How to have meaningful conversations: A guide for leaders
When’s the last time you had a truly meaningful conversation with someone at work? Not a status update. Not a WIP review. A real conversation — the kind that made you feel seen, heard, and supported.
According to a recent Gallup study among nearly 15,000 employees, only 16% said the last conversation with their manager was extremely meaningful!
Yet when those conversations do happen, the impact is powerful: employees who receive meaningful feedback weekly are more than twice as likely to be fully engaged.
And engagement directly correlates with productivity, retention, innovation and wellbeing. It’s not a nice to have, it’s mission critical.
Gallup’s long-standing research, based on meta-analytics of 100 million employee interviews, shows that 70% of the variance between highest engaged teams and persistently disengaged teams is the manager.
They found that great managing is an act of coaching (rather than directing or bossing).
So why aren’t more managers doing it?
Because it requires time, patience and intent. It’s not passive. It’s active engagement in your people’s development. And, most managers have never been taught how to do it well.
This guide gives you a practical framework to be more intentional about feedback and the conversations you’re having with your team members.
A practical framework for meaningful conversations
So, here’s a guide to
🕒 Time: 15–30 minutes
🔁 Frequency: Weekly
👥 Style: Informal, one-on-one
Focus areas:
Genuine recognition or appreciation for recent efforts
Acknowledgement of their strengths/what they do well
Goal check-ins and support needs
Help connect them with the right team members for collaboration and support
Encouraging their voice: ideas, concerns, questions
Wellbeing
Conversation starters:
How have you been feeling — in and out of work?
What’s energising you lately, and what’s draining you?
What’s been the highlight of your week so far?
What’s something you’re proud of that I might not have seen?
Do you feel like you have what you need to do your job well right now?
Is there anything blocking your progress or slowing you down? How can I help?
What’s something you'd like to explore, learn, or try in the next few months?
Which of your strengths have you been leaning on the most lately?
Where do you feel your strengths might be getting in the way?
What they are
When approaching meaningful conversations it’s easy for us to slip back into what we know, but it’s important that they don’t become status updates or project tracking meetings.
✅ A check-in on how your team member is feeling and doing.
✅ A chance to celebrate what’s going well.
✅ A way to show you care.
✅ A space for listening to ideas, challenges and aspirations.
✅ An opportunity to connect them with the right people and resources.
These are relationship-building moments — and they compound over time.
What they’re not
❌ Working meetings
❌ WIPs
❌ Task checklists
❌ Opportunities to offload your to-do list
❌ A balancing act of equal critue and praise (true coaching means leaning heavily into what your people do best)
They are not transactional. They are relational.
Using your superpowers to drive better conversations
These conversations may feel small — but they’re not. They are the quiet, consistent moments that build trust, engagement and loyalty.
And here’s the twist: you don’t need to become someone else to have better conversations — you simply need to leverage your own superpowers.
For example:
If one of your top CliftonStrengths talent themes is Analytical then you seek to understand how things work — you like data, patterns, evidence, and logical thinking. In conversations, this can be incredibly useful for bringing clarity, cutting through emotional fog, and helping team members make sense of challenges. You might use it to:
Look for patterns in your team member’s behaviour or performance over time and use those as a basis for reflection.
Offer insights that separate fact from assumption — helping them focus their energy where it counts.
Or, if you have Maximizer in your top 10 talent themes you are naturally talented at seeing areas for greatest potential. You can use this superpower in conversations to be inspire, energise and focus on amplifying your team member’s strengths. You might use it to:
Celebrate excellence: pointing out what your team member does exceptionally well, not just what they do adequately.
Coaching toward quality, not quantity — helping people focus effort where they can have the most impact.
You don’t need a script to be a great coach. You need presence, curiosity, and a willingness to use your strengths — not just to perform, but to connect.
Because leadership isn’t about holding power — it’s about creating possibility.
Ready to have better conversations?
Whether you're new to people management or ready to deepen your impact, our leadership coaching can help you tap into your strengths and grow the kind of culture where people thrive.
Get in touch to learn more about 1:1 leadership coaching or tailored programs for your team.