Want to lead? Ask smarter questions. Ditch the FAQ for the infrequentlyAQs instead
Most executives walk into an interview prepared to answer tough questions. But the real power move? Knowing how to ask them.
If you’re stepping into a senior leadership role, you’re not just looking for a job—you’re stepping into a system. A culture. A battlefield of expectations, competing priorities, and unspoken rules.
And the last thing you want is to realize six months in that you walked into a situation no one warned you about.
That’s why the best leaders don’t ask, “What’s the culture like?”
Because the answer will be exactly what they want you to hear.
Instead, they ask:
👉 “When was the last time leadership changed its mind on something because of employee feedback?”
Now you’re not just getting a description—you’re uncovering alignment (or lack of it).
They don’t ask, “How does the leadership team collaborate?”
They ask:
👉 “What’s something the company has been ‘talking about doing’ for years but hasn’t acted on?”
That answer tells you how power actually moves inside the company.
And they definitely don’t ask, “What’s the biggest challenge I’d face in this role?”
They go deeper:
👉 “What’s a strategy that’s worked well for you in the past but wouldn’t work here?”
Because now, you’re learning about bureaucracy, resistance, and real operational hurdles.
The Difference Between Good and Great Leadership
A good executive prepares to deliver impressive answers during an interview. A great executive prepares to ask the kind of questions that make people pause.
Why? Because when people pause, when they have to think, when their answer isn’t perfectly polished—that’s when you learn the truth.
If you ask about the company’s biggest priority, and the interviewer struggles to articulate it, that tells you strategy isn’t clear.
If you ask what makes top talent stay, and they default to “competitive pay,” it tells you retention isn’t built on engagement or purpose.
If you ask how senior leaders navigate disagreement, and they sidestep the question, it tells you conflict is avoided, not managed.
These moments matter because they signal what leadership actually looks like behind closed doors.
Operational and Strategic Clarity—Before You Say Yes
Culture matters, but so do strategy and execution. You need to understand what’s working—and what’s holding the company back.
👉 “If the company had to double revenue in three years with no additional headcount, what would need to change?”
This question reveals operational inefficiencies and growth bottlenecks.
👉 “What’s a process or system that everyone here quietly hates but hasn’t been fixed?”
You’re now learning where frustration brews and what’s stopping innovation.
👉 “What’s a decision that had to be made faster than leadership was comfortable with? How did it go?”
This tells you how the company reacts under pressure—and if agility is part of its DNA.
These aren’t just interview questions. They’re leadership due diligence. They help you understand how much power you’d actually have, where resistance will show up, and what kind of transformation is possible.
Because taking a new executive role isn’t just about the title. It’s about stepping into the right arena—one where you can actually win.
Final Thought: Flip the Script
If you’re being interviewed for a top role, assume you’re already qualified. The real question is: Is this the right move for you?
Instead of trying to prove yourself, flip the script. Make them prove that this is the kind of leadership team you want to join.
And the only way to do that?
Ask the kinds of questions that don’t just get you answers—but reveal the truth.
My best, always,
Shar
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P.S.
If you’re preparing for a leadership transition and want to make sure you’re asking the right questions, let’s chat.
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P.P.S.
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