Delegation That Actually Works (And Why Yours Keeps Coming Back to You)

Delegate verb

1. To entrust to another
2. To appoint as one’s representative

Intransitive verb

1. To assign responsibility or authority

The end.

It doesn’t have a caveat at the bottom that says “ … and then insist you do the work yourself after they’re done.”

My son is in Kindergarten. There is nothing I can delegate to him that doesn’t also still require my involvement. One of the ways he contributes to the household is by emptying the dish washer and managing a large portion of his laundry. But I’m putting the extracted dishes in cabinets he can’t reach, or standing next to him when he starts the dryer to allay his fears of starting a fire.

It’s not reasonable for me to expect that he’ll be able to take full ownership of most tasks and as a result, I’m still needed.

Your employee on the other hand, is absolutely able to do so and their seeming inability isn’t theirs at all, no matter how frustrated you might get. More frustrating still, is the fact that the failure is yours and yours alone.

But to quote my son, “That’s okay.”

The problem

It goes without saying that failed delegation is all too often related to control and a dash of well-earned arrogance.

I mean, you and I both know that you could do it “better” right? Probably faster too. And while we’re talking about speed, it’s usually faster to do it yourself than to try to explain and hand it off.

The quality of your work is far superior anyway so it’s just best for you to keep doing everything yourself … or fixing the work that others have done.

Except …

Is it best?

In Dan Martell’s book Buy Back Your Time he uses the phrase “80% done by someone else is 100% freaking awesome!”

You not having to come in on the weekend to get caught up is 100% freaking awesome.

You not having to miss your kids’ game or a friend’s birthday party is 100% freaking awesome.

You not having to spend half your week doing something you hate for the hundredth time is 100% freaking awesome.

And he’s not wrong. You delegated it because it didn’t need to be done by you. Because you didn’t want to do it or it wasn’t the best use of your time. Either way, you already made the decision, now stand by it and enjoy the capacity and the time it opened up for you.

When delegation finally works, the relief is immediate.

Additionally, if you think about delegation failure from the standpoint that the new owner truly didn’t hit the mark, there are three basic reasons why that happens:

1. The outcome was never clearly defined
   1. “Just handle it” or “You do this now” is not an outcome
   2. The team doesn’t have a good understanding of what “done” looks like
2. The process lives in the owner’s head
   1. Steps, edge cases, judgment calls are all invisible
   2. The team is guessing in the absence of guiding structure
3. There’s no check-in rhythm
   1. Owners either hover or disappear
   2. Both lead to rework

As with much of business, delegation is a system, not a single action you take. In those moments of overwhelm where you finally tip over and admit you need help, it’s important to understand that asking for help isn’t delegating. Designing a way for work to move forward without you is delegating. That necessarily involves systems, processes, and prioritization.

Your strategy work helped you determine what to focus on, what matters most. Efficiency is about figuring out who does what and how it gets done.

In light of the three reasons above, here’s a way to think about the simple system your delegation needs:

1. A clear outcome
   1. What does “good” look like?
   2. What’s the deadline?
   3. What decisions are they allowed to make on their own, or if it’s shorter, what decisions do they need you to make?
2. Visible process
   1. Checklist, screen recording, or comprehensive example
   2. Not perfect, just usable
3. Predictable check-in
   1. When will you review it?
   2. How will issues surface?
   3. What happens if something goes wrong?

Think of these three as legs on a stool. If one leg is broken or is missing, you’re hosed.

Let’s say you want to offload your email and your calendar work to an assistant. It’s low value work that’s eating up high value time. And while sifting through your inbox and scheduling your appointments seems easy, these same principles apply.

What does good look like? When, how quickly, or how frequently do you expect the work to be done? What should be flagged for your personal review, and what can they handle on their own?

You want your email responses to be prompt, and by prompt you think a response should be provided within 2 hours of receipt. If the email pertains to the list of specific people or topics you wanted to handle yourself, they’re flagged and you’re notified in under 2 hours.

You provide sample emails that you’ve written to give them an idea of how you communicate. You give them access to your email account and you let them know that for the first week you want to review samples of their work at the end of each day for 15 minutes. This is a perfect opportunity for them to bring questions, or offer suggestions.

Finally, when issues arise, or mistakes are made, you give them a direct means of contacting you. Text message, Slack, or something that will catch your attention immediately. You are there to support them, not co-work with them.

Pretty soon you’re feeling like you just graduated and you don’t have homework anymore. What are you going to do with ALL THIS TIME?!

As a comparison, imagine you just hired a person, gave them access to your accounts, and told them they were responsible for your email and scheduling from now on. Are you feeling more stress or less?

The payoff

In your line of work you’re familiar with the various ways you add value for your clients. There are of course financial benefits, but there are also emotional and psychological benefits as well. The same is true for delegation. When it’s done well, you get to put down the emotional and psychological burden you’ve been carrying. You get to feel relieved instead of anxious. That task is managed and you don’t even have to think about it.

You start developing trust with your team, and get to feel what life is like when you aren’t responsible for everything anymore. Your capacity to prioritize what’s important expands, and that ceaseless exhaustion fades. Ultimately, it creates a team that grows, is fulfilled and motivated, instead of waiting for the other shoe to drop.

The business can run without you doing everything.

That’s the goal.

In the next week, pick one task you currently redo or double-check every time. You know the one even as you’re reading this.

• Define the outcome
• Record yourself doing it once
• Set one check-in point
• Then step back

Congratulations. You’ve built a stool. And that’s where the analogy ends. Stools don’t give you time back in your life, but delegation will. It’s not about randomly or blindly casting off responsibility. It’s about assessing what would be better managed by someone else, trusting them to own it, and supporting them. It’s a system. Next week we’ll look at the rhythms that make those systems stick.