Before You Hire a Coach for a Senior Leader, Ask These 5 Questions

(And why they’re the right ones)

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TL;DR

Coaching can be game-changing — or a complete waste of time and budget. These five questions help CEOs and CPOs vet whether a coach will actually help a senior leader lead better, faster, and with less drag on the business.

The best coaches don’t just support the person. They change how the work gets done.

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Hiring a coach for a senior leader isn’t a casual decision.
The stakes are high, and the impact—positive or negative—ripples fast.

If the fit is off, it doesn’t just waste time. It slows the business down.

These five questions come up again and again in early conversations with CEOs and CPOs.
They’re not hypothetical. They’re the ones people ask when the decision really matters.

1. Will this actually move the business forward—or just help someone feel better?

Coaching isn’t a wellness benefit. It’s a performance lever.

That means it only works when it helps a leader operate differently in the context they’re in—in ways that drive the business forward.

Often, the issue isn’t a lack of skill. It’s a lack of honest feedback. The higher up leaders go, the less truth they hear—and the harder it is to see how they’re actually landing.

That might mean helping a CSO stop talking in ways only scientists understand—and start speaking in terms investors care about.

Or working with a VP who’s made their mark as a technical expert—but now needs to operate as an enterprise leader, not just a functional one.

When those patterns shift, the business moves with them.

2. Will my executive actually listen to this coach?

This is a credibility check—and it matters.

Senior leaders don’t need a coach to make them feel good.

They need someone they’ll respect enough to let in—someone who can push their thinking, say what others won’t, and hold their own when the pressure’s on.

That might mean working with a Medical Affairs lead who’s trusted scientifically—but struggles to influence peers in Commercial or Clinical.

Or supporting a CMO under board scrutiny during a high-stakes quarter.

It helps when the coach isn’t starting from zero on the context—when they know the terrain, understand the dynamics, and can speak the language without needing a glossary.

That kind of fluency often comes from both industry experience and having led—or coached—at a comparable level. It’s hard to guide a C-suite leader if you’ve never been in the room where those decisions get made.

3. How do we balance confidentiality with alignment?

Leaders need a private space to work through challenges honestly.
But that space still has to connect to what the business needs from them—now, not six months ago.

That’s the real challenge: making sure the coaching supports the leader’s growth, reflects the company’s goals, and stays connected to what sponsors are expecting to see shift.

When alignment slips, the coaching loses traction. Either the work gets too narrow—focused only on the leader’s perspective—or too vague, with no clear tie to what matters in the business.

The right process builds alignment in from the start.
That means structuring regular check-ins between sponsor, coach, and leader—not for status updates, but to stay focused on the right outcomes.

When it’s done well, the leader gets the space they need.
And the business stays confident that the right work is happening.

4. Is this the right moment?

Coaching is most effective at points of transition or stretch.

Maybe it’s a big-pharma exec moving into biotech.
A CMO stepping into industry after a career in academia.
Or a high-potential VP stepping into enterprise scope for the first time.

In each case, the leader is capable—but the context is new, the pressure different, and the expectations higher.

That’s where coaching creates real leverage—not because the leader is weak, but because the game just changed.

5. Is this going to lead to change—or just more conversation?

Coaching that stays in abstract insight doesn’t help.
Leaders don’t need to reflect endlessly on tendencies.
They need to do things differently—where it counts.

That could mean:

• Running meetings in a new way.

• Communicating in a way that resonates across functions.

• Making decisions when there’s no script.

If those changes aren’t happening, the coaching isn’t working.

Final Thought

These five questions don’t just help companies vet coaches.
They clarify what effective coaching should actually do.

It’s not about helping a leader become someone else.
It’s about helping them show up differently in the moments that matter most—so the business gets what it needs from them.

When that shift happens, the value of coaching isn’t theoretical.

It’s obvious.

Ready to Talk?

If these are the questions you’re asking, you’re already ahead of the curve.

I built my practice around helping senior leaders make these kinds of shifts—quietly, effectively, and in ways the business can feel.

If you’re considering coaching for a high-stakes role or inflection point, let’s talk.

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