7 Prompts to Unlock Better Hiring, Culture and Performance

These questions are simple to ask, hard to answer and (sometimes) harder to hear.

Use them if you can stay quiet, really listen, and act on what you learn. If you can, they’re game-changing.

“If you wouldn’t let your daughter work for them, why are you letting others’?”

Every CEO has faced the dilemma: the leader who delivers. Smart, commercially invaluable.

But behind them... churn, distrust, quiet exits from good, capable, values-led people. (Often women,) And they’re not leaving because they’re not ambitious, but because of who they’d have to follow. Here is what they’re not saying out loud:

“I don't trust their character.”

“They're manipulative. Sometimes cruel.”

“They lead with ego, not integrity.”

“If something goes wrong, they'll throw me under the bus.”

And yet somehow, it doesn't rise to the CEO’s agenda - even when it’s dominating everyone else’s. Because it’s uncomfortable? Because they deliver? Because... maybe it’ll sort itself out? This, despite the 360s, the psychometrics, the feedback, the exits, the whistle blows. The truth is already on the table. What's missing is the will to act.

That’s when to ask this question; it clears the fog. Because we’ll tolerate more for ourselves than we ever would for someone we love.

If the answer is no, they shouldn’t be leading anyone. Culture isn’t what you preach, it’s what you tolerate.

Your best people are watching. Not what you say about values, but what you protect. If you shield poor character because it delivers results, don't be surprised when trust disappears, and your talent follows.

You don’t need perfect leaders. But you need leaders who people are proud to work for.

“If you had to find a problem with what I’ve suggested, what would it be?”

Most leaders say they want challenge, ideas, debate, people speaking up. But behaviour says otherwise. The silencing isn’t always obvious or intentional. They’re not shutting people down.

They’re just ... hard to interrupt. Maybe so compelling that people get on the bus, so creative it feels disloyal to poke holes, so intelligent no one wants to look stupid, so pacey no one wants to brake, so enthusiastic no one wants to burst their balloon. These are strengths. Unchecked, they become silencers.

If you want challenge, don't just tell them they can. Require it.

Not “Any thoughts?” Not “Do you agree?” Those invite consensus.

This demands dissent. How you respond sets the tone for whether you’ll get it again. Flinch, defend, dismiss, or punish? No more challenges! Thank them, probe, stay open - you create something rare.

You don’t need to be less compelling, creative, smart or fast. Just aware of what those strengths might suppress.

“Where do you feel clear, and where are you guessing?”

Be honest, how many times have you said “over to you” ... and then quietly braced for the rewrite? It’s not that the work is terrible. It just comes back, well different. Not what you pictured, not quite what you meant. And the team aren’t at fault; they nodded, smiled, left the room, and then had to reverse-engineer what you actually wanted.

So they guess. They second-guess. They make assumptions. And you end up fixing things no-one knew were wrong in the first place. That’s not delegation - that’s outsourcing the guesswork.

This question surfaces friction before time gets wasted. It lets your team admit what they don’t know without looking incompetent. And it saves you both from the slow erosion of trust that comes when clarity is missing.

Clarity isn't overkill; it's a performance advantage.

“Is this your best work?”

You assign a task, step back, and get underwhelming work. You fix it. Next time, they try less - why bother if you'll redo it? A silent deal forms: deliver “good enough,” and you’ll patch it up. This leads to disappointment and lowers standards.

The fix? Before accepting work, ask this question. Say it without sarcasm. Just calm, clear, curious. You’ll learn two things immediately:

1.     Whether they own the output

2.     Whether they know what good looks like

It shifts the quality bar from your standard to theirs. Not “Will I approve it?”, but “Will you stand behind it?”

If you keep finessing things behind the scenes, you’re not helping. You’re enabling a loop of dependency, resentment and underperformance. Great teams aren’t built through rescue; they’re built through responsibility.

“Whose voice is missing from this decision?”

Most decisions fail not because the thinking was wrong, but because it was narrow.

Smart people in a room. Well-intentioned, experienced and aligned on a goal. But something gets missed: the client’s reality, the employee experience, the person who will have to execute it, the view that challenges your own. And that gap is where risk lives.

So before you charge ahead, ask: who isn’t here? Or even: who are we not hearing from, even if they are?

If the missing voice is always the same - junior staff, your customer, the only woman in the room - that's not a gap, that's a pattern.

“What’s one thing that’s making your job harder than it needs to be?”

Most teams don’t fail because they’re lazy or incapable. They fail because they’re quietly battling systems and habits that make good work unnecessarily hard.

The fourth sign-off on simple comms? A sacred but pointless meeting? The “urgent” presentation that’s never used?

Everyone knows it’s ridiculous. No one says it. This question signals trust without therapy sessions, invites feedback on systems (not people), catches the small stuff before it becomes resentment and flips from “how can you improve?” to “how can we stop making it harder?”

Once you’ve asked, don’t defend, don’t explain - just listen. The answer tells you where the friction is. Fixing friction is faster than another away day.

“What role have you played in creating the culture you don’t like?”

We run a lot of executive team days, and when the topic is culture, the pattern is almost always the same. People are quick to name what's not working:

“There's a lack of trust.”

“Too many side conversations.”

“Not enough challenge.”

“We're tolerating mediocrity.”

“It's not safe to speak up.”

All true. And then, at the right moment, we ask this question, and the room goes quiet.

Because the truth is, this isn't someone else’s culture - it’s yours. Even if you didn’t cause it, you’ve likely enabled it.

This question matters because it forces a shift, and that’s where change starts. You can’t build a better culture without holding a mirror up to the people shaping it (especially the ones at the top). Because naming the problem isn’t leadership; owning your part in it is.