On Leading Friends
How to be a good leader when you’re also friends with the person
👋 Howdy! Claire here, Founder & CEO of Canopy. The topic of “being a leader when my friend is my direct report” came up in a training I led this week, and so I wanted to write my thoughts on it in more detail here.
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Arguably the hardest thing to do as a leader isn’t telling someone they’re underperforming, giving feedback on a touchy subject, or even firing someone — it’s doing any and all of those things when you’re also friends with the person.
When you’re friends, things get, well, complicated.
You have history. This person has been through thick and thin with you. They know what you’re really like after the Zoom call has ended. They laughed at your jokes before you’d gotten your fancy “Director” title.
You have a shared outside-of-work life. You see them on weekends at the tennis court. You regularly call them up to go for a run. Perhaps your kids even go to the same school.
You likely have mutual friends — a friend circle, who you might regularly hang out with. So you’re not just applying your own self-judgment to the situation: You anticipate the judgment of others you care about, too.
This inevitably colors your leadership. Not necessarily worse or better, just different. Imagine if this person you were leading were someone else. Someone who didn’t know you in college, who didn’t participate in the same soccer league as you on weekends.
This difference is sometimes what makes delicate situations especially hard: When you need to tell your friend they came unprepared to the meeting, or when you need to tell your friend they didn’t get that promotion.
The good news is, being an effective leader and being friends with someone doesn’t have to be as daunting as it seems.
At the core, when we’re managing friends, there’s one thing to keep in mind…
Two roles, two approaches
The most helpful grounding point is this: The role of a leader and the role of a friend are two distinct roles.
To remind yourself of this, ask: What is the true purpose of a leader?
The true, ultimate purpose of a leader is to help a group of people (a team) accomplish something together that an individual typically couldn’t achieve alone. A leader exists to make that end outcome happen.
Now, I want you to consider: What is the true purpose of a friend? Is it to “accomplish” anything? No, no — I think most of us would say that a true friend is someone who supports us no matter what, who brings us joy and laughter, who help us feel good.
A leader is there to help the team get something done. A friend is there to help you feel good. Those are different things.
And that’s precisely why combining the two roles is so challenging.
It also underscores this truth: If we want to be a great leader and a great friend, we need to avoid conflating the roles. Instead, we need to keep them distinct and clear — and know which role we’re operating from, and when.
Here are a few ways to do that…
“Can we switch gears here?”
One of the trickiest parts of leading friends is figuring out when one role ends and the other begins.
Let’s say you saw your friend (who’s also your direct report) over the weekend at a basketball game. Monday morning rolls around, and you realize they’ve missed a critical deadline. You know you need to hold them accountable, just as you would anyone else — but it feels weird when you were just swapping stories 24 hours ago at Chase Center.
What do you do?
You acknowledge that the roles are shifting: That you’re now at work, and stepping into your role as a leader.
A simple phrase to signal this shift is: “Can we switch gears here?”
In this example, you might say:
“Hey, now that we’re back at work, can we switch gears here? I noticed we’re overdue on this deadline. Can we figure out how to move this forward so we can deliver on it as soon as possible?”
“I know you value that we can have an honest conversation”
One of the most beautiful, incredible aspects of friendship is the inherent trust that is built in. When you’re friends with someone, you trust them to have your back, to look out for you, and to have your best intentions in mind.
Because of this trust, you should in fact feel more empowered to have a difficult, honest conversation with your friend. They already trust your intentions — and so when you’re in the leader role, you’ll want to affirm that.
You might say:
“I know you value that we can have an honest conversation…”
“I know you trust me to give you real feedback…”
“I value that I can be super frank and open with you…”
I know many of us fear saying the wrong thing and negatively affecting or hurting our friendship in a work environment — but if we can lean in and highlight the trust that is already there, then we mitigate that risk almost completely.
“The work requires…”
I once worked with a CEO who had a co-founder who was a close friend of his. While they were trying to recruit and hire employees for meaningful, senior roles, the CEO noticed that his co-founder would show up, unprepared and ask questions that were “off script” and led the candidate is a totally different direction than what the interview was supposed to focused on.
“I don’t know exactly how to steer my co-founder back on course because (1) he’s my co-founder, not my direct report, and (2) he’s a good friend of mine and I don’t want to hurt his feelings,” this CEO told me.
Here’s what I shared with the CEO: The quickest path to course-correction is to focus on what the work itself requires, not on what you think the person is or isn’t doing. When you anchor your request in the needs of the work, the project, or the company, people who care about those things are more likely to adjust.
In this case, the company requires top-level talent — and that means interviews need to be tightly edited and focused, rather than sprawling and unpredictable. When the CEO communicated this to his friend, the co-founder, he almost immediately changed his behavior in the next interview.
“Can I put my ‘friend’ hat on?”
The nature of duality is that it is indeed two-sided: Sometimes, we must inhabit both roles at once, and some situations require that we switch our roles.
I worked with a senior leader once who needed to let their direct report (a close friend of theirs) know that they didn’t get a promotion. Stomach in knots, the senior leader just couldn’t imagine how they’d be able to share this information with a straight face, knowing that their friend had tried their very best and would be gutted by this news.
I understood. In moments like this, both roles are called upon: Leader and friend.
Here’s what I recommended to the senior leader: Deliver the news professionally and clearly, as you would for any team member. Then, when you want to show empathy as a friend, name the shift.
A helpful phrase to do this could be: “Can I put my ‘friend’ hat on?”
You might say:
“You weren’t selected for the promotion this time. The feedback I received was [insert reason]. I know you gave it your all, and I believe more opportunities will come. That said… can I put my ‘friend’ hat on? Ugh. This freaking sucks. I’m so sorry.”
This way, you honor your role as a leader by calmly and fairly sharing the difficult news — while also creating space to show up as a friend and honor your friend’s experience.
You don’t have to be everything everywhere all at once
I love that we have friends in the workplace. I personally know the feeling of working alongside close friends — it makes the time at work richer and more rewarding. Yes, it can also feel a little more precarious, a little more sensitive... But to me, that’s a signal we care. We care about these relationships.
And with that care comes clarity: You don’t have to cram the role of “leader” and “friend” into one voice, one moment, one interaction. You can choose which one you need to step into, which hat to wear, when the situation requires.
They are two roles. And when you treat them as such, you’ll show up as both a better friend and a better leader.
-Claire
If you resonated with my writing this week, feel free to “like” or “share” the post — it helps other folks who might find this piece similarly useful see it for free 🫶
In case you missed ‘em, here are two other recent pieces I wrote to help support your team’s performance (whether or not you are close friends with each person 😅)…
If you found this piece helpful and are looking for deeper guidance as a leader, here are ways you can directly work directly with me, Claire, Founder & CEO of Canopy:
📣 Invite me to deliver team keynotes and workshops, remotely or in person on topics for leaders including “Avoiding Leadership Pitfalls” and “Giving Difficult Feedback Well.”
🚂 Partner with me to roll-out a leadership training program for your managers to avoid key mistakes such as being overly nice and hard performance conversations.
🌿 Use Canopy, our lightweight leadership learning app, in your day-to-day.
🤝 Explore 1:1 executive coaching with me personally to help you elevate your leadership keep your best people. (I periodically have spots upon up throughout the year — I’ve had the privilege of coaching leaders at companies like Apple and Uber, and welcome the opportunity to share those learnings in-depth with folks one-on-one.)
I’d be honored to chat and see what might be the best fit for you. Feel free to reach out to me directly here 💚