Cofounder Alignment

There’s one relationship that—if you let it sour—often kills startups: the cofounder pair (or trio+).

I made SO many mistakes with my cofounder, but I’m called to share my lessons because ultimately I think we had a strong relationship.

Jeff & I bonding over food (as usual!)

My cofounder at Chewse, Jeff Schenck, is an amazing person through and through. He is one of the major influences in my leadership and life. His vulnerability, flexibility to work any job, genuine curiosity, and kind heart shaped me forever. I guess this is a bit of an ode to him.

These principles also scale beyond your cofounder. I was able to use them effectively with my COO, Aakash Mathur, who also shaped me. He is one of the greatest problem solvers I’ve ever worked with, and I will always be grateful for his ability to embrace a love culture while bringing excellence.

My personal entrepreneurial story is built on the deep connection I shared with my co-founder and COO – that dynamic doesn’t just happen; it’s carefully crafted through a deliberate set of actions and mindsets.

This post is a practical application for how to help cofounders and CEO-COO pairs find their aligned groove. Finding product-market fit is hard enough, finding cofounder fit is even harder.

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Principle of Super Alignment

When you hear the story of a company’s success, the product, strategy, and fundraising often gobble up the headlines. What’s rarely discussed is the rock-solid alignment between the co-founders at the helm.

The bond between startup co-founders is almost spiritual. It’s not just about running a business; it’s about negotiating the vision, merging cultures, and ultimately creating magic. How do you turn two people into a single, united force?

Super alignment is the ideal state between the cofounders. It’s a state of transparent, open alignment that is forged out of deliberate discussion, honesty, and authenticity.

Like any partnership, cofounder alignment is fluid. It can be built or lost in a matter of days or hours. That means its always yours to gain or lose.

I believe there is no neutral relationship with your cofounder: it’s either good or bad. While this feels binary, it highlights the need to continually stay aligned. Because even 2% misalignment on a Monday can become 30% misalignment by Friday given the speed of startups.

We’ll walk through four key steps to fortify your alignment.

1. The Weekly Alignment Meeting

First, you need to build a cadence for alignment. Daily contact involves Slacks and meetings that you and your cofounder share. But the Alignment Meeting is the bedrock1.

This is a 2 hour weekly meeting that is sacred. It’s the easiest meeting to blow up because its long and minimally structured — so why do it?

This is the time to carefully sift through the last week with your partner and determine where the cracks in your foundation are. This is NOT your standard 1:1 where you go through tactical items. You can have a loose agenda, but I found these meetings were best served when we came in without a suffocating set of bullet points.

Instead, we started with a personal check-in. How is the other person actually doing? We give space beyond the “I’m fine” answer to check in on the human underneath. This helps suss out if any tension you feel is from issues not related to the business.

From there, we go to the bird’s eye view of the company. How are we feeling about the overall business? Is the market changing beneath our nose and we’re not catching it? Are we noticing early trends with customer conversations that are making us a little uneasy? This is where the non-obvious items start to come to light.

If nothing emerges there, we meander into details of the business. Is there a teammate that’s starting to bug us? A deadline that continues to slip? Dive into the mechanics that aren’t being addressed in your weekly Goals meeting.

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2. Open and Honest Communication

What happens when you uncover misalignment? You disagree on how to handle the employee conflict or they aren’t seeing your fears about the market?

You must build a bedrock of openness between you two. I think about cofounder openness at the depth of 3 levels:

Level 1: How you are outwardly feeling about a situation (ex. “I don’t think our contractor is moving quickly enough for what we pay him.”)
Level 2: How you are inwardly feeling about a situation (“I’m scared about the rates we pay our contractor. We don’t have much runway left.”)
Level 3: How you are inwardly feeling about our relationship (“I’m worried you won’t hold the contractor accountable and we won’t find alignment here.”)

You can express all the levels, but I find that it speeds up the process to dig down and share Level 3 as quickly as possible (especially if you’re at an impasse). Get to the undercurrent of your gridlock. Now resolve it.

3. Resolving Conflicts

There are two guidelines I hold dear for resolving cofounder conflict: expose your story and assume best intentions.

First, expose your story. When I get to a Level 3 share, I like to separate the data from the story I built from that data. An example is me saying, “I see that your contractor missed his deadlines 3 weeks in a row. And I didn’t hear you address that in the meeting. ” That’s your data. That’s what a camera would capture if it was recording the meeting. No emotions at this point.

Then here’s the story I built from it, “I tell myself the story that you are afraid to hold the contractor accountable. Help me out, is that story true? What’s going on for you?”

Labeling the story separate from the data is critical. This helps you draw out fact from fiction. Then you can acknowledge what is unverified fiction and invite your cofounder into the conversation to fix the storyline2.

Note: Sometimes our stories are true. But they remain stories until they are verified. And unverified stories can take up a large portion of our brainpower.

Second, assume the best intentions of your co-founder (the only assumption I endorse!). Startups are beyond stressful, and in stressful environments it’s easy for us to turn our partner into our enemy. Whenever I felt this, my cofounder would sense it. So adjusting your mindset is your #1 job ahead of resolving a conflict.

4. The “No Gossip” Rule

It was common to see teammates low key complain or gossip about one cofounder to another. The more we tolerated this behavior, the more it happened.

We finally got to a place where we decided to put boundaries on this behavior. We created a rule where if someone came to us complaining about the other, we would tell them, “I want you to know I have every right to share this information with my cofounder. However, I’m happy to help you strategize how to approach this person if you are open to sharing this feedback.”

This stopped a lot of he said-she said behavior.

Does it risk you getting less feedback? Absolutely. But that doesn’t stop the flow of information, it forces people to be considerate of their language and asks.

Keep in mind you still want to build other healthy feedback channels. We found that complaining to us wasn’t one of them.

Cofounder as a Teacher

My bond with my cofounder transcended merely running the business. He was an incredible teacher to me about leadership and being human. Our mix of vulnerability and execution showed me a whole other level of how two people can support and partner together. I had never experienced anything like it at that point in life.

Take the time and be deliberate with your cofounder. With the right amount of structure and trust, I hope you too can find the blessings of a beautiful, authentic relationship with your cofounder 🙂

I appreciate you!

If you’re managing your inner work alongside your outer work of building a company, you may benefit from my coaching work. If you book a consult, I’m happy to chat more.