Meeting with Your Manager Every 90 Days
The 90-day cadence for check-ins isn’t your typical status update or performance review. It’s more like a real conversation, a moment to reflect, realign, and think more deeply about where I’m going and what’s working (or not). And honestly? I wish more teams made space for this kind of dialogue.
Below are some of the prompts I like to use in these check-ins, and why they matter.
How am I doing, really?
This isn’t just about KPIs or timelines. It’s a conversation about what’s going well, where I’m feeling stuck, and how I’m showing up, not just in terms of outcomes, but in how I live the company’s values every day. It’s a mix of performance check-in and personal reflection.
You can ask yourself: If I gave notice today, what would the reason be? Not because you’re planning to leave, but because that prompt often reveals small things that, if left unspoken, can build into something bigger.
What am I afraid of?
It’s a vulnerable question, but such an important one. You might open up about fears of stagnation, burnout, not growing fast enough, or imposter syndrome.
Sometimes the pressure is internal, not external. Saying it out loud builds trust and usually leads to more meaningful conversations than pretending everything’s fine.
What do I want next?
This is the forward-looking part. What are my personal and professional goals? What am I working toward beyond this quarter? Revisit the goals you set last time, what you have accomplished, what shifted, and what still needs work.
Then you can talk about what’s next: projects you want to explore, skills you’re hoping to build, and how the company is (or isn’t) helping you get there.
What needs to change?
This is where things get real. You talk honestly about what’s not working, from leadership to culture.
- What would you change in the company if you could?
- What would you change in how we lead, collaborate, or communicate?
- What do you wish we talked about more often?
It’s not always easy to name these things, but it’s part of building a workplace where people actually want to stay.
Why this works
Taking time every 90 days to step back will help you feel more connected to your work and more aligned with where you’re headed. It also creates space for honest feedback, which is critical in fast-paced environments.
If you’re a manager, I highly recommend building this into your team rhythm. And if you’re an individual contributor (IC), don’t wait for someone else to create the space. Suggest it. Try it. Bring a simple agenda. You might be surprised at what comes up.
Curious to hear:
Do you have regular check-ins like this with your manager?
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