When your boss is a poor delegator

We know 82% of managers don’t get foundational training.

This probably includes your boss.

If your boss isn’t giving you meaningful work because they are a poor delegator, this framework is for you.

Principle First:

Delegate

This can be used as a noun and a verb. The pronounciations are different, but the meanings are related.

1.  noun. /De-lə-git/ a person acting for another: such as a representative to a convention or conference

2. verb. /De-lə-gāt/ to assign responsibility or authority.


 🧠Today’s Framework: The Commitment Conversation

📚Today’s Story: Prying work from a bad delegator


 📝Today’s Quote:

“Delegation requires the willingness to pay for short-term failures in order to gain long-term competency.”– Dave Ramsey


🧠Framework: Fred Kofman’s Commitment Conversation

To help steer this situation in the right direction, we turn to Fred Kofman’s “Commitment Conversation.”

This framework revolves around four critical questions that ensure clarity and agreement between you and your boss.

Poor delegators are often worried they won’t be able to explain the task well enough to another, or never considered they wouldn’t do a task personally, or that they are the only ones with the skills to do it. These are all recipes for burnout.

Here we’ll start with some questions to help your boss realize they should ask for help by delegating, and then we’ll bring in Kofman’s framework to ensure alignment, giving your boss some relief that the baton has been passed in a skillful way.

Some questions

Here are some questions designed to encourage your boss to reflect on their workload and recognize the benefits of delegation.

Believe me, they know they are overloaded. They just don’t know how to get the team to help.

These questions aim to illustrate you are coming with helping hands, and should help prevent a defensive response:

  1. “What part of this project is taking up the most of your time right now?”
  2. “What do you wish you were spending more time on? What are you actually spending your time on?”
  3. “What aspects of this task would you like to focus on more closely?”
  4. “Is there any part of this project where my involvement could free you up for other priorities?”
  5. “Are there elements of this task that I could take on to help speed things up?”
  6. “What can I take off your plate that would allow you to focus on [a specific strategic priority]?”
  7. “If I were to help with this, what part would be most useful for you?”
  8. “How do you see us dividing the workload on this to make the most impact?”
  9. “What support do you need to ensure this project meets its deadline?”
  10. “Where do you think my involvement could make the biggest difference in our current priorities?”
  11. “Is there a part of this that you feel could be more efficiently handled if we shared the responsibility?”
  1. “Would it be helpful if I took over [specific task] so you can concentrate on [another task or goal]?”
  1. “What’s the most challenging part of this project for you right now? Is there any way I can help ease that burden?”

These questions are designed to help your boss reflect on their workload and see the value in delegation.

They guide the conversation toward identifying areas where you can contribute, ultimately leading to a more effective and balanced distribution of work.

Once they agree on your help, move to Fred Kofman’s “Commitment Conversation” from his book Conscious Business.

The Commitment Conversation

Use your active listening skills and ask questions until you can answer YES to all four of these questions:

1. Do I understand what the other is asking of me?

Seek to understand the request fully. Clarify the expectations, deliverables, and timeline.

2. Do I have the skills and resources to do it?

Assess if you have what’s necessary to accomplish the task. If you lack certain resources or skills, this is the time to discuss them. Refer to this graphic to help you and your boss think about resources:

The 6 types of resources a team may need: job related informaiton, material and supplies, tools and equipment, work environment, customer and supplier participation, budgetary support.
Adopted from: Trent, Robert J. 2016. “Understanding the Many Factors That Affect the Success of Organizational Work Teams.” Journal of Business.

3. Am I convinced that those on whom I depend will deliver for me?

Determine if you can rely on any teammates or stakeholders involved in this task. Identify potential dependencies and address concerns early.

4. Am I willing to be held accountable for anticipating potential breakdowns?

A commitment isn’t just about saying “yes”; it’s about owning the process. You should be prepared to monitor progress and proactively handle obstacles.

The key here is to keep asking questions and seeking clarity until you can confidently answer “YES” to each of these questions. Only then can you and your boss be aligned on the request, setting you up to deliver successfully.

There are only six possible answers you can give to a request:

1. “Yes, I promise.”

Full commitment, indicating you understand and accept the task entirely.

2. “No, I do not commit.”

You can’t fulfill the request, though you might offer to help in other ways.

3. “I need clarification.”

You require more details before committing.

4. “I commit to respond by [a definite date].”

You’ll provide a definitive answer by a specific date.

5. “I accept conditionally. I can commit to do what you ask if [a mutually observable condition] happens. Would that work for you?”

You agree, provided certain conditions are met.

6. “Let me make a counteroffer. I can’t commit to doing X by Y, but I could do S by T. Would that work for you?”

You propose an alternative that you can commit to.

This approach not only helps you pry work away from a hesitant boss but also demonstrates your commitment to ensuring tasks are managed properly.

Remember, there’s a 82% chance they don’t have training. Accept their imperfections, and offer helping hands.

📚The Story: Prying work from a bad delegator

Early in my career, I had a boss who we’ll refer to as Michael.

Michael was an excellent individual contributor and was promoted to manager. He was then promoted to senior manager, meaning he was now running a team of teams with several managers working for him.

But he never learned to delegate when he first became a manager.

So now he’s got managers working for him. And the managers have teams. The teams are looking to the managers for context, but they stuggle because they lack the context from Michael.

The managers started to leave in frustration. This left Michael with even more responsibility.

It wasn’t that he didn’t trust his team; he simply didn’t know how to let go.

I really liked this guy, I had known him for 10 years. I knew his family. He’s incredibly smart. He never carries a notebook, he manages to hold everything in his mind and can synthesize meaning without apparent effort.

But he just didn’t know how to turn his personal meaning into shared purpose.

And how to ask for help.

I had a weekly one on one with Michael.

For a while I’d use that time to complain about how things were going. But then I changed course – I started asking open-ended questions.

“How confident are you that this aspect of the project will come to a successful completion?”

That tapped into his anxiety in a productive way. He started describing all the things he was worried about that he needed to do, but didn’t have time.

“Is there any part of this project where my involvement could free you up for other priorities?”

Boom – a project started to get defined.

He was still nervous of letting go. He was afraid I didn’t completely understand. He had been in so many discussions and thought about this for so long only ever considering he’d do the work.

Enter the Commitment Conversation.

1. Do I understand what the other is asking of me?

I asked questions until I could repeat back the objective and timeline required.

2. Do I have the skills and resources to do it?

I thought about my own personal skills, and used the graphic above to help think through resouces to ensure I had what I needed.

I remember him allocating some budget to buy some tools and software that he had but my team did not have.

3. Am I convinced that those on whom I depend will deliver for me?

I considered my teams current workload. I negotiated some relief on some tasking to make room for this new priority.

4. Am I willing to be held accountable for anticipating potential breakdowns?

I acknowledged knew I didn’t have all the history as I hadn’t been in every room Michael had been in. I also defined some risk I could see on achieving the deadline, but closed with a confidence level on success.

By the end of the discussion, Michael had a clear understanding that I was prepared and equipped to take on the project. He was more comfortable letting go, knowing I was committed to its success.

Over time, as we had more of these conversations, Michael learned that he could trust me and other team members. Eventually, he became more adept at delegating, freeing him to focus on strategic aspects of his role.

The team and I felt much more empowered, and a weight was removed from Michael’s shoulders.

He was incredibly relieved. He finally shared with me his wife had some health issues and he wasn’t sure how he’d balance it all…

📕1 Book, 🎧 1 Podcast, 📺1 Video, 📰1 Article

Here’s the best stuff I’ve found while researching this.

 📕Today’s Book:

I’ve recommended this book many times. Fred Kofman was the Vice President of Executive Development of LinkedIn while CEO Jeff Weiner was scaling the company from 337 employees to 16,000. LinkedIn founder Reid Hoffman calls him “The High Priest of Capatilism.”

Kofman offers dozen of simple frameworks and today’s “Commitment Conversation comes directly from this marvelous work.

“Conscious Business: How to Build Value Through Values by Fred Kofman.

🎧Today’s Podcast:

This episode dives into the nuances of managing your newly promoted boss by taking work OFF her plate, not putting work on it.

“The Look & Sound of Leadership” – Episode 125: “Managing Up” (or on Apple Podcasts). (10 Minutes)

📺Today’s Video:

Williamn Ury’s TED Talk “The Walk from ‘no’ to ‘yes’ ” isn’t directly about delegation, but it’s a brilliant story of managing limited resources, and a reminder find perspective by “Going to the Balcony”.

“The Walk from ‘no’ to ‘yes’ ” by William Ury. TED Talk. (18 minutes)

📰Today’s Article:

Some comedic relief, the hilariously true stories of bad management behind many of the iconic Dilbert cartoons.

“How to Dilbert Practically Wrote Itsself” by Meghan Ennes, Harvard Business Review.

author avatar
Evan Hickok
Evan Hickok has over twenty years of experience designing and managing high-complexity systems in high-consequence environments. As a Systems Engineer and Program Manager, he has guided projects through every phase of the product life cycle—from concept, detailed design, transition to production, production, installation & activation, and operational support. A dedicated researcher of team dynamics, Evan focuses on building high-performing teams capable of delivering exceptional results in the most challenging environments. He shares his insights and frameworks in the Lighthouse Leadership newsletter, published almost weekly at evanhickok.com.

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