Sweet Dreams of Learning for Small Teams
Why most education and leadership advice is built for a reality we don’t have
Accepting the obvious
A few years ago, we were developing our organization’s strategy. The goal was not just to produce a strategy “as a document,” but to create a tool that would help the organization survive and grow in a radically changed environment.
I was sent to study. It was an online strategy course at Harvard Business School (of course, online — we are not Google)!
Big, crazy smart, crazy-crazy ambitious. Theory, cases, peer-to-peer sessions. It was exciting and challenging. Like opening a window into the biiiig world.
And then you return to your own context and suddenly realize that all this knowledge… is not about you.
It’s like assembling a wardrobe using a 150-page IKEA manual, but 90% of the parts are missing, and the remaining ten percent belong to a completely different piece of furniture.
And then…. you go through all the stages.
Shock and denial. “No, I just didn’t fully get it. I need to reread it. More sessions. More sticky notes.”
Anger. “I hate corporate education! Why does nobody say that the real life of small teams is different?”
Bargaining. “Okay, maybe I just need to figure out which parts are useful, and which ones are clearly designed for very big, very “adult” companies run by very, very-very serious people.”
Grief. “F**k it! This is pointless! Nothing works. The frameworks don’t work. I’m just bad at this.”
And only then — acceptance.
Most advice, courses, and guides on leadership and management are written:
for teams you don’t have!
for resources you don’t have!
for capacity (personal and team), you don’t have!
for people who are not like you!
for a context radically different from yours!
It is important to understand:
Most small projects, initiatives, teams, organizations, or businesses are not “early stages of something big.”
They are a different species. A parallel branch of evolution.
That means we need a different education. Education and knowledge for small teams, resource-scarce initiatives, ten-person nonprofits, and for people who want to become leaders and grow in exactly this context.
Traps, Gap, and a bit of Slack
There are several reasons behind this gap between what the education industry offers and what small teams actually need.
1. Scale trap
Most leadership advice, courses, and programs assume management through layers. You have roles, departments, and processes. And you are taught to manage those layers and mediators.
But in small teams, there are almost no layers!
Most advice we get from courses only looks behavioral (“delegate,” “coach,” “set OKRs”), but in reality, it is structural.
For example, one of the most popular ideas in courses, books, and yes, on Substack too: “Leaders should be strategists, not executors!”
Sounds applicable? Try dropping your share of operational work in a six-person team.
Or this one: “Build a leadership pipeline.”
Sure. In a nine-person team, the pipeline usually looks like this: “One person is holding everything together, and two others are on the verge of quitting.”
At that point, it stops being inspiration and starts feeling like mockery.
Especially when Bezos’s “two-pizza team” rule is not a rule for you. It’s already the absolute maximum of what’s possible.
2. The “Slack” Gap
Many change and innovation frameworks are built on the idea of organizational slack—surplus time, people, money, and expertise that can absorb inefficiencies during periods of change.
We are told:
“Spend 20% of your time on innovation,” or “Run a three-day strategic offsite.”
But we don’t have that slack. Every hour spent on Harvard-style strategizing is an hour when work that brings money or real outcomes right now does not get done.
We are offered tools for optimization, while small teams need tools for growth survival.
3. Expectation trap
You complete a course. You read the book. You feel energized. And new expectations appear! Expectations of a new version of yourself, and of the environment around you, which now somehow should match all those cases you “lived through” during the course.
But in terms of resources, you are still the same. And the surrounding reality is the same, too.
It’s like giving Kai from The Snow Queen shards of ice with the letters S H I T on them and asking him to assemble the word “Eternity.”
Yes, consciousness shapes being to some extent (sorry, Karl), but not that much.
The result is often the same: you may become more knowledgeable, but more often you simply become more unhappy.
4. The specialization trap
In large teams, the efficiency of a leader (and of the team) is often achieved through narrowing the scope of responsibilities.
Small teams survive through hybridity.
You can’t “delegate marketing” when you don’t have a marketing director. That’s it.
You are the CEO. You also write the copy. You also pay the bills.
5. The time horizon trap
My favorite one!
Classic strategy teaches you to look three, five, ten years ahead. Sustainable competitive advantage and all that.
For us (small teams), “long-term” often means the next quarter.
Applying long-term planning tools (like complex scenario analysis) to an organization facing a cash gap next month is like choosing curtain designs in a burning house.
7. Causation trap
Business courses are almost always causation-based:
goals → plan → resources → execution.
In our reality, resources appear only after something actually works. It’s a kind of bricolage, for god’s sake!
I’ve written more about bricolage as a managerial state of mind in a separate post, if you want to go deeper.
6. Follow the Money!
Small teams don’t pay.
Who at Harvard or Bocconi School of Management needs your fifty dollars for a course? Those “small” online courses priced at two thousand dollars are just a flashlight at the entrance of an MBA sales funnel.
The entire body of knowledge is created for the paying client. And it is not us.
Once, I attended a training on security and AI. We were told that it is absolutely critical to have a department responsible for data security. A department!
In a ten-person team, that “department” is a morning slot in someone’s calendar.
That training is clearly something they roll out for their regular clients. And we… yes, once again, we are not them. And yes, we’ve made a mistake in choosing this training provider. And yes, they didn’t adjust anything.
Four Shifts: A Learning Manifesto for Small Teams
I may have painted a pretty grim picture. But let’s get out of this lonely tunnel of despair (layered with even more despair) for a moment. What do we actually need? We need just four fundamental shifts.
Shift 1: From Content Consumption to Contextual Connection
Traditional education sells content. But today, content is a commodity. You can Google anything in three seconds, and ChatGPT or Gemini will explain it to you with examples for free.
What you cannot Google is how to apply that model in your specific context, when Patrick, your accountant, is about to quit, your day already feels 32 hours long, and Susan, your lead project manager, has just burnt out after a six-week sprint.
You need a similar context and comparable experience.
That is why education for people and teams like us should be Cohort-Based and Peer-Driven.
In the world of small teams, an “expert” is not a professor who studied markets back in 2010 or the Chief of Marketing of Amazon who decided to teach. An expert is a fellow founder, team lead, fundraiser, or marketer who solved your current problem in a similar context just last Tuesday.
What does this look like in practice?
Guided masterminds: A co-development format where five leaders dissect one participant’s real-life case.
Community environment as curriculum: Instead of buying a “course,” you buy access to an environment (like Reforge or Lenny’s Newsletter community). You aren’t paying for video lectures; you are paying for the chance not to be alone, for access to shared knowledge, and for the ability to actually talk to people who “get it.”
Lunch and learn: If someone on the team solves a problem or learns something new, they share it and teach the rest. This isn’t just shared ownership of new knowledge and expertise; it is a way of documenting and reflecting that allows the team to “repeat” success.
Shift 2: From “Just-in-Case” to “Just-in-Time”
To stock up on all the necessary knowledge for a small team of generalists that might be useful someday to someone, you would have to simply never start working. You cannot hoard knowledge for the future! You can’t take three-month pauses for courses — no one is going to pay for that.
We should learn in the flow of work. Moreover, you need to learn exactly at the moment when your new knowledge and skills have an immediate application: you grow while solving a task you couldn’t solve before.
For example:
Continuously updated micro-courses: 5-minute modules on specific tasks, pains, and situations, contextually linked to what you are doing right now. A “for right now” library: created and updated somewhere by someone—or even by your own team.
Newsletter courses: Instead of sending a manager to a generic leadership course, subscribe them to a curated newsletter that delivers tools weekly. If knowledge cannot be applied today or tomorrow, it is not education—it is Edutainment.
On-demand micro-education: Community-based practical education. Today, you ask a question, voice a problem, or say what you wish you knew how to do. Tomorrow, you receive three 1-minute videos and a short guide on how to solve it.
Shift 3: From Prescriptive Ideals to Descriptive Sensemaking
Most courses teach you how things should be (The Norm). But small teams live in chaos. Trying to stretch an ideal textbook model over that chaos only creates anxiety and a sense of inadequacy (can education at least stop making us feel inadequate, please?)!
Karl Weick described what growth and education for leaders — especially in small teams! — actually looks like. He called it Sensemaking:
Something happens → we try to understand it → we act → we re-assemble our understanding.
Instead of theories and frameworks created for someone else, this approach focuses on reflection and the iterative sensemaking of experience. It’s the iterative growth of expertise and skills.
This means analyzing decision logs and data after something has already happened!
As noted in a post by The Effective Project Manager:
“Making mistakes is human. But repeating mistakes makes me frustrated.”
Mistakes are the stimulus and the very object of learning, specifically so they don’t become repeated mistakes.
What does this look like?
Retrospective Sessions: Moderated (or not) sessions to analyze what happened after the work is done.
Community-based or peer-to-peer retrospectives: Breaking down what was done, what went wrong, and what was problematic with a group of people in similar shoes.
Shift 4: From The Heroic Leader to Collective Agency
All we ever read is: “the leader must,” “the leader should.”
90% of educational products are targeted solely at the leader, as if everyone else in the office were just mindless blobs wandering aimlessly down the corridors.
Leadership and business education must be grounded in and develop distributed agency, where the unit of learning is not the individual but the team:
Democratized knowledge: No more “secret management courses.” The principles for creating and executing strategy, finance, and developing corporate culture, along with all the tools (everything!) must be open and accessible to the entire team.
Leadership for non-leaders: There must be courses and accessible knowledge on leadership and management for people who are not managers. The best youth football academies (like my favorite, FC Barcelona) train thousands of kids as if every single one of them is a future Messi. Only a tiny fraction will make it to a professional career, but they teach EVERYONE the same way and EVERYONE the same thing: how to play great football.
Education for small teams and resource-scarce initiatives is educational bricolage (I love this word, it feels both sophisticated and a little bit spicy 😅 ).
We take whatever is at hand, mix it with the experience of a neighbor (Peer Learning) or a group of neighbors (Community and Cohort-based learning), apply it immediately (Just-in-Time), and make sense of the results together (Sensemaking).
It might not be as prestigious as a Harvard diploma. But it is exactly what allows us to survive and grow.
If you’ve read this to the end, thank you!
If you disagree, feel something important is missing, or have anything on your mind, I’d love to hear it in the comments.
Your article does a great job of describing a reality a lot of small-team leaders feel but rarely see reflected: most leadership education is optimized for scale, not scarcity. I personally struggled to coach a company of 3 last year and felt like my impact just wasn't there.
I do like the shift toward sensemaking, peer context, and just-in-time learning, it treats leadership as an evolving practice, not a credential.
Curious: if you were to design the first learning artifact for say a five-person team (one habit, ritual, or tool), what would you start with? Thanks!
Great piece. This captures something many small teams experience.
Not every small company is “at the early stage of something big.” Some are a different species entirely - with different constraints and realities.
I’ve seen the same thing happen with processes like Agile. Teams try to force-fit frameworks because “that’s what good companies do,” even when the structure behind those frameworks simply doesn’t exist.
Corporate logic doesn’t always translate to small teams.