Why Can't You Delegate to the Team You Trust?
How founder loyalty masks the talent gaps quietly limiting your growth.
I had an operations manager who'd been with me since almost the beginning. He was one of my first hires—showed up when we were five people crammed into a sublet office, figured things out without a playbook, and never complained when the job description changed every six months.
By the time we hit 30 people, he was running operations. By the time we hit 50, he was struggling. Deadlines were slipping. Projects were falling through the cracks. I kept stepping in to fix things, telling myself I was just helping out during a busy stretch.
It took me way too long to see the real problem. The role had outgrown him. The company needed someone who could build systems and manage managers, and that wasn't his skill set. But I couldn't bring myself to make a change because I remembered everything he'd done for us early on. I felt like I owed him.
That loyalty cost me. Not just in operational headaches, but in the A-players who quietly decided the company wasn't serious about performance and started looking elsewhere.
I call this the Loyalty Trap—the pattern in which founders keep people in roles based on history and trust rather than current capabilities. It's one of the most common problems I see when coaching founder-CEOs of companies between $5M and $50M, and it's one of the hardest to fix because it feels like doing the right thing.
What the Loyalty Trap Looks Like
The pattern usually starts with someone who was essential early on. They were there when things were scrappy. They figured out their job without training. They stayed when others left. The founder trusts them completely—and that trust is earned.
But as the company grows, the role changes. What used to require hustle and improvisation now requires process and structure. What used to be a team of three now has fifteen people and needs a real manager. The person who was perfect for the early stage isn't necessarily right for the next stage.
The founder sees the gaps but explains them away. "She's been overwhelmed lately." "He just needs more support." "Once we hire underneath her, things will smooth out." The conversation about whether this person is actually the right fit never happens—because the founder can't imagine having it.
Meanwhile, the rest of the team sees everything clearly. They see the underperformance. They see the founder making excuses. And they start drawing conclusions about what kind of company this is.
Why Founders Fall Into This Trap
Loyalty is a virtue. Founders are supposed to take care of the people who took care of them. Letting someone go—especially someone who's been loyal—feels like betrayal.
There's also a practical fear: what if you can't replace them? Early employees often hold institutional knowledge that isn't documented anywhere. They know how things actually work. The idea of losing that knowledge, on top of losing the relationship, is enough to keep most founders from acting.
And then there's identity. Many founders see themselves as the kind of leaders who stand by their people. Admitting that someone isn't working out feels like admitting failure—either in hiring, in developing them, or in building a company where they could succeed.
So founders wait. They hope things will get better. They invest in coaching, restructure responsibilities, and hire support staff to compensate. Sometimes that works. Often, it just delays the inevitable while the real costs pile up.
What This Pattern Costs Your Business
The highest cost isn't the underperformance itself. It's what happens to everyone else.
A-players don't want to work alongside B- and C-players. They notice who's pulling weight and who isn't. When they see underperformance tolerated—especially at the leadership level—they start questioning whether this is a place where excellence matters.
Some will say something. Most won't. They'll just quietly update their LinkedIn and start taking recruiter calls. By the time you realize what's happening, your best people are already halfway out the door.
The second cost is the founder becoming a bottleneck. When someone can't fully own their role, the founder steps in to fill the gaps. They review work that should be final. They make decisions that should be delegated. They spend their time managing around the problem instead of leading the company.
This creates a ceiling on the business. The company can only grow as fast as the founder can personally compensate for talent gaps. And that's not a scalable strategy.
What a Real Talent System Looks Like
Strong companies don't rely on loyalty and gut instinct to manage talent. They build systems that create clarity about expectations, performance, and development.
Role scorecards define what success looks like in each position. Not activities—outcomes. What does this person need to deliver, and how will we measure it? When the scorecard is clear, conversations about performance become objective rather than personal.
Regular talent reviews force honest assessment. At least quarterly, leadership teams should evaluate every key player: Are they meeting expectations? Are they growing? Are they in the right role? This isn't about being harsh—it's about being honest.
A-player standards get defined explicitly. What does an A-player look like in your company? What behaviors and results separate them from B-players? When you can articulate this clearly, you can hire for it, develop toward it, and make decisions based on it.
Development paths give people a chance to grow into roles—but with timelines and milestones. "We think you can get there" is different from "We're going to invest in your development, and here's what we need to see in the next 90 days."
Honest conversations happen early. The longer you wait to address a performance gap, the harder the conversation becomes. Great leaders give feedback quickly, directly, and with genuine care for the person. That's not cruelty—it's respect.
How to Know If You Have This Problem
There's a simple diagnostic. Take out a piece of paper and list your leadership team. Next to each name, write A, B, or C.
A-players consistently exceed expectations. You'd enthusiastically rehire them into their current role.
B-players meet expectations. They're solid, but you're not sure they can grow with the company. You might rehire them, but you'd have some hesitation.
C-players are below expectations. If you're being honest, you wouldn't hire them again for the role they're in today.
Now look at your C's. How long have they been C's? If the answer is more than a quarter or two, you have a Loyalty Trap problem. You've been tolerating underperformance, and everyone on your team knows it.
Where to Start
You don't need to fire anyone tomorrow. But you do need to get honest.
Start by building role scorecards for your key positions. Define what success looks like—specifically and measurably. Share those scorecards with the people in the roles. If there's a gap between where they are and where they need to be, name it.
Then have the conversation you've been avoiding. Not a vague "we need to step it up" talk—a real conversation about expectations, timeline, and consequences. Give people a genuine chance to rise to the challenge. Some will surprise you. Others will confirm what you already knew.
The goal isn't to become ruthless. It's to become honest. The best thing you can do for your team—including the people who are struggling—is to be clear about what you need and whether they can deliver it.
Questions for You and Your Team
Before moving on, take a few minutes to reflect on these questions. The goal isn't to have comfortable answers—it's to surface the gaps between what you believe about your team and what's actually true.
If you rated every member of your leadership team as an A, B, or C player in their current role—not their past contributions or future potential—how many C's would you have? This forces honesty about where you actually are versus where you wish you were.
How long have your lowest performers been underperforming? Weeks, months, or years? Duration reveals whether you're managing performance or avoiding it.
Have you lost any A-players in the last year who might have stayed if the team around them was stronger? This is the hidden cost most founders don't calculate.
What to Do Next
If this pattern sounds familiar, you're in good company. Most founders I work with have at least one person they've been avoiding a hard conversation with.
If you want to see where your People systems stand relative to other growth companies, take the Growth Readiness Assessment. It's a free 15-minute diagnostic that scores your business across six dimensions, including People.
Take the Growth Readiness Assessment
If you'd like help thinking through your talent strategy or preparing for a difficult conversation, I offer a free 60-minute consultation.
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About the Author
Bruce Eckfeldt is a strategic business coach and exit planning advisor who helps founder-CEOs of growth-stage companies scale systematically and exit successfully. A former Inc. 500 CEO who built and sold his own company, he brings real-world operational experience to strategic planning and leadership development. He's a certified ScalingUp and 3HAG/Metronomics coach, Certified Exit Planning Advisor (CEPA), an Inc. Magazine contributor, and host of the "From Angel to Exit" podcast. Bruce works with growth companies in complex industries, guiding leadership teams through growth challenges and exit preparation. Reach him at bruce@eckfeldt.com with any questions or if you want more information or to book a call with him.
