70 Coaching Questions to Elevate Your 1:1 Conversations

Most 1:1s are well-intentioned—but too often, they stay surface-level.
Task updates, status checks, a few polite nods... then back into the daily churn.

But great 1:1s? They’re something else entirely.

They unlock trust, spark motivation, build clarity, and re-energise your team members toward what matters most. They create space for meaningful reflection, bold ideas, and aligned action.

I’ve been helping leaders shift from “check-in mode” to “coaching mode” for over 20 years through 1:1 coaching and leadership programs.

In my Elevate in 90 Days Leadership Program, we dedicate an entire lesson to conducting powerful 1:1s—because when done right, these conversations become a cornerstone of purpose-led leadership.

To help you elevate your own 1:1s, here are 70 coaching-style questions to bring out the best in your team members.

 

🔹 Clarity + Direction

These questions help uncover alignment, confusion, and deeper career aspirations:

  • What’s feeling clear in your role right now—and what’s not?

  • What parts of your role feel most aligned with your strengths?

  • What does “success” look like for you with your career/this year/this quarter?

  • Where are you spending the most energy—and is it where it matters most?

  • What would a more purposeful version of your role look like?

  • If your role was 10% more fulfilling, what would be different?

  • Where do you feel you’re making your greatest impact?

  • What feels off-track or out of alignment right now?

  • What’s one part of your role that drains you—and why?

  • If you could redesign your role tomorrow, what would change?

 

🔹 Growth + Possibility

These help uncover stretch goals, new skills, and bold thinking:

  • What’s one area you’d love to grow in this year?

  • What would challenge you in a good way?

  • Where do you feel like you’re holding back?

  • What’s one skill you’d love to develop—but haven’t had the space for?

  • What stretch assignment would excite you?

  • If you had more confidence, what would you pursue?

  • What kind of leader (if relevant) do you want to become?

  • Where do you want to feel more empowered?

  • What feedback would help you grow right now?

  • Who do you admire professionally—and what can you learn from them?

 

🔹 Momentum + Action

These are about moving forward with clarity and purpose:

  • What’s one decision you’ve been avoiding?

  • Where are you stuck—and what would help you get unstuck?

  • What’s one action that would move things forward right now?

  • What’s something small you could complete this week that matters?

  • Where can we remove friction or blockers for you?

  • What’s been on your mind that we haven’t talked about yet?

  • What are you procrastinating on—and why?

  • What support or resources do you need to move forward?

  • If nothing changes in the next 6 months, how will that feel?

  • What would momentum look like in your week ahead?

 

🔹 Purpose + Values

Questions that connect people back to what really matters:

  • What energises you most in your work?

  • What do you want your work to mean?

  • What impact are you proud of recently?

  • What values guide your decision-making?

  • What kind of difference do you want to make through your role?

  • What lights you up about your career?

  • Where do your strengths meet the business needs?

  • What kind of legacy do you want to leave in this team?

  • Where do you feel most aligned with your purpose?

  • What’s your bigger ‘Why’ right now?

 

🔹 What support do you need to be at your best?

These questions invite reflection, unlock honesty, and strengthen the two-way trust that’s essential in great leadership:

  • What kind of support helps you show up at your best?

  • Is there anything that's frustrating you or getting you down that you'd like to share?
  • Where do you feel stretched too thin, and what would help?

  • What do you need more of—or less of—from me as your leader?

  • What would help you feel more confident navigating current challenges?

  • Where are we unintentionally making things harder than they need to be?

  • What’s one thing I could shift to better support your focus, energy, or growth?

  • What boundaries or flexibility would help your work feel more sustainable?

  • Where do you feel disconnected from the bigger picture or the team?

  • What conversations do we need to have more regularly?

  • What’s one thing that would make your day-to-day feel more energising?

 

🔹 If you were in my shoes…

These questions invite upward insight and shared ownership of the team or culture:

  • If you were in my shoes, what would you do differently right now?

  • What would you prioritise or explore that’s not currently on our radar?

  • What would you change or communicate to better align the team?

  • What needs addressing that may have been overlooked or avoided?

  • What would you do to help the team feel more connected, focused or empowered?

  • If you were leading this team tomorrow, what’s the first thing you’d do?

 

🔹 Ask me anything

These questions open the door to curiosity, transparency and deeper conversations:

  • What question do you wish I’d ask—but haven’t yet?

  • What’s one question you’ve always wanted to ask me?

  • What’s something you’ve been wondering about our team, strategy or direction?

  • What do you think I might not be seeing that’s important to address?

  • Is there anything you’re holding back that we should talk about?

 

Want to go deeper?

If you’re ready to become a more intentional, coaching-style leader who leads with purpose, clarity and energy—I'd love to support you.

In my Elevate in 90 Days Leadership Program, I provide tools, templates and coaching frameworks to help you have more meaningful conversations, grow your people, and make a lasting difference as a leader.

👉 Explore Elevate in 90 Days Leadership Program

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