OTL Newsletter - Why You Should Help Your Star Player Quit...

Observation 🧐

As sales leaders, we often face a bittersweet reality: the better we are at hiring and developing top performers, the more likely we are to lose them. 

While it's tempting to hold onto these stars at any cost, true leadership requires putting their growth ahead of our own immediate interests.

The real challenge—and opportunity—lies in how we support their growth, even when that growth might lead them away from our team. This approach, while seemingly counterintuitive, is crucial for several reasons:

1. Your reputation as a leader who develops talent becomes your strongest recruiting tool. When you champion people's growth, you attract more top performers. This creates a virtuous cycle: great talent attracts great talent.
2. Supporting individual growth creates a culture of excellence and ambition. When team members see their colleagues advancing—even if it means leaving the team—it sets a powerful example that performance and potential are truly valued. This motivates everyone to raise their game.
3. Today's departing star could become tomorrow's strategic partner, client, or senior executive champion. By supporting their journey, you're not just doing the right thing—you're making a long-term investment in your professional network.

Common Mistakes That Drive Away Top Performers

Unfortunately, many sales leaders inadvertently sabotage their relationships with top AEs through well-intentioned but counterproductive actions:

👎The Golden Handcuffs Approach

Some managers try to retain top performers by making them financially dependent on their current role. 

👎Information Hoarding

Keeping top performers in the dark about growth opportunities or limiting their exposure to senior leadership.

👎The Comfort Zone Trap

Sometimes managers avoid challenging their star performers with stretch assignments, fearing it might prepare them for roles elsewhere.

👎The Guilt Trip

Using emotional manipulation ("the team really needs you" or "we're in a crucial period") to discourage career moves.

The long-term impact of these mistakes extends far beyond losing the individual AE. It damages your reputation as a leader, makes recruiting harder, and creates a culture of stagnation rather than growth.

Maximizing Impact While Supporting Growth

So how do we balance team performance with individual career development? Here are strategic approaches that serve both objectives:

1️⃣ Create a Clear Development Path. 

Understand their career aspirations and create specific development plans. This might include:

• Identifying skills they need for their next role
• Creating opportunities to develop those skills in their current position
• Setting clear timelines and milestones for progression (timelines are key to setting expectations for both parties, the leader and the AE) 

2️⃣ Build a Strong Bench

Knowing that star performers will eventually move on, focus on:

• Having your top AE mentor other team members
• Documenting their best practices and processes
• Creating systems that help institutionalize their knowledge

3️⃣ Leverage Their Expertise While You Have It

Make the most of their time on your team by:

• Having them help shape sales strategy and processes
• Using their insights to improve team training
• Creating case studies from their successful deals

4️⃣ Be Their Career Champion

Position yourself as an ally in their professional journey by:

• Making introductions to senior leaders
• Recommending them for growth opportunities, even if outside your team
• Providing honest feedback about their readiness for next roles

The Long Game of Leadership

Remember that your job as a leader can sometimes mean making decisions that hurt in the short term but create lasting value.

When you become known as a leader who genuinely supports career growth, several things happen:

• You attract more top performers who want to work with you
• Your alumni network becomes a powerful source of business opportunities
• Your reputation as a leader grows stronger
• Your team develops a culture of high performance and continuous growth

The paradox of great leadership is that the more willing you are to let people go when it's right for them, the more people will want to stay and work with you. 

By focusing on developing people rather than just deploying them, you create a legacy of leadership that continues to pay dividends long after individual team members have moved on.

Remember, your star AE's success story should include you as a catalyst, not a roadblock.

Thought Starter  🤔

Love 🥰

A great book about building a high performing team culture is “Leaders Eat Last” by Simon Sinek. It is the ultimate guide to building a strong and inspiring team, and creating a supportive work environment, where everyone can thrive.