The Hard Truth About Delegation

How I Learned to Lead and Let Go

I was talking recently with one of my favorite colleagues about the challenges we’ve both faced when it comes to delegation. As leaders who have led large teams, we’ve both constantly battled the ability to effectively delegate, ensuring we are meaningfully moving work down the organization, allowing us to elevate and improve our overall impact on the business. 

From my past experience, there appears to be two types of leaders when it comes to delegation: 

  1. Those That Delegate Too Much

  2. Those That Delegate Too Little

For those that delegate too much, they’re the kind of boss that forwards on requests via email, essentially reducing their role to one of air traffic controller. For those that delegate too little, it’s a boss who finds themselves constrained by a desire to control, holding onto too many tasks and underutilizing their teams. 

Like my colleague I was catching up with, over the course of my career I’ve found myself in the camp of a boss who doesn’t delegate nearly enough. While I mean well, and certainly believe in my team, there are a few reasons I still struggle to delegate:

The Four Reasons I Don’t Delegate Enough

  1. I Worry About Our Team’s Capacity: The most common concern I have is that the team doesn’t have the capacity to take on additional work. When I sense the team reaching capacity, with our top talent already taking on so much, I’ll often find myself withholding work in an effort to not overload their plate.

  2. I Worry About Our Team’s Capability: It’s uncomfortable to admit, but there have also been times when - while the team may have capacity - I worry the individual may not have the capability to get the job done, either in its entirety or to my expectations.

  3. I Worry About My Capacity: In the cases where the team may not have the capability to execute the given project or task, I should be investing the time and energy to train talent and up-level the team. Unfortunately, there are times when I find myself prioritizing my own schedule. In these moments of weakness, I tell myself it would be faster if I just did this item myself, rather than slow down to train the team on how to handle it.

  4. I Worry About Being Liked: Finally, it pains me to admit that there have been times when I will withhold delegating in an effort to not upset someone. In these cases, which often involve after hours asks that I take on myself, I’m prioritizing being liked by the team over the priorities of the business.

Over the course of my career, I have worked hard to correct the above mentioned bad habits. While I’m far from having mastered delegation, along the way I have learned a few things that have helped me make noticeable improvements in this area. 

If you too struggle with delegation, perhaps the following can be of service to you: 

Six Lessons In Learning To Let Go

  1. When We Don’t Delegate, We’re Doing Our Team A Disservice: We may tell ourselves that we’re looking out for our team, but the truth is, when we choose not to delegate due to capacity concerns we are doing our team a huge disservice. Our team deserves the right to weigh in on their own capacity and they deserve the right to take on more if they think they can manage it. We aren’t protecting our team if we aren’t allowing them to speak for themselves. 

  2. Capacity Should Be Objective, Not Subjective: Capacity should be an objective conversation, not a subjective one. When approaching delegation, we should strive to shift the conversation from one of feelings to one of facts. By utilizing time tracking, coupled with scoping incoming requests, we can have fact-based conversations related to how much one person can reasonably take on.

  3. When We Don’t Slow Down And Solve for Capability, We’re Destined to Repeat: If the issue at hand is that the team doesn’t have the capability to execute, it’s incredibly short sighted to take on the work ourselves. Sure, in the short run, this will be the fastest solution, but by not slowing down and training up the team, we’re bound to find ourselves in this situation again.

  4. Expectations Should Be Expressed, Not Implied: When we find ourselves withholding work because we worry we can do a better job than the team, we should keep in mind that it’s our job to express our expectations, not merely imply them. Have we been clear on what the expectations would be for the project? Have we communicated that to the team and given them the opportunity to articulate their own opinion on their ability to execute against these expectations?

  5. It’s Not Our Job To Do It All, It’s Our Job To Get It All Done: As the boss, it’s not our job to do everything, it’s our responsibility to get everything done. That means intentionally managing, utilizing, and applying our resources to meet the needs of the business that we serve. When we free ourselves from the misconception that we must personally do the work, we’ll find ourselves getting far more done.

  6. If Our Team Isn’t Making Mistakes, We Are: This one was one of the hardest truths that made the biggest impact on my ability to start letting go. Mistakes are cost of entry for an organization that wants to move fast and make meaningful change. And while we certainly can’t accept an unlimited number of mistakes, one thing that is clear is that if your team isn’t making any mistakes, you’re making a big one: You simply aren’t delegating enough. 

Bringing the above lessons from idea to execution takes more than just an appetite for change. On my own road to addressing my weaknesses with delegation, I developed a four-step approach that has proven to be as simple as it is effective:

The Four Step Delegation Cycle (A.k.a “DEEA”)

The objective of the Four Step Delegation Cycle is to provide managers with a framework to approach delegation. Its focus is on creating a learning cycle that allows managers to push work down the organization, while elevating their role and the work they do. It goes as follows:

  1. Delegate: Delegate work down the organization, providing more junior employees the opportunity to expand their responsibilities and increase their impact on the business.

  2. Elevate: Elevate your own role, focusing your efforts on projects of higher priority, shifting from executing tactics to developing strategy.

  3. Evaluate: Evaluate the team’s effectiveness in executing the newly delegated projects and tasks.

  4. Adjust: As needed, move back down into the organization to address issues arising from delegated work. For issues of capacity, provide or address resource constraints. For issues of capability, treat the symptom and address the root cause.

The above is designed to be a cycle, so as you parachute in to adjust, strive to extract yourself as soon as is reasonably possible, returning to delegate new tasks and projects to your team. 

As the cycle progresses, you continue to learn more about yourself and your team. You understand where there are core competency challenges and where there are resource management issues. When done effectively, everyone is left feeling challenged, with the business benefiting as a result. 


While I wish I could tell you I’ve mastered delegation, the truth is I have a long way to go. For all my own weakness as a leader, of which there are many, delegation continues to be a challenge. 

That said, whenever I talk to a colleague about their own struggles with delegation, I am comforted in knowing that I am not alone.

The hard truth about delegation is that there is no finish line and that the work is never done. 

And yet, despite this fact, we owe it to ourselves, our team, and our organization, to pursue it anyway; to embrace delegation, to lean into this learning cycle, to challenge ourselves and our team, to finish each day better than we started.

Editor’s Note

An early version of today’s post was originally published to LinkedIn back in May of this year.

As I have been onboarding new clients at Kanahoma, and subsequently growing the team to support the new work, it has resurfaced how critical this conversation is, which inspired me to resurface the post, rework it a bit, and give it a share.

If you have your own recommendations on how best to approach delegation, please don’t hesitate to share. I could use some added inspiration as I continue to work on self-improvement in this area.