Issue 168, Part Time CEO Newsletter

Hey, it's Dhiren 👋,

I'll be honest, this one frustrates me.

Everyone tells founders to "be vulnerable." LinkedIn is full of it. Coaches preach it. Leadership books won't shut up about it.

But the same people telling you to be vulnerable will be the first to judge you for it.

You open up to a client and they question your ability to deliver.
You admit uncertainty to your team and you can feel the confidence leave the room.
You share a doubt in a peer group and suddenly you're the "struggling one."

Even at home. Your partner asks "how's the business?" and you say "fine" because you can't dump that weight on them too.

So you learned the real lesson. Not from a book. From experience:

Keep your mouth shut. Sound certain. Carry it alone.

I don't blame you.

The business world trained you to perform certainty because certainty gets applause, closes deals, and keeps people calm.

But certainty doesn't get you truth.

And without truth, every decision you make is built on what people think you want to hear.
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🧠 Certainty gets applause

Here's what happens underneath all that certainty.

Your team stops bringing you real problems.
They bring you what they think you can handle.
They filter bad news.
They sugar-coat reports.
They manage up instead of speaking up.

You end up making decisions based on a version of reality that's been cleaned up for your comfort.

I know because I did this for years.

Early days at Cloudscape, I believed if I said "I don't know," my team would stop respecting me. So every question, I had an answer. Even when I didn't.

It took working with my coach Warsha to see what I was actually doing. I wasn't protecting my authority. I was suffocating my team.

And it cost me.

I made hires that weren't a fit because nobody felt safe enough to flag the doubts.
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I had clients who were unhappy at the end of projects because they were unhappy at the start and nobody told me.

The signs were there.
My team saw them.
But I'd built a room where certainty was the only language allowed. So that's what I got back.
Certainty. Clean updates.
And problems that only surfaced when it was too late to fix them.

I thought I was leading. I was making decisions with half the picture.
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🧠 Safety gets truth

Vulnerability isn't oversharing.
It's not being emotional.
It's not a therapy dump in the middle of a team meeting.

Vulnerability is saying something that gives the other person the opportunity to judge you.

That's what it actually costs.

"I'm not sure."
"I might be wrong about this."
"Help me think this through."

Three sentences.
Hardest words a founder will ever say.
Not because the words are complicated.
Because the risk feels enormous.

Inside the Part-Time CEO Council, we run every conversation on one rule: no judgment, no solutioning.
When a founder shares a fear or a doubt, nobody jumps in to fix it. Nobody raises an eyebrow. We hold space.

And every time, the same thing happens. A founder who hasn't admitted uncertainty in years finally says it out loud. The room doesn't flinch. And the real conversation starts.

You can build this in your business.
Next time a team member brings you a problem, don't solve it.
Say "tell me more about that" and go silent.
Five minutes. That's it. No fixing. No advising. No jumping in.

The first time someone experiences that from you, they'll bring you something real.
Something they've been sitting on for months.

You're still the one who decides.
You're not giving up authority.
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You're giving your team permission to help you decide well.

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Your Turn

One question: when was the last time someone on your team openly disagreed with you?

Not behind your back. To your face. In the room.

If you can't remember, you trained them not to.

Try this tomorrow:

Say "I don't know." Say "tell me more." Shut up.

🧭 Know a founder who needs to hear this?
Forward this. It could be the push they need.
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📢 Dhiren’s Updates

Quick question for any coaches in this community.

You're good at coaching. You know that. Your clients get results.

But packaging what you do? Pricing it? Selling it without feeling like a used car salesman? Delivering it without burning out?

That's a completely different skill set. And nobody teaches it.

I'm designing a live workshop for coaches who want to build their signature product. The thing you're known for. Packaged, priced, and ready to sell.

If that's you or you know a coach who needs this, reply with "WORKSHOP" and I'll share details as they come together.

📌 Dhiren’s Pick of the Week

Usually I recommend books or podcasts.

This week, I’m recommending a drink.

Iced Americano with pistachio cream from Starbucks.

I don’t know who invented this. They deserve a raise.
I’ve told everyone I’ve spoken to about it.
You’re not escaping either.
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That's me sipping on one while writing this issue. 👆

Check your local Starbucks before they rotate it off the menu.

You’re welcome.

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ps: did someone forward this to you?​
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Cheers,