#411: Why the Best Sales Teams Make Leadership Harder (and How to Thrive)
The Paradox of Great Sales Teams!
You’ve built a dream team of top-tier sales reps and rockstars who crush quotas and win deals. So why does leading them feel more demanding than ever? Because the best people don’t bring you solutions, they bring you the problems they can’t solve.
Why Does This Happen?
High Performers Tackle the Easy Stuff
Top reps are self-sufficient. They close straightforward deals, handle objections, and manage pipelines without hand-holding. You’re not wasting time reteaching the basics, which should free you up for strategic thinking, or so you thought.
They Escalate the Tough Stuff
When they hit roadblocks such as unpredictable buyer behavior, competitive disruptions, or internal bottlenecks, they turn to you, the sales leader, for answers. These aren’t simple fixes; they’re complex challenges from your best performers, positioning you as the expert they trust.
The Stakes Are Higher
Because these reps are your top talent, their problems often involve your most significant accounts, most formidable competitors, or most critical quarters. They’re closing five- and six-figure deals all day, but the roadblocks they can’t clear are the seven-figure whales that can transform your business.
Is This a Problem?
As I learned in Sales 101, there are no problems, only opportunities. This isn’t a flaw in your team; it’s a sign of their strength. Yes, it stretches your boundaries, but it also means your team is tackling opportunities that can scale your company. They’re closing smaller deals faster and more efficiently, boosting productivity and profitability while eyeing the big wins they believe they can land.
Years ago, an interviewer asked me if I had "glass window syndrome." I had no clue what it meant. He explained: "Are you comfortable cold-calling a Main Street shop but hesitant to walk into a 20-story highrise, thinking you’ll get there someday?" Someday is now for your team, and your leadership makes it possible.
Turning Chaos into Opportunity
Yes, it’s demanding, but it's also a chance to grow your team and yourself. Encourage your reps to escalate problems early, not just when they’re stuck, as by then, it might be too late. Top performers hate admitting defeat, so prompt them with questions during status updates to uncover issues sooner.
Stop being a fixer and become a coach. Don’t just hand them answers, guide them to solutions. For example, ask: "What’s the buyer’s biggest hesitation, and how can we address it together?" This builds their skills and your team’s resilience.
As Sun Tzu wrote over two millennia ago, "In the midst of chaos, there is also opportunity." Your best reps may bring you chaos in the form of their most challenging problems, but within that chaos lies your chance to lead with innovation, build resilience, and create an unstoppable team, not just today but for years to come.
Upgrade Your Leadership
To lead a top-tier team, you may need to upgrade your problem-solving skills. At Kole Performance Group, we specialize in helping sales leaders turn chaos into opportunity. Contact us for a free 30-minute consultation to see how we can help you build a stronger, more resilient team. It’s hard work today, but it’s the path to a better tomorrow.