Becoming Your Future Self

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.”

Types of bottlenecks

There are three common ways in which startup leaders can fail to scale up:

  1. 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.
  2. 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.
  3. They’re good but not great at the job. Some people simply hit a limit in what they’re able to do. Maybe someone is good at managing 3 people but not 8 people. Or they work well with managers, but not managers of managers. If these people don’t improve their skills, they end up holding the company back. “Good” may be good enough on a small team, but it’s not sufficient when dozens or hundreds of people depend on a single person. The danger to a company is even greater if a key person isn’t great at their job but thinks they are.

Are you a bottleneck?

One of the challenges with scaling up is that people often don’t realize that they’ve hit a wall. They get promoted from contributor to manager to director and think everything is going great, when in fact they’re no longer performing well at their new level. It’s hard to stay self-aware when your environment is changing rapidly. Here are some tips for figuring out if you’re transitioning from an asset to a bottleneck:

A thought experiment on personal scaling

The best way to avoid being a bottleneck is to not become one in the first place. One thought experiment that I sometimes suggest to founders is to consider what their future selves will have to do.

Thought experiment: What will your job look like in 1 year? In 5 years? Which existing responsibilities will you no longer have and what new responsibilities will you accumulate?

This perspective can make your career path clearer. Here are three examples of how responsibilities may evolve over time:

  1. You’re an early-stage CTO who currently splits time between managing 3 engineers and writing code. What will your role look like in a year? Your team will probably grow to 5-10 people, so you’ll have more management responsibilities and less time to code (if any). What will your role look like in 5 years? If the company does well, it might have 100 engineers. At that point, you’re either purely a manager or purely an engineer, and very unlikely to be doing a mix of both.
  2. You’re a CEO and you are starting to build out a sales team. Your company is young, so you’re doing most of the selling. You’re also personally training each sales hire. What will your CEO role look like in a year? As your sales team grows, you’re probably doing less selling and training, and focusing more on hiring a VP of Sales. In 5 years, you’re likely delegating everything sales-related to your VP of Sales.
  3. You’re an engineer at a Series A company, and your team is doubling every 6-12 months. What will your role look like next year or in 5 years? Your department might be 2x-4x bigger next year and 20x or 50x bigger in 5 years. You have a lot of career options in a company that’s growing that quickly: remain an individual contributor, become a tech lead, shift from engineering to product management, become a manager, or even work your way up to VP-level. Each of these options requires a different, intentional plan of action, and if you’re not pursuing a specific plan then there’s a good chance you’ll still be an individual contributor in 5 years. Maybe that’s what you want, and maybe it’s not.

Becoming your future self

Once you have a sense of how your role is likely to look in 1-5 years, the next step is reverse engineering a path that gets you to that destination. There are 4 main courses of action:

Miscellaneous tips

As your role evolves, one of the toughest things to do is to prioritize the right tasks and activities. Here are a few assorted tips for doing that:

Perhaps the most important thing to consider is that if you don’t actively think about what Future You will be doing and how to get from where you are to where you’ll need to be, then Future You will look a lot like Present You.† If you want to scale in tandem with your company, then start moving in the right direction today.

† This is true professionally and personally.

Thank you to Natalie Dillon for giving me feedback on this post.

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