Lessons For Going Into Business With Your Friends

I’m a cofounder and the Head of Innovation at Fringe. We are an HR Technology startup focused on transforming the work experience.

It was December 2022, after the end of what was one of the most challenging years for our startup. Over the course of the year, the team had more than doubled, my role had evolved at least three times, my dad passed away, and in the midst of all that we raised our Series A—which was nothing short of an eight-month slog.

My team in particular had missed our revenue forecast. I wasn’t happy with how things had gone and was determined to right the ship but had kept most of those feelings to myself. All the while, there was growing frustration among my other co-founders. It culminated in a “come to Jesus” moment with my good friend and co-founder. As I drove to a hole-in-the-wall diner to meet him, thoughts raced through my mind. I felt hurt, frustrated, even scared.

I had failed to communicate what was going on in my heart and mind over the past few months. In particular, I had failed to simply say out loud “I’m sorry things didn’t go as well as we thought, and I take responsibility for my team’s part in that.” But in the absence of communication, many do what is natural and fill the narrative gaps with their own story.

Taking responsibility is crucial.

One leadership lesson I’ve learned is that it’s your fault, even when it doesn’t seem fair. And it’s also your responsibility to learn from what didn’t go well, adapt and move forward. I’ve come to accept failure and shortcomings as part and parcel of growing and becoming better.

As we sat down to coffee, all I could think about at that moment was that the most important thing to me right then was my relationship with the person sitting in front of me. We had been through a lot together over the 10 years that we’d known each other—both in business and in life.

But as we spoke, it was clear, we were there for each other. The ground from which we were starting was our friendship and love for one another. That gave us the space to speak openly about ways we felt hurt. It gave us space to speak about our frustrations and to truly hear and empathize with each other. And it gave us space to reconcile.

Over the course of that day, I spent time individually with all of my co-founders. I’ve dubbed it the “reconciliation tour.” It was exhausting, but as the five of us sat together at the end of the day, we reflected on how much closer and stronger our relationships felt and how critical that is to not just our friendships but also our success as a team working together.

Whether you’re in business with your friends or not, here are some takeaways that could transform your leadership and relationships:

Go first.

Don’t let tension linger and fester. If you know there’s something that needs to be addressed, have the courage to go first. That doesn’t mean lead with aggression or accusations. Be the first to acknowledge that you likely have ownership in whatever isn’t going right. Lean into that, and be willing to accept critical feedback.

This isn’t about being gregarious and outspoken, and it’s certainly not about being willing to call people out. This is about moving into potentially messy situations with the aim of growth. If you want to stagnate as a person, avoid difficult conversations. If you want to grow, lean in. If you have conflict with someone, ask if you can talk about it with them. Let them know you want to hear their perspective and acknowledge you want to work through it together.

Start from a place of humility.

If you’ve read The 7 Habits of Highly Effective People, you’ll know this mantra: “Seek first to understand, then to be understood.” I’ll be the first to admit that when I have a point I want to make, I tend not to listen. But that shuts you off from true listening, and the lack of listening closes off your ability to learn from the person in front of you.

Focus on listening to what the other person has to say. Ask follow-up questions to clarify things they may have said. Don’t invalidate their feelings no matter how hard it may be to hear or how wrong you may think they are. Be curious about the other person and what you might learn from them. Think of the Socratic paradox, “I know that I know nothing.” Adopting a humble attitude means acknowledging you have limits and room to learn and grow.

Prioritize the relationship.

There are some things that are more important than business, no matter how important the practical needs may seem in the moment. When people reflect on the greatest leaders they’ve had, it rarely comes down to business ingenuity; it often comes down to how that leader made their followers feel. You may even find that your greatest relational conflict has been with your closest friends.

Conflict in relationships is a universal reality. But optimal relationships can move through the conflict and reconcile quickly. In fact, the conflict often makes the relationship stronger. When a difficult conversation is back-stopped by the reality of a relationship, it allows both parties to be vulnerable in the ways needed to grow. We all have areas of our lives in need of pruning, and prioritizing authentic relationships allows us to snip off the areas that are hindering our growth.

Here’s to more authentic, vulnerable and truly courageous leadership!

Forbes Business Council is the foremost growth and networking organization for business owners and leaders. Do I qualify?