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  • Jason R. Waller

How to Delegate Like a Boss



Last week, a client asked me, “How can I delegate more effectively?” It made sense that she wanted to dig deeper into this. Delegation is a superpower for leaders — it’s one of the most powerful ways to scale yourself and your impact. I strongly believe: great leaders delegate better than average leaders.

Part of this is causality, though. If you don’t delegate, you’re probably going to burn yourself out as an average leader and never finish the journey to becoming a great leader.

In some ways, delegation was always one of my strengths. But it was also something I leaned into too much once in a while. I was quick to pass on responsibilities and give others opportunities, but it was sometimes a scattershot approach. And it didn’t always come with the clear guidelines and support that makes delegation effective.

So, where is the balance? How can we unlock this deep well of efficiency and effectiveness? Like most leadership topics, it begins with the leader.

1. Address Your Own Control Issues

I agree with Harvard Business Review when they said, “One of the most difficult transitions for leaders to make is the shift from doing to leading.” But one of the core reasons this is true is because of selection bias: people who do the best at their job are often the ones promoted to be leaders.

Think about that for a second. People are usually promoted because they can do things faster, better, and easier than their peers. That makes it very, really, super hard to let go of control and that high bar when leading a team. Important deadline? Just do it yourself and get it done. High visibility presentation? Just manage it yourself so it doesn’t get messed up.

The rope here is only so long. A new leader can only get up early, go to bed late, and manage every detail for so long. A candle can’t burn at both ends forever.

The entry point to becoming good at delegating, then, begins with each of us, as a leader, stepping back and asking ourselves “What is it that I’m struggling to let go of and why?” High-achievement, perfectionism, insecurity — they’re all qualities that made us amazing as individual contributors but will hold us back as leaders.

We need to move from the idea that there’s only one way to do things and into the idea that there are many different ways of doing things, even ways that might not be quite as good. We need to move from the idea that we can do everything and into the idea that we can’t and shouldn’t do everything, and get ruthless about prioritizing. We need to move from the idea that failure is unacceptable and into the idea that, in a system, some failure is normal, and decide where we’re willing to give and where we’re not.

What’s holding you back?

2. Decide What to Delegate

Once we’re willing to delegate, the next question becomes which things to delegate. Delegating everything is no better strategy than delegating nothing.

I love this article by Jenny Blake that details six T’s of what to delegate: tasks that are tiny, tedious, time-consuming, teachable, (you are) terrible at, and time-sensitive. It’s a great way to think about which things to let go of and delegate.

Here’s a simple construct. Right now, take 30 minutes out of your calendar and just write down every task that needs to be done. Think about your major categories or activities as buckets to help brainstorm these tasks.

After you have a big, healthy list, go through and ask yourself: which activities could I delegate or outsource? These are the tasks that someone else could do reasonably well. Note that I said reasonably well here, not perfectly. I like thinking about the 70 Percent Rule as guidance here. If it can be done by someone else with about 70% the same level of quality and/or speed, just delegate it. This is the part of leadership where you get to practice letting go of perfection in favor of progress. It also creates great moments for mentorship and coaching.

After this, take another pass and ask yourself: which activities should I delegate or outsource? You might find that there are tasks you could outsource, but the outcome really needs to be controlled or it’s simply your job to do it. You also might find new tasks that you can’t outsource yet but should figure out a way to in the future.

Think about not just yourself and what you can get off your plate but also what is going to lead to better outcomes. Both matter. By better outcomes, this could be that the task is completed more quickly, to a higher standard, or in a new, novel way that you hadn’t thought of. A better outcome could also mean creating an opportunity to develop someone or make them feel ownership.

This list becomes your starting point of what to delegate. As a rule of thumb, a leader should focus on bigger, more strategic efforts and outsource operational tasks that are more repetitive or routine. In the earlier-mentioned article, Jenny also provides a link to a Google Doc that highlights 75+ tasks she delegated in a year.

3. Decide How to Delegate

Once we know which tasks to delegate, the next question is how to delegate them effectively. I think of this in four steps:

  • Own the “what”

  • Share the “why”

  • Pass on the “how”

  • Pass on the “wow”


How leaders actually delegate matters a lot to the outcomes.

Own the “What”

Just because we delegate something doesn’t mean that we get to be hands-off and point the finger when things go wrong. We delegate authority, but never responsibility, what I call the “what” of a task.

This means that, even if we delegate, we still own the outcome. Leaders are always accountable for the results, and this should be clear when tasks are handed down. Don’t “fire and forget.” Check-in, offer support. Set clear deadlines and be specific about what success looks like.

As a frequent delegator, this was my cardinal sin. I would be too hands-off and just expect people to figure things out. This left them feeling confused and unsupported, not empowered as I had hoped. And it meant that when things went off the rails, not only was I accountable for bad results but also I was responsible for not providing clear guidance and resources along the way.

Share the “Why”

This is huge. People are motivated by “why.” They’re inspired by it, intrigued by it. If we pass along a task without the context, we’re just like the parent saying “because I told you to.”

Making sure we still own the “what,” but let’s not forget to pass on the “why.” It doesn’t need to be long or elaborate, but it does need to be meaningful. What is the purpose behind this task? What will it accomplish? How does it feed into the bigger picture and higher-level goal?

This isn’t just for motivation, by the way — this is also practical. By sharing the reasoning behind a task, we open the door to innovation. We invite others to brainstorm new ideas and think about different ways to solve the problem, not just check a box. When people understand the bigger picture, they can be inventive, creative.

In the Army, we called this “commander’s intent.” The mission was important, but knowing why, the commander’s intent, let us be more nuanced in our execution and think outside the box when things got messy.

Pass on the “How”

The “how” is what we really, truly delegate to someone. This is the responsibility for others to figure things out and come back with a solution. Not passing on the “how” is micromanagement, which is actually a great short-term strategy. It’s just a strategy that’s impossible to sustain and scale.

When we pass on a task, we need to give others the opportunity to figure it out. This is 80% of the work anyway. Passing on the “how” breeds ownership and responsibility. It encourages diversity of thought. When you give someone a task, focus on the outcomes, the deliverables. Resist the urge to walk step-by-step into each, tiny detail. Instead, ask how they would do it.

How to do a task should be owned by the person that we delegate to, but it doesn’t mean it can’t be informed by our experience. We can offer resources and share what we’ve seen work before. But the bright line here is that the other person still steers the process.

Pass on the “Wow”

Along the way, we can’t forget to celebrate success and acknowledge a job well done! This not only reinforces the ownership in others but also reinforces the power of delegation in ourselves.

Of course, this isn’t to say that everything is going to be on time and that we should pat people on the back for poor quality. But it’s important to remember the 70 Percent Rule and recognize that perfection isn’t the goal, progress is. And even in complete failure, we can celebrate the opportunity to coach and train others. We can celebrate the effort made.

We can also celebrate that we’ve empowered others and freed up our own time to focus on what really matters. Delegation is hard. When things don’t turn out according to plan, let’s not view this as a failure but rather as another learning point. Let’s celebrate that we’re practicing this core leadership skill.

In Summary

“If you really want to grow as an entrepreneur, you’ve got to learn to delegate.” — Richard Branson

Before even beginning, the first step is to try to figure out if something’s holding you back from delegating. Probably, you are better at doing these tasks than most. How can you let go of your high standards and perfection?

The second step in delegation is to decide what to pass on to others. What can be delegated? What can be outsourced? What should be? Make a list and start today.

The third step in delegation is to decide how to delegate. Never let go of your accountability for results, always own the “what.” Always share the “why” and how the task is important. Pass on the “how” and let people own the process, guiding them along the way. And also pass along the “wow” and celebrate the empowerment that you create in others, as well as the freedom you create for yourself.

To reiterate, delegation is a skill that separates great leaders from average leaders. And like any skill, it can be learned and honed. Check yourself on where you are with this skill. Find mentors to make it more real and relevant. Get feedback from others along the way about how it’s going.

You’re going to do great.

#leadership #delegation #management #personalgrowth

Originally published in The Startup