One of the most debated questions in leadership isn’t about strategy or structure—it’s about relationships. Specifically: Can or should managers be friends with their team?
This question took center stage in our inaugural CoachEm “Closing Arguments” Sales Leadership Debate, where two respected voices, Kevin Gaither (CEO, Inside Sales Expert) and Mark Kosoglow (CEO, Operator), tackled it head-on. The debate was lively, real, and packed with lessons for any manager leading in today’s performance-driven, people-first world.
Here’s what I took away and why I believe most sales leaders are better off being friendly, but not friends.
The Challenge: Friendship vs. Accountability
Friendship at work feels good. It creates connection, fosters trust, and makes the workday more enjoyable. But as Kevin Gaither wisely pointed out, it also creates risk, especially when leaders avoid the hard conversations.
“When you’re friends with your reps, it’s harder to hold them accountable. Feedback feels personal. Decisions feel political. And the line between empathy and favoritism starts to blur.” — Kevin Gaither
I agree. In my experience coaching and leading sales teams, most managers don’t struggle with connecting; they struggle with confronting. They delay performance conversations. They sugarcoat feedback. They over-index on likeability and lose sight of their leadership mandate.
The irony? Many of these managers are incredibly well-intentioned. They care deeply. But without structure and discipline, that care becomes counterproductive.
The Trap: Wanting to Be Liked
During the debate, Mark Kosoglow argued that friendship deepens trust and makes accountability easier. He’s a world-class leader, and his point is well taken. The difference? Mark knows how to coach with clarity, even when emotions run high. He has a discipline KPI and PIP process, and he leans into challenging conversations with authenticity and brutal honesty.
That’s rare.
He even loves our tool…
“CoachEm gives me the data and structure to have the hard conversations I don’t want to have. It helps me lead with objectivity, not emotion.” — Mark Kosoglow
I love that quote because whether you lean toward Kevin’s caution or Mark’s connection, structure is the equalizer. Tools like CoachEm remove the guesswork from coaching and give managers the confidence to hold the line, even when it’s uncomfortable.
The Solution: Be Friendly, Not Friends
So, at the end of the debate, what’s the answer? I actual disagree with the audience that voted 60/40 towards being friends with your team.
For most sales leaders, the safest and most scalable model is “friendly, not friends.” Here’s what that means:
- Be approachable and warm, yes.
- Ask and listen about personal context, but only when it impacts performance.
- Care deeply about your team and their success, but maintain clear authority and professionalism.
- Lead with transparency and objectivity, not emotion or loyalty.
- Share some of yourself and your personality as it relates to the business, but draw lines you won’t cross about your personal life.
That’s not cold. That’s wise. It protects the organization, the leader, the employee, and the culture.
Final Word
Being a sales manager means caring enough to challenge someone. It means balancing empathy with high expectations. It means knowing that respect is earned through accountability, not popularity.
Let your team know you’ve got their back. But don’t confuse being a great leader with being a great friend.
Friendly is good. However, friendship at work can come at a cost that most leaders cannot afford.
👉 Want to give your sales managers the tools to coach with confidence and clarity? Book a demo of CoachEm.
Let’s help managers have difficult conversations and start leading with impact, just like our two panelists did in this debate.
