Learning How To Delegate: A Guide To Letting Others Make Decisions

Startup heads can’t just sit around answering employees’ questions all day.

Learning How To Delegate: A Guide To Letting Others Make Decisions
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Most self-employed people get caught in the delegation trap. You’re busy doing everything yourself. You know you need help, but to find and train someone would take more time than you have. So you keep working harder until you break.


Here’s my tale of how I broke into the delegation mind-set.

In 2001, CD Baby was three years old. I had eight employees, but I was still doing “everything else” myself, working 7 a.m. to 10 p.m., seven days a week. Everything still went through me. Every five minutes, my employees had a question for me:

Derek, some guy wants to change the album art after it’s already live on the site. What do I tell him?

Derek, can we accept wire transfer as a form of payment?

Derek, someone placed two orders today, and wants to know if we can ship them together as one, but refund him the shipping cost savings.

It was hard to get anything done while answering questions all day. I felt like I might as well show up to work and sit on a chair in the hallway, just answering employees’ questions full-time.

I hit my breaking point. I stopped going to the office and shut off my phone. Then I realized I was running from my problems instead of solving them. I had to fix this, or I’d be ruined.

After a long night of thinking and writing, I got myself into the delegation mind-set. I had to make myself unnecessary to the running of my company.


The next day, as soon as I walked in the door, someone said, “Derek, someone whose CDs we received yesterday has now changed his mind and wants his CDs shipped back. We’ve already done the work, but he’s asking if we can refund his setup fee since he was never live on the site.”

This time, instead of just answering the question, I called everyone together for a minute. I repeated the situation and the question. I answered the question, but more important, I explained the thought process and philosophy behind my answer.

Yes, refund his money in full. We’ll take a little loss. It’s important to always do whatever would make the customer happiest, as long as it’s not outrageous. A little gesture like this goes a long way towards him telling his friends we’re a great company. Everyone always remember that helping musicians is our first goal, and profit is second. You have my full permission to use that guideline to make these decisions yourself in the future. Do what makes the musicians happiest. Make sure everyone who deals with us leaves with a smile.

I asked around to make sure everyone understood the answer. I asked one person to start a manual, and write down the answer to this one situation, along with the philosophy behind it. Then everyone went back to work.


Ten minutes later, a new question. Same process:

  1. Gather everybody around.
  2. Answer the question and explain the philosophy.
  3. Make sure everyone understands the thought process.
  4. Ask one person to write it in the manual.
  5. Let everybody know they can decide this without me next time.

After two months of this, there were no more questions. Then I showed someone how to do the last of the stuff that was still my job. As part of learning it, he had to document it in the manual, and then show it to someone else, too. (Learn by teaching.)

Now I was totally unnecessary. I started working at home, not going into the office at all.

I had even taught the employees my thought process and philosophy about hiring new people. So our two newest employees were found, interviewed, hired, and trained by other employees. They used that manual to make sure all new employees understood the philosophy and history of CD Baby, and knew how to make decisions for themselves.

I’d call in once a week to make sure everything was okay. It was. No one had any questions for me.


Because my team was running the business, I was free to actually improve the business! I moved to California, just to make it clear that the running of things was up to the employees. I was still working 12-hour days, but now I was spending all my time on improvements, optimizations, and innovations. To me, this was the fun stuff. This was play, not work.

While I was away, my company grew from $1 million to $20 million in four years, and from eight to 85 employees.

There’s a big difference between being self-employed and being a business owner. Being self-employed feels like freedom until you realize that if you take time off, your business crumbles. To be a true business owner, make it so that you could leave for a year, and when you came back, your business would be doing better than when you left.


This article is adapted from Anything You Want: 40 Lessons for a New Kind of Entrepreneur by Derek Sivers, in agreement with Portfolio, an imprint of Penguin Publishing Group, a division of Penguin Random House LLC. Copyright © Derek Sivers, 2011. It is reprinted with permission.