How to Stop My Boss from Wasting My Time with Their Bad Delegation

Oct 16, 2023 6 Min Read
frustrated man at work

Vector image is from by @freepik.

You can lessen your frustration and help solve bad delegation by aligning expectations.

Why Do I Even Try?

Declan paced back and forth, fuming. “I busted my ass to get this done. Made sure it was perfect and met every one of the project’s requirements. I met with my boss today and she blew it off. She’s a poster child for bad delegation.”

“What did she say?” we asked.

He let out an exasperated sigh. “She looked at what I’d done and frowned.”

“Pretty soon she says, ‘This isn’t what I wanted.’”

“But it’s what you asked for!”

“Yeah, but I don’t like this. It’s not what we need. We need to do this differently.”

Declan folded his arms. “I did exactly what she asked, but then she criticises the work and makes me start over? I’m so over this. If she’s just going to waste my time, why bother trying?”

Later, talking with Declan’s manager, she was grateful for Declan’s work, but also confused. “Why would he be satisfied with something that doesn’t do what we need it to do?”

Declan was frustrated—and so was his manager.

Why Your Boss Might Waste Time with Bad Delegation

At the heart of their frustration and disappointment with one another is an expectations conflict.

Declan felt like he had clear parameters, knew the assignment, and got to work. He expected that by fulfilling those parameters, he’d done good work and that his manager would acknowledge that work.

If you’re like Declan, that probably all makes sense.

And, if you’re like Declan, when you delegate, you probably think through the success criteria and give someone clear outcomes to meet. So, you expect other people to do the same.

But what’s happening with Declan’s manager?

She has different expectations. Her expectation likely include the opportunity to iterate. To see something before she can respond to it and know if it’s going to work, make sense, or meet the needs. To do what matters most.

For this kind of leader, their ability to see and touch a work product is crucial. Once they can see it and feel it, then their brain fires up and starts making connections. Sometimes those connections result in those “fun” last minute enhancements that keep everyone working way past deadline, but genuinely make a better product.

Other times, seeing and touching a work product makes them realise just how much something different will better meet the team’s or customers’ needs. So, they scratch out everything and start over. But they couldn’t have told you that before they saw, touched, and felt something tangible.

If you are like Declan’s manager, you probably hope that the first iteration you get will meet your expectations. But often, you receive a work product that disappoints you. It didn’t meet expectations you didn’t know you had—until you saw something that didn’t meet them.

How to Help Your Boss Stop Wasting Your Time with Bad Delegation

There are steps you can take to help align expectations, lower your frustration, and help your boss stop wasting your time with bad delegation.

  1. Clarify Intent
  2. Draw Out Details
  3. Focus on Proof-of-Concept
  4. Explain Tradeoffs
  5. Bonus: for Manager’s Who Struggle with “Bad Delegation”

1. Clarify Intent

The next time your manager brings a project to you, ask about their intent. You might recall the past situation and clarify your intent for the conversation. For example:

“I recall last time we worked on a project like this. I put in lots of time on it and then you wanted to go a different direction. My intent is to ensure I understand what you’re looking for and minimise frustrations. Is this a project like that where you would like something to respond to? Or do you see it as complete and finished the first time?”

If they clarify that they need to see it in order to know for sure, now you know how to proceed. Set up a timeline that allows for iteration and an initial proof of concept (see step 3).

2. Draw out the Details

Next, you want to draw out as many details as possible about what the task will achieve. It’s not enough to get specific details about what they think they want. Ask them what it will do. What will it accomplish? How will it improve the customer’s experience? Or your team’s efficiency?

Focus time on the outcomes they want to achieve. Once you know those outcomes, you’re able to ask questions and help them think through the details. This will reduce the number of iterations you need to make (and establish you as a more strategic thinker).

3. Focus on Proof-of-Concept

If you clarify success criteria and then work hard to build a perfect solution, try a fresh approach. You can save time and frustration by starting with a proof-of-concept.

Instead of delivering a finished product, start with a light version. What is a draft of the task that gives your manager something to respond to?

Provide enough detail that you can ask, “Is this on the right track? Is it feeling good to you?”

As you draw out details, you might hear your manager say things that feel ambiguous, like “It needs to sing” or “I want it to have youthful enthusiasm.” These are subjective standards that will vary—and they fall into the category of “I’ll know it when I see it.” So, give them something to see before you go to all the effort of building something that isn’t what they ultimately want.

4. Explain the Tradeoffs

Even when you clarify intent, draw out the details, and focus on a proof-of-concept, you will still have moments of frustration where your manager asks for more, changes their mind, or wants to go a different direction.

You might feel frustrated and ask yourself, “Don’t I have time for that? Don’t they understand what they’re asking?”

The short answer is often, “No, they don’t know.” They’re living in a world of possibilities and guiding the team to create a future that doesn’t exist. So you need to help them understand the tradeoffs.

Just spell it out. “Here’s what we can do—and here’s the tradeoff that will require.”

Your manager might decide the current version is sufficient. Or that another project can wait. Or they’ll find more resources. But they can’t make any of those decisions unless you give them the information.

(For more on this, check out How to Lead Through Chaos—without Burning Out Yourself or Your Team)

5. Bonus: What To Do If You’re the “Bad Delegator”

If you are more like Declan’s manager with a frequent need to respond and iterate, be clear about that from the beginning. This will help your people draw out the details and focus on proof of concept. They’ll also be able to budget time and mental energy for enhancements or a full re-start when needed.

Also, when you respond to work product, manage your communication so you aren’t critical of their work. Telling someone their product sucks when they poured their heart into doing what they thought you’d asked often comes across as criticism of their work.

But it’s not, or at least, it shouldn’t be. You can try something like “This is what I asked for—and you did a good job building that out. And, as I’m seeing it, I’m recognising this will not work the way we’d hoped. Here’s what I’m seeing… What would you add?”

This response empowers your people, avoids demoralising your team, and includes them in the problem-solving.


Supporting Managers in a Tug-of-War: Balancing Leader and Employee Expectations

Your Turn

You can help manage the frustrations that come from a boss who wastes time with bad delegation by taking responsibility for your communication. Align expectations by clarifying intent, drawing out details, providing a proof-of-concept, and explain the tradeoffs. Together, you and your manager will build far more effective products, services, and projects—with less wasted time and headaches.

We would love to hear from you: What’s one of your techniques when working with a manager who isn’t so great at delegation?

 This article was originally published on Let’s Grow Leaders.

Edited by: Kiran Tuljaram

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Karin Hurt helps human-centered leaders find clarity in uncertainty, drive innovation, and achieve breakthrough results. She’s the founder and CEO of Let’s Grow Leaders, an international leadership development and training firm known for practical tools and leadership development programs that stick, and the author of four books including Courageous Cultures: How to Build Teams of Micro-Innovators, Problem Solvers and Customer Advocates.


David Dye helps human-centered leaders find clarity in uncertainty, drive innovation, and achieve breakthrough results. He’s the President of Let’s Grow Leaders, an international leadership development and training firm known for practical tools and leadership development programs that stick. He’s the author of several books including Courageous Cultures and is the host of the popular podcast Leadership without Losing Your Soul.


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