65% of startups fail due to co-founder conflict, largely because trust and commitment between founders often get lost amid the endless to-dos and chaos of building a company. As trust erodes, co-founders can become less in sync, leading to unpredictable behaviors and surprise reactions that undermine the partnership. I spoke with Annie Garofalo, an expert in preventing co-founder conflict, about the “Weekly 20”- a weekly ritual she recommends to manage co-founder conflict.
What is the Weekly 20?
“Weekly 20” is a dedicated, 20-minute conversation between co-founders focused solely on their partnership. This regular check-in is designed to keep trust strong and prevent issues from festering.
Schedule it weekly (ideally on Monday or Friday).
Keep it brief and consistent — it’s about maintenance, not crisis management.
Missing too many sessions can be a warning sign; agree up front how many skips are allowed and hold each other accountable
The Three-Part Agenda
Each Weekly 20 follows a simple structure, with both co-founders taking turns on each part:
Appreciation: Start by sharing something you genuinely appreciated about your co-founder in the past week. This could be a work-related gesture or a personal kindness, helping to ground the conversation in trust and positivity.
Micro Frustration: Next, each person names a small frustration — not a major issue, but something that might otherwise go unsaid. The goal is to practice raising minor concerns before they become bigger problems, without blame or defensiveness.
Support Request: Finally, ask for support in a specific area. This should be personal or leadership-related (not just a tactical business task). For example, you might ask your co-founder to help you stick to a gym routine because it helps you perform better at work
What the Weekly 20 Is and Isn’t
The Weekly 20 is a space for routine maintenance, not for airing existential or high-stakes conflicts.
If a major concern arises, use the session to flag it and schedule a separate, longer discussion.
The goal is to make these meetings something you look forward to — a time to reconnect, not to dread.
When to Seek Outside Help
If these sessions start to feel unproductive or become dominated by major conflicts, it may be time to bring in external support. This could mean working with a facilitator, mediator, or participating in a structured partnership agreement program to reset the relationship and communication habits
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