when things go off the rails.

Think of it like setting gates along a ski course. Too many gates and you’re micromanaging — frustrating the high-agency people you depend on. Too few and it’s chaos — everyone skiing different lines to different endpoints.

Our job as leaders is to determine the finish line and figure out how many gates to put along the course. The ask of our teams is then clear: “Get to the finish line, make sure you go through these gates. But for the rest of the run, do as you see fit.”

That’s leadership rooted in purpose. Not a list of attributes to perform, but a clear function to fulfill.

Why Leaders Are Chosen

Clarity and order are the product. But before anyone experiences your leadership, they have to decide you’re worth following.

Research on social perception consistently shows that when we evaluate leaders, we’re asking two primal questions: Does this person have my best interests in mind? And are they capable of doing anything about it?

Charisma is displaying warmth first, then strength.

Without warmth, strength becomes threatening. Without strength, warmth is welcome but not reassuring. The leaders people choose to follow are the ones who check both boxes. And the most effective charisma is rooted in truth — you have to actually care, and you have to actually be capable.

Who Leaders Are

If leadership is a means, and its purpose is providing clarity and order, and it requires warmth and strength to attract followers — then what does the actual profile of a good leader look like?

Not what you’d expect. I once took an extensive executive coaching assessment that ranked 25 personal skills. My “leadership” ranking? Number 23 out of 25. And yet I had started, grown, and successfully exited a business with happy employees and anonymous reviews saying “I can’t imagine a better boss.”

There’s no single profile. Effective leadership is one mountain with many paths to the top. But there are traits common to effective leaders regardless of path — four pillars built on one shared foundation.

Communication — transmitting your reality to your team’s understanding. Not so little detail that they’re guessing, not so much that they’re overwhelmed.

Empathy — cognitive empathy specifically. The ability to see the world through someone else’s experience and use that insight to make better decisions.

Strength — not just one kind. Physical, intellectual, emotional, relational, volitional, and moral strength all play different roles at different times. The goal isn’t excellence in one but adequacy in all.

Executive mindset — the ability to zoom in and out across different scales of the business and act at the right level. Not stuck in the weeds, not floating above them, but moving fluidly between the two.

And beneath all four: self-awareness. Without it, none of the others improve. You can’t fix your communication if you don’t know how you’re coming across. You can’t develop empathy if you assume others think like you. You can’t assess your strength honestly if you only see where you’re confident.

The path isn’t a straight line. Most leaders improve quickly early on, hit the false summit of Mount Stupid, tumble into the Valley of Realization, and only then begin the real climb toward mastery.

Traits Without Infrastructure Is How Good Leaders Fail

I’ve met business owners who had every trait on the list. Empathetic, strong, self-aware, great communicators. And their businesses were still struggling — because the leader was the only thing holding it all together. Every decision ran through them. Every fire got put out by them personally. Every new employee learned how things worked by asking them directly.

They had the traits. They didn’t have the systems. And when they burned out, got sick, or simply couldn’t be in three places at once, the organization stalled.

Because if leadership is a means in service of business goals, then personal traits are only half of what’s required. The other half is what you build. Sound decision-making frameworks so your judgment scales beyond your personal bandwidth. A deep understanding of what actually drives the people on your team. And the organizational systems and structures that keep things running when you’re not in the room.

Teams can only perform at the level of competence their leaders are able to provide.

The traits tell you who a good leader is. The frameworks, people insights, and systems tell you what a good leader builds. Without both, leadership stays personal — and personal doesn’t scale.

Raising the lid of your leadership is a lifelong pursuit. But the alternative is a business that plateaus at the limits of the person at the top. And good people don’t stay long in organizations that can’t grow past their leader.

This article draws from Part 3 of Craft: The Expedition of Business. The rest of the book covers the decision-making frameworks, people insights, and organizational systems that make good leadership sustainable. You can learn more about the book at: https://TheExpeditionofBusiness.com

You already use them, whether you’ve named them or not. Supply and demand is a mental model. So is the 80/20 rule. So is thinking about your business as a funnel, a flywheel, or a machine. Each one gives you a shortcut for interpreting what’s happening and deciding what to do next.

First principles thinking is a specific type of mental model. Instead of reasoning by analogy — “what did someone else do in this situation?” — you break a problem down to its most fundamental truths and build your reasoning up from there.

The term gets thrown around a lot, usually in the same breath as Elon Musk or Aristotle. But at its core, first principles thinking is just asking: what do I know to be true, independent of what anyone else has told me? And what can I build from there?

Strategic thinking ties both together. It’s the ability to step back from the day-to-day, see the bigger picture, and make decisions that move your business in a deliberate direction rather than just reacting to whatever lands on your desk.

All three — mental models, first principles, and strategic thinking — are ways of making better decisions. And for business owners, that’s the whole game. Every day is a series of decisions, and the quality of those decisions determines the trajectory of the business.

So far, so good. But here’s where most business owners run into trouble.

The Problem with How We Actually Make Decisions

Most of us think we’re making strategic, principled decisions. In practice, we’re usually doing something much simpler.

We’re copying. We heard a peer describe how they structured their sales team, and we did the same. We read a book about a company that scaled with a particular operating system, and we implemented it. We saw a competitor run a certain type of promotion, and we followed suit.

There’s nothing wrong with learning from others. It’s how we all start. But if we’re honest, a lot of the decisions running our businesses weren’t made from deep thinking — they were inherited, borrowed, or defaulted into.

Why do you have a 40-hour work week? Why do you do annual reviews? Why is your pricing structured the way it is? If the honest answer to any of those is “because that’s how it’s done,” then the decision wasn’t really made at all. It was absorbed.

In my experience running a business for twelve years, and now working with other business leaders, I’ve found that most decision-making falls on a spectrum. In Craft: The Expedition of Business, I call it the Mountain of Why — five levels that describe how deeply we’re actually thinking when we make a choice.

• Level 1 — Mimicry. We do something because someone else did it. It’s the default when we don’t have enough information or experience to decide differently.

• Level 2 — Heuristics. Rules of thumb from our own past experience. “It worked last time.” Useful, but inconsistent — we’re often missing key variables.

• Level 3 — Frameworks. Structured models for thinking about a problem. EOS, Scaling Up, SPIN Selling, Porter’s Five Forces — these all live here. They help break complex decisions into manageable pieces.

• Level 4 — Synthesized Strategies. Taking a framework and adapting it to your specific business, market, and team. Not following a playbook, but bending one.

• Level 5 — First Principles. Identifying what you believe to be fundamentally true and building your decisions from that foundation.

Most business owners operate between Levels 1 and 3. And for a while, that’s enough. Level 3 frameworks in particular feel sophisticated — they come with diagrams, workshops, and certified coaches. They give your team a shared language and they beat operating on gut instinct.

But as I wrote in the book:

All are general in their approach. Their design is for the average business, not necessarily your business. To find better tailored solutions, we need to climb yet higher on The Mountain of Why.

A framework designed for the average business is optimized for nobody in particular. Your industry, your team, your customers, your competitive landscape — none of that is baked in. The framework is a starting point, not a destination.

What First Principles Thinking Actually Looks Like in Business

Before the Wright brothers, everyone trying to build a flying machine started from the same mental model: birds fly, so we should build things that look like birds. They sewed feathers onto wings. They strapped on contraptions that flapped. They jumped off cliffs.

They all failed.

The Wright brothers asked a different question. Not “How can we fly like birds?” but “What are the fundamental requirements for controlled flight?”

The answers — more power without control is useless, three axes of control is the minimum, marine propellers don’t work in air — had nothing to do with birds. Once they identified what was actually true, the design that followed looked nothing like what had come before.

Business decisions work the same way. The question isn’t “What did the successful companies do?” It’s “What do I believe is fundamentally true about my customers, my employees, my market, and what makes a business work?”

Jeff Bezos decided customers always wanted low prices, fast delivery, and lots of choices. Amazon was the extrapolation of those core beliefs. Netflix decided convenience trumped everything else in entertainment. A client of mine planted their flag on the belief that people want to feel included and hate uncertainty. They added one simple meeting in the middle of their process. It cured both problems and resulted in a measurable difference in engagement, morale, and project quality.

None of these came from a framework someone bought at a conference. They came from leaders who did the harder work of identifying what they believed to be true — and then building from there.

How to Start Climbing

This isn’t about throwing out every business book and starting from scratch. That would be its own kind of hubris. The frameworks at Level 3 are valuable — but they’re raw material, not finished product.

When you encounter the next “proven” system, try treating it as a Level 3 input rather than a Level 5 answer:

• What specifically is this designed to do? Does that match what my business actually needs right now?

• What assumptions is it making about the industry, the team, or the customer? Do those hold for me?

• What would this look like if I adapted it to my situation rather than adopting it wholesale?

And the most important question: what do I already believe to be true about my business that this either reinforces or contradicts?

If you can’t answer that last one, no framework will save you. It’ll just become the next thing that didn’t work.

Why This Is a Competitive Advantage

Here’s what most business advice leaves out. Your competitors are Googling the same best practices. They’re reading the same bestsellers. They’re implementing the same frameworks.

If you do what they do, at best you get what they get. And most of them are camped at Levels 1, 2, and 3 on the Mountain of Why. They have the same mental models, the same borrowed strategies, the same playbooks.

The advantage goes to the leaders willing to climb higher. To do the harder, less comfortable work of figuring out what they actually believe, testing those beliefs against reality, and letting those principles — not someone else’s system — shape the decisions that run their business.

That’s not a program you can buy. It’s a way of thinking. And it’s the difference between a business that looks like everyone else’s and one that actually becomes what you set out to build.

This article is adapted from Craft: The Expedition of Business by Zack Tomlin — a guide for leaders of small and mid-sized businesses who are done borrowing answers and ready to build their own.

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“Business is hard enough even if we assume everyone is operating in the same reality. When everyone perceives the same information in different ways, it gets that much more difficult. Unfortunately, we tend to overestimate how often we’re on the same page.”

The below is an excerpt from Part 2 - Chapter 6 of “Craft: The Expedition of Business”:

“Mr. Tomlin, I’ve been trying to reach you for weeks. I’m out of patience and am turning this issue over to my attorney.”

It wasn’t the voicemail I wanted to find when I returned from lunch, nor was it a message that I could make much sense of. I knew the number and the voice. He was a client, and two or three weeks prior we had met to resolve an issue on a project. A meeting that I thought had put matters to rest. I had not heard from him since. I was as much perplexed as concerned.

My return call keyed me in on a few pieces of information. He had my email address wrong, those messages I had “ignored” never made it to me. His phone calls that I “didn’t return”—until that day they never ended with a voicemail. I did not know that he had called.

Now I had clarity on the “out of patience” part of his message, but “my attorney”? I thought this was resolved. It turns out he did too—until he talked with his boss. He had different ideas as to who bore responsibility.

The entire episode had started months prior when they contracted us to provide some design services. They presented “what they had budgeted” to my project manager, and my project manager saw his task as giving them the design “they asked for.”

I’m not sure the client disagreed until the piece of equipment didn’t work. “We should have raised our concerns” was my take on the situation, but I was still unclear on just what had happened.

There was much to understand. Why the voicemail? How did this design come to be? Why the change of heart? It took a while, but once I could understand everyone else, I could finally be understood, and a resolution could be reached.

Understanding is also the first step in getting people aligned within an organization. What is their starting point? What is their perception of reality? Those are the foundations needed to build a usable model. One that explains what someone might want and how they are likely to respond. Without that foundation, the world can be a strange, confusing, and frustrating place.

You’re probably familiar with the classic party game “Telephone.” Someone starts the game by whispering a message to the person next to them. That person does the same, and by the time you’ve reached the end you’re left with some altered version of the original message.

A more modern take on the game, and a better analogy for our struggles related to perception, is the game Telestrations®. In that game, players alternate between drawing a picture of the “secret word” and writing a description of the previous player’s drawing.

As you might imagine, hilarity often ensues. What started as “A rabbit wearing a top hat” turns into “Richard Nixon taking a bubble bath.” Unfortunately, with business and getting our teams aligned, we often get the confusion but rarely the comedy.

There is no “secret word” in business. Instead, we’re awash in information: calls, emails, tone, body language, and there’s more. At any moment we’re also processing our entire field of view: the sounds around us, the feeling of the air and objects we’re in contact with, and whatever smells our noses may be picking up.

In effect, all that incoming information is the world and our immediate place in it. To keep it from being overwhelming, our brains filter out nearly all of it. What we’re left with is the small slice we focus on: our attention. What we pay attention to gets filtered through our perception of the information we are aware of.

Without attention and perception, it would all be noise. With it, we create a mental model to approximate reality. We can’t absorb all of reality at once, so we develop a low-resolution view to make sense of that small slice of reality we pay attention to. And that perception becomes one’s reality.

Unfortunately, in business, this chain of approximations often becomes our own game of Telestrations®, and it’s not as much fun.

Like me, you receive an angry phone call from a customer. Now the words they say didn’t fall from heaven. They start as the customer’s perception, a product of the slice of reality they paid attention to. Maybe they’re right to be upset, maybe they’re not; but in the moment, their approximation of reality takes shape in their mind, and the resulting action is to give you an earful.

They then make yet another approximation. They can’t express 100% of what they’ve experienced, how they feel, and what they want you to do about it. That all exists in their head, but to convey it to you they’re left to approximate the best they can. They do so with words, their tone of voice, and maybe—if they still have a landline—slamming their phone down.

So now it’s your turn. You’ve paid attention to some slice of the information sent screaming at you. You’ve perceived it the best you could, constructed your own approximation of reality, and now you must do your best to approximate the situation to an employee who can fix it. An employee who is the next link in the chain of “world”, attention, perception, and action.

With each step, the picture, the “reality”, our communication, and expectations all drift further from the truth of the situation.

Business is hard enough even if we assume everyone is operating in the same reality. When everyone perceives the same information in different ways, it gets that much more difficult. Unfortunately, we tend to overestimate how often we’re on the same page.

Research has shown that nearly 60% of us overestimate how effectively we communicate. And it’s a problem in both directions. A person communicating with you is likely to assume they’ve delivered a clearer message than they have, and you’re likely to err in the same direction about your communication with someone further down the chain. It’s how we get from Peter Rabbit dressed for a night on the town to the 37th President taking a dip in the tub. And it’s how we find ourselves befuddled over what “made sense to us.”

There’s a long list of what makes getting others to share our version of reality difficult: our varied histories and past experiences, words and their multiple meanings, the non-verbal cues that can enforce but also derail our messages, our tendency to fill gaps in information with assumptions or our memories, and that we all are likely to focus our attention on different pieces of information.

Some people spend a career researching all the different factors that influence our specific perception of reality. But for a business leader, one question is essential: “What do I do about it?”

Thankfully, there’s a four-step process that can help us make sense of things.

R.E.A.R.

Relate to their perspective. Explore what they think is happening and why. Affirm your understanding by repeating back. And then, but only then, Respond....

When’s the last time you found others living in a different reality? With the right steps, you can likely bridge the gap.

Learn more about my new book at: TheExpeditionofBusiness.com

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“The question isn’t whether a business is pulling each of these levers, but how? There are limitless ways, and an equal number of suggestions of what’s best. Books, courses, podcasts, consultants, coaches, and gurus. There is a river of information, but it all flows towards pulling one of the four levers.”

The below is an excerpt from Part 1 - Chapter 4 of “Craft: The Expedition of Business”:

The Wright brothers, our friends from Chapter 2, spent decades tinkering and toiling with mechanisms, gadgets, and gizmos of all types before finally setting their sights on airplanes. A short five years later, they were ready to make history on a December morning at the Outer Banks of North Carolina.

It was cold, windy, and miserable; but it was also perfect conditions for flight. Wilbur had won a coin-toss to be first in the saddle, but his attempt to be “The First in Flight” had ended with a crash a few days prior. Orville would be at the controls.

The motor was humming, the wind was blowing, and once the restraining wire was cut, the plane started bouncing down the launch rail. Speed increased, wind rolled across the airfoil of the wings, wheels lifted off the rails, and there it was. Orville was in flight.

We can all relate to some version of toil and struggle before finally, success. I thought and schemed for some time before launching my first business. Landing those first clients, seeing the first checks roll in, hiring the first staff. No one is going to commemorate my story in a state motto or on a license plate, but the feeling seems parallel to Orville’s as things finally got off the ground.

I don’t know his specific reaction, but as he was soaring high above the ground in a contraption that made the flying car from “Chitty-Chitty-Bang-Bang” look like a Learjet, part of me suspects his reaction was just like mine and that of many business leaders new at the controls: “Oh shit, now what?”.

For Wilbur, that answer lay in the levers he had at his disposal. A lever for the speed of the engine. A lever for the angle of the wing. A lever for the pitch, roll, and yaw of the plane.

For me, the answer was in levers as well. Four of them. The four levers that any business is trying to control. Those that get (and keep) their organization soaring.

One for Energy. Hire it, grow it, buy it, cultivate it.

Another to Unify. Getting everyone aligned and moving in the same direction.

The third for Resistance. Lowering obstacles, working smarter, finding the best path.

And the last for Yield. Marketing and selling results for maximum return.

Keeping the plane in the air was about E.U.R.Y. and finding the right balance and tradeoffs between the four.

Every business has a form of the E.U.R.Y. model. They are all paid to do work. Something their customer or client can’t or would prefer not to do themselves. An opportunity they forgo because the resistance between them and the outcome they desire is too great.

The business exists because it can amass the energy needed to do the work. Unify it in a single direction. Lower the resistance to doing the work. And finally, maximize the yield they receive for a job well done.

These are the four variables of the infinite number of paths to success, and each business does (and should do) it differently.

A local plumbing company builds its…

Energy and their team by targeting recent high school graduates, partnering with a local community college to train them in the trade, and creating a profit-sharing plan to boost engagement.

Unity comes via their creed “treat every home like your own”, clear job descriptions, and documented SOPs. Everyone focused and aligned.

Resistance is lowered via larger trucks re-stocked daily with parts to avoid return trips. Customers being able to upload photos and videos of their plumbing issues, giving technicians the chance to prepare better before they arrive. It all makes the work easier.

Yield increases by offering preventative maintenance plans after a repair, asking for online reviews and testimonials, and by tracking the install dates of water heaters. That way they can contact customers when it’s time to be replaced. One customer, multiple benefits.

The question isn’t whether a business is pulling each of these levers, but how?

There are limitless ways, and an equal number of suggestions of what’s best. Books, courses, podcasts, consultants, coaches, and gurus. There is a river of information, but it all flows towards pulling one of the four levers.

“Hire slow, fire fast,” Energy

“Everyone rowing in the same direction,” Unify

“Work smarter, not harder,” Resistance

“Land and expand,” Yield

Best practices, effective strategies, common tactics, and even the clichés; they all find a home here. It’s our job as leaders to sift through all the information we come across. To figure out how it best serves us when sitting at the levers of control.

So, just how do we pull those levers?...

The next decision you make, stop an ask, what’s the intent here. Raise the energy? Unify it better? Lower the resistance? Or maximize the yield?

Learn more about my upcoming book at: TheExpeditionofBusiness.com

Learn more about Your Craft Your Climb, my business coaching and consulting practice at: YourCraftYourClimb.com