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Sharpening Delegation Skills Can Be a Major Growth Opportunity.

Two people sit together, one is on a couch and one is on a chair, and they are learning how to delegate

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Learning how to delegate 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: 

  1. Have I hired someone I trust to perform the task efficiently?
  2. Are documented processes in place, or does everything “live” in my head?
  3. Is there a method of ensuring accountability? 
  4. Can Istep away and allow the other person to do the task?

Some of these, like number four, require a simple mindset shift; addressing the other three concerns can support that shift. So, what is the first and foremost obstacle to effective delegation? Read on.  

The Most Significant Obstacle to Effective Delegation: Lack of Communication 

There are many obstacles to effective delegation, but a lack of communication tops the list.  

As a business owner, I delegate tasks to the 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.” The person you delegate to 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’re delegating it. However, if you don’t provide the SOPs and training necessary for the employee to perform the task, it’ll simply boomerang back to your plate again.  

So, what’s the solution? How do you overcome this obstacle and learn how to delegate effectively? The answer is to build 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 and SOPs 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 most common challenges when learning how to delegate.

1. The entrepreneur has a hard time letting go of the task.

It can be challenging to learn how to delegate and 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. Perhaps you 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 didn’t 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.  

Another reason you may hesitate to delegate is that the task being delegated is complex and hard to explain. 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 and starts the process.

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.  

How to Delegate: Build the Systems that Support You 

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. 

Learn how to delegate from entrepreneurs who have been in your shoes.

Adi Klevit is co-founder of Business Success Consulting Group and an EO Portland, Oregon member. 

This article was originally published in 2024 at 

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