Today I listened to a really good interview with Ted Roden of personal assistant service Fancy Hands, who talked about how one of the biggest challenges with their service is getting people who have already paid to actually use it.

As a Fancy Hands user myself, this struck a chord. I don't use it as much as I thought I would and exactly for the reasons he talks about. People either think their task is too easy and not worth it, or it's too hard and only they can do it.

This got me thinking. We don't learn how to delegate.

Delegation is not natural, it's a skill and an art. Some of the most successful and noteworthy people got to where they are due to their ability to let go of control and delegate. Others usually get swamped and stressed due to the fact that they never let go of control and have never learned the art of delegation.

I will confess that I find it hard to delegate and ask for help. Many times I take the "It'll be better if I do it myself attitude." This is not good and as we say in the web world it's a habit that won't scale. Delegation is a habit and like all habits it takes practice and discipline to get it right. In fact, I think there are three dimensions to delegation that we have to master.

The first is knowing what you can delegate.

There are some things that you cannot delegate. Going to the bathroom, eating, sleeping and your art. Your art is the thing that you do that no one else does, and hopefully you get paid for it. My art is being able to program and to take complicated business rules and requirements and boil them down to simple applications. Maybe your art is customer service, blogging, serving the best coffee you can etc. Once you know what you can't delegate, everything else is fair game.

Almost everything. I like to stick by the 2 minute David Allen rule defined in Getting Things Done. If the thing you are trying to do can be done by you in 2 minutes or less, do it and do it then and there. Otherwise, Delegate.

The second is knowing how to delegate.

This is the actual act of delegation. Asking someone else to do something for you. This is also a skill/art that requires practice. In the 7 Habits of Highly Effective People Stephen Covey talks about stewardship delegation in contrast to gopher (go-for) delegation.

Stewardship delegations defines the rules of the game and the desired outcome but leaves the details to the delegated. Gopher delegation is micromanagement at its worst. You define every step with so much detail you may as well do it yourself. The more trust you have in the people you are delegating to the more natural stewardship delegation becomes, but it takes practice and trust.

A service like Fancy Hands doesn't lend itself to this kind of delegation at the beginning since the trust is low and you have no idea who is doing the delegating, but if you listen to that interview I linked above you will likely develop more confidence in their service. I did. I have vowed to try to use this kind of stewardship delegation as much as I can.

Don't forget. Ps and Qs go a long way in this step.

The third is actually doing it.

Putting on your shorts and shoes is great, but it will do you no good unless you go for a run. (Anne Fenwick Proverb)

You must take the plunge and start delegating! Play the WTWTCH (What's the worst that can happen) Game. For example, when I used the acronym WTWTCH, I hoped you read the explanation and chuckled at the ridiculous use of an acronym in that situation. But maybe you didn't. Maybe you think I'm an idiot and aren't even reading this anymore. That's about the worst that can happen. So I did it. Same goes for delegation.

Ask yourself What's the worst that can happen?

Someone will say no.

Okay, then ask someone else.

Someone will do it wrong.

Yes, that's true. However, use it as a chance to learn and get better at delegating. Did you define the task enough? Did you define it too much? Did you give the person any resources or recommendations that might have been helpful? Don't assume right away that because it wasn't done right it must be their fault. It's likely partially or fully your fault.

That being said, if you have a mission critical report due in a few days and you need someone to check your references, then maybe you don't want to delegate that. Maybe if you are writing a more casual memo and need some background info that would be a good one to practice with. The more you delegate the better you will get at it and you will strengthen the habit of delegating.

Learning how to let go is one of the hardest things for us to do. That's why great things happen when we do.