Most sales leaders don’t fail because they lack intelligence or effort—they fail because they step on landmines they never saw coming. Managing a sales team isn’t just about setting quotas and reviewing the pipeline. It’s about hiring the right people, developing them, and avoiding the subtle leadership missteps that can derail performance.
Kevin Gaither has seen it all. As the former sales leader at ZipRecruiter and now the CRO of Inside Sales Expert, he’s built, scaled, and fixed sales teams across multiple startups. And he’ll be the first to tell you—he’s made thousands of mistakes along the way. In our latest Coach to Scale podcast episode, Kevin shares the hard-earned lessons that every Chief Revenue Officer (CRO) and frontline sales manager needs to hear. If you want to avoid the most common leadership traps and build a high-performing sales team, read on.
The Myth of Being “Friends” with Your Sales Reps
One of the first mistakes new sales managers make? Trying to be friends with their reps. Kevin calls this out as one of the biggest myths in sales leadership. The thinking goes: if you build a personal friendship with your reps, they’ll work harder for you and be more loyal. But in reality, the opposite is true.
Friendships blur the lines of accountability. When a tough decision has to be made—whether it’s performance management, coaching, or even letting someone go—personal relationships make it harder to act in the best interest of the business. Worse, the perception of favoritism can destroy team morale. As Kevin puts it, “It never becomes a problem—until it becomes a problem.” And when it does, it’s often too late to fix.
Sales leaders need to build strong, professional relationships with their teams, but they shouldn’t cross the line into friendships. Being respected is far more important than being liked.
The Six Traits Every Sales Hire Must Have
A great sales strategy is worthless if you put the wrong people in the seat. Kevin believes most hiring mistakes happen because leaders overlook the must-have traits that define top sales talent. He doesn’t just have a wish list—he has a non-negotiable hiring framework:
- Need for Achievement – High performers have an internal drive to win. They push themselves harder than anyone else ever could.
- Competitiveness – Sales is a game, and the best reps hate to lose. They’re always looking for ways to be the best.
- Optimism – Rejection is part of the job. The best reps bounce back quickly and don’t dwell on losses.
- Coachability – If they can’t take feedback and improve, they’ll never get better.
- Continual Learning – Sales is evolving fast. The best reps actively seek new ways to improve.
- Organizational Skills – Success in sales isn’t just about hustle; it’s about managing pipeline, time, and priorities effectively.
If a candidate lacks even one of these traits, Kevin doesn’t hire them. And neither should you.
Why Most Sales Coaching Fails
Here’s a hard truth: most sales “coaching” isn’t really coaching—it’s just pipeline management in disguise.
Kevin points out that too many managers spend their 1:1s reviewing deals instead of developing reps. Real coaching isn’t just about getting a deal across the finish line; it’s about making sure reps consistently get better at the skills that drive long-term success.
That means coaching conversations need to be intentional. Are your managers helping reps sharpen their discovery skills? Are they working on objection handling, negotiation, or deal strategy? Or are they just running through the forecast? If it’s the latter, you’re leaving massive performance gains on the table.
Managers Need Training, Too
Many CROs assume that because a rep was a top performer, they’ll automatically become a great manager. Kevin calls this one of the biggest leadership blind spots.
Most frontline sales managers have never been taught how to coach. They don’t know how to run effective 1:1s, develop struggling reps, or hold their teams accountable in a way that drives improvement. They end up overwhelmed—juggling their own quotas, corporate tasks, and the pressure to hit team numbers—without the skills to effectively lead.
Without a structured approach to coaching, new managers default to what they know: focusing on deals instead of people. That’s why so many sales teams struggle with inconsistent coaching and unpredictable results.
Avoiding the Landmines in Sales Leadership
Kevin’s biggest takeaway? Sales leadership isn’t about being the smartest person in the room—it’s about building systems that help other people succeed. That means:
- Hiring the right people with the right traits.
- Coaching to skills, not just deals.
- Training managers so they can actually develop their reps.
- Keeping professional boundaries to maintain respect and accountability.
If you’re a CRO or frontline sales leader, this episode is a must-listen. Avoid the mistakes that have tripped up even the best sales managers, and start building a team that wins—consistently.
🎧 Listen to the full conversation with Kevin Gaither on Coach2Scale
