Is the fear of wasting time with mistakes keeping you from delegating? Worried you'll spend more time explaining or fixing than getting stuff done? It’s hard to trust other people, and it’s easy to get frustrated when people don’t get what you mean. While it may seem that good help is hard to find, maybe seeing mistakes in a different perspective can help you get over this challenge.

I know what it’s like. I tend to assume that my instructions are clear, even though I know people can’t read my mind.  I tend to assume that my instructions are clear, even though I know people can’t read my mind. Even when you work with good people, people aren’t always going to know what you expect from them. Yes, the first few tasks are going to be frustrating, but hang in there. You could have a great team. Don’t let those initial frustrations get in your way.

A mistake isn’t wasted if you squeeze everything you can learn from it. We learn more from our mistakes than we do from our successes. Remember: you’re learning about managing people at the same time that they’re learning to work with you! Let me tell you a story about the first task I gave a new assistant.

You see, I’ve been curious about how delegation can help with my writing and sharing. I recently hired a writer through oDesk. I wanted her to help me go through a transcript and pull out good Q&A opportunities for follow-up blog posts. That way, good ideas didn’t just languish in hour-long podcasts or long documents. I interviewed one of the candidates on Skype, and by the end of it, we were both excited by the possibilities.

I thought I sent my new assistant a link to the document that already had the transcript that another assistant prepared. I expected the task to take 30 minutes, maybe one hour at most. It’s a good thing I checked on her using oDesk’s automatic screenshots. I realized that instead of pulling Q&A from my existing transcript, she transcribed the audio file I sent. Uh oh. She had spent five hours doing the wrong task.

One of the things about being a good manager is deciding that yes, the buck stops with you. I wondered where I’d gone wrong. Were my instructions unclear? Did something get lost in transmission? I talked to her to clarify what had happened. It turned out that she didn’t see the Trello card with my instructions, only the folder with the audio file. I hadn’t made sure she knew where to look for her current task. I hadn’t confirmed that she understood my verbal instructions, which turned out to be ambiguous.You might think that this would have been a complete waste of time and money, but it wasn’t.

You might think that this would have been a complete waste of time and money. It wasn’t. It was a great opportunity for both of us to learn more about delegation. Yes, we spent an hour together as I outlined my goals and made sure she understood where we were going to begin. There was a lot of information packed into that hour-long session. While she thought she knew what I expected of her, I never asked what she thought her task. She told me later that she had been looking forward to starting the project. But moving had tired her out and all the new information overwhelmed her. We both assumed we knew.

Mistakes happen, and there’s always more than one reason. (The Swiss cheese model of errors is an amusing visual.) It’s good to ask lots of “Why?” questions to find the root causes so that you can do better next time. Every mistake points out several opportunities to grow. For example, next time I hire someone and give them their first task, I’m going to make sure I send them a direct link to the instructions. I’ll ask them to explain what they will do. I’ll check in with new assistants, perhaps staying on the line with them as they do the task for the first time. (Google Hangouts, Skype, and other screen-sharing programs make this easy.)

My new assistant offered to take that time off the record so that I didn’t have to pay for it, but I told her to keep it on. After all, the work that she did was useful too. I rarely assign duplicate work, but having that second copy makes it easier for me to see the differences between the way people do things. And hey, it’s no big deal in the long run, which brings me to the second reason why mistakes are great and you shouldn’t be afraid of them.

Mistakes give you a chance to be a good manager. Contractors deal with many uncaring clients who blame them for all the mistakes that happen. Here’s your chance to be different, and to build a closer connection with someone whom you might come to trust even more. Take a thoughtful approach to solving problems and helping people move on. You might find it easier to engage and keep people who will bring more of themselves to the work. You can pay for grudging compliance with tasks and specifications. You need a special connection for creativity and initiative. A mistake is a good opportunity to connect as a human being. If it’s your mistake, ‘fess up. If it’s the other person’s mistake, be understanding. In both cases, be human.

What about situations where you keep getting the wrong results? Maybe there’s a mismatch of skills or expectations. I recently ended a contract with another assistant who couldn’t deliver what I was looking for at the time. Sometimes it’s just not the right fit. If you like people and they have other skills you need, see if you can work around their weaknesses and play to their strengths. If they’d be better suited to other teams or other kinds of work, then it’s good for everyone to move on. Think about how you'll change your processes for interview, onboarding, or probation. You can get the benefits of that mistake too.

Don’t let the fear of making mistakes stop you from delegating. There’s so much to learn from them. Think of your inevitable mistakes as the tuition you’ll pay to learn how to tap other people’s skills. Good luck!

Author's note: In fact, I asked Amanda Bassett to draft this blog post (based on an outline I gave her) as her second task. She more than made up for the flub with the first task. =) I revised her draft in real-time while she watched and added comments (hooray Google Docs!). I think that editing process will be a good blog post to share too. Learning as we go! – Sacha