Learning to Decide: The Founder's Edge

How Navigating Chaos Builds Leadership Competencies the Future Demands

It's Tuesday afternoon. Sarah sits across from me, her laptop open, notes scattered across the table. Five different conversations are playing on loop in her mind. Her advisor told her to focus exclusively on product-market fit - nothing else matters yet. An investor said she needs a technical co-founder immediately or the opportunity will close. A successful founder she admires insisted she should be implementing AI into her customer service this week. Her business partner thinks they should bootstrap another six months. Her mentor from the accelerator says raise now, before the market shifts.

She looks up. "How am I supposed to know who's right?"

The silence hangs between us. Then I say what she isn't expecting: "You're not supposed to know. You're supposed to decide anyway."

Her face shifts - confusion, then something like recognition. This is the paradox every founder lives inside. Pulled in five directions by people who've succeeded. Contradictory wisdom from those who've been there. No clear path forward. Yet the business doesn't pause. Customers need answers. The team needs direction. Decisions stack up whether she's ready or not.

What looks like chaos, I've learned, is actually something else.

What Gets Built in the Crucible

Three months later, Sarah sits in the same chair. She's made perhaps two hundred decisions since our last conversation. Hired that technical person - though not a co-founder, someone junior she could afford. Tried a basic AI tool for customer support, watched it fail, adjusted it, watched it improve. Chose to raise a small friends-and-family round instead of waiting for a Series A. Each decision made with a fraction of the certainty she wished she had.

She's not less overwhelmed. The conflicting advice hasn't stopped. But something has shifted. She moves through it differently now. Faster. With more conviction. She describes a pattern she's starting to recognize: this mentor's advice tends toward caution, that one toward aggression. This framework works for B2B, that one for consumer. She's developing an internal filter - not perfect, but improving.

"I'm learning to trust my own read on things," she tells me. "Even when I'm not sure."

This is what I see happening, week after week, in coaching sessions with founders. The overwhelm doesn't break them. It builds them. The conflicting advice, the absent certainty, the pressure to decide without knowing - these aren't obstacles to overcome. They're the crucible where something essential gets forged.

Deciding Without Knowing

Watch founders closely and you see three capabilities emerging. Not from training programs or frameworks. From repetition. From necessity. From having no choice but to develop them.

The first is learning to decide without knowing.

When five mentors offer five different paths, founders can't wait for consensus. They can't defer to authority because authority is divided. They can't collect more data because the data itself is contradictory. They operate in huge complexity and unforeseeable uncertainty as their baseline condition.

So they learn to ask different questions. Not "What's the right answer?" but "What's true for my situation?" Not "What do experts recommend?" but "What can I test this week?" Not "How do I know for certain?" but "What will I learn by trying?"

They make decisions with half the information they wish they had. Not because they're reckless or impatient. Because standing still is worse than moving forward imperfectly. Because the cost of delay often exceeds the cost of being wrong.

This happens twenty times a week. Every week. The pattern recognition sharpens. The internal compass calibrates. Not confidence that they're always right - that would be delusion. Confidence that they can handle being wrong and adjust course. That's different. That's something you can't learn any other way.

*

Learning by Doing

The second capability: learning by doing, at velocity.

Founders can't wait for courses to be designed or best practices to emerge. The landscape shifts too quickly. Thirty-nine percent of skill sets will transform within the next five years, which means the textbook for what they need to know doesn't exist yet.

So they learn through a different rhythm. Try something Monday. Break it Tuesday. Fix it Wednesday. Get feedback Thursday. Iterate Friday. Repeat.

When Sarah needed to understand whether AI could handle her customer inquiries, she didn't take a course on large language models. She watched a fifteen-minute YouTube tutorial, signed up for an API, built something basic, shipped it to ten customers, collected their feedback, adjusted. Within a week, she had real knowledge - not theoretical understanding but practical insight into what worked for her specific use case.

This velocity compounds. Month one: she learns one new tool. Month six: she can evaluate and implement three tools in a week. Month twelve: she's teaching her team and spotting opportunities others miss. Not because she knows more in absolute terms, but because she learns faster. The gap widens.

*

Building Resilience Through Repetition

The third capability is harder to name. It's something like resilience, but more specific. It's what gets built through making two hundred decisions, watching some work and others fail, adjusting, and continuing.

Every decision carries risk. Every choice Sarah makes could be wrong. And many are. The AI tool she implemented in week one needed major changes by week three. The junior hire she made struggled for a month before finding their rhythm. The funding approach she chose meant saying no to opportunities that might have been better.

But here's what develops through this repetition: the ability to be wrong and keep going. The capacity to say "I don't know yet, but we'll figure it out" and mean it. The trust in her own judgment after testing it hundreds of times. The humility to ask for help without feeling diminished. The confidence to lead while still learning.

This doesn't come from one big challenge overcome. It comes from a thousand small ones. From making a decision on Monday that feels uncertain, seeing the result by Friday, and discovering she survived it. Again. And again. Until the survival part becomes assumed and the learning part becomes the focus.

*

The Corporate Reality

Now I move to my afternoon sessions. Different context, same capabilities needed. Opposite environment.

Michael leads the marketing division at a medtech company that's been around for fifty years. Smart, capable, experienced. He wants to experiment with a new approach to customer engagement. Something that might work, might fail, but seems worth trying.

What follows is familiar. He'll need to develop a business case first - two weeks of work. Present it to his skip-level manager and get initial alignment - another week. Coordinate with three other departments whose work intersects with his - stakeholder management meetings scheduled over the next month. Submit for budget approval, which runs quarterly - wait for the next cycle. Present to the steering committee - they'll want more analysis on the risk profile. Address their concerns with additional research - another few weeks.

By month four, the landscape has shifted. The opportunity looks different. The approach needs revision. The business case requires updating.

Michael spends perhaps seventy percent of his time not deciding, but coordinating about decisions. Aligning stakeholders. Managing up and sideways. Getting buy-in from people who have veto power but no accountability for the outcome. The ability to decide with incomplete information - to say "I think this is worth trying, let's see what we learn" - that muscle atrophies. Not because Michael is incapable. Because the system doesn't allow it.

Where Learning Slows

The learning environment looks different too. Michael's company invests significantly in executive development. Formal training programs. External consultants brought in to teach frameworks. Seventy-eight percent of companies have mandatory training sessions for executives, and his company exceeds that. He attends these sessions, takes notes, finds them intellectually interesting.

Then returns to his regular work. The gap between learning about something and learning through doing remains unbridged. He knows the theory now. But he hasn't broken anything and fixed it. Hasn't felt the consequence of choosing wrong and adjusting. Hasn't developed the tacit knowledge that comes only from trying.

Sarah learns by building something that might fail. Michael learns by listening to someone explain how to build it. One creates capability. The other creates awareness of capability. These are not the same.

Where Resilience Can't Grow

And then there's risk. Or rather, the prevention of it.

In Michael's environment, every significant decision must be triple-checked. Risk-assessed. Precedent-supported. Guaranteed to succeed before approval is granted. This makes sense from a governance perspective. The company has obligations, stakeholders, regulatory requirements. The caution is rational.

But here's what it prevents: you can't build comfort with uncertainty in a risk-free environment. You can't develop resilience without failing and recovering. You can't learn to trust your judgment without testing it repeatedly, including when you're wrong.

Sarah fails constantly. Small failures. Recoverable ones. Each teaches her something and builds the muscle. Michael's system is designed to prevent any failure, which means the muscle never develops. When he eventually faces true ambiguity - and he will, because only one percent of organizations have fully matured their new capabilities - he hasn't had the reps.

Why This Matters Now

Here's why this matters beyond the startup-versus-corporate comparison.

The world Sarah inhabits - constant ambiguity, rapid learning cycles, moving forward without certainty - isn't unique to startups anymore. It's the water we're all swimming in now. Markets shift faster than strategic plans can accommodate. Technology evolves continuously, making last year's expertise less relevant. What worked doesn't guarantee what will work.

The competencies founders are developing through necessity - deciding without knowing, learning by doing, building resilience through repetition - these aren't startup skills. They're the essential leadership capabilities for a world where ambiguity is permanent, not temporary. Where learning velocity matters more than accumulated knowledge. Where perfect planning loses to rapid iteration.

Established companies try to maintain business architectures while startups radically change their operating models. The difference isn't intelligence or resources or strategic intent. It's these three capabilities, developed through daily practice.

And founders are getting thousands of reps while corporate leaders are stuck coordinating about getting ready to begin.

The Questions

So I sit with Michael and ask questions I know might be uncomfortable.

When did you last make a significant decision with less than half the information you wanted? Not a small operational call, but something meaningful. Something where you said "I believe this is right, let's move forward" knowing you might be wrong.

He pauses. Thinks. "I'm not sure I'm allowed to do that anymore."

When did you last learn something new by actually trying it yourself? Not attending a presentation about it or reading a case study. Actually implementing it, breaking it, fixing it, seeing what happens.

Another pause. "That's not really how we operate at my level."

When did you last try something that might genuinely fail? Small enough that the failure would be recoverable, but real enough that you'd learn something valuable if it did.

He smiles, but there's recognition behind it. "I think I see where you're going with this."

The gap between what leadership requires now and what most organizational environments permit has grown stark. Not because people are incapable, but because the systems we've built prevent the very capabilities we need most. The permissions, the processes, the risk-management frameworks - they made sense for a different era. They're actively harmful now.

The Opening

But here's the opening.

You can't develop these competencies in your current environment without changing something. The environment shapes what's possible. So change the environment, even in small ways.

Michael and I talk about this. What would it look like to create space for development?

He could make one decision this week faster than his system typically allows. Set a deadline - forty-eight hours - and decide with whatever information he has by then. Not for everything, just one thing. Notice what happens. The decision might be imperfect. He'll survive it. He'll learn something.

He could learn one new capability by actually doing it himself. Not delegating it or watching someone present about it. Try the tool. Build the prototype. Run the experiment. Break something. Fix it. See what he discovers. Not theoretical knowledge. Practical capability.

He could try something that might fail. Small enough that if it doesn't work, the cost is minimal. Significant enough that success would teach him something valuable. Create the conditions for small, contained failures that build the muscle.

These aren't revolutionary acts. They're modest experiments. But they're reps. And reps are what build capability.

Six Months Later

Six months after that first conversation, Sarah sits across from me again. She's made perhaps a thousand decisions by now. The company is growing, the team is expanding, the challenges are more complex. She still gets conflicting advice from mentors. She still doesn't know the right answers.

But watch her process it now. Someone suggests she should pivot her entire strategy. She listens, asks clarifying questions, considers it against what she's learning from customers. Decides to test one aspect of the suggestion rather than wholesale adoption. Makes the call quickly. Implements within days. Learns whether it works. Adjusts.

This happens across multiple decisions simultaneously. She's not operating from some perfect framework. She's developed a feel for it. Pattern recognition built through repetition. Comfort with uncertainty earned through surviving it hundreds of times. Confidence in her own judgment forged through testing it constantly and adjusting when wrong.

"I'm still overwhelmed sometimes," she tells me. "But I move through it faster now."

That's the edge. Not having the answers. Moving forward without them. Learning by doing. Building resilience through repetition. These capabilities can't be taught in a classroom. They're developed through practice, necessity, and thousands of small acts of deciding anyway.

*

In a world that still rewards certainty - or at least the appearance of it - what Sarah represents flips something fundamental. What if true leadership doesn't begin with knowing the answer? What if it begins with the willingness to decide without knowing, learn through action, and build conviction through practice?

The founders aren't succeeding because they're smarter or younger or more aggressive. They're succeeding because they're getting daily reps in exactly what everyone needs now. Deciding without complete information. Learning by trying. Building resilience through small failures.

That founder who asked "How do I know who's right?" She doesn't. She probably never will. The advice will keep conflicting. The uncertainty won't resolve.

But she's learned to decide anyway. And that might be the most essential leadership capability there is.

ABOUT THE AUTHOR

Karin Wellbrock, Partner Kay Group K.K. Japan - Leadership and Team Coach and Organizational Consultant. She helps her clients buid capabilities formal training can’t teach. She works across startip and corporate worlds, partnering with leaders to develop what matters the most in an ambiguous world: deciding without knowing, learning by doing, and thriving in uncertainty. Contact Karin for exploration (karin.wellbrock@kaygroup-asia.com)

References

Zahra, S. A. (2024). How startups create new knowledge that spark disruptive innovations. Canadian Journal of Administrative Sciences, 41(4). https://onlinelibrary.wiley.com/doi/10.1002/cjas.1771

World Economic Forum. (2025). Future of Jobs Report 2025. Retrieved from https://www.weforum.org

Astera Software. (2025). 5 Competencies for a Successful AI Strategy in 2025. https://www.astera.com/type/blog/five-competencies-successful-ai-strategy/

McKinsey & Company. (2025). AI in the workplace: A report for 2025. https://www.mckinsey.com/capabilities/mckinsey-digital/our-insights/superagency-in-the-workplace-empowering-people-to-unlock-ais-full-potential-at-work

Hahn, R. (2020). Artificial intelligence technologies and entrepreneurship: A hybrid literature review. Review of Managerial Science. https://link.springer.com/article/10.1007/s11846-025-00839-4