“Figure It Out” Is Not Leadership: Why founders accidentally set their first leaders up to fail

“Figure it out.”

It’s a phrase that sounds empowering on the surface.

But most of the time, it’s not empowerment.

It’s leadership abandonment.

And founders and CEOs need to hear this.

I’ve seen this happen over and over again in early-stage companies. In fact, it happened to me more than once earlier in my Customer Success career.

A founder or CEO pulls you aside and says something like:

"Kristi, this is a big opportunity. You've never done this before, but I believe in you. Go figure it out."

In the moment, it feels incredible.

They trust you.

They see potential.

They believe you can do something big.

So naturally, your response is something like:

"10-4. I'm on it."

And off you go.

But here’s what actually happens next.

The Reality Behind “Figure It Out”

Once the excitement fades, reality starts to set in.

You don’t know where to start.

You’ve never built this before.

No one has shown you what “good” looks like.

Nothing else has been taken off your plate.

There is no playbook.

No mentor.

No framework to guide your thinking.

So now you're left doing what most first-time leaders do in this situation.

You scramble.

You guess.

You work nights trying to figure things out.

You make avoidable mistakes because you’re building the plane while flying it.

And eventually the cracks start to show.

Revenue starts slipping.

Customers begin to feel the impact.

Internal pressure builds.

Then the narrative quietly becomes:

"They just couldn't deliver."

But the truth is something very different.

They were never set up to succeed.

Responsibility Without Support

What those leaders were actually given was responsibility without support.

They weren’t given:

Coaching

Budget

Clarity

Tools

Time

They were given expectations.

And expectations without support almost always lead to frustration, burnout, or failure.

I see this happen constantly with first-time Customer Success leaders.

These individuals are often incredible operators. They understand the product. They know the customers. They’re respected by the team.

Then they get promoted into leadership.

Suddenly, they’re responsible for building a Customer Success strategy, designing onboarding, defining health scores, building retention motions, and hiring a team.

And the guidance they receive is:

"Go figure it out."

That’s not empowerment.

That’s abandonment.

What Real Leadership Support Looks Like

Promoting someone into leadership is not just about giving them a title and more responsibility.

It’s about giving them the structure and support needed to succeed in a role they’ve never held before.

If you're a founder or CEO promoting someone into leadership, you should be asking yourself a few questions:

Do they know what success looks like in this role?

Do they have access to coaching or mentorship?

Have we defined the outcomes and priorities clearly?

Have we given them the time and resources to actually build?

Because leadership development isn’t automatic.

And building a function like Customer Success from scratch requires experience that most first-time leaders simply haven’t had the opportunity to gain yet.

That doesn’t mean they’re not capable.

It means they need guidance.

The Cost of Getting This Wrong

When leaders are left to “figure it out” without support, the consequences rarely stay contained.

It impacts:

Your customers

Your retention

Your revenue

Your team morale

And often the person who ends up carrying the blame is the very person who was set up to struggle from the start.

That’s not a leadership failure on their part.

That’s a support failure from the organization.

What Great Leaders Do Differently

The best leaders I've worked with didn’t just give people opportunities.

They gave them the resources to succeed.

They provided guidance.

They helped define what success looked like.

They opened doors to mentors and experts who could help fill the gaps.

They understood that belief alone isn’t enough.

Support is what turns belief into results.

And when leaders receive both the opportunity and the support to succeed, their careers can change forever.