When investors trust founders to “figure it out”
Why trust without challenge quietly creates drift
When I speak to investors, I often hear a sentence I agree with at a fundamental level:
“We invest in the founder and the team. We trust them to figure it out. We don’t want to tell them what to do.”
At a principle level, this is right.
Founders live closest to the problem.
Context matters.
Advice given from the outside is often wrong.
And micromanagement destroys ownership.
So yes. Trust matters.
But there is something we talk far less about: what this kind of trust actually does to founder behaviour over time.
What trust produces in practice
When founders are trusted to “figure it out”, they usually do exactly what they are best at.
They solve.
They build.
They dive deeper.
They handle complexity.
They stay busy.
This often looks like competence. And often, it is.
But there is a risk embedded in this dynamic.
Founders who are trusted to figure things out rarely stop to ask whether they are still solving the right problem in the right way. Not because they don’t care. But because they are inside the problem every day, and momentum becomes hard to question from within.
This is how teams disappear into complexity without noticing.
The rabbit-hole trap
I’ve seen this pattern repeatedly, both in startups and in innovation initiatives inside larger organisations.
Progress looks real. Work is happening. Things are moving. Slowly.
Yet over time, fewer people can clearly explain why this is still the right direction.
At a detailed level, everything makes sense.
At a strategic level, clarity slowly disappears.
Why advice doesn’t fix this
The usual response is advice.
More ideas.
More suggestions.
More opinions from people who mean well.
Ironically, this often makes things worse.
Advice adds pressure.
It adds activity.
It increases noise.
It pushes founders to react instead of reflect.
There’s another reason advice rarely helps at this stage. Going back or reconsidering your entire approach is rarely seen as a real option. Once movement has started, both founders and advisors tend to assume the direction is broadly right. So the company keeps moving, even if the course is slightly off.
When things eventually get difficult, the response is rarely to rethink direction.
Instead, teams start cutting.
Cutting initiatives. Cutting scope. Cutting cost.
That’s often how companies optimise their way into a dead end.
I’ve lived this myself. Not in theory, but in practice.
Between advice and letting you work things out on your own, something important is missing.
What’s missing is not control. It’s judgment support.
Good support is not about telling founders what to do.
And it’s not about stepping away entirely.
It’s about helping them step out of the problem to question their own momentum.
The most valuable intervention is often a question, not a suggestion.
• What are we assuming to be true right now that we haven’t actually checked in a while?
• Which problem are we solving out of habit rather than conviction?
• What are we still working on mainly because we already invested time or money in it?
• If we were forced to simplify our strategy tomorrow, what would we immediately stop doing?
These questions don’t tell founders what to do.
They don’t remove founder autonomy.
They strengthen it.
Trust without challenge creates blind spots
There is a subtle tension here.
Trust is necessary for founders to operate.
Challenge is necessary for founders to course-correct.
When trust exists without structured challenge, blind spots grow quietly.
When challenge exists without trust, founders shut down.
The balance is fragile, and it’s rarely discussed explicitly. But this balance is exactly where drift either accelerates or slows.
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Previous posts
If you missed my previous posts in this series, here they are: