Delegate Well or Not at All

One thing that often happens to founders trying to grow their companies is the need for delegation.

As a founder of a small company, you start by doing everything from unlocking the door in the morning to closing up at night. You grow it by bringing in other people to take on the tasks you originally did yourself, one by one.

I’ve been through that process myself. In the early days of Palo Alto Software I did the programming, the documentation, the marketing, the administration, and the technical support. And I answered the phone.

As we grew, I shed those tasks one by one. My first hire was someone to answer phones, and the second hire was someone to handle tech support. Then came a bookkeeper, which led, over time, to a controller. I hired somebody to handle the documentation, and somebody to manage the programming.

Something I learned along the way: if you delegate a task to somebody else, and then second guess the results, that person won’t accept the next task. Instead, you’ll be stuck with micro managing, whether you like it or not, because that person will ask you all the details so that you decide, rather than risking being second-guessed again.

So, for example, if you ask a marketing person to design and implement a brochure, and you don’t want to deal with the details during the process, then you’d better damn well shut up and like the brochure when it’s done.

If you don’t let it go, and instead of that you wish it had a different headline or a different size or a different color, then you’re not delegating; you’re micro managing. The person you’re second guessing won’t take initiative in the future. Instead, he’ll come back at you over and over asking you to decide every detail along the way.

I’m guessing that this seems obvious when you read it, but I know from experience that it’s very hard to do. I’ve learned the hard way. I had some smart people who helped. But it wasn’t always easy. So, If you’re trying to grow a company, then you probably need to delegate. If that’s the case, then I suggest you take a step back, and test yourself: watch yourself in action.

If people keep coming back to you asking you to decide the details all the time, that’s a good indication that you’re not really delegating or you are second guessing and making your would-be delegates miserable. Get a clue: if people don’t seem to want to make decisions, maybe that’s because you make them suffer when they do.


  • Tim Berry says:

    Re energybyte, good point, but I certainly lived with a bootstrapping business throughout the growth period I was describing. It was all bootstrapped. So I was always facing the tradeoffs of the leverage of more people vs. the increased risk and fixed cost. Tim.

  • Small Business Entrepreneur blog says:

    Hi Tim,

    When you are delegating in a bootstrapped business, things are a little more complicated because you get the feeling you are cutting the profits by hiring. I wrote an article about this, you might find it interesting

  • Kelly says:


    That is so well said! Yes, it's hard to do, but essential for staff to believe in themselves and your company. When you step back, you allow them to take ownership. When you don't you make them feel like wage slaves, and then you are just a replaceable paycheck, not a company they're an integral part of.

    It's about trusting the employee, but maybe there's a bit more, too: do you not trust your own hiring abilities, if you can't let the person do the job you selected him or her for? As owners letting go of being chief cook *and* bottle washer, we have to trust ourselves to hire great bottle washers.



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