Scaling a company is one of the hardest things a founder will ever do — and not just technically or tactically. The real challenge is emotional. Many founders underestimate how much of their company’s future depends on their own evolution as leaders.
The truth is that as your company grows, your role must grow with it. The instincts that got you from zero to one — making every decision, driving every initiative, keeping everything in your head — often hold you back at one to one hundred. The startup that once needed your fingerprints on everything eventually needs you to take your hands off the wheel.
To explore how to make that shift, we sat down with Edward Sullivan, CEO of Velocity Coaching. For more than a decade, Edward has coached founders and CEOs of high-growth startups like Slack, DoorDash, and Airtable, helping them navigate the messy middle between scrappy beginnings and sustainable success. His leadership frameworks have been featured in Harvard Business Review, Forbes, and Fast Company. He’s also the co-author of the WSJ bestseller Leading with Heart. His central message is simple: scaling your company means scaling yourself.
Over the years, Edward has seen the same five leadership mistakes appear again and again — pitfalls that quietly stall growth. Here’s what they are, and how to avoid them.
1. You’re Fueling Growth, But Not Reducing Friction
Most founders are wired for acceleration: raising capital, hiring fast, pushing hard. But few pay attention to friction — the invisible drag that slows a growing team. As Edward puts it, “Organizational velocity equals fuel minus friction.”
“Velocity isn’t just about fuel — like capital, headcount, or go-to-market,” he says. “It’s also about reducing friction: poor decision-making, weak delegation, backchanneling, conflict, and toxic personalities. Most founders focus on acceleration. But speed comes just as much from removing drag.”
True leadership isn’t about pushing harder. It’s about clearing the path so the team can run faster with less effort. The best founders are friction hunters, not just growth drivers.
2. You’re Still in the Center of Everything
In the early days, founders are the company’s nervous system. Every decision, every customer call, every hire flows through them. But as the team grows, that structure collapses. Founders often stay in the center not because of ego, but because of missing systems.
Delegation isn’t abdication. Over-delegation can create chaos just as micromanagement kills trust. Effective delegation begins with defining what good looks like, then letting go of how it’s achieved. Systems replace supervision. Clarity replaces control. The founder’s job evolves from doing to enabling — from being the center to setting direction.
“If a decision is low-cost, low-scope, and reversible — someone else should own it,” Edward explains. “Founders get their time back by defining thresholds for their involvement and sticking to them.”
“When you clearly define what good looks like,” Edward says, “you can let go of the how — and trust your team to figure it out.”
3. You’re Avoiding Hard Conversations
Few founders enjoy giving tough feedback. Many avoid it out of fear — fear of conflict, fear of demotivating people, or fear of losing someone they need. But avoidance breeds mediocrity. When underperformance goes unchecked, it quietly tells the team that accountability doesn’t matter.
“Start by understanding the thinking behind someone’s work,” Edward says. “There’s almost always a nugget of genius in it — something to build on, even before you course-correct.”
Founders who normalize feedback build resilient, self-correcting teams. The best cultures treat feedback as fuel, not fire.
“Leaders need to create a culture where critique is safe — not brutal,” Edward says. “That’s how teams stay sharp without becoming scared.”
4. You’re Sending Mixed Signals About Accountability
As startups scale, accountability often blurs. Expectations live in people’s heads instead of systems. Rewards are inconsistent. Consequences are unclear. Over time, performance drifts.
Edward introduces the ARC Framework — Agreements, Rewards, and Consequences. “Clarity is kindness,” he says. “That means clear agreements, clear rewards, and clear consequences when expectations aren’t met.”
Accountability isn’t about punishment; it’s about creating a culture of trust and transparency.
“We get more of what we reward,” Edward notes. “Recognition — especially when it’s public and immediate — can be more motivating than long-term incentives.”
5. You’re Burning Bright — But Headed for Burnout
Startups have a way of turning urgency into identity. Founders sprint for months or years, mistaking constant motion for progress. But sustainable velocity requires pacing and renewal.
“Even an engine performs best at 80% effort,” Edward says. “If you’re redlining constantly, performance drops and burnout spikes.”
Longevity in leadership means managing energy, not just time. A burned-out founder can’t lead a high-performing team.
“Sailboats are built for sailing — not sitting in harbor, and not thrashing in hurricanes,” he explains. “Founders should aim for flow: that sweet spot between boredom and overwhelm.”
Scaling Yourself to Scale the Company
Scaling isn’t just about hiring faster or raising more money. It’s about removing friction in your leadership style, creating clarity, and building systems that let your company move without you in the center. Founders who evolve unlock growth at every level — in themselves, their teams, and their companies. It all starts with three principles: clarity, candor, and care.
Edward shared these lessons during our monthly founder-exclusive webinar series, one of the many ways we support portfolio founders at Right Side Capital Management. If you’re building something bold, you can apply for funding directly on our website.
To learn more about Edward’s work, visit Velocity Coaching or reach out directly at hello@velocitycoaching.com.
