Check-ins are like dates.
- Andrew Daub
- Mar 31
- 2 min read
Updated: Apr 21

Two people coming together, having a conversation, trying to make sense of things and figure out what’s next - all with their own exact, at times hidden alchemy of preferences and past experiences.
And, given that it’s work, given that there is power in the room (even and especially when not acknowledged), given that we’re bringing different identities, lived experiences, and relationships with power, it’s important to pause and establish a strong foundation, together. To share what we expect from one another, what we like, and what we don’t like.
There’s a lot that goes into this. I’m a particular fan of Priya Parker’s work on gatherings, including the importance of centering in purpose and leveraging ritual. Trust and psychological safety are also key to nurturing a strong, healthy, human relationship so that check-ins in turn are also strong, healthy, and human.
And, where do you even start?
I find good conversation can spring from just a circle and pen. All you have to do is…
✏️ Draw a circle. Simple, right?
⭕ Inside the circle, put the specific things you want in an ideal check-in. What do you want to experience? What do you want to do and feel each time you meet?
⏺️ Outside the circle, put the specific things you don’t want in an ideal check-in. What do you not want to experience? What do you want to avoid? What are the dealbreakers?
✅ Share your circle with your colleague and have a conversation. If you're a manager, consider how you show up - how much airtime you take, how much presence your preferences occupy, how you honor the other person's wants, needs, dreams, fears, and expectations.
🟣 Talk about what you have in common. Where are there similarities? How do we want to honor those shared preferences?
🔵 Talk about where things diverge. Where are there differences? How do we want to honor or adjust any of those individual preferences?
🟡 Anticipate the future. Where are things in conflict with one another? How do we want to reconcile those differences, and how might we respond if we find ourselves butting up against one of these gaps in our preferences?
Of course, putting things to paper doesn’t just make things a reality. It takes more work to deepen and preserve trust, and to turn a shared vision into regular practice. But taking time to pause and clarify what we want most in how we work together can ensure that we’re able to speak a shared language, operate with similar expectations, anticipate potential conflict, shift power, and co-construct how we do our work together.
Here’s an example of how I’ve filled out my circle - so swipe right if you also are not a morning person or someone who wants to check in on a Friday…