Like a Boss Series: Learn to Delegate

Old habits die hard, and if you’re an entrepreneur, one of the hardest to conquer is the mindset “If you want something done right, you have to do it yourself.”

Entrepreneurs are characteristically task-oriented, meticulous go-getters with a pre-established way of doing things. When you’ve built a business from scratch, it’s extremely difficult to let go of the idea that any other way of doing things could be better than (or as good as) your way. The hard truth is that if you don’t “let go,” your business will stagnate. You will become the main detractor to your company’s growth and success.

So how do you master the art of letting go and learning how to delegate? Well, at first it will take practice and a lot of willpower. After all, you’re trying to squelch the very traits that make you an entrepreneur. To get you started, we’re going to discuss a checklist of items you’ll want to review each time there’s a project to be handed off to one of your employees. With time, these items will become second nature.

The Delegation Checklist

As you’re handing off an assignment, check off these 7 points:

  1. Clearly define the project.
  2. Have the employee repeat the request.
  3. Explain why it must be done.
  4. Explain how it must be done.
  5. Have the employee repeat the above.
  6. Set a deadline.
  7. Make sure the employee agrees to and understands how to meet deadline.

Checklist Breakdown

Let’s talk about these points in more detail.

Clearly define the project.

Being a good manager means understanding how your employees take instruction and guidance on an individual scale and working with them to accomplish efficiency and productivity. How you communicate, or “hand off,” a project to someone will depend on yours and the employee’s preference, whether it’s through a ticket, email, task-management software, or otherwise. The main objective is to ensure that the full scope and content of the task is communicated thoroughly.

Have the employee repeat the request.

The best way to ensure that the task is understood is to ask the employee if they understand, and even ask them to repeat what it is to be done so that you can work out any miscommunications on the spot rather than waiting for the incorrect end result.

Explain the “why.”

If you’ve done the hiring process well, your employees aren’t stupid. You can explain why you need a project done a certain way without being or sounding patronizing. This is part of thoroughly handing off an assignment. You want your employee to have the full picture.

Explain the “how.”

Here will be the hardest part to communicate without micromanaging. Depending on the task, there may be an exact process that must be followed, which you can teach, or there could be a number of ways to complete the project well. Here is where you’ll need to allow the employee some freedom to deliver the end results their way. You’ll need to trust them, remembering with humility that your way may not be the only way or even the best way.

Make sure the employee understand the “how” and “why.”

Ascertain that your employee has a full comprehension of the scope of the project as well as the desired end result. You can do this by having them repeat it all back to you in their own words.

Set a deadline.

A lot of factors will determine the necessary deadline, including external demands that neither you nor the employee can control. Depending on these factors, you should strive to set reasonable deadlines that will both serve the company and set your employee up for success, not certain failure, while applying a dose of healthy (yes, certain types of stress can be healthy) stress and responsibility.

Agree on the deadline.

Allow your employee to have some input on the deadline. You’re working with a human, after all, and not a robot. As their manager/boss, it also wouldn’t be amiss to ask the employee if they have everything they need to get the job done. Remember, it’s your job to make sure the necessary resources are at their disposal; it’s their job to use them efficiently.

Ready, Set, Delegate!

What has been the greatest advice you’ve ever received about delegation? Have you had any experiences with failed delegation? Share in the comments!


Kennedy, Dan. “Become a Master Delegator in 7 Simple Steps.” (January 28, 2015.)