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.
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?
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?
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?
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?
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?
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?
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?
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?
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.
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