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5 Delegation Tips for Freelancing Perfectionists

freelancer and client bumping fists

Congratulations — you’re taking the first steps

If you’re reading this, we’re going to assume two things:

  1. You’ve admitted that you need help with your day-to-day operations, whether through expanding your team or through outsourcing.
  1. You’ve admitted that you might have just a little bit of difficulty letting go of your complete control over those operations.

We’re here to let you know that what you’re feeling is completely normal.

For self-proclaimed perfectionists, one of the biggest barriers to expansion and growth is the ability to delegate. They most likely have high quantities of anxiety in general related to the quality of their output, and adding yet another variable seems almost unbearable.

Realistically though, if you’re going to make the transition someday from a small-time freelancer to an agency owner, you’re going to have to loosen your grip on the reins. 

Why It’s Hard to Let Go

group of freelancers looking at a computer

If the thought of entrusting your agency’s output to someone else’s hands gives you hives, it’s going to make it difficult for you to effectively get work done —delegating tasks is meant to relieve stress, not pile it on!

Let’s look at some of the reasons you might be feeling this way.

Pride in what you’ve built

The fact that you’ve come far enough to even consider allowing someone to take over part of your workload means that you yourself have done all of the work up to this point, and it’s been a success! You should be extremely proud of yourself.

In any industry, especially in the tech and digital world, success can be temporary and fleeting. It’s probably terrifying to imagine that all the work you’ve put into your project and the rapport you’ve been building with your clients could come to a screeching halt at the hands of someone you hired.

The brunt of accountability — and responsibility

You might fear the possibility of help from someone else sabotaging your business, but not only because of a potential quality drop-off.

You realize that the blame for any setbacks or discontent on your clients’ end ultimately comes back to you.

You might be afraid of your churn rates increasing, or, even worse, a mass-exodus of your hard-earned clients from your project—all because you entrusted your work to someone else.

General Trust Issues

Most of the issues related to delegation difficulties can be traced back to trust issues in general. You want to believe that someone else could put the same amount of passion and effort into your sites as you do, but you’re just not 100% sure.

Above all else, remember that the reasons listed here, or any other causes of your hesitation, do not make you a bad person or a bad leader. You’ve simply got to work through these issues in order to push forward and pursue growth for your budding agency!

Let’s Break Down Your Excuses

group of women working around a table

It’s time to take a look at some of these common excuses that you might be using to put off delegating tasks to someone else.

“They don’t care as much as I do about this

You’re probably right.

Even if it’s not what you wanted to hear, they probably don’t care about your freelance project or agency as much as you do. After all, it’s your baby, not theirs. 

But if you’re hiring and delegating to the right kinds of people, it won’t make a difference.

“They won’t be able to match my style

That’s highly unlikely, but we’ll talk about how to put yourself at ease a little bit further on.

“I’ve been burned before when I trusted someone else with my project”

And you’ve probably also had hot pizza burn the roof of your mouth before, but did you stop eating it forever?

Right; we didn’t think so.

“The client pays to work with me, not with them”

This is probably the most valid excuse a freelancing perfectionist might have, and this most likely varies from client to client. Let’s explore this a bit further down the road.

If you’ve found yourself nodding your head, or even grimacing, while reading those excuses, consider some of the following tips to make the process a little bit easier on your perfectionist brain.

5 Tips for “Hopeless” Perfectionists

two women discussing an assignment

Try out these tips, and let your perfectionism take a back seat for a while.

1. Gradually increase responsibility

Difficulties with delegating that stem from general trust issues are obviously the most difficult to conquer, so why not take it slow? 

If you’re outsourcing from an agency, request a probation period to not have it feel like such a gut-wrenching commitment. Have the potential “hire” create a few test assignments. If you find that they’re at least satisfactory, bring them on.

You don’t have to entrust your newest colleagues with the project/agency secrets all on the first day. Build your confidence in them,–like this BBC WorkLife article suggests–and in yourself, by not setting either of you up for failure at the outset.

2. Develop clear, distinct communication

If you’re worried about a potential source of help not being able to match your tone, style or expectations, examine the way you’re delivering your message to those who work with you. Are you being abundantly clear with your ask? Are you laying out steps or providing demonstrations to show exactly what you want and need?

Armed with all of the necessary information to create what you’re looking for, and with a little patience on your part, you can gradually put your mind at ease.

Avoid being patronizing with your comments and directives, though. If you speak to those around you like an overlord, you’re going to undo any trust and confidence you’ve been building.

 office worker

3. Use tools to maintain accountability

Is the fear that your colleagues aren’t quite getting the concept keeping you awake at night? Consider using services such as Slack or monday.com for easy contact and communication. Even if you’re only communicating with one or two team members, there are budget-friendly plans that allow you to participate without affecting your margins. 

But be forewarned—this can be a slippery slope into micromanaging. Only use this if, or until, you can maintain yourself sufficiently hands-off.

4. Maintain a healthy dose of empathy

You might be a perfectionist, but you’re not perfect.

(There, we said it.)

It’s highly probable that earlier in your career or when first starting out as a freelancer, you were the source of ire and impatience for another perfectionist. It might have even shaped you into the freelancer you are today. 

Try not to let past transgressions or negative experiences stop you from finding the help you need to achieve your growth goals. A little bit of understanding and patience goes a long way.

5. Bring in pre-vetted help that is as excited as you

As we’ve discussed, it’s difficult to find someone that’s truly as enthusiastic about your project as you are, but you can assure that you’ve got capable and enthusiastic hands on deck by either outsourcing through companies like us at GoWP or hiring through a selective headhunter.

If you think that problems could potentially arise from any particular client, you’ve got to do a bit of management and relations work. 

You could start by highlighting the fact that the benefit of having two people working on their site allows for more proactivity and attention. Introduce the employee who will be helping you if it’s appropriate. If they’re still not convinced, ask them if they’ll consider a probationary period. 

Moving forward

woman smiling in front of a group of freelancers

You’ve been given a few tools to help you move forward in your freelancing journey, but it’s understandable that you still might be having doubts. After all, it’s the first day towards the new, improved owner and manager that is you.

”What if it never gets easier?”

It will, trust us.

Just like any critical skill in life, letting go of control is something to be practiced and mastered, and chances are, you’re probably going to slip back into old habits occasionally! As long as you maintain a conscious effort, you’re making progress.

Self-reflection as a key to successful leadership

By admitting that you find delegation difficult and feeling a need to change your approach, you’re already lightyears beyond others in the same position (In fact, according to Business 2 Community, you’re on the first of 15 steps!) 

Be proud of what you’re attempting. It means that, with a little work, you’re going to make an amazing leader.

Patience and persistence

Changes like these don’t happen overnight. Be patient with yourself and with the people trying to make your job easier. Remember that everyone makes mistakes, even you, you perfectionist.

We assure you that you won’t regret it. 

And who knows? You might find that delegating your tasks is the perfect solution after all.

diversity and inclusion free

For more encouragement and insight about releasing yourself from the fear of outsourcing and delegating, check out this blog post by our very own Morayo Orija.
And if you’d like to connect with other agency owners that have most definitely experienced the same feelings and discover how they worked through their issues, join our Digital Agency Owners Facebook group!


Abigail Brooks Santana

Abigail Brooks Santana

Abigail Brooks Santana is a Dedicated Copywriter with GoWP who loves to work with words and challenging ideas! Abigail is a native of Montgomery, Alabama, but now lives in the Portuguese countryside, where she and her partner breed and train Lusitano horses.

You’ll be joining a community of highly-vetted digital agencies and web professionals with one common goal — growth! Learn more. 


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  • Daily security scans and malware cleanup
  • Maintenance dashboard
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