Overcoming Blocks to Delegation

As the 30-day delegation challenge continues, I wanted to share some thoughts on overcoming limiting beliefs related to delegation and outsourcing.

Last week I invited others who are doing this challenge with me to share their blocks in this area. What thoughts, beliefs, and attitudes hold us back when it comes to delegating and outsourcing?

Here’s a summary of what people shared, paraphrased into one-liners:

Fairness / assumptions about other people’s values

  • It’s unfair to make someone else do tasks that I wouldn’t want to do myself.
  • I’d feel bad outsourcing tasks to people in another country for low pay.
  • People would be better off working on their own projects than on mine.
  • People should be independent, not dependent on me.
  • I don’t want to have power over other people.
  • I only have enough work for part-time people, and people won’t want to work only part-time.
  • It’s embarrassing to have someone clean my bathroom or do my laundry.


  • No one will be as good at these tasks as I am.
  • It’s important to me to stay in control.
  • My way of doing things is too unique.
  • I actually like doing laundry, grocery shopping, and other seemingly unimportant tasks.
  • Some tasks just can’t be delegated.


  • It’s tough to find people I can trust.
  • If I trust someone with access to my files, systems, bank accounts, passwords, admin access, etc. then they might screw me over.
  • If I find someone who’s really good, they might eventually quit and start their own business… and maybe copy my business model and compete against me too.
  • How do I know if a complex task was done properly without inspecting all of the steps in fine detail?

Not feeling ready / not seeing the value of delegation

  • My systems aren’t good enough that someone else could effectively run them.
  • The timing isn’t right for hiring someone yet.
  • I need to figure out how to do each task first (and get good at it) before I can effectively assign it to someone else.
  • I’m only a student, mom, artist, etc.
  • I’m not in a position to delegate since I don’t have a business.

Self-esteem issues

  • Who am I to delegate?
  • Who’d want to work for me?
  • Who am I to 10x my business?


  • I can’t afford to hire someone (or to build a team).
  • I need to make a certain amount of money first before I’m ready to think about delegation.
  • I’d have to pay more than a task is worth to me.
  • I can’t afford the quality I’d want.
  • I have more time than money right now.

Time / impatience

  • I’m too busy to find the time for this.
  • The tasks I have to delegate are too small, so it would be faster to do them myself.
  • It will take a long time to see positive returns from investing in delegating.
  • The hiring process takes too long.
  • It takes too long to find someone good.
  • Explaining tasks and documenting processes would take longer than just doing the tasks myself.
  • Other people work too slowly.

Lack of skill

  • I’m not good at delegating.
  • I don’t know how to delegate.
  • I’m not organized enough to handle a team.
  • I haven’t mastered my personal productivity yet, so I’m not ready to manage people.
  • Where would I even start?
  • I’ve tried delegating / outsourcing before, and it didn’t work out.
  • I’m only a Winnipeg Jets player.

Challenge of finding good people

  • I probably can’t find someone to delegate what I’d actually like to get off of my plate.
  • Even I find someone good, they might leave shortly after I hire them.
  • The person I hire won’t care as much or won’t be as motivated as I am.
  • It’s tough to find someone with the right skills, experience, and values.
  • It’s hard to find someone trustworthy and dependable.
  • Many people just don’t follow directions well.
  • How would I even find someone reliable?

Fear of judgment

  • I don’t want to be seen as lazy, spoiled, or elitist.
  • If I outsource creative work, I’ll be judged for taking advantage of people and trying to pass off their creative work as my own, and maybe it means I lack integrity.

Worries about complexity

  • It’s simpler and easier to do everything myself.
  • Delegation will make my life more complicated.
  • What if I end up really stressed with too many people to manage?
  • I hate micro-managing people.
  • The thought of growing my business seems scary.
  • I might lose flexibility if I build a team.
  • Do I really want to be responsible for other people’s livelihoods?

Fear of mistakes and failure

  • I might screw up and hire the wrong people.
  • It would be really tough if I had to let someone go.
  • Other people’s mistakes could cost me a lot of money.
  • What if delegation makes me go faster in the wrong direction?
  • What if I’m underpaying or overpaying?
  • What if I assign more responsibility to someone than they can handle?
  • What if I run out of money and have to lay people off, especially people who are counting on me?
  • I could ruin other people’s lives if I screw this up.

Avoiding confrontation

  • I’m not good at confrontation, like if someone does a bad job.
  • I don’t like following up, especially when I might not like what I find.

Please don’t get hung up on my classifications since some of these could have been sorted differently. The groupings are just for convenience.

If we condense the big list to these summary groups though, we get this shorter list:

  • Fairness / assumptions about other people’s values
  • Control
  • Trust
  • Not feeling ready / not seeing the value of delegation
  • Self-esteem issues
  • Cost
  • Time / impatience
  • Lack of delegation skills
  • Challenge of finding good people
  • Fear of judgment
  • Worries about complexity
  • Fear of mistakes and failure
  • Avoiding confrontation

This is more manageable, although we lose a bit of detail.

Now let’s consider a ridiculously simple delegation situation. Imagine you’re going to a Starbucks to delegate latte-making to a professional barista, i.e. you go there to order a drink for yourself. What would these same objections look like for this scenario?

  • Fairness / assumptions about other people’s values – The barista probably has better things to do than to make me a drink.
  • Control – No one makes a macchiato like I do. I’m a macchiato goddess!
  • Trust – What if they’re lying and their soy milk isn’t really organic? What if they’re secretly using GMO soy because it’s cheaper?
  • Not feeling ready / not seeing the value of delegation – It’s too early for coffee. In fact, maybe I shouldn’t be drinking coffee at all.
  • Self-esteem issues – Who am I to sit at a hipster table with my crusty, non-Apple laptop?
  • Cost – Who in their right mind would pay $8 for a latte? I can make my own for 25 cents.
  • Time / impatience – The line is too long. And so is the menu.
  • Lack of delegation skills – What if I don’t say my order right… and I hold up the line… and the people behind me get annoyed and call me stupid?
  • Challenge of finding good people – All of their pimply faced baristas suck. And they never fill my drink to the top – it’s always a half-inch below the rim. And they keep misspelling and mispronouncing my name.
  • Fear of judgment – What if people think I’m a total bourgeois snob for liking Starbucks? No one can know.
  • Worries about complexity – How am I supposed to decide what to order when there are so many options? And don’t even get me started on Starbucks Reserve.
  • Fear of mistakes and failure – What if I order a drink that I’ve never tried before, and I don’t like it? That would suck.
  • Avoiding confrontation – What if they screw up my order, and I have to ask them to remake it?

So here’s the thing. All of these concerns are valid. Maybe the Starbucks version makes them seem a tad silly, but these objections can all be real issues for people. Any one of these reasons can be used to decide not to go to Starbucks… or to avoid just about anything else in the modern world.

Maybe you can make a better drink yourself. A latte can be expensive. It’s not an essential need. People might judge you for it. You may make a mistake, or they might make a mistake. Lots of things could go wrong.

And yet you could probably still do it if you wanted to, especially if you can handle some occasional human imperfection. It can work out, and you could have a good experience. Success is possible and maybe even probable. Even if you get off to a rough start, you can build skill through experience and get better over time.

Millions of people will patronize Starbucks today. And millions of people will delegate tasks today. There are valid reasons not to do these things, but people cope.

If we frame these potential problems as reasons not to try, we hold ourselves stuck and prevent further growth along a given path of development. But we could also frame these problems as potential growth experiences.

Let’s look at these objections from a growth perspective. What’s the growth potential for each one?

  • Fairness / assumptions about other people’s values – Maybe I’d really enjoy having people serve me now and then, and maybe they’d enjoy it too if I appreciated the value they provide. A little gratitude goes a long way. Perhaps I could learn to be more appreciative and to say thank you more.
  • Control – Maybe I could learn not to be such a control freak and loosen up a bit more, which could make my life easier and more flowing. Needing to control everything is limiting me anyway.
  • Trust – Wouldn’t it be wonderful if I could trust the universe more and surround myself with trustworthy people who genuinely care about my best interests? There are trustworthy people in the world. Maybe I could work on becoming a more trustworthy person too.
  • Not feeling ready / not seeing the value of delegation – Most people don’t feel ready when they step into delegation, and yet they still lean into it. Delegation is a skill, and like any other skill, it takes time to develop. It’s unrealistic to expect to feel ready since it’s outside of my comfort zone, so of course I’m not going to feel ready when I start. My comfort level will improve with experience.
  • Self-esteem issues – It would be nice to believe that I deserve help and that people feel good about helping me. It would be nice to feel that I matter and that my goals and projects matter too. This means that I’ll have to start working on goals and projects that truly matter to me. If I don’t respect and value my work, how can I expect anyone else to?
  • Cost – Maybe I’ll have to start small for budget reasons, but I could invest a little in this, or I could find people who’d be willing to help me for free if I’m working on something interesting and worthwhile. I can also delegate tasks that will directly help me generate more income. There’s room to grow here. I can begin with what’s accessible to me now, even if it’s only a baby step.
  • Time / impatience – What if I had the attitude of a wise investor and developed the patience to invest in long-term results? There may be some work up front, but in time I’d be reaping significant rewards.
  • Lack of delegation skills – Imagine what life will be like when I’m really good at delegation, and lots of things are getting handled that I don’t have to personally attend to. This is one of the best skill paths I could possibly pursue. Without good teamwork I’ll always be limiting myself.
  • Challenge of finding good people – How amazing will it be to master team building and to know how to attract amazing, talented, and heart-centered people to help me with any project I desire? And I’ll have fun doing it too.
  • Fear of judgment – Judgment isn’t the real problem; my fear of judgment is. I need to invite this judgment, so I can get past it and stop being so timid. Maybe I can cultivate a better sense of humor about this too.
  • Worries about complexity – If I was better at delegating, it would actually make my life simpler since people would be handling things for me, and I could spend more time exploring and leveraging my strengths.
  • Fear of mistakes and failure – Think of how much faster I could learn and grow if I stopped fussing so much over making mistakes. Mistakes are lessons that help me grow stronger. It makes more sense to embrace them than to fear them.
  • Avoiding confrontation – To step into my power, I need to learn how to stand up for what I want and help other people raise their standards too. I can’t expect people to be perfect, but I can expect them to improve. And if they can’t or won’t meet my standards, then I’ll have to let them go. I deserve to work with smart people who care about quality.

Before I began this 30-day challenge, I had many of these limiting beliefs, mostly hiding in the back of my mind. I let them stop me from taking action. Some of them seemed like valid objections. I could always make the case that the timing wasn’t ideal. I could always worry that adding people would complicate my life. I could always avoid the possibility of having to let someone go for poor performance or misaligned values.

What finally got me to say yes was the amazing growth potential within these challenges. It may not be easy, but this path will be full of interesting lessons, experiences, and personal and professional gains.