Your Best Employees Should Leave Your Team
(And Why That's Your Win)
The Contrarian Truth: If your top performers aren't outgrowing you, you're not developing them, you're just using them.
I watched Chris, a manufacturing supervisor I coach, stare at the resignation letter on his desk, his heart sinking.
Marlin, one of his most promising team members, was leaving for a new role at another company. As he read the gracious note thanking him for "showing me what being a supervisor should look like," he felt a mix of pride and loss. This was the third person from his team in two years who had been promoted or recruited elsewhere because of the skills they had developed under his guidance.
"I invest so much time developing these people, and then they leave," Chris admitted when we met later that day. "Sometimes I wonder if I'm just training talent for other teams and companies."
I understood his frustration completely—because I used to feel exactly the same way.
When I Got It Wrong
Early in my career, I took every person moving on personally.
When someone on my team got promoted to another department or left for a better opportunity, I felt like I was losing something. Worse, I felt like I was *being* lost, like they were choosing something better than me. I remember one particular team member (let's call her Sarah) who I'd invested countless hours developing. When she came to tell me she'd been offered a position at another organization, I felt my stomach drop. Instead of celebrating with her, I found myself thinking, "After everything I did for you?"
My response was polite but cold. I gave her the standard two-week transition, wished her well, and internally resented what felt like abandonment. I saw her departure as my failure, not her success.
Looking back now, I can see how insecure and short-sighted that mindset was. I was measuring my worth by whether people stayed, not by whether they grew. I wanted to be needed more than I wanted to develop people. And that meant I was more focused on my own validation than on their success.
It took a long time and a good mentor for me to finally understand: I wasn't upset because I was losing good people. I was upset because I'd made their growth about me instead of about them. That realization changed so much for me.
When Chris shared his frustration about Marlin leaving, I heard my younger self in his words. So I asked him the question someone asked me years earlier: "Chris, do you remember what you told me last month about your team's performance?" "That we've exceeded our targets for six consecutive quarters?" "And why do you think that is?" Chris paused. "Because the team is highly capable, motivated, and up for the task." "Exactly. You've created a culture where people grow. Yes, some of them will inevitably leave, but think about the legacy you're building. How many former team members still call you for advice? How many people credit you with changing their career trajectory? That's the effect of being a multiplier."
The Courage to Be Outgrown
Here's what Chris was missing—and what most supervisors miss when they obsess over the wrong kind of retention: His success should mean that his direct reports might outgrow his guidance.
We've built an entire management philosophy around retention metrics, as if keeping people is the ultimate goal. It's not. Developing people is the goal. Sometimes development means they grow beyond your team, your department, or even your organization.
Traditional supervisors hoard information, maintain tight control, and create dependency on themselves. They fear that developing others too much will diminish their own value. But the multiplier mindset recognizes something counterintuitive: investing in people's growth, even knowing they might leave, creates something more valuable than forced loyalty. It creates legacy.
The Multiplier Effect in Action
Let me tell you the rest of Chris's story. That team member who left, Marlin? He went on to become a department head at his new company. Within a year, he had developed three new team members using the principles he learned from Chris. Those three, in turn, began developing others. Chris's initial investment in Marlin ultimately influenced dozens of people he never met.
This is the ripple effect of true development. Every person you develop has the potential to develop others, creating impact that extends far beyond your direct influence.
But here's what happened on Chris's team in the meantime: The people who stayed became more engaged, not less. They saw that Chris genuinely invested in growth, not just productivity. They trusted that if they gave their best, he would give his best to help them advance, no matter where that advancement led.
New hires started seeking out his team specifically. Word got around that if you wanted to actually grow as a professional, Chris's team was the place to be. His retention of high performers who wanted to stay actually improved, while those who needed to leave for their next chapter did so with his blessing and support.
The Real Cost of "Retention at All Costs"
When you prioritize keeping people over developing them, you create several hidden costs:
1. Stagnation becomes your culture. When people sense that growth opportunities are limited, the ambitious ones disengage mentally long before they leave physically. You get their time but not their best thinking.
2. You attract the wrong people. When your reputation is "stable but stagnant," you'll attract people seeking comfort, not challenge. The high-potential talent you actually want will look elsewhere.
3. You become a bottleneck. If your value comes from being indispensable, you can never scale. You have to manage everything because no one else is being developed to lead.
4. Your best people leave anyway, they’ll just be bitter. Eventually, people who want to grow will leave. The question is whether they leave grateful for what you taught them or resentful about what you withheld.
From Gatekeeper to Gateway
In my book Lead. Manage. Win!, I discuss the crucial shift from being a gatekeeper who controls access to opportunities to becoming a gateway that opens doors for your team's success. This requires a fundamental mindset change:
The Gatekeeper Mentality:
Controls information flow to maintain power
Makes themselves indispensable by hoarding opportunities
Views team members' success as potential threats to their status
Focuses on what people can't do rather than what they can do
Creates barriers to growth instead of removing them
The Gateway Approach:
Opens channels of communication rather than controlling them
Creates pathways to opportunity instead of blocking them
Amplifies team voices in important conversations
Connects people with resources and influential networks
Removes obstacles that prevent the team from succeeding
The gateway supervisor asks, "How can I help my people reach their potential?" rather than "How can I maintain control?"
The Development Pipeline: Making Growth Systematic
If you're going to embrace the reality that your best people should outgrow you, you need a systematic approach to developing them. Here's the framework I use with the supervisors I coach:
Stage 1: Recognition
Not everyone wants to move into leadership, and that's okay. The key is identifying those who have both the desire and potential. Look for:
Initiative: Do they tackle challenges without being asked?
Influence: Do others naturally seek their guidance?
Growth Mindset: Are they eager to learn and improve?
Courage: Do they speak up when necessary and take intelligent risks?
Empathy: Do they genuinely care about others' success?
Stage 2: Development
Create intentional experiences that build capability:
Immediate Opportunities (30 days):
Shadow you in important meetings
Lead a small project or initiative
Represent the team in cross-functional meetings
Mentor a new team member
Short-Term Growth (90 days):
Act as department representative on company-wide initiatives
Lead process improvement projects
Handle difficult situations with your coaching
Facilitate team meetings or workshops
Long-Term Development (12 months):
Serve as acting supervisor during your absence
Lead significant change initiatives
Participate in formal leadership development programs
Build external professional networks
Stage 3: Advocacy
Here's where most supervisors fail: they develop people but don't actively advocate for them. True cultivation requires you to:
Nominate them for stretch assignments in meetings where they're not present
Recommend them for promotion and recognition
Share their successes with senior leadership
Defend their decisions and approaches
Ensure their voices are heard in important conversations
This is where the courage comes in. You're putting your credibility on the line. You're creating situations where they might outshine you. You're potentially losing them to other opportunities.
And that's exactly the point.
The Real Questions You Should Be Asking
Stop measuring your success by retention rates. Start measuring it by:
How many people you've helped reach their next level, wherever that level exists
How many former team members still seek your advice
How many people credit you with changing their career trajectory
How quickly high-potential talent seeks out your team
How engaged your current team is because they know you invest in growth
How many leaders you've influenced who are now developing others
The supervisors who truly understand this become magnets for talent. People want to work for someone who will invest in their growth, even if it means eventually letting them go.
Your former team members become ambassadors of your leadership. They join your informal network. They remember who invested in them when they were still rough around the edges. And when they're in positions to hire, partner, or recommend? They remember.
The Courage to Begin
Transformation like this doesn't happen overnight. It requires courage because it means:
Sharing credit and spotlight
Prioritizing long-term capability over immediate results
Accepting that some people you develop will leave
Trusting others with increasing responsibility
Measuring success through others' growth, not just your own achievements
But here's what I've learned coaching supervisors through this shift: The ones who embrace being outgrown don't just build better teams, they build better careers, better organizations, and better industries.
They create the “multiplier effect”, where their influence extends far beyond their immediate sphere through the people they've developed who go on to develop others.
Your Next Step
If you're ready to shift from retention-focused supervision to growth-focused development, start here:
This week, schedule 15 minutes with each team member and ask:
"What's one thing you need more support with?"
"What's one area where you need more challenge?"
"Where do you want to be growing in the next year?"
Then listen. Really listen. Don't immediately try to solve or categorize… just understand what they need and why it matters to them.
Some of those conversations will reveal people ready to grow beyond your team. That's not failure, that's your win. Because you'll know you've created the kind of environment where people don't have to leave to grow, but they're free to leave when growth requires it.
The Real Question: Are you developing people or just trying to keep them?
Your answer to that question will determine whether you're building a legacy or just managing a team.
Want to dive deeper into developing situational fluency as a supervisor? Check out my book "Lead. Manage. Win! Mastering When to Manage and When to Lead" which is releasing very soon! CLICK HERE to join my mailing list and get updates on the release date, insights to book and an introductory price.
