What to Delegate in Your Business: The 3-Box Test

How Do You Decide What to Delegate in Your Business?

Use the three-box test: if a task meets all three conditions — you don’t have to be the one to do it, you don’t like doing it, and someone else can do it — delegate it. Start with standardized, repeatable tasks like admin, scheduling, bookkeeping, and data entry, where the process is consistent and help is widely available.

I’m ready to delegate, but how do I know what to delegate?

Delegating sounds great… on paper

You hand-off work you shouldn’t be doing to someone else, so you can focus on the high-impact priorities in your business you actually enjoy. 

Hooray, everyone wins! 

Unfortunately, it’s not always easy to resist our primal founder instincts of holding onto absolutely everything — if something’s going to get done “correctly,” we have to do it ourselves, right?

But like I said last month, we can’t control everything. (And just like last month, I still hate it, too.)

Sometimes we learn this the hard way: things start falling through the cracks, you catch yourself saying “I don’t want to do this” more and more about certain tasks, or you experience one of those fun moments when a client “politely” asks:

“Hey, uh, have you thought about getting an assistant?”

No matter how you got here, if you’re finally ready to embrace delegation with at least somewhat open arms, I salute you.

You’ve decided you’re not going to be an island-of-one doing every single thing inside your business forever — that’s a big deal. 

Of course, now you’ve got a new question in front of you:

How do you decide what tasks you should delegate?

That’s what we’re going to unpack in this issue.

(By the way, if you’re thinking to yourself, “Wait, I don’t even know who to delegate my work to,” good news — I’m going to talk about that in a future issue.)

If it checks these 3 boxes, delegate it

When I work with clients who need help deciding what to delegate, this is where we start.

If a task checks all three of these boxes:

  • You don’t have to be the one to do it.

  • You don’t even really like doing it.

  • Someone else can do it for you.

… you should probably delegate it.

Scheduling meetings, filing out paperwork, running errands, checking boxes on admin work, some operations tasks, and bookkeeping are good examples. Often, these involve standardized, repeatable processes, which are much easier to outsource. (For instance, bookkeeping has standards and rules, and you’re largely going to do the same thing every month.) 

Plus, more standardized tasks can be handled by a virtual assistant, accountant, or another specialist who are generally in good supply and have a standard range of rates. There is help for every budget, even if just a few hours a month.

Now, what you choose to delegate will be relative to you. 

For example, I hate managing email, so that was one of the first things I delegated. But most people I know hold onto their email tighter than Rose gripped that Titanic door. (Sorry, Jack. Wisconsin will always remember.) 

On the other hand, despite many offers, I have not delegated travel booking because I love playing the points/cards/miles game. Maybe I’d give it up before I let the love of my life drown. (I’ll save that one for a future reality TV newsletter edition.) 

Delegation is a true “choose your own adventure.” Others will have suggestions, but ultimately, you decide what stays and what goes. 

Whatever you decide, your goal here is simple: find other people to do the stuff that will free you up to be really efficient at what you’re good at and like doing (at least most of the time). 

Delegation is an ongoing evaluation process

Over time, you should plan to revisit what it is you do and don’t do inside your company.

For example, once you’ve got all your “I don’t want to do this, I don’t need to do this” stuff handled by someone else, the next step up the delegation ladder is evaluating what needs to be delegated away from your role, including things you’re good at or enjoy.

You may reach a point where you need to look beyond delegating transactional work. You may need to hire specialists who can scale what you can deliver. Heck, a few years from now, you might realize you need to hire strategic leaders to own the core functions of your business, rather than trying to do it all yourself. 

For some of you, that may be an exciting thought. 

But for the rest of you, don’t worry — that is not a problem for today-you to solve.

Today-you only needs to take those first steps toward not being an island-of-one. 

Remember, your only goal with delegation right now is:

“I want to make myself a more efficient executive.”

To achieve that, regularly audit your contributions by asking:

“What does the business need overall, and what does the business need from me specifically?”

Not everything may be a good use of your time, even if it’s still good for the business..

So, if the business needs something, but not specifically from you, move it off your plate. 

Then, just take it one day at a time.

Start-stop-keep: delegating edition

That was a lot, so let’s make your next steps easy:

  • START small. Look at your to-do list for today. Is there anything on it that (a) you don’t have to do, (b) you don’t like doing it, and (c) someone else can do it? Write down the obvious ones and pick one to delegate to someone else now.

  • STOP holding onto tasks because you’re convinced you’re the only person who can do them “right.” I understand the urge, but that’s how work starts falling through the cracks. Your growth will come from documenting repeatable standards and procedures, not from finding the perfect human.

  • KEEP revisiting what belongs on your plate by asking: “What does the business need overall, and what does it need from me?” If the business needs it but not from you, assign it to someone else.

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