Overcoming the Fear of Delegation

Kelsey Opel
SquaredAway
Published in
3 min readMar 4, 2021

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‘Why is delegation so hard for us?’ This usually comes down to 3 perspectives:

  1. The delegation process takes too much time
  2. The belief that delegation is wasted time
  3. Self-improvement bias

Let’s break these down further:

  1. Delegating takes too much time — This is a false perception that is fueled by emotions regarding delegation.
  2. Delegation is wasted extra time — This is also false as long as you are using the time to delegate effectively (more on how to delegate below).
  3. Self-improvement bias — Some managers don’t want to give up the “go-to” title for specific projects or tasks or feel they need to ‘perfect’ the project themselves by supervising all completed work. This mindset can result in micromanaging and cause a bottleneck in the workflow.

How to Delegate:

  1. The End Goal: Explain the end goal to the individual you are delegating to. A bulleted list, main points about the pieces of the task/project, or details on where you need help are great ways to explain this.
  2. Vulnerability: Explain how you feel about the task/project. Vulnerability is essential; this allows the individual working on the project to better gauge how you may react to the task and how you may share your recommendations.
  3. Plan: Define the areas where you feel you can delegate pieces of or the whole task/project.
  4. Ask questions of the individual you are delegating to: “Is this something you are confident in handling?” “What is confusing about what I am delegating?” “What do you need to be successful with this task?”
  5. Set a deadline for the project/task: This will give both the managing individual and the individual handling the delegated task a clear end-date or time for the project/task. This allows both parties to communicate on the status of the delegated item.

Trust the process, delegation takes some time upfront, but the long-term rewards are effective productive workflows.

Experiences in Delegation: Will it make you want to live on an island?

Think of the worst thing that could happen from delegating the task or project. If the “worst-case” is something that could be career-ending or cause you to want to go live on an island, it’s best not to delegate it. If the task you’re considering delegating is a low-risk task that you don’t enjoy doing or is something that you regularly handle, delegate it and see how much time you save in your life.

The first thing I ever delegated was a social media graphic on Canva. I shared our brand guide, gave set parameters, and asked the assistant to run with it. This saved me 15 minutes in total (it usually would have taken me 20-minutes to complete the task, and I spent 5 minutes delegating it and answering questions). Start small and work your way up to the vital areas of your business.

I can now delegate other areas that have a more substantial impact on the company, but the trust-based relationship has grown to a point where I’m comfortable with this. I have learned that this is how companies effectively scale, through continued teaching, delegation and trust.

Delegation + Software = Productivity

Automations make a lot of workflows more straightforward, and software improves our access to automation. These are Project Management software that we recommend.

  1. AsanaA platform that allows you to manage projects and tasks with automation and streamlined requests.
  2. monday.comA visual-focused platform that allows you to create a project workflow in seconds.
  3. Trello A cross between Asana and monday.com, Trello focuses on simplicity and a card-centric workflow.
  4. BasecampThis platform was built by a remote-first company, and it focuses on everything living in one place, from check-ins to message boards and to-do lists.

Are you ready to start your delegation journey? We challenge you to find three areas in your life that you can begin to delegate; whether it’s outsourcing your grocery shopping, getting help with your next trip, or getting all of your admin needs ‘squared away,’ delegation is the key to a productive lifestyle.

If you’re ready to get Squared Away, visit us at GoSquaredAway.com or grab some time for a call.

Drop by our social media and say hi👋 Instagram, Twitter & Facebook.

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Kelsey Opel
SquaredAway

Startup Operator // Snowboarder // Taco connoisseur. Follow along for my journey in operations and lessons learned in this territory.