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The Top 3 Obstacles to Effective Delegation, and How to Overcome Them
November 14, 2025
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Delegation is one of the hardest skills for entrepreneurs to master because it challenges trust, communication, and control. A business systems expert breaks down the top three obstacles — poor communication, difficulty letting go, and lack of accountability — and offers practical ways to build systems that make delegation work smoothly.
Delegation is an enormous challenge for any entrepreneur. Often, you’ve built your business yourself, and handing any piece of that business to another person can be difficult.
There are four primary concerns most business owners have when determining whether to delegate a task:
- Have I hired someone I trust to perform the task efficiently?
- Are documented processes in place, or does everything “live” in my head?
- Is there a method of ensuring accountability?
- Can I step away and allow the other person to do the task?
Some of these, like No. 4, require a simple mindset shift. Addressing the other three concerns can support that mindset shift.
So, what is the first and foremost obstacle to effective delegation?
The Most Significant Obstacle to Effective Delegation
There are many obstacles to effective delegation, but a lack of communication tops the list.
As a business owner, I delegate tasks to employees I trust to give it their all. It could be that the employee had special training in the area or previously demonstrated intelligence and teamwork. Most entrepreneurs hire people they trust to do a good job.
However, their doing a good job does not translate to “mindreading.” Your delegatee cannot read your mind and figure out how you perform a task. Instead, you must communicate how the task is done competently and provide support as they learn the ropes.
This can feel frustrating, as you likely want the task off your plate. That’s why you are delegating it. However, if you don’t provide the SOPs and training necessary for the employee to perform the task, that task will boomerang back to your plate again.
So, what’s the solution? How do you overcome this obstacle and effectively delegate? By building well-structured and time-tested processes and procedures. And, if you need to delegate before your processes are mature (which many of us need to do), then it’s wise to bring the employee in on the ground floor and ask them to help you build the new process or update an existing one.
A process provides a baseline from which you and the employee can communicate. Additionally, having to-dos in writing (or on video) provides a resource to which the employee can refer. That frees up your time while giving employees the support they need. And it makes for more substantive communication because you are both operating from the same foundation.
Two Other Common Obstacles to Effective Delegation
In my decades as a business consultant, I have encountered many other obstacles to effective delegation. The following are two of the more common challenges.
1. The Employer Has a Hard Time Letting Go of the Task
It can be challenging to let go of a task for many reasons.
It could be a task you enjoy. You may feel like no one can do it as well as you. You may have a small company and worry that an additional task will scare off your best employees. Your employees may not be trained in some specialized aspect of it. Or, you may think of yourself as a hands-on boss.
The best way to fully delegate a task is to identify why you are hesitant to let it go. Often, there is an underlying issue that you can solve.
For example, I have a background in accounting. I like accounting. It’s fun and easy for me. However, when considering why I did not want to delegate the task, I had to admit that accounting was not the best use of my time. I would not pay an accountant my rates to accomplish the accounting work for my company. So, I determined that it was time to delegate.
It may be a longer process for you. For example, if specialized training is required for the particular task you want to delegate, you have two choices:
- Train an employee to do it.
- Hire someone who already has that specialized training.
Making that choice does not automatically allow you to delegate because you must train an employee or hire someone. But it highlights your next step.
2. There Are No Accountability Systems in Place
Without accountability, delegation is almost impossible because you cannot determine if the task is being done effectively.
The solution is straightforward: Set up an accountability system. One-on-one meetings, metrics tied to particular tasks, and daily check-ins can go far toward ensuring delegated tasks are being completed — without stepping on toes.
Ultimately, business owners must be willing to delegate to grow their business. One person with a specific skill set — no matter how broad — can only do so much. Work with your team to build business processes, create accountability systems, and ensure that proper training is taking place. That way, you can delegate as your company grows, enabling you to achieve your business goals.
Contributed by Adi Klevit, an EO Portland member who is the co-founder of Business Success Consulting Group, which helps leaders create and document custom processes and tailor-made management systems that ensure consistency.
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