Dear CEO

5 Questions That Might Haunt You.

What if the people in your company could ask you one honest question about how you lead?
Would you want to hear it?

Now flip it — what are the questions you should be asking yourself?
Not the leadership book ones.
The real ones.
The ones that sit in the back of your mind when it’s quiet…
and no one’s watching.

With thousands now reading this newsletter — many of whom are CEOs, founders, and senior leaders — I thought:

What if I put some of those questions out there?

Not for judgment. Not for show.

But because in this climate — with everything people have endured and the culture cracks growing louder —
we don’t need more performance metrics.
We need more bravery.

I’ve spent two decades in and around leadership —
helping people grow, watching companies shift, and seeing first-hand what happens when leadership gets it right… and when it doesn’t.

And here’s the truth no one wants to say out loud:
Most people no longer believe leadership at the top will ever truly change.

They’ve seen too many cycles.
Too many reshuffles.
Too many moments where doing the right thing got buried under performance pressure, politics, or personal preservation.

They’ve learned:
As long as the results are strong, the system tolerates the cost.
Even if that cost is toxic behavior.
Even if the culture is cracking.
Even if belief is quietly dying.

But I still believe something else is possible.
I believe we can win — and still do it right.
I believe you can lead with strength, conviction, and care — and walk away proud.

But Only If You’re Willing to Ask the Right Questions

The kind of questions you don’t ask in a boardroom.

The kind you sit with alone — early in the morning, late at night, or in the silence between quarters.

Not to impress anyone.
Just to know — deep down — that you’re living and leading in a way that would make the people you care about most… proud.

1. When I say people matter — have I backed that up in who I’ve rewarded, promoted, and protected?

Your team watches what you tolerate.
They see who gets the benefit of the doubt.
They know what gets rewarded — and what gets overlooked.

Culture isn’t built in slide decks.
It’s revealed in decisions — especially the quiet ones.

2. Have I created the kind of place I’d want my own child to work in?

Not for the brand name. Not for the salary.
For the experience.

Would you want your son or daughter to report to one of your leaders?
To navigate the politics, pressure, and priorities you allow?
To spend years of their life inside the system you shaped?

3. Have I been brave in my leadership — or just careful enough to survive?

Because playing it safe is easy.
So is staying quiet, looking the other way, or protecting your reputation while others take the hit.
But if you’ve never risked anything to do what’s right —
don’t fool yourself. That’s not leadership. That’s self-preservation.

4. Have I made it easy for people to tell me the hardest thing they need to say?

Because if they can’t…
You’re not leading. You’re commanding.

And no amount of pulse surveys will ever fix what fear keeps hidden.

5. If the people I love most — my spouse, my kids, my parents — saw every decision I made as a leader… would they be proud of how I treated people?

Not the strategy.
Not the speeches.

But the moments I chose belief over fear.
Humanity over politics.
Bravery over self-preservation.

Let That Last One Sink In.

Because legacy isn’t what you say about your career.

It’s what others say — the people who worked under you, and the ones who watched how you moved through the world.

Your most cherished relationships… they know your character.
And whether you meant to or not, you’re leading in a way that tells them something about who you are.

So ask yourself:
Would they be proud?

The Real Bottom Line

Leadership is the single most powerful force in any organization.
It shapes futures. It builds belief.
Or it breaks both.

And at some point, we all have to decide:

Is it enough to win the game?
Or will I care about how I played it?

Because you can rise fast, win big, and still lose your way.

But you can also lead with strength, integrity, and heart —
and still build something extraordinary.

Something that performs.
Something that matters.
Something that means something.

That kind of leadership is rare.

But it’s possible.
And it’s worth it.

So, dear CEO… what will it be?
And what will you do — today, tomorrow, and every day after — to lead in a way that you, and the people you love, would be proud of?

With Absolute Sincerity,

Ed Clementi, Founder & CEO of Inspired Fire, LLC

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