I'm a national bestselling author (still feels weird to say!), keynote speaker, podcaster, and educator. In college, I started a small Etsy shop and blog from the storage closet in my sorority house. Fancy, I know. A few years later, that small Etsy shop grew into an internationally recognized sweatshirt brand & that dinky little blog led to bestselling books and publishing career. Now, I'm obsessed about helping other women pave their own path and work from home in their pajamas, too.
Every Wednesday, I send my insiders exclusive resources, ideas, and advice directly from me.
Calling my fellow recovering perfectionists! This is allll for you, my friend! Let me help you ask for help as a perfectionist.
A reader named Elizabeth recently sent in a message and asked, “Can you offer some advice on how to delegate and ask for help when you’re a perfectionist?”
I immediately resonated with that struggle because I tend to be a bit of a perfectionist, which can also mean I can turn into a control freak.
I’ve heard it said that you should delegate a task that someone else could do 80% as well as you could. Apparently that’s supposed to be encouraging but to my perfectionist brain, 80% just doesn’t seem acceptable! That’s a B and I tend to be of the mindset that if it’s not an A+, is it even worth doing? I didn’t want to ask for help as a perfectionist, it just didn’t make sense at the time!
My fellow perfectionists will understand.
Anyway, while I wouldn’t say I’ve totally overcome the struggle, I have learned a thing or two about having to delegate as a perfectionist.
If you relate to this struggle at all, buckle up. I’m going to give you four tips to doing this so that you can begin entrusting tasks to others instead of trying to do it ALL yourself.
When I first realized I needed to delegate some things in my work (but also in my house, like cleaning when we’re out of town for two weeks at a time), I had a hard time not micro-managing. I wasn’t sure how to ask for help as a perfectionist yet.
Then, I realized that was probably because I gave up way too much control, too fast. I basically handed a whole process off to my assistant (because that’s what I thought I was supposed to do) but then I ran into problems because I expected it to be done exactly like I would have done it. On the flip side, it was a lot for her to learn and implement the same way I would that quickly.
She still did a great job. But my control freak side didn’t have the easiest time with it…
That’s when I realized two things about asking for help as a perfectionist. The first was that I didn’t give her a very clear system to follow. It was a general overview of what needed to be done but without providing her steps, it did make it difficult for her to follow the pattern of how I would do something.
So, that’s when I started a big, massive document titled Jordan Lee Media Systems, Procedures, and Standards.
I broke down every process my team members will handle by going through the processes themselves. Some are actually still a work in progress, and those are usually what we are co-handling or building together.
But putting a huuuuge chunk of our weekly work into systems on paper and having a reference point gave me so much peace of mind. That way, we’re all as clear as possible on what needs to be done and HOW it needs to be done.
What I mean by that is that many of the processes have a “Standards Guide,” which is essentially a checklist of items that must be checked off before marking the process complete.
For example, we have a checklist for blog posts that must be completed before hitting publish.
A few of the line items include…
If you have a small business or an assistant, go through those processes yourself and write down every step to develop a system that you can hand off. Walk your assistant through that process.
If there’s another area of your life that you need to delegate some tasks, such as home maintenance, you can follow a very similar framework. Develop a system by mindfully going through the process you follow, probably without even realizing it, when you do the task (for example, cleaning your floors).
Instead of just zipping through it as you normally do, carefully track every step you take AS you do it.
I always recommend creating systems by actually going through the process yourself. This helped me SO much because when I’ve tried to write down systems to the things I just naturally did without actually going through the meticulous steps, I often found that I forgot a step or two because they were things that I didn’t even think to write down.
Why? Well, because when you’re used to doing something a certain way, it can be easy to think others would do it the same way. To you, it’s essentially second nature, but to someone else, it may not be so obvious.
Make it as easy on them as possible by being as meticulous through the process up front.
I’m much less of a control freak when I’ve communicated clearly, which leads me to my next point…
I also realized from my first experiences attempting to delegate (and failing miserably) that I personally do better when I give one small task at a time, see that someone has mastered it, and then give up more from there. Then, I can hand off the next step in the process, and perhaps even co-work alongside them as they take it on for a few days, until I feel comfortable that they’ve mastered it.
Being able to delegate a little bit at a time doesn’t only allow the person you’re delegating to learn at a steady pace, it also helps YOU learn how to delegate.
I’ve come to find that delegating and giving up control isn’t necessarily something that comes natural to most of us, and therefore, it’s something we must learn how to do. It’s essentially an acquired skill, and when you take pride in your work, or your home, or in whatever you’re delegating, it only makes sense that you want it to be done right! I mean, it’s not easy to ask for help as a perfectionist so it makes sense that things will be shaky in the beginning.
On the front end, creating the systems and procedures with the standards guide can be a really helpful tool for communicating expectations. Additionally, inviting and encouraging them to ASK you questions if they’re not sure, especially in the beginning, can be really powerful. Again, learning how to ask for help as a perfectionist is a step by step process.
I didn’t realize it before but sometimes people won’t ask because they don’t want to bother you or appear as if they weren’t paying attention when you trained or showed them what to do… and because they’re not comfortable coming to you with questions.
It’s on YOU to create this open door policy.
Now, if the question asking on the same type of thing goes on for six months, that may be when you remind them that they’ve been through this before and are capable of doing it, and that you trust them.
In the beginning, people need to feel comfortable asking questions until they get something down.
Then at some point, they need to be empowered to do the job you hired them for.
In addition to communicating expectations upfront, it’s also important to remind people of those expectations and even point out adjustments you’d like made when you’re not satisfied with something they did.
This is a suuuuper tough one for me because I never want to come across as bossy. But that’s the risk when switching things up and learning how to ask for help as a perfectionist
Maybe you can relate.
However, I learned the hard way after a couple of years. For a long time, I had a hard time just straight up saying what I did and didn’t like, and what was acceptable and what was unacceptable for me.
I never wanted to hurt someone’s feelings… but in avoiding that potential awkwardness, I ended up making it harder because the same things kept happening and I’d have to get in and “fix” it to my liking.
This only created more work for me and probably more tension for my team because I was essentially redoing their work without actually telling them exactly what I didn’t like.
When I brought on a content manager, she really emphasized her desire for me to be super straightforward and honest with her about what I didn’t like, and to show her changes I’d make to copy she wrote or graphics she made.
I appreciated that she invited this and it gave me the freedom to be a little bit more honest and upfront. Then, when she’d send me a caption to a post she wrote and I didn’t love it, I’d screen record myself making adjustments to her caption in the notes section on my phone and send it to her so that she could see what I changed step by step.
This proved to be so helpful! And I, as a leader, felt empowered to be more straightforward.
And one day I had this realization: People can’t read your mind, J! You have to show them what you want!
They may be doing great work but if it’s not quite how you’d want it, you HAVE to tell them.
However, I know it can be uncomfortable to point out something that seems negative or offer critique.
So, here’s what I try to do: balance every critique with two affirmations.
For example, if I like the photo my manager posted, as well as the timing of when she posted it, but didn’t love the caption, I might send her a screenshot and say, “Hey! Just a heads up! This photo looks great and the time you posted it was perfect! Just a quick heads up that I don’t love the line that says “(Insert Line Here),” because it doesn’t really sound like something I or my brand would say. Reminder, our goal is to appeal to (this person our company serves) and deliver messaging (this way that we’ve talked about). Can we make this adjustment? You’re doing great!”
The pattern I try to follow is something like Affirmation, Affirmation, Critique, Affirmation.
Of course, I don’t do this perfectly every time, especially if I’m in a hurry. But if I can offer critiques or communicate what I don’t like in this fashion MOST of the time, I consider it a win.
It’s usually received well and I don’t feel like a total brat for telling them.
One other way to do this well is to have monthly or quarterly reviews. When you see something you don’t love that someone did, but can live with for a bit so that you can show them, write it down or take a picture of it. Then, when you go through the quarterly review, you can show them what you liked and didn’t like — and work on how to make improvements.
This can also be a great chance to invite THEM to tell you where YOU can improve (you may be a perfectionist but you’re not perfect! ;)).
Maybe the disconnect is happening in the work they’re doing because they didn’t fully understand what you meant or because you’ve changed your mind a couple of times (this is something I’ve been guilty of…).
Gathering their feedback and giving your feedback makes this communication pattern feel more like a two way street, which makes for a healthier relationship and when there’s a healthy relationship, you can expect healthier results!
Lastly, there’s one thing you have to realize: The sky is not falling when they inevitably drop the ball.
When someone is learning something new, whether it be a process in your business or in your home, they’re learning how to do it like YOU prefer it to be done.
That’s kind of like learning to walk — any toddler learning to walk is bound to wobble and fall down a few times before they really get their footing, right?
This is similar. They may be a professional at the task or type of work but learning to fit into YOUR systems and preferences does come with a learning curve.
I know it can be scary to delegate and risk something getting messed up. But it’s so important to know when and how to ask for help as a perfectionist.
But here’s something I’ve learned: Even if I don’t delegate and try to do it all myself, there’s still a pretty high chance that something will get messed up. I can drop the ball, too, especially if my plate is full and I’m trying to do it all… something is bound to slip from my control.
When my husband first started producing my podcast, there were a TON of moments I had to bite my tongue because he just wasn’t doing it exactly how I was used to. One time he didn’t have a chance to review an edited episode before it aired, and it ended up airing with a bunch of missed edits.
People started messaging me asking why the episode sounded so unprofessional… and I started to panic.
I listened back to the episode and wanted to crawl into a hole! There were several spots where we had to start over and that never got cut out.
For a moment I thought, “this is why I don’t like to ask for help as a perfectionist,” I wouldn’t have made this mistake!
I was so embarrassed! Especially because that was a year into having a podcast as a seasoned podcaster, not the first couple weeks as a new podcaster!
At first I was SO mad. I tried not to be mad at him, I knew he didn’t do it on purpose, but it was SO hard not to express my dissatisfaction. Honestly, it made me want to produce and manage and edit the whole podcast myself!
I could totally do it better, I thought.
Total lie. There’s no way I could handle that whole process AND create the content and manage the rest of what I do well.
It’d all crash and burn because it’d be way too much for me to handle on my own.
However, in the moment, I wanted to reach for control and do it all myself so that would never happen again.
But then I remembered what one of my friends said to me when Matt first started working with me, “This is going to be an adventure, and you probably have your ways of doing things, J. But you HAVE to let him drop the ball, and when he does, you have to put the ball in his court to make it right. You can’t just come in and start controlling him. It’ll hurt your relationship and your business.”
So, I know it’s hard to hear, especially as a perfectionist, but I’m passing on that same advice. You have give them the room to succeed…but when you do that, you inevitably give them the room to make a mistake.
And the fact is, they probably will make several mistakes.
When they do, you have to make it clear that the mistake isn’t acceptable but you also have to give them grace, remember the sky isn’t falling when it happens (even if it’s totally embarrassing or even costly) and empower them to make it right.
If it continues over and over again, that may be when you consider making a personnel change.
But it typically helps me to keep in mind the net positive to the net negative. If someone I delegate a portion of work to is succeeding and crushing it 95% of the time but has a margin of error of about 5%, that’s a pretty good ratio.
We calculated this with the podcast example by looking at all the episodes that went live under my husband’s management. There were about 42. Of those 42, only 2 ever had an issue. That meant he had a 95.3% success rate. When I looked at the big picture, I realized he’d provided much more of a net positive than a net negative to that part of my work (even if the mistake seemed massive in the moment).
Bottom line, no one will always bat 100.
So it’s important for you to decide what you can live with and what you can’t, to give grace, and to empower them to fix the mistakes they inevitably will make rather than micro-managing.
I know it’s not easy but you’ve totally got this! I believe you’re going to understand how to ask for help as a perfectionist in no time.
Tell me: What do you need to delegate or outsource in your life or business? What’s your biggest roadblock to actually doing it?