Understandably, many founders take on low-level tasks in the early days. However, as the business becomes more profitable, we naturally expect them to hand over those tasks. But that isn’t what always happens. Many still hold on tightly to work they should no longer be doing, and it often slows growth more than they realize.
Delegation isn’t a skill everyone has naturally. While some can easily assign work to others, many would rather overwork, and even when they decide to share the work, they feel clueless about how to do so. However, it’s a skill that founders (managers and executives, too) must have.
In this article, we’ll break down the main reasons these founder delegation struggles exist and share practical tips to help you overcome them. Let’s start with why delegation feels so tricky in the first place.
Why Founders Struggle To Delegate
Fear Of Losing Control
Many founders hold on to tasks because they can’t stand the idea of things going wrong. They worry that they can’t direct the outcome to the tiniest detail when someone else takes up the work, which will affect how the final output looks.
At a stage where every task feels critical and personal, full control is non-negotiable. Many tasks become less personal later on, but the mindset doesn’t always grow with the company. The desire for total control stays the same, decisions bottleneck around the founder, and everything slows down.
Perfectionism And High Personal Standards
The belief that their own way is the only right way to get things done makes many founders fear delegation. They feel it’s better to keep doing the things they are good at on their own, since they don’t see anyone else meeting their standards. When they think of delegation, all that comes to mind is the risk of losing time due to errors.
Those who manage to assign tasks tend to overedit the results or micromanage the assistants they assign them to. The assistant may actually perform well, but they’ll still make changes because it is not exactly how they’d prefer. This pressure to make everything “perfect” reinforces the idea that delegating leads to mistakes.
Lack Of Trust In Others
As a founder, you know your business is your priority—something you’re giving your best efforts to—so you stay extremely dedicated to it. But it’s hard to trust that someone else who doesn’t have your vision will care about it as much as you do. Yes, they may do a good job when assigned tasks and responsibilities, but you wonder if that’s really the best they have to offer.
This distrust usually surfaces when founders have dealt with inconsistent work or unreliable contractors in the past. Now, they are over-scrutinizing candidates, and even when they find someone they can trust a little, they’ll be skeptical about handing over meaningful tasks to them.
Unclear Or Undocumented Processes
Many founders can handle certain tasks and responsibilities well on their own, but the problem arises when it’s time to transfer that knowledge. They either don’t know how to explain it in words, or they haven’t written it down well enough for someone else to understand by simply reading and asking a few questions.
When the methods for doing a task well only exist in your head, handing them off puts your assistant in guessing mode. It gets even worse if it’s not a general task but one that requires acquiring specialized knowledge.
Without a clear structure, even defining what “good work” looks like becomes difficult. Your VA may assume the work is good when it has no grammatical errors or fluffy sentences. However, for you, it also has to be free of any plagiarism.
Difficulty Identifying What To Delegate
Picking some tasks to hand out from the many that make up their day is where the delegation problem begins for some founders. Questions about which ones are appropriate or safer to delegate make them stall, especially when everything feels too important.
For some, everything also feels interconnected. Take a simple task like “sending weekly client updates.” You can’t send the update without collecting client data, and you can’t collect the data without checking project status, which you can’t do without asking the team for progress notes. Even the progress notes require creating a note format for them to follow. Taking one out to assign to a VA feels like disrupting the whole process.
All these can make the founder feel overwhelmed, leading them to give up on delegation completely.
Belief That Delegation Takes Too Much Time
Have you ever felt like you will spend more time explaining the process of performing a task than you will actually spend doing it? Many founders think that way, too. So, aiming to speed up the process, they simply do the task by themselves.
Founders build this mindset when they are overloaded with work. Always seeing a bunch of tasks ahead of them keeps them on their toes. They feel every second spent showing someone how to perform a task is time they could have spent either doing the task or some other high-level work.
Emotional Attachment To Work
A founder may have made handling a task part of their identity within the company. This could be because they’re exceptionally good at it, or maybe the task tells a story of their early struggles building the company. That emotional attachment can make it hard to let go of such tasks.
Maybe when the business started, the founder served as the project manager. So, even as it expands, they hold onto the role, not because they can’t afford to hire one but just because it keeps things familiar. Letting go of this responsibility also feels like betraying the business’s roots. They expect that it will change the work vibe and that change is not something they’re willing to embrace yet.
How Founders Can Overcome These Delegation Struggles
Start With Small, Low-Risk Tasks
One of the safest ways to get into something you aren’t familiar with is to start small. Go for work that is easily repeatable and won’t cause major issues if it isn’t perfect. Examples include finding available time slots for meetings or renaming and organizing files into the correct folders.
Giving these small tasks out shows you how helpful delegation can be. It also helps you build familiarity with how the system works and establish a working relationship with those who can help. As you gain experience and confidence from handing off low-risk tasks, you can gradually move on to bigger, higher-risk responsibilities, like creating SOPs for entire departments and responding to comments or messages on your brand accounts.
Document Tasks In A Simple, Repeatable Format
Delegation becomes far easier when you don’t have to explain how to go about the task every single time. That’s where documentation comes in. There are several ways people document processes: short written steps, infographics, checklists, and screen recordings are just a few. You can combine as many forms as you need to explain the processes well enough.
When you have the steps clearly documented, anyone assisting you knows what to do and what completes the work. Your assistant won’t do it based on what they think is good, but on how you prefer it done. For example, if they handle social media, they know whether all your posts should include images, and if they edit videos, whether to keep your logo at the end, throughout the clip, or completely absent.
Documentation also ensures you don’t spend too much time answering questions. They can always refer to the documented process whenever they are confused, and only reach out to you when their confusion goes beyond what you shared.
Set Clear Expectations From Day One
Some assistants can actually meet your expectations if you share them. You may have heard that many assistants don’t meet deadlines, communicate properly, or meet the quality standards you set. However, these could be because these details weren’t properly communicated to them.
Include all these details in the SOPs you’ll share with your assistants. For instance, for each task, you can specify how tasks should be created, prioritized, and marked as completed. Maybe you can ask them to log all tasks in your project management tool and document any blockers directly in the task comments. Without this level of clarity, assistants may maintain their own task-management style, which can lead to missed steps or delays.
When they understand your deadlines and quality requirements, they can aim to meet them. They can also work confidently, which yields faster results, and independently, freeing up time for you.
Establish A Predictable Communication Routine
Keeping your work visible is not as hard as people think. One way to do so is by establishing communication rules that help your assistant keep you adequately updated on the progress of the task they’re working on. You can also use shared CRM tools for communication as they allow you to see tasks’ progress in real time and share comments.
Have regular check-in sessions, too, so that you and your assistant remain aligned on what you aim to achieve. When you’re both on the same page, mistakes reduce, and the back-and-forths you’re scared of disappear. The result is a stable working relationship between you and your assistant.
Hire Based On Skills That Match The Work
There are different kinds of virtual assistants, so you want to be sure you’re hiring the right one. Just as you won’t hire just any job seeker to take a role at your company, you also have to go for an assistant with the needed skillset. If you don’t know how to go about picking the right VA, this guide on what to look out for during a VA interview will help.
Besides skills, you also want to know a candidate’s technical abilities, so you can be sure of their training needs. Another important thing to look out for is their communication style, and see if you’re comfortable with it or if it will work with yours. Finally, you want to know how reliable they are—their track record and professional credentials can help with this.
Practice Accepting "Done Well" Instead Of "Done Exactly Your Way"
Working with others requires allowing for different working styles. What matters is that the results meet the needed standards. Different people have different styles of working and various methods of arriving at a given result. So, it doesn’t always have to be your way. In fact, you should encourage those who work with you to use their own strengths and methods. That’s how you get their best.
When you stay flexible, you reduce the need for unnecessary oversight. You may only need to step in when the methods they use are inefficient or not good enough for the results you’re aiming for. Plus, you also get to learn new ways of doing things, which you can adopt or borrow from to help your business grow faster.
Redirect Your Time Toward Higher-Level Work
The aim of delegation is actually to free up time for high-level work, so do just that. While your assistant responds to your customers’ inquiries or conducts your research, don’t micromanage them. Instead, pursue those partnerships and decide which direction your product will go next.
Constantly monitoring tasks will defeat the purpose of getting an assistant in the first place. Let your assistant work independently and check in on them from time to time. That way, even if you aren’t impressed with their work, you wouldn’t have wasted the whole time breathing down their neck.
What This Means For You As A Founder
If you are a founder having difficulty delegating tasks, you likely saw the reason in this article. We hope that reading through the tips we shared will help you to overcome your founder delegation struggle. Delegation is a skill, so give yourself time to learn it as you practice and adjust as needed. Eventually, you’ll become a pro at it.
Remember that overcoming these challenges saves you from burnout, frees you for high-level work, and pushes you closer to achieving your business goals. If you start small, stay consistent, and build the right systems, you’ll eventually become a pro at handing off tasks effectively. Delegation will stop feeling risky and become a real advantage for you.
