If your check-in meeting feels like a status update, you’re doing it wrong.
Executive Summary
Your one-on-one check-in meetings should NOT be about micromanaging your employee. Instead, they SHOULD be about co-creating momentum. As a result, leaders who use their check-in meetings as coaching moments are able to meet the unique and context-specific need of the individual sitting across from them. Check-in meetings can shift an employee from apathy to engagement, from confusion to clarity, from disappointment to hope.
How to Improve Your Check-In Meetings:
- Let them lead. The employee owns the agenda: what’s working, where they’re stuck, and what they need.
- Then You listen. Ditch the advice-fest and lean into Inquiry Over Advocacy. Ask before you answer.
- Connect it back. Help employees see how their efforts tie to the larger change vision or organizational strategy. This small effort is all it takes to show the employee how to build meaning (which will sustain them through work challenges more than reviewing metrics).
- Follow through. A quick recap email does more than document. It shows your employee, “I heard you.” It also gives you something to reference, so you can be sure to follow through on any tasks or action items you took on. You can also reference it for brief check-ins before your next check-in meetings (How’s “x” going?).
When leaders start coaching this way, they don’t just get updates, they get insight, alignment, and buy-in…and THOSE are the experiences that build a strong culture AND will make change stick.
7 Steps to Making Check-In Meetings a Powerful Change Management Tool
Let’s be honest: one-on-one check-in meetings in corporate life can feel like one of those things you have to do…that are really just calendar clutter, pulling everyone away from the real work that needs to get done.
But here’s the truth: in times of change, those 30 minutes are gold because they’re your front-row seat to what’s really happening beneath the surface, what people feel, not just what they do.
When done right, a one-on-one becomes your most powerful change leadership tool. It’s where trust gets built, resistance gets decoded, and your culture shifts one conversation at a time.
1. Redefine the Purpose
In change-intensive environments, your one-on-one check-in meetings aren’t just performance check-ins; they’re sensemaking sessions. So a great change leader uses them to:
- Surface hidden resistance or fatigue
- Reinforce meaning and connection to purpose
- Clarify shifting priorities and expectations
- Co-create small next steps that maintain (or start/re-start) momentum
Your leadership role moves from task review (THIS is the activity that leaves you both thinking your check-in meeting could have been an email) to trusted translator between the employee’s lived experience and the organization’s change vision.
2. The Employee Leads the Conversation
To build ownership and accountability, employees should come prepared to share:
- Successes: What wins (large or small) they’ve had since the last check-in.
- Work in Progress: What they’re focusing on and how it connects to broader change goals (don’t skip this part!).
- Where They’re Stuck: Obstacles, ambiguity, or emotional blocks.
- What They Need: Specific asks for tools, clarity, or leadership support.
Change Management Lens: This aligns with the Prosci ADKAR model, particularly the Knowledge and Ability stages. You’re teaching employees to self-diagnose what they need to succeed.
3. The Leader’s Job: Listen Like a Coach
In OCM, listening is a strategic act. Therefore, you need to:
- Use Inquiry Over Advocacy: stay curious longer before offering solutions.
- Reflect patterns: “I’ve noticed you’ve mentioned uncertainty about X the last two meetings. What’s behind that?”
- Validate resistance as information, not defiance.
- Use coaching language: “What feels hardest about that?” instead of “Why haven’t you done that?”
Change Management Lens: Every time a leader listens well, it then builds the Desire and Reinforcement stages of ADKAR. And this is where psychological safety and trust are reinforced.
4. Then Ask Change-Focused Questions
Beyond the operational, weave in reflection that connects to the change journey:
- “What feels different about your work since the change started?”
- “Where are you seeing progress?”
- “What are people not saying out loud?”
- “How do you think your peers are experiencing this?”
- “What would make this transition easier for you or your team?”
These questions create feedback loops that help leaders spot risks and resolve challenges early.
5. End With Empowerment
Close each conversation with:
- “What’s one thing I can remove from your plate or clarify?”
- “How can I better support you so you can be successful?”
(Leadership Tip: Some employees may need examples of what this could be if they are either high-performing autonomous performers or haven’t had supportive leaders in the past). - “What’s one commitment you want to make before our next check-in?”
This creates shared accountability and reinforces the “we’re in this together” mindset that sustains change.
6. Document and Reinforce
Finally, follow up with a short email:
- Summarize key points (successes, focus areas, asks, and commitments)
- Thank them for their openness
- Note how their efforts tie back to the larger initiative
Why it Matters: The written recap is both psychological reinforcement and your audit trail for adoption tracking. It signals attentiveness, builds trust, and reduces misalignment.
7. Coaching Assignment for Change Leaders wanting to Level-Up their Leadership
Then, in between check-in meetings, leaders should reflect on the following:
- What themes am I hearing across my team?
- What barriers are within my control to remove?
- How am I modeling the change I’m asking for?
Follow-Up: Leaders should bring these reflections to their own check-in meetings with their leaders and change management staff, including identifying some potential action they plan to take in response to these reflections.
Final Thoughts: “Less Manager, More Mirror.”
Great leaders don’t just direct. Great leaders reflect. They help people see themselves in the story of change. Every one-on-one check-in is an easy opportunity to listen deeply, ask better questions, and model the kind of curiosity that turns skeptics into supporters.
You don’t need a change management framework to make your check-in meetings meaningful.
You only need presence and empathy. And maybe a little courage to stop talking so much. Because real change doesn’t happen in a mass email or a leadership offsite. It happens one conversation at a time, between two people willing to get real.
