Problems and Solutions, Doers and Managers


One of the biggest differences when transitioning from doer to manager is how best practices on communication change.

When you’re a doer executing for a boss, the best bet is to lead with solutions.

Every executer worth their salt eventually realizes that just pointing out problems doesn’t really help the team.

That just creates work for someone else

(Potentially the exact person deciding whether you stick around to get a raise).

So it’s better to carry the ball all the way down the court:

“Hey boss, I found X issue, so I did Y, Z, and B. Here’s a draft of an email you can use to tell the C-Suite. Have a nice weekend!”

At Deloitte, we called this “managing up.”

And it’s how you proved your worth and moved up in the org.

But when you transition to being a manager or a CEO,

Your mentality has to shift.

It's not longer about being execution-focused;

You need to become results-obsessed.

It’s not your job to map out every step anymore;

It’s your job to set the goals and track the outcomes.

Sure, you’ll still get your hands dirty sometimes.

But if you hold onto a “lead with solutions” reflex as a boss,

You risk steamrolling employees’ ideas, limiting their growth,

And keeping yourself stuck in the weeds on tasks you meant to delegate.

Instead, you have to fight your prescriptive impulses with discipline.

Practice patience. Stay open to other solutions.

Yes, there will be things you prescribe, demonstrate, and hand down.

And in a crisis with a known playbook, you should be directive.

But most sophisticated work is better learned by doing

By trying, screwing up, and problem-solving.

Can't afford to let people learn?

Then it's YOUR job to fix your org so they have the overhead.

Or to hire someone who already has the reps.

If you want your org to scale,

They have to skill up

And so do you.

Your Daily CFO,

Lauren

Founder-Friendly Finance

CEO-turned-CFO & finance instructor, Lauren Pearl, drops a daily tip that helps startup founders grow their businesses and control their destinies. Learn why this growing list with a 60% open rate led to LP being named top 25 Finance Thought Leader and host of the #3 CFO podcast for 2025

Read more from Founder-Friendly Finance

Recently, I read a comment from a startup advisor peer about the lack of women in VC-funded startup leadership. Essentially: "Maybe this is just a product of preference. Maybe women are just more risk-averse. And maybe men are simply dumb enough to try." While framed as flattery, it disguises something ugly- It’s a tidy explanation for the funding gap That promotes a dangerous narrative Which is also - blatantly - wrong. Women do start venture-backed companies - many of them. About 1 in 5...

AI is supposedly making us faster. In conversations with founders and engineers, I’m hearing the same story: Prototypes that once took weeks now take days. Code that required whole teams now gets drafted in an afternoon. Experiments are cheaper, iteration is faster, and the barrier to entry for creating new products has never been lower. But speed in one part of the system often exposes constraints elsewhere. Recently, I’ve been reading Abundance, Ezra Klein and Derek Thompson’s new book on...

The junior employee who says: “Managers are a complete waste of money - they just sit around doing nothing while others work.” The first-time founder who says: “Big-firm lawyers are a total rip-off. I’m paying $700/hour for a contract that should just be a free template.” The nursing student who says: “Ugh, doctors don’t know ANYTHING.” The independent consultant who says: “Those jerks at McKinsey are a scam. People pay them millions and all they do is create a PowerPoint and walk away.”...