Co-Founder Monthly Check-In Guide
Why do co-founder monthly check-ins?
It is a healthy and proactive practice to schedule regular check-in meetings with your co-founder. The goal is to take a pause from the hustle of building to reflect on how you are doing being teammates and partners to each other.
If we don’t bring stuff to the surface, we run the risk of assumptions and bad feelings creeping in and eroding trust. When we surface misunderstandings or misalignments frequently and process them, we’re more likely to build a positive and productive collaboration.
You can have these conversations alone or invite a third party, like a coach, to facilitate the check-in meeting for you. The benefit of having a mediator join is that you both get to fully participate. Sometimes it’s also really valuable to have a trained facilitator share observations and offer a neutral perspective to help you and your teammate learn from the past and improve how you work together moving forward.
The process:
It’s smart to have a co-founder check-in meeting at least once a month. Spend some time at least one day before the check-in meeting reflecting on how this past month has gone and write down some reflections so you can make the most of your time together.
Agree on the Questions
It’s a great practice to agree on the questions you will discuss ahead of time so you can have a game plan and structure for the conversation. It is helpful to have the same questions every time so you get used to this routine and habit. Of course, you can modify and add questions as you see fit. It’s nice to keep your notes in the same folder or in one long document so you can look back and see patterns over time as well.
Discuss Process
Depending on your preferences, you can share your notes ahead of time to allow the other person to preview the content - or you can save the notes and use them to help you during a live conversation. It’s a good idea to have this process conversation ahead of time - some people get extremely nervous walking into a conversation without some mental time to prepare for what’s coming.
Reflect in Advance of Your Meeting
Here are some questions you may want to consider discussing together:
Successes
Share a success you’ve had this past month.
Share a success that your co-founder had this past month.
What was a success that the company or team had this month?
What is one way that your co-founder helped you or supported you this past month?
What would you like for your co-founder to keep doing this month that’s working really well?
What do you want to keep doing as a team, because it’s working really well?
Challenges
What was a challenge you faced this past month?
What was a challenge your co-founder faced this past month?
What was a challenge your team or the company faced this past month?
What would have helped you overcome these obstacles more effectively?
What do you want to try to do differently as a team in the future, based on our learnings from the challenges you faced this past month?
Coming Up
What do you anticipate will be hard or challenging this coming month?
How do you think you will overcome them?
Do you have any requests for help and/or support from your teammate?
Next Steps
What are some next steps we might want to take to help us make progress?
Make an Action Plan
At Founder to Leader, we have a bias towards action, so we always love leaving meetings with concrete and clear next steps. What do you want to do more of? Do less of? Try differently? How will we check in on how these changes are going? A month is a long time in any start-up so think about when and how you want to experiment as co-founders and align on what that looks like.
Wrapping Up: How’d We Do?
Not to get super meta on you, but it’s always healthy to talk - at the end of a hard conversation - about how that felt. What was hard for you? What felt vulnerable? How do you feel now that you’re wrapping up? You don’t need to do a wild deep-dive into your feelings but part of this co-founder check-in process is figuring out how your partner (or partners) operates; asking these questions is one way to keep deepening your understanding of each other and keep the door open for sharing insights and requests.