Why You Don’t Delegate (And What to Do About it)

It's 6:32pm, you're still working, and you've got 5 things left to get done today. 

You're going to miss dinner with your family for certain, and you're not happy.

One by one you watched your team members sign off from work, and you're frustrated that you have to keep working AGAIN.

You wish you could delegate SOMETHING to a team member, but it's too late now. The work just has to get done.

And you don't really trust that they'd do a good job anyway...

Why You Don't Delegate 

You don't delegate to others for one of these reasons:

1. You Wait Too Long :: If you wait until a task is due (or worse: LATE), you've no margin to actually delegate to someone else for them to get the work done in time.
2. You Don't Think You Have Enough Time :: You know delegating well takes time, but you already feel overwhelmed with your schedule, so you don't know when you'd actually take time to do it.
3. You Don't Trust Your Team :: Listen, we get it. You're really talented. We're not saying you're not, but if you've caught yourself saying, "They won't do it as well as me", then you don't trust your team.
4. You Feel Bad Burdening Your Team :: You might trust they can do the work, but you don't want to burden them with the work if they're already busy. Even worse, you might not like the task, so you don't delegate it to your team because you think they won't like it either. 
5. No One's Ever Taught You to Delegate Well :: You may have tried and failed to delegate in the past, and simply given up on it. It could simply be that you need a better framework. 

The GREAT news is all of these are solvable, but first lets cover why delegating will be such a win for you.

Why You SHOULD Delegate

It's obvious that you should delegate work to give you time back, but there's actually many more valuable reasons to do so. Even if you are working the amount of hours you want to work each week, delegation should be a part of your Weekly Planning Meeting. 

You Will Maintain Your Highest Sustainable Pace

If you're working more than you want to work, the frustration and overwhelm actually changes the way you work. Instead of collaborating, we work on items ourselves "because it's faster". Instead of seeking creative high impact solutions, we seek the quickest solution "because I'm behind already". The quality of our work actually gets worse. Time Boss "Highest Sustainable Pace" thinking ensures you are rightsizing the amount of work you put in daily & weekly to maximize the impact of the work you actually do, and delegating is a key strategy here. 

You Will Work on Higher Impact Items

When you delegate, you free up time for you to work on higher impact items that have a greater likelihood of helping you accomplish your goals. By not delegating, you're actually holding back your company or team from experiencing greater results, because you could have higher impact. Not to mention the career growth you'll experience from upgrading what you work on. 

You Will Develop Your Team Members

When you delegate, you create a growth & development opportunity for your team. Particularly if you don't think your team can do it as well as you, delegating the work creates the opportunity for them to learn to do the work as well as you, provided you delegate well via a defined process (full step-by-step guide below on how to do so).

What You Should Delegate

Jim Schleckser, author of the book "Great CEOs Are Lazy", says you should delegate anything that someone else can do 70% as well as you. The obvious implication is that there is work that only you can do that you should keep. 

So what should you actually give away:

1. Recurring Tasks :: These are the easiest things to give away because the requirements are well established (even if it's only in your head right now). When you delegate a daily / weekly / monthly recurring task, you're getting back the time you'd spend running it daily / weekly / monthly.  For example, if you delegate a 1 hour weekly task, that's 52 hours back every year - the rough equivalent of an additional work week! 
2. Projects (in Whole or in Part) :: Every project you're working on has SOMETHING that you could delegate, possibly the entire thing. You simply need a delegation process you can rely on (see below!).

How to Delegate

Step #1 is to plan ahead so you actually have time to delegate, and no better way to do this than a Weekly Planning Meeting. Every week this meeting helps you get everything out of your head and into a system, get clear on your priorities and break them down into manageable tasks, get those tasks to your calendar, and deal with the tasks that don't fit (such as... you guessed it... delegating 🎉). 

Once you've planned ahead, the actual steps to delegate vary based on what you're delegating, but the core idea is the same:

1. You want to set up your team member for success
2. You want to verify the work was done to your standards

How to Delegate Recurring Tasks

Take a quick audit of your recurring tasks (daily / weekly / monthly / quarterly / annual) and look for items someone else can do 70% as well as you. Found one? Here's what to do next:

1. Record Yourself Doing the Task :: Whether you delegate a recurring task or not, guaranteed you're going to do it at least one more time, even if that's during training of another team member. Next time you do the recurring task, record yourself doing so using a tool like Loom, or Mac or Windows built in tools. Ensure audio is on, and talk out loud as you complete the recurring task. You want whoever you're delegating to to understand how and why you are doing what you're doing. This is setting your team member up for success. 
2. Ask Your Team Member to Write a Recipe :: You heard that right. YOU don't have to write the documentation to delegate well, but SOMEONE does. By having the team member you're delegating to write a recipe, they have to watch the video and compress it down to written words, dramatically increasing their ownership of the steps to complete the recurring process. In addition, they can always return to the video as a reference point if they are confused, reducing the future interruptions to whatever higher impact task you're going to be working on. 
3. Review the Recipe for Understanding :: By reviewing the recipe, you ensure that the process was documented correctly, and can coach up your team member on their documentation skills.This is verifying the work is done to your standards. For example, if they are vague in their language or miss a key step, it's an opportunity for you to show them the standard you expect for recipes, which will only improve their ability to receive future tasks you might delegate to them. 

How to Delegate Projects

For the purpose of this section, when we say "Project" we mean either an entire project, or a subset of a larger project. 

Projects are more difficult to delegate because they do require more prep work on your part

Low-risk Projects :: The 10-80-10 Method.

The net effect of this method is you spend 80% less time spent on whatever you delegate. We repeat: 80% LESS TIME SPENT ON WHATEVER YOU DELEGATE. Don't believe me? Here's how: the 10-80-10 rule (courtesy of John Maxwell).

 The idea is this: you take 10% of the Project to ideate on what needs to be done, and create requirements and direction to set up your team member for success. The team member then completes 80% of the work. You then work with the team member on the last 10% to verify the work was done to your standards. This works well for low-risk projects, where there's time for you to help get the deliverable up to your standards in that last 10% portion. 

1. 10% - Create Requirements & Direction for the Project :: This step creates boundary conditions for the project. What must happen within the 80% phase NO MATTER WHAT. Up until now you did this implicitly simply by how YOU did the work. For you to grow as a leader and delegator, you need to put those things on paper for the team member you're delegating to. Need a template to get started? Try our free guide "How to Crush Your Quarterly Goals". A quarterly goal is simply a type of "Project" (and you should be delegating at least some portion of your team members to help anyway). 
2. 80% - Your Team Member Does the Work :: Pretty straight forward here. Your team member should simply be making the project happen based on your requirements and direction. For more complicated projects, you can ask them to give you a detailed project plan (The "How to Crush Your Quarterly Goals" free guide can also serve as a template for this) to ensure they are locked in with a good plan, and you should consider adding a weekly project check-in (either meeting or via email/messaging) to ensure your team member is on track and not blocked by anything. It's hard to understate how much this will impact you and your team members. You get time back to run at your Highest Sustainable Pace, and to work on higher impact items. Your team member gets to upskill and develop as a professional. 
3. 10% - Verify the Work and Coach it to Completion :: Up until now, you may not have delegated because you didn't trust your team to do the work as well as you. The magic of 10-80-10 is that no trust is required. You are verifying the work at the end, leaving time to ensure you can add whatever special touches you want, and coach your team members up to your standards. You get the results you want from the project, and your team member learns and develops, helping them be that much more effective for the next item you delegate. 

High-risk Projects :: The Apprentice Model

10-80-10 works great when you've got room to iterate. But what about the work that has to be right the first time? The change order going to a client. The schedule update that drives the whole job. The deliverable where a 70% first attempt could blow up the relationship.

For high-risk work, you need a different model. We call it the Apprentice Model, and it's how craftspeople have developed people for centuries.

Before we get into the steps, here's the most important shift you need to make: delegation is a process, not an event. The number one reason high achievers don't delegate is trust. We have high standards, and we don't believe anyone else can hit them. The Apprentice Model is a zero-trust way to delegate. You don't have to trust the person when you start. You build the trust through the process itself.

Here's how it works:

Stage 1 - You Do, They Watch :: You're already doing this work today. The only change is you bring a team member along to observe. They watch every decision you make. You talk out loud as you work, explaining the why behind each step. Quiz them as you go: "What would you do here? Why?" They're getting reps by watching, and you're not putting the deliverable at risk because you're still the one doing the work.

Stage 2 - You Do, They Help :: Same situation, but now you hand them portions. They take a piece, you take a piece. You're still owning the outcome, but they're getting hands-on reps on smaller chunks. You watch their work before anything leaves your desk.

Stage 3 - They Do, You Help :: Now they lead. The controls are in their hands. You're right there watching, ready to step in if needed, but they're the one making it happen. Either way, you get the 100% deliverable you need.

Stage 4 - They Do :: Eventually, they just do it. They've stacked up enough reps and enough coaching to hit your standard. The work is off your plate, and you've developed someone who can run it without you.

The magic that makes this work at every stage is a framework we call honor and extend.

Every time your team member does the work (or part of it), they're going to do some things right and some things wrong. If you only point out what's wrong, they get discouraged and stop trying. If you only point out what's right, you never raise the bar. You need both.

Honor what they got right, and be specific. "You handled that step exactly the way I would have. You caught that issue before it hit the client." This reinforces the behavior you want repeated.

Extend their context where they fell short. They didn't get it wrong because they're bad at their job. They got it wrong because they don't yet have the experience you have. Fill in the gap. Walk them through the missing context, the decision you would have made, the standard you expect. Then run it together.

That's the whole loop. Honor what worked. Extend what didn't. Run another rep. Each pass gets closer to your standard, and your trust in that team member grows alongside their capability.

So when do you use the Apprentice Model versus 10-80-10?

Use the Apprentice Model :: When the work is high-risk, complex, or requires judgment that's hard to put on paper, and you CAN NOT afford it to be wrong. 

Use 10-80-10 :: When the work is lower-risk, the requirements can be clearly written, and you have time to work back and forth with the team member if it's not up to your standards. 

Both models develop your people. Both get work off your plate. The right one depends on the risk of the task and where the team member is in their development.

Delegation is One Part of Mastering your Week

We believe you have what it takes to master your week to get the results you want: life-giving personal or financial freedom, career growth like you’ve never experienced, and contribution to the things you care deeply about.

Mastering your week is simple in nature, but hard to follow through in practice, and Time Boss is here to help. Stay connected to the blog, subscribe to the newsletter, grab a free Time Boss resource, or even jump in a “Master Your Week” course (offered quarterly).

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