A high-performing remote team starts with organic core values, intentional hiring for accountability, and incentive structures tied directly to individual results. Justin Benson, founder of Bara Agency, shares how his team runs on values like ‘leave people better than you found them’ and ‘do what you say you’re going to do,’ plus quarterly in-person retreats that rebuild relationship currency. This episode is essential for any owner building or scaling a distributed team.
This episode is part of the Team Culture, Dynamics & Tough Personalities series. Browse all episodes →
Mic drop moments
“…the friend zone is synonymous with avoiding hard conversations, avoiding giving the hard feedback, avoiding doing the corrective stuff.”
“…the more you have these conversations upfront, the more you give feedback, the more you are addressing things before they turn into bigger problems, the easier these hard conversations get.”
“…as the boss, you aren’t friends with your team members, and you can absolutely be friendly. You can care deeply about them and their families and their lives.”
“Saying whatever you’re feeling stuck with and naming it, this doesn’t weaken your credibility as a leader. This strengthens it.”
Episode highlights
The signs you have been friend-zoned by your team
It does not announce itself. It creeps in. Someone texts you about their yoga class to get out of a meeting. Another person pushes back on feedback like you just insulted a buddy at brunch. A third keeps bending the work-from-office policy because they know you hate conflict. Lia’s clearest tell: if you are avoiding hard conversations, or quietly routing them through someone else, you are in the friend zone.
Being friendly and being a friend are not the same thing. You can care deeply about your people’s lives and still hold a professional boundary. The problem is that most leaders who end up here are people-pleasers who never meant to blur the line. Small teams make it worse because everyone is together constantly and a collegial vibe feels natural.
Why this happens and why your team is not the villain
Lia is direct: your team members are reading the signals you send. If you never established expectations, stayed flexible on everything, and avoided every uncomfortable moment, they adapted to that environment. They are not trying to take advantage of you. They are just doing what the signals told them was okay. The fix is to change the signals, not punish the people.
Step one: put your leadership style on the table
The first move is a conversation that most leaders skip entirely. Go to your team and say you have been reflecting on how you want to show up as a leader and you want to share that, and understand how they like to receive feedback and have hard conversations. This one move does two things at once. It resets the dynamic by signaling a different kind of relationship, and it gives you real information about how to have the conversations that are coming. Naming a struggle, such as saying you have been avoiding direct feedback because you want everyone to feel good, does not hurt your credibility. It builds it. This is not a conversation you would have with a friend, and that is exactly the point.
This step matters most if you hired someone you already knew, whether a former peer, a personal contact, or a family member. The relationship outside work and the one inside work can both be strong, but they are not the same relationship.
Step two: set boundaries and actually hold them
Boundaries are not about becoming cold. They are about creating a structure that makes trust and accountability possible. Practical examples: not attending every team lunch or every after-work event, setting clear hours for when messages get answered, and defining what belongs in a text versus Slack versus email. Lia’s caveat: if you set a boundary, you have to respect it yourself. Sending a message at 9 p.m. and expecting a quick reply cancels out every boundary you announced. Mixed signals land worse than no signal at all.
The specific norms will vary by industry. Events, production, gyms, salons, and similar businesses have legitimate after-hours demands. The goal is not a rigid corporate schedule but a set of shared expectations that reduce the blurry, anything-goes feeling that feeds the friend zone.
Step three: have the hard conversations, and stop outsourcing them
This is where Lia gets specific about a pattern she sees constantly. A founder or owner has an ops manager, office manager, or chief of staff who holds the line and delivers hard messages. Then when a team member goes directly to the owner, the owner softens everything. That person becomes the good cop, the ops manager becomes the enforcer, and the team starts to resent the enforcer because leadership never backed them up.
If someone on your team has been told by your ops manager that extended unpaid leave is not available, and then they come to you and you say you think it is probably fine, you have set both people up to fail. Consistent messaging is not optional. Coach whoever is delivering hard messages to do it empathetically, and then say the same thing yourself. That is a united front.
What shifts when you get out of the friend zone
Lia closes with the outcome, because it is not obvious until you have been through it. When the friend zone dynamic breaks, feedback flows more easily, people step up more proactively, and psychological safety actually increases. When everyone is protecting the vibe, nobody feels safe taking a real risk or speaking an uncomfortable truth. A clear leadership relationship removes that tension. The hard conversations get easier the more you have them, and the whole thing becomes, in Lia’s words, game changing.
Related episodes in this cluster
- Ep 224: Why certain team members bug you (and how to actually handle it). When a team member drives you up the wall but is technically doing their job, the problem is rarely performance. Lia breaks down three specific archetypes that trigger leaders, explains what each one is actually signaling, and gives you a concrete strategy for each. This episode is especially useful for owners and founders who keep dreading their own one-on-ones.
- Ep 144: How to motivate and align your team when everyone feels like they are sprinting a marathon. Motivating a team under tight deadlines comes down to shared context, early visibility, and a culture where people feel seen beyond their project output. Alison Curtis and Janessa Mason, leaders at creative agency Skona, share how they align client services and creative teams through transparent communication, collaborative timeline-setting, and deliberate relationship-building at every level. This episode is especially useful for founders, agency leaders, and anyone managing across departments that can feel like they have competing agendas.
- Ep 141: How to manage former friends without making things weird. Managing former peers and friends is genuinely hard, and pretending nothing has changed is the fastest way to make it harder. Lia walks through three moves: name the relationship shift out loud, co-create norms for feedback and hard conversations, and own your authority instead of downplaying it. This episode is especially useful for new managers who got promoted from within their own team.
- Ep 118: How to build a high-performing remote team with real accountability and culture. A high-performing remote team starts with organic core values, intentional hiring for accountability, and incentive structures tied directly to individual results. Justin Benson, founder of Bara Agency, shares how his team runs on values like ‘leave people better than you found them’ and ‘do what you say you’re going to do,’ plus quarterly in-person retreats that rebuild relationship currency. This episode is essential for any owner building or scaling a distributed team.
Want to go deeper?
The Unstoppable Team. How to build a team that runs without you in the room.
Full transcript (click to expand)
But what’s not so awesome is when you have to be the boss and give the hard feedback or hold people accountable. And they look at you like, come on, dude, like, we’re just out here having beers. The truth is, as a leader, as the boss, you aren’t friends with your team members, and you can absolutely be friendly. You can care deeply about them and their families and their lives. But as the boss, there has to be a bit of a boundary there.
Welcome to Leading Small Teams, a Real Talk podcast tackling the ins and outs of leading teams in the modern workplace. I’m Leah Garvin, your host, with a decade of experience driving team operations in companies like Google, Apple, and Microsoft, bringing you insider strategies to make you a more confident and effective leader. From delegating to feedback to avoiding micromanaging and more, this podcast gives you the tools to empower your team, scale yourself as a leader, and grow your business.
Whether you’re managing a team of one or 100, everyone is welcome to hang out with Leading Small Teams. You did everything you could to avoid it. You thought, okay, I’m going to hire people and set these clear expectations, and we’re going to do great work. And all of a sudden, you ask someone to do something, and they kind of slack on it. Or you give feedback, and they’re like, whoa, I don’t really need to do that.
Or you’re getting texted all hours of the day with people’s excuses about their dentist’s appointment, their yoga class, and why they can’t finish something. And you realize that against all your best judgment, you are friend-zoned by your team members. And this is something that happens to all of us leaders who are maybe a little bit people-pleasing or want to be friendly in relationships with our team members. It’s completely natural, especially if you have a smaller team.
You’re all sitting together, you’re meeting all the time, and it would be awesome if we could all just be a group of friends. But what’s not so awesome is when you have to be the boss and give the hard feedback or hold people accountable, and they look at you like, come on, dude, we’re just out here having beers. But the truth is, as a leader, as the boss, you aren’t friends with your team members. And you can absolutely be friendly.
You can care deeply about them and their families and their lives. But as the boss, there has to be a bit of a boundary there. And that’s what we’re talking about on today’s show. What do you do if you wake up one day and you realize, oh, God, yep, I am friend-zoned, hardcore with my team, and I got to figure this out. Now, what are some of the tells that you’re in the friend zone? Well, I mentioned a few of them.
One of the big ones is folks are coming to you with all their little excuse-y things that probably if they had a corporate job or a job where they didn’t think of the boss as a friend, they wouldn’t do that. So that is when maybe they’re not honoring the work-from-office policy. Or when you have it, they’re always asking for edge cases. Maybe it’s, yeah, them texting you and saying, oh, I had this thing come up. Or, you know, I’ve got that thing going on where it’s not a medical issue or a child care thing.
Or something like, yeah, you know, I had that yoga class. I’ve been really trying to get in with that new teacher, and it’s like, this is not really a work issue. And they’re trying to, like, miss an important meeting or something like that. Something that you really would make an excuse about breaking off with a friend plan, not work. And a lot of times, it looks like a real resistance to feedback because we’re not used to getting feedback from our friends about things that we’re not doing well, and this is with constructive feedback specifically.
So if you’re nodding along like, yes, yes, and yes, all of the above, I’m in the friend zone. Is it too late for me? What do I do? First of all, no, it is not too late. You can always fix any of the challenges, anything that we talk about this show, we’re talking about it because it’s fixable. But we have to do it with intentionality, and we actually have to shift and rebuild the relationship that we have with our teams, and that might be a little bit awkward.
Like we’re probably in the friend zone in the first place because we don’t really want to have conflict. We don’t like having awkward conversations. Feedback’s uncomfortable when someone gets defensive, so we avoid it. Or we know the team members that we really can’t give feedback to versus others. So we’ve kind of categorized folks in these buckets, and everyone’s just kind of thinks like, oh, yeah, she’s cool, he’s cool, they’re cool, whatever. I can do this. And your team members don’t, I would say, let’s give them the benefit of the doubt and think they’re not trying to take advantage of you.
They’re not doing this to get one over, but they’re reading the cues that you’re sending. And if you are signaling, yeah, I don’t have a ton of boundaries, or I’m flexible as stuff, or you’ve never established that, then it is time to reset those signals. But this doesn’t mean you have to be like, okay, now I’m the boss now, like, wow, listen to me. Because that’s going to throw people off a lot. And they might leave if you turn into another person, or they might feel like, well, this isn’t the environment I wanted to come to, or this is, you know, who are you right now?
So it’s a course correction that’s not a blindsiding. And there’s a few things that I think are critical to do when we find ourselves in the friend zone. The first one is to talk about your leadership style, like put it out there in the open. And this can feel a bit awkward, like as a leader, I like to do this, but no, that’s not what we’re talking about, right? This is real talk. So we can talk.
It is saying, hey, you know, I’ve been reflecting on what’s really important to me as a leader and how I show up, and I’d like to share that with you. And I’d like to understand, you know, how you like to have feedback and so that we can figure out, you know, the dynamics of when we have to have a hard conversation, how can we do that respectfully? If I have to share constructive feedback, what works for you simply by having this conversation, you are putting it out there like, yeah, we have a different relationship.
We’re not just hanging out like on the back patio, having beers, right? We are in a different situation. If you’re anything like me, you’ve had those nights where you wake up at three in the morning wondering, gosh, are people working on the right things? Or what’s the status of that project? And obviously you can’t email folks at that time, but the tools you’re using, ClickUp or Asana or Slack, it’s just too detailed. You need a bird’s eye view.
Enter the snippets template. At the end of each week, your team member fills out the highlights from the week, any places they’re stuck, and the top parties for next week. So you’re never wondering, are folks working on the right things? Are there things that they haven’t brought up that really should be on my radar? And most importantly, what wins can we celebrate as a team? Grab your copy at liagarver.com slash snippets. So literally talking about your leadership style, this is what I am excited about as a leader.
This is some of the challenges I’m working with through. Maybe it’s saying I struggle with giving direct feedback because I want everyone to feel always super positive with their work. And that’s something I’m reframing for myself. Saying whatever you’re feeling stuck with and naming it, this doesn’t weaken your credibility as a leader. This strengthens it. And by virtue of having the conversation, this is a two for one, you are asserting yourself as a leader. I am the leader.
These are the characteristics. I am asking you to have this conversation. I’m inviting you into this and you’re resetting because this is not a conversation you’d have with your friends. So you’re starting to shift the dynamic. And these conversations are extremely, extremely helpful and critical. If you are managing folks that you had worked with more on a peers capacity or a friends capacity, maybe you have hired someone, you know, very personally, small business owners, maybe you hire a family member.
We’ve got to reset this dynamic completely with folks that we know well, because the relationship that we have outside of work is completely different than the one we have inside. They can both be fantastic, beautiful relationships, but they’re not the same. So resetting and having a conversation about this is my leadership style. Here’s how I like to give feedback. How do you like to have hard conversations? Let’s talk about this. Let’s get on the table. How do you like to receive recognition and praise?
We don’t know that either in this person, this new capacity. And that is going to go such a long way to starting to reset. Okay. So that’s our step one. We’ve, we’ve reset, we’ve named the dynamic change. Our second step is to actually hold some boundaries. We might hold boundaries where we don’t go to lunch with the team every day, or we don’t go out with everyone to the bar after the Christmas party, you know, or we don’t invite folks to our house, or we aren’t answering text messages at all hours.
We say, Hey, these are the work. These are the hours that I’m answering messages and emails, you know, outside of an emergency. This is when I’m available. And we start to put up some boundaries of this is when I’m available. Here is, you know, when you have access to me or not. This is going to also set an emotion that we’re not just on a shorthand and you can, you can get me whenever you need me.
Now it goes both ways. If you’re going to set that boundary, you’ve got to respect your team members boundaries. And this is where I think a lot of us go wrong is we want to have boundaries, but we think of something at nine at night and we’re like, and we’re expecting our team over to respond. And then we’ve sent a mixed signal. So, so think about what kind of boundaries that you want to set is going to be a lot of this will relate to the industry you’re in.
If you work in events or in production or a company like a gym or a men’s bar or salon where you have evenings and weekend work, again, events and production has late night last minute stuff that has to be figured out that will all those sorts of industries, those jobs, those companies will have all different kinds of norms that are appropriate and expectations you can set. I think the thing with the boundary is not only about time you’re available, it’s things that you can text versus Slack versus email about or call.
Nobody calls anymore, but let’s throw that one in there. If you have to, you know, call out sick or have a last minute emergency, maybe it is a phone call. So you can talk through and talk about a coverage plan instead of a text or something has to be requested instead of announced right in Slack. Those kinds of things are going to establish a little bit more formality that can be really helpful in not having feeling like, oh, I don’t want to be the bad guy, right?
That’s a friend zone feeling of, I don’t want to upset anybody and I don’t want to be mean and all these things. It’s not mean to have boundaries, right? This is how we are actually able to scale ourselves and your team members are going to want their own boundaries too. So they’re going to, this is going to be much appreciated across the board. So once we frame this leadership conversation, once we’ve set these boundaries, now you’re going to rip the bandaid off my friends.
We got to have some hard conversations. The friend zone is synonymous with avoiding hard conversations, avoiding giving the hard feedback, avoiding doing the corrective stuff like saying, Hey, this thing didn’t work because we like the friendly thing and we like the vibe in the office and we don’t want someone to start to be grumpy or frustrated or they’re really important for this deadline and we don’t want them throwing it off. You’re a leader. You’ve got to face those things even if they’re uncomfortable.
You’ve got to face it. If you’re not sure if you’re in the friend zone, the number one tell is if you are avoiding hard conversation. And again, this is real talk. I get that it’s hard, but if you are not having the hard conversations or you’re sending someone to have them for you and then maybe you’re having a little bit of a different conversation, okay? I see this a lot. My business owners that have an ops manager or an office manager or a chief of staff, they’re sending that person to really hold the line, hold people accountable and share the hard messages.
Then when the team goes to them, that business owner directly, that founder directly, they’re kind of good cop. They’re the nice guy and they’re not operating consistently and you are not setting up that chief of staff or office manager, ops manager for success. If you’re playing, you know, friend boss when they’ve had tried to hold them accountable and you don’t have that united front, that’s a signal that you’re stuck in that friend zone. If something needs to change, it needs to be fixed on it.
Support that person. Empower your office manager. Empower them with having a consistent communication down the chain. If there’s a, let’s say a vacation policy that you want to enforce or I have a client that someone on their team keeps asking for unpaid leave, like weeks and weeks of extra sort of vacation time because they are okay with it not being paid because they have other income streams. Well, that’s not the whole point of the vacation policy is to make sure there’s coverage so that there’s enough work getting done, right?
So this has been a challenge. Now, if that’s what the business owner feels, they have to say the same thing as the, as the ops manager. When the ops manager shares that policy, if the team member comes back to the boss or the, you know, the business owner and says, Hey, can I take some unpaid leave? Like, yeah, I think you can. Whoa, you have just set both people for failure because you’re not, you’re not enabling that person to be a leader.
Now I call that out specifically because that is one of the things I’m seeing my friends. I’m seeing it every day that we want someone else to enforce some of our policies or deliver the hard messages. And then when we’re kind of called on it, we don’t, we don’t say something consistent and instead we’re like, Oh yeah, no, I mean, I don’t know if that was a big deal. I hope when you’re hearing this, you’re realizing how problematic that is.
We’re going to say it’s so problematic to do that because you, this is why a lot of times folks resent the ops manager or the office manager or the accounts team or the chief of staff because you have this enforcer and you’re not backing them up. Now, what do we do when we are trying to avoid friend zone? Being a friendly boss, being the person that everyone still wants to come to, but we’ve also haven’t disrupted this sort of flow across your team is we coach the enforcer how to deliver these messages empathetically.
And we also deliver them empathetically and they’re the same message. And that means we’ve got to have hard conversations again. It’s part of being a leader. It is what you signed up for. And the more you have these conversations upfront, the more you give feedback, the more you are addressing things before they turn into bigger problems, the easier these hard conversations get. So this my friend is how we both recognize and avoid getting stuck in the friend zone because what happens when we’re in the friend zone is we can’t have the hard conversations.
We can’t give the feedback. We actually find we have lower psychological safety where people don’t feel comfortable speaking up and taking risks because they don’t want to rock the boat because it’s everybody’s in the friend zone. Now, when you shift that, you start to see, okay, it’s easier to hold people accountable. People are actually stepping up more proactively. They’re solving problems in a bigger way. It is game changing and such a freaking relief for you as a leader.
All right. So remember, we want to talk about that leadership style. That’s step one. Set and hold those boundaries. And then we have to have the hard conversation or operate in alignment with whoever else is having those hard conversations. Do those three things and you will be out of the friend zone and into a productive positive place that is way more sustainable. See you next time. Thanks for tuning in and I hope this podcast makes leading your team feel just a little bit easier.
If you liked this episode, check out my most popular tool for staying in the know of what your team is working on without having to micromanage at leahgarvin.com slash snippets. And if you’re looking for more support for yourself as a leader or for the team you’re managing, don’t hesitate to reach out at leahgarvin.com. See you next time.
Questions this episode answers
How do I know if I'm in the friend zone with my team?
The biggest tell is that you are avoiding hard conversations. Other signs include team members texting you with non-urgent personal excuses to miss work, pushing back on feedback as if it does not apply to them, or routinely asking for exceptions to policies. If you find yourself categorizing certain people as ones you simply cannot give feedback to, that is a clear signal the dynamic has shifted too far toward friendship and away from a functional working relationship.
How do I reset the relationship with my team after I've let things get too casual?
Start by having a direct conversation about your leadership style. Tell your team member you have been reflecting on how you show up as a leader and want to share that with them. Ask how they like to receive feedback and how they prefer to handle hard conversations. This single conversation does two things at once: it opens a dialogue about expectations, and it signals that the relationship has a different structure than a friendship. You are asserting yourself as a leader without blindsiding anyone.
What kind of boundaries should a leader set to avoid being too friendly with their team?
Start with time and communication norms. Define when you are available to respond to messages outside of a true emergency, and be clear about what should be a Slack message versus an email versus a phone call. Also consider whether you want to limit things like going to lunch together every day or socializing heavily after work events. The key is that whatever boundaries you set, you have to respect your team members' boundaries too. If you text them at nine at night expecting a response, you have already sent a mixed signal.
What should I do if I've been sending my office manager to deliver hard messages while I play the nice boss?
That pattern is a problem and you need to stop it. When a team member comes to you after the office manager has already delivered a message or enforced a policy, you have to say the same thing your office manager said. If you soften or contradict that message, you are undermining your office manager and making it impossible for them to lead effectively. The result is that your team ends up resenting the person you put in charge of holding them accountable, while you stay comfortable. Consistent communication from both of you is what protects everyone.
Can I still be warm and caring with my team without getting friend-zoned?
Yes, and that is exactly the goal. You can be friendly, care deeply about your team members' lives, and still maintain a clear boundary as the leader. The distinction is that a friend does not give you constructive feedback or hold you accountable for your work, but a good leader does. When you hold that boundary with consistency and empathy, people actually feel more safe to speak up and take risks. It creates a more productive environment for everyone, and it is far more sustainable for you as a leader.