30 Questions Great Leaders Ask Their Teams
- Nancy Maher
- 6 days ago
- 5 min read
Updated: 2 days ago
"If you can build a culture where people listen to one another, they will start to fix things you as the boss never even knew were broken" - Kim Scott, Radical Candor
Great leadership starts with great questions. Through our work, we’ve seen how thoughtful dialogue shapes workplace culture for the better.
If you want to influence your team’s culture, generate trust, create ownership and unlock growth, start by asking the right questions.
Don't know where to start? We've got you.
We've compiled a list of 30 questions great leaders ask their teams and grouped them into leadership conversation themes.
Contents
The Impact of Leaders Who Ask
Leaders set the tone for team culture. When you ask open questions, you invite everyone to contribute, learn, and feel ownership. This leads to higher employee engagement, better performance, and stronger, more adaptable teams.
70% of team engagement is determined solely by the manager or team leader - Gallup
We believe that the best leaders focus more on asking than telling.
When leaders ask instead of tell, they show trust, encourage autonomy, and help teams become stronger and more resilient. This approach is at the heart of must-read leadership books such as Radical Candor, The Fearless Organization, The Coaching Habit, and Unleashed. Leaders who ask good questions help teams feel heard and valued. This builds psychological safety and drives better results.
👉 Check out our 25 Must-Read Leadership Books 2025 for more recommended reading 📚
30 Questions Great Leaders Ask Their Teams
These 30 questions span key themes – from showing that you care personally to encouraging experimentation as well as supporting individual ways of working. Use these as conversation starters in meetings or one-on-ones to spark dialogue, align priorities, and foster a stronger workplace culture.
🔍 Care Personally
Opening up human-to-human conversations is the foundation of great team culture. When leaders take an interest in their people as individuals, rather than just employees, trust grows. This is supported by workplace culture statistics, which show that meaningful conversations are crucial to employee engagement. By tuning into individual needs, leaders create workplaces that work for everyone.
Questions to ask:
How can I support you to do your best work?
What’s one thing we could change to help you feel more comfortable and supported at work?
How do you prefer to receive support - hands-on guidance, a sounding board, or space?
What does "doing your best work" look like for you right now?
What part of your role feels most energising - and why?
🔬Encourage Experimentation
Curiosity is fuel for growth. Great leaders ask questions that encourage experimentation and innovation. If teams feel that "failure" will have repercussions for them, they won't challenge the status quo. This limits your chance of innovation. Leaders who role model a continuous improvement approach build innovative cultures.
HBR reports how Jensen Huang, cofounder and CEO of Nvidia has highlighted the importance of asking questions. "Through probing, I help [my management team]…explore ideas that they didn’t realise needed to be explored."
Questions to ask:
What’s possible here that we haven’t tried yet?
What would you try if you knew you couldn’t fail?
And what else?
What’s something we might be missing?
What’s a risk worth taking together?
🎯 Clarify Direction and Goals
Clear direction and knowing how your work contributes to shared goals transforms team performance. Experience tells us that when leaders are clear on direction, remove blockers, and listen to what people truly need, employee engagement and results improve.
Questions to ask:
How can I create more clarity for you?
What’s one decision you’d like me to make (or unblock) so you can move forward?
What are you saying "yes" to that might be distracting you from what matters most?
What’s unclear or ambiguous about your current priorities?
What’s one thing you’d like to improve about your work?
👏 Evolve Team Culture
Team culture doesn’t happen by accident – it’s shaped by the way we work together. Healthy cultures are intentional: they prioritise effective collaboration, constructive feedback, and meeting habits that drive progress. Strong team cultures are linked to higher productivity and lower staff turnover.
Questions to ask:
How do you like to be recognised for your contributions?
What’s one small ritual or practice that would build more connection on this team?
What’s one thing we could do to improve how we work together?
How can we make team discussions feel safer and more open?
How do you prefer to give and receive feedback?
💬 Champion Inclusion
Inclusive leadership creates cultures where everyone’s voice matters. Time and again, we’ve seen the impact of inclusive culture work in transforming teams. McKinsey highlights that diverse organisations are better at attracting and retaining talent, decision-making and driving innovation.
Questions to ask:
What helps you feel included and valued here?
Is there anything about our culture or processes that makes it harder for you to contribute?
What’s one thing we could do to make our team more inclusive?
Are there any barriers you’ve noticed that we could remove?
How can we better support each other’s unique backgrounds and experiences?
🌱 Support Career Growth
Knowing that your boss cares about your future career is motivating. These questions help surface aspirations, hidden strengths, gaps, and opportunities in a way that empowers people to take ownership.
Questions to ask:
What is your hope for the future?
What’s one thing you’d like to learn this year that could accelerate your growth?
What’s one responsibility you’d like to try outside your current role?
If you could shadow someone for a month, who would it be and why?
How can I best support your career growth?
Why These Questions Matter
They build trust and psychological safety: People do their best work when they feel safe and heard.
They drive inclusion: Everyone’s voice matters, and different perspectives make teams stronger.
They support wellbeing: Understanding needs helps prevent burnout and supports employee wellbeing.
They encourage ownership: Empowering teams to experiment and come up with their own solutions increases ownership.
To Sum Up
Great workplace cultures aren’t accidental - they’re built with intention, curiosity, and action. Having regular check-ins with your team, supporting them on both their everyday tasks and long-term career aspirations, creates a great workplace culture and is beneficial for the business.
