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