Hi there,

You're delivering results, hitting your targets, but here's what managers like you tell me: "I sit down for a one-to-one, and it turns into a a big status review. I leave thinking, 'I should have coached them, but I’m not sure how to go about it.'"

Sound familiar?

The truth is, coaching conversations are what separate managers who get promoted from those who stay stuck. And it's not because you don't care, it's because you haven’t learned the best questions to actually ask yet.

Why This Matters for Your Career

Coaching builds trust, connection, and engagement. It creates empowered teams that solve problems themselves. And here's the thing, senior leaders notice managers whose teams actually perform.

In our increasingly AI-driven world, the ability to connect with people becomes disproportionately important. The machines can handle the data, but only managers who can develop people will get promoted to the top.

5 Questions That Change Everything

This week's video shares 5 coaching questions that will transform your one-to-ones, they work like tools in your leadership toolbox, that you can quickly reach for in any situation.

Here are the first two to get you started:

Question 1: "What does success look like for you this quarter?"

This isn't about their to-do list. This gets them thinking beyond tasks to outcomes. When someone can clearly articulate what success looks like, everything else becomes easier to prioritise.

Why it works: Instead of "I need to finish the project," they might say, "Success looks like delivering a solution that reduces customer complaints by 20%." See the difference? One is a task, one is an outcome that actually matters.

Question 2: "What's your biggest challenge right now - and what's working well?"

Notice you're asking for both the challenge AND what's working well. Most managers only focus on problems, but great coaches help people recognise their strengths too which are a lot easier to leverage.

Why it works: This gives you real insight into what they're actually experiencing, not just what you think they might be experiencing. Your job is to understand, not to immediately fix.

The Missing Piece Most Managers Never Ask

What separates the best leaders from middle managers stuck in the day-to-day is that they help people focus on what actually moves the needle, not just what feels urgent.

There are three more questions that complete this framework, including the one question that forces strategic thinking and gets your boss to notice your team's results. Plus there is free coaching guide to go with the video.

​Watch the full video here ->​

Try This Week

Pick ONE of these questions for your next one-to-one. Don't use all 5, that would feel a bit like an interrogation. Just one question, listen more than you speak, and notice how the conversation shifts from administrative to developmental.

Your team member will leave feeling heard and challenged in the right way. And you'll start building the coaching reputation that gets you noticed for promotion.

Let me know how you get on, I’m at the end of this email.

Keep leading brilliantly,

Helen

P.S. If you found this helpful, forward it to another manager who's ready to level up their coaching skills. They'll thank you for it.

P.P.S If you got this email from a kind colleague and liked it, sign up here to get weekly leadership lessons straight into your inbox.

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