I was wrong about this one thing, and it almost ended my entrepreneurial career

Years ago, during my leadership journey, I had the chance to sit down for dinner with Ben Chestnut, co-founder and former CEO of Mailchimp.

"How do you manage your time?" I asked him. "You do so much. What's your productivity secret?"

I expected him to have the ultimate productivity hack. I worked hard to keep my inbox at zero, to manage my tasks, and to find time to accomplish my work. 

"You have a productivity problem?" he asked.

"Yes," I said. "I think I could do more."

"You don't have a productivity problem," he replied. "You have a people problem. You need to delegate. Are you delegating? Do you have the right people you can delegate to?"

Boom. Ben’s statement hit me like a ton of bricks.

I was running myself into the ground, spending all my time putting out fires. I was constantly searching for more time. How could I get the time so I could accomplish more? Getting as much done with the time I had felt like it had been one of the secrets of our progress so far.

But Ben was telling me that I needed to totally reframe the problem. It wasn’t about making my time more productive; it was about having the right people and giving them the right challenges so I could end up with more time to work on different classes of problems.

That moment with Ben changed how I saw the team and managed my time moving forward.

I quickly started giving the senior management team more ownership– I realized I had never fully delegated to them before. Rapidly, things changed. Some people started scaling more than I had ever seen, and others quickly started failing. It was enlightening, painful, and amazing to see what happens when you delegate the right things.

I learned that delegation wasn’t just about surviving in business. It could help me thrive as a leader and ultimately help the company scale.  

Once I mastered the art of delegation: 

• I had more energy and time to do the things I was uniquely capable of doing to move the business forward.

• Others began growing faster and took on way more than I expected. With more ownership, their domain expertise began to impact the company positively.

Here’s how I think about delegation after doing it for more than a decade now:

1. If someone can do something 80% as well as me, I delegate it. If you can do something uniquely valuable, you should figure out how to keep doing it.

2. Delegate the opportunities and challenges, but hold the strategy close. Figuring out the right balance of goals and objectives can allow you to spread ownership of different problems across the business. The key I’ve found is having a strategy that A. Is clear enough it allows everyone to remain highly aligned. 2. Grants ownership so that teams can work independently. Highly aligned, and loosely coupled is the way Netflix puts it.

3. Temper your failure tolerance for the long term. Here’s what I mean: Some projects and people will fail. This is okay and expected if you take enough risks, but ideally, each failure is small and something you can learn from. If you see a mistake or potential failure happening, the calculus around balancing the effort to help, the magnitude of the failure, and the likelihood of the person learning from the failure should all be considered when deciding if you should get involved or not.

4. Delegation without feedback is bad. When delegating well, you want to provide a lot of feedback, especially when beginning new types of projects.

5. Communicate, communicate, and then communicate some more. We’ve found that the larger the business becomes, the more we must repeat the strategy, values, and mission. Keep the big things the same, and let the small things change more.

So remember, productivity hacks are nice, but they run out of runway when you start to get more people. 

Thank you, Mr. Chestnut, for that dinner conversation.