What I Learned About Leadership by Getting It Wrong the Hard Way

I used to think good leadership meant knowing all the answers.

Spent years proving I knew more than everyone around me. Made sure my team understood I was the expert.

The result, I lost a lot of good people that way.

The Pattern I Created

Would give my team direction. Assume they understood. Get frustrated when they don't execute the way I expected.

• Focus on high-value opportunities.

• Target the right stakeholders.

• Prioritize likely deals.

Made sense to me. It should've been obvious to them.

But it wasn't.

What I Didn't See

My team was guessing about everything.

• Which opportunities were "high-value"? 

• What made someone the "right" stakeholder? 

• What made a deal "likely"?

They'd make reasonable assumptions. Do what seemed logical. Execute based on their best guess.

Which was usually not what I meant.

Then I'd get frustrated. "Why aren't you doing what I asked?"

They'd get defensive. "I am doing what you asked."

Both viewpoints are true. Both views are missing the point.

When Someone Finally Told Me

Sales rep quits. Exit interview, she was honest.

"I never knew what you actually wanted. Everything was vague. I spent more energy trying to figure out what you meant than actually doing the work."

Ouch!. Because she was right.

I wasn't giving clear directions. I was giving expert-sounding vagueness and expecting my team to read my mind.

That's not leadership. That's lazy.

What Changed

Started being specific. Painfully specific.

Felt awkward at first. Like I was talking down to people by spelling everything out.

But the team? Relief.

Finally knew what they were supposed to do. Could actually execute instead of guessing.

Turnover dropped. Not immediately, but over a few months, the team stabilized.

Execution improved. Because people spent energy doing work instead of decoding instructions.

What Specific Actually Looks Like

Don't say: "Focus on qualified leads."

Say: "Focus on Title I funded districts with intensive intervention needs, 6-9 months from budget approval."

Don't say: "Target decision-makers."

Say: "Build relationships with curriculum directors. They pick products. Then get in front of superintendents for budget approval."

More words. Way more clarity.

Still Make Mistakes

I remember telling my team, "Prioritize the pipeline. Focus on what matters."

Three people. Three different interpretations. All reasonable. None of what I meant.

One prioritized the biggest contracts. 

One prioritized closest to closing. 

One prioritized strategic accounts.

Had to go back and be specific: "Prioritize deals with signed LOIs and budget approval in the next 60 days."

Should've said that first.

Still reminding myself: what's obvious to me isn't obvious to anyone else.

Why This Is Hard

When you're good at something, shortcuts make sense. A "High-value opportunity" means something specific to you. Whole context attached.

Your team doesn't have that context. They're hearing words without the years of experience that make them meaningful.

You think you're being efficient. You're actually being vague.

And vague direction costs way more than the time you saved by not explaining.

What I See in Other Founders

Watch founders do exactly what I did.

Give vague direction. Blame the team when execution suffers. Convinced they have a talent problem.

They don't. They have a clarity problem.

Recently worked with a founder losing reps every few months. Kept saying: "Can't find good people."

Sat in on a team meeting. His direction?

"Go after districts that need us." "Focus on the right opportunities."

His reps had no idea what that meant. They were guessing about everything.

Told him what someone told me: Not a talent problem. Direction problem.

Once he got specific about which districts, which opportunities, and who decides, turnover stopped.

Same pattern I lived through. Just watching it from the outside now.

The Real Lesson

Good leadership isn't about having all the answers.

It's about being clear enough that your team can execute without guessing.

Not about proving you're the expert. About making sure everyone knows what success looks like.

Took me way too long to learn this. Cost me good people. Cost them frustration.

Still learning it. Still default to vague direction when I'm in a hurry.

But every time I catch myself and get specific instead? Team performs better. I perform better. Work gets done.

What This Means

If your team seems confused, probably not because they're not smart enough.

Probably because your direction isn't clear enough.

Test yourself: Could three people interpret what you just said in three different ways?

If yes, rewrite it. Be specific. Remove interpretation.

Your team doesn't need you to have all the answers.

They need you to be clear about what you want them to do.

Big difference.

What did you say recently that your team might have heard differently from what you meant?