How to Navigate Difficult Conversations with your Co-founder

A sneak peek into Project A’s new Personal Coaching and Development Program: Leading tough conversations

By Alena Hilbig

Having a co-founder is great: You provide valuable support to each other and complement the other’s skills, knowledge, and experience. You share the workload, decision-making, and accountability, helping each other navigate the ups and downs of entrepreneurship.

Building a solid relationship with your co-founder is crucial and requires a lot of dedication. As you’ll face various challenges along the way, you must establish a good foundation and prioritize this relationship to ensure your startup’s success.

A primary building block is preparing for difficult conversations. Remember, difficult doesn’t mean having different opinions; diverse viewpoints on building and running your company can be valuable and healthy. Avoiding tough conversations and lacking the skills to negotiate, resolve conflicts, and find common ground is what guarantees failure.

In this article, you’ll find tips on leading those tough conversations, making the time for them, and which critical topics co-founders should discuss regularly.

The how

Communication between two people happens on various levels, from small talk to a deep emotional exchange:

  1. Informational – talking about the weather, weekend, or sports.
  2. Transactional – talking about my role, our strategy, or your task.
  3. Relational – talking about emotions and impact.

Take a moment to reflect: How often have you engaged in level 3 conversation with your co-founder, if at all?

Don’t confuse “expressing your opinion” with level 3 communication: Tough conversations mix Transactional and Relational topics and sound like, “I’m worried because I feel we’re going in the wrong direction” or “I’m angry you didn’t deliver on time.”

It may seem like you’re talking about strategy or performance, but you’re really sharing your fears and gauging mutual trust.

Here’s a simple script that can inspire a genuinely intimate and honest conversation:

“I’ve noticed that…” → Only mention what you can see or hear

“It makes me feel…” → Describe how the above affects you

“What’s your take on that?” → Ask for their perspective and experience

“It’s important to me that…, so I propose we…” → Explain your value, offer a solution

“What can we agree on?” → Find common ground

The when

What if you can’t find the time for those conversations, as your schedule is already full?

Assuming you have regular check-ins with your co-founder, allocate some of that time to introduce difficult conversations. The sooner you integrate those topics into your meetings, the quicker you build trust and resolve potential issues.

💡 Co-founder check-in: A weekly session with a predefined agenda that leaves room for discussions on critical issues. More than a status update, which you can do async, this meeting is where you align on product strategy, discuss the company’s direction, set priorities, hold each other accountable, offer feedback, and ask for help.

Adopt this routine at the earliest stage (~5 employees).

The what

Reading through Amy Buechler’s (aka The Founder Coach) User Manual for Founder Psychology, I found this list of meaningful talking points and guiding questions for co-founders:

  • Vision: What are our dreams for this company? Are they aligned? Do we believe in what we’re doing? What motivates us? What values are important to us? Do we agree on that?
  • Equity: How did we decide on our equity split? Are we 100% comfortable with it? Can we imagine a scenario where we won’t be, and how do we plan for that?
  • Responsibilities: Do we have a clear view of our roles and responsibilities? Are we comfortable with them? Do they fit our individual strengths and capabilities?
  • Performance: Is our workload balanced? Does one of us bring more hard or soft skills than the other? Is there a skill set that’s currently more critical to our startup? Are we equally dedicated and committed?
  • Third parties: Are we distracted by external forces (social life, family, fundraising, press, etc.)? Are we choosing the right investors? Are we focused on our vision or allowing a third party to lead us?
  • Decision making: How do we reach an agreement when we have different opinions? For example, will the technical co-founder always have the last word on product decisions?
  • Org building and hiring: Are we aligned on which people to hire next? What should our organizational structure look like?
  • Roadmap: Are we using the right metrics? Are we achieving our goals, or any goals at all? How much influence should users have on our roadmap? When do we prioritize data over intuition?

Time to take action

Discuss what’s relevant to you and integrate these topics into your regular check-ins. Tip: Forward this article to your co-founder so they know where you come from.

💡Getting nowhere with a specific topic? Struggling to resolve your difficulties? A coach can help lead and direct the conversation as a neutral third party.

We’re excited to introduce Project A’s exclusive Personal Coaching and Development Program for founders. The program is a unique opportunity to work one-on-one with an experienced coach, set personalized goals, and achieve sustainable change.

Have questions about tough conversations? Need more input about our program? Let’s continue the conversation on our social media channels.

Which coaching or personal development topic would you like to read about next?