In my five years as a VC, I’ve worked closely with the founders of 50+ companies. Many of these companies have grown headcount substantially since I first met them. One of the biggest challenges that founders and early employees face is scaling up personally to meet the ever-growing needs of a business. People sometimes gets stuck and become bottlenecks because they are reluctant to delegate the things they are great at, or they don’t want their role to include new tasks that arise as a company grows. As executive coach Marshall Goldsmith says, “what got you here won’t get you there.”
They’re good at some parts of the job but bad at other parts. Jobs often require multiple skills, and key employees have to be great at all of those skills. For example, an early-stage CTO should be a great engineer, a great recruiter, and a great manager. If they’re not good at one or more of these things, the engineering team will struggle as it grows.
They’re unwilling to delegate. In growing companies, strong performers gain responsibility quickly. If you’re good at your job you can quickly move from individual contributor to manager to executive. This transition requires letting go of making personal contributions, and people are often reluctant to do that. A company ends up having a CEO who wants to spend 10% of their time defining the product strategy, or a CTO of who manages 8 people but still wants to check in code for core features. The result is that these people become bottlenecks. The CTO becomes rusty and their code quality worsens, but they also hold up their teammates who are waiting for work that the CTO committed to but doesn’t have time for.