THE CONFESSION:
“Lately I feel like I can’t do anything without running it past my Co-Founder.
I know they care and want visibility, but it just feels like they’re second-guessing everything I do. I feel monitored, and it’s impacting my confidence.
It’s like I’m spending more time going through everything with them, than actually doing the work.”
This is such a common pain point, and whilst it can seem like this is about control, the themes I often find underlying this sort of situation are clarity, trust, and pace.
A few things to think about here:
1. Intention and perspective
Sometimes “checking in” is framed as collaboration, but received as micro-management. Naming this gap is powerful.
So ask: “When you check in with me, what are you looking to get from it?”
”Here’s how it feels on my side…”
”How could we make this feel more collaborative?”
You might find that one of you is looking for reassurance or connection, while the other is receiving it as doubt. It’s all about intention and perspective.
2. The stage of the business
At early stages, founders are in everything together. But as you grow, the need shifts from visibility on every decision to clarity on ownership and outcomes.
If your partnership hasn’t reset, the same habits that were strengths in the early stage can become friction points when you scale. It’s time to look at roles and responsibilities, and your decision making processes.
3. Your own patterns at play
Notice what this checking dynamic stirs up in you personally. Is it just about pace and autonomy? Or does it touch something deeper - like self-worth, not feeling trusted, or fear of making mistakes?
Triggers often show up in disguise, so part of the work is teasing them apart.
Owning that means you’re not making your Co-Founder responsible for your feelings. They’re yours to understand and navigate, and that ownership creates space for a clearer, calmer conversation.
4. Redesign your accountability systems
Instead of ad hoc monitoring, design structures: weekly check-ins, clear reporting lines, agreed ways to share updates.
When you both agree on these processes, it stops feeling personal, aligns expectations, and boosts productivity and confidence.
This shift is part of your business growth and highlights how effectively you communicate and resolve challenges together - see it as an opportunity to level up your partnership. And if self-doubt still creeps in with new systems in place, it’s a cue that it’s less about your Co-Founder and more about your inner narrative - something everyone needs to work on as they grow as a leader.
A QUESTION FOR YOU ALL TO ASK YOUR CO-FOUNDERS:
“HOW WELL ARE OUR ACCOUNTABILITY STRUCTURES SERVING US RIGHT NOW?”
This edition was published on the 22nd August 2025