Lessons to do business with your friends

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I am co-founder and Head of Innovation at Zoom. We are an HR technology startup focused on transforming the work experience.

It was December 2022, after the end of 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 father died, and in the midst of it all, we brought our Series A – which was nothing short of eight months of slogging.

My team in particular had missed our revenue forecast. I wasn’t happy with how things had turned out and was determined to make things right, but had kept most of those feelings to myself. All the while, frustration was growing 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 diner to meet him, thoughts raced through my mind. I felt hurt, frustrated, even scared.

I hadn’t been able to communicate what was going on in my heart and mind for 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 role in that.” But in the absence of communication, many do what is natural and fill the gaps in the story with their own story.

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Taking responsibility is crucial.

A leadership lesson I’ve learned is that it’s your fault, even if it doesn’t seem fair. And it is also your responsibility to learn from what went wrong, adapt and move on. I have come to accept failures and shortcomings as an essential part of growing and getting better.

As we went for coffee, all I could think at the time was that the most important thing for me at the time was my relationship with the person sitting across from me. We had been through a lot together in the 10 years we had known each other, both professionally and privately.

But as we spoke, it was clear, we were there for each other. The basis from which we started was our friendship and love for each other. That gave us the space to talk openly about ways we felt hurt. It gave us space to talk about our frustrations and really 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 called it the “Atonement Tour.” It was exhausting, but as the five of us sat together at the end of the day, we thought about how much closer and stronger our relationships felt and how critical that is to not only our friendships, but our success as team working together.

Whether you do business with your friends or not, here are some tips that can transform your leadership and relationships:

Go first.

Don’t let the tension linger and fester. If you know there is something that needs to be addressed, have the courage to go first. That means not leading with aggression or accusations. Be the first to recognize that you probably own everything that isn’t going well. Lean into that and be prepared to accept critical feedback.

It’s not about being sociable and candid, and it’s certainly not about being willing to invite people over. This is about entering potentially messy situations with the goal of growing. If you want to stagnate as a person, avoid difficult conversations. If you want to grow, lean in. If you have a conflict with someone, ask if you can talk to them about it. Let them know you want to hear their perspective and acknowledge that you want to work through it together.

Start from a place of humility.

If you have read The 7 habits of highly effective people, do you 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 cuts you off from true listening, and the lack of listening hinders your ability to learn from the person in front of you.

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

Prioritize the relationship.

Some things are more important than business, no matter how important the practical needs may seem at the moment. When people think about the best leaders they’ve had, it rarely boils down to business savvy; it often comes down to how that leader made his followers feel. You may even find that your biggest relationship conflict has been with your closest friends.

Conflict in relationships is a universal reality. But optimal relationships can weather the conflict and quickly reconcile. In fact, the conflict often makes the relationship stronger. When a difficult conversation is interrupted by the realities of a relationship, both parties can be vulnerable in the ways it takes to grow. We all have parts of our lives that need pruning, and prioritizing authentic relationships allows us to cut off the areas that hinder our growth.

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


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