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March 1, 2016
Growth  |  6 min read

How to Delegate Like a Boss

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Ellis Friedman

Back when you started your business, it was just you. But now that you’ve got a team of people to do the things you used to do, now you’ve got to learn how to be, well, a boss. How on earth do you do that?

Lynn Perkins, CEO of UrbanSitter, sat down with us to give us her tips and experience on delegating like a boss and how to scale a small business.

It takes a heavy dose of open communication to be an effective delegator, and you’re going to have to put your ego aside and learn how to let someone else take the reins, which is perhaps the hardest part of being the boss.

Check out Lynn’s tips in the video below:

Not up for a video right now? Check out our summary below:


This week’s question was from Greg: 

Now that I've hired a couple of teams and a few dozen people at my company, I find I'm still having trouble letting go of all the responsibilities and day to day tasks that I used to handle. I don't want to be a micro-manager and I want to be able to work on my business at a higher level but it's hard to let go. How can I be a good and effective delegator?

Lynn Perkins, CEO of UrbanSitter, gave her advice in transitioning from working in your business to working on your business, and she advised with starting small. Start by delegating tasks that can be separated down into smaller components so that you can start to build trust for the people that are working for you and also, they can start to learn your work style and what's expected. 

Be very candid with the person you're delegating to and say, "Listen, this is the first time we're working on something like this together. Why don't we start this one small?" Start by telling what you want the end result to be. Make sure you're really clear in communicating with them and letting them know what you hope the outcome is. That way, they know what their expectations are and break the problem or project into different components and agree to check in with him after the first component. 

And you should expect mistakes the first time, so be patient and go through the project together, to show encouragement and to make sure you’re checking in and giving good feedback. That will help build a relationship.

To know who the best people to delegate to are, look at your team and their strengths and weaknesses . Not only the roles that they're in today but the things you’ll be asking them to do in the future. That's how you retain employees and you get them to become better in their careers. Then pick a task that you're delegating that matches that person's strength. 

Keep your eye out for people who are exhibiting excellent communication skills and are able to surface up questions when they have them. That way you know that you're going to get feedback from them if they get stuck along the way. 

If a project didn’t come out the way you were expecting, you have to take a step back and say, “Okay, not all of the work that's being done in this company is going to end up the way I would have done it, but you know what? That's actually a good thing. I should be hiring people who are owning areas where they have more expertise and better knowledge than I do. Or I should be delegating to people who have the bandwidth to actually learn to do something in a way that I haven't.”

Lynn shared an anecdote of her own to illustrate the point:

When I hired the woman who runs our operations and finance, she did a great job getting up to speed for me. Later she came back to me with the quarterly report and said, "I know this is going to look different than how you've done it in the past but I think this is actually where we would need to take it." There was a piece of me that initially was a little bit offended. Like “Oh shoot, I didn't do it the best way.” But then I had recognize that given the resources we had at the time, I did the best I could and I brought the right person in. You have to put your ego aside. 

If one of your people brings work to you that was done in a way that clearly isn't correct, then you do need to have that conversation with them, identify the mistake, help them understand the best solution. Most of all, you need to ensure they understand that you support them and show them that it's okay to make a mistake as long as it can be used as a way to improve performance for the future. Then tell them how you’d like to see it done next time and give them another chance.

To be a good delegator, you need to recognize what you’re delegating. Are you delegating something that's right for that person's skill set? The worst thing you could do would be to set someone up for failure by giving him something outside his skill set or not providing the right tools. 

It's really tempting to give people the things that you least want to do. But you need to ask yourself, “Is this something that the company has either seen me do or would feel that I was capable of doing?” You want to show that you're giving people interesting projects.

Pick recurring or incremental projects and work with the person as closely as you can so that they see your work style. Then, next time give them a little bit more. By the time they're on project number three, they're running the show. 

And when it comes to training your new reports, make sure that you're not delegating when your workload is so chaotic that you can't give them ample time for training. Think of training as mutual training—you’re each learning how to work together, what each of you can handle and how long things take. 


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