If you’re asking yourself this question, you’ve already gotten past the first big hump with delegation.

You’ve realized you don’t need to personally do everything inside your business forever, because your success shouldn’t come at the expense of your sanity, your sleep schedule, or your health.

That’s a big deal, because most founders don’t get stuck on figuring out what work needs to be done. They get stuck on actually letting the work go.

Delegation sounds like a fantastic idea… right up until it’s time to give someone else the keys.

Even when you’re drowning, looking at a pile of work and saying, “Some of this does not need to be me,” isn’t easy. It’s your business. Your vision. Your ideas. Handing even small pieces of that off to someone else can feel like the moment when you say, “OK, cool, so this is where it all falls apart.”

But now that you’re no longer an island-of-one, you’re standing in the next question. And this is the question that actually determines whether delegation works or becomes a frustrating science experiment:

“I know what work I want to get off my plate. But where does it go? Who (or what) takes over this responsibility?”

The answer isn’t always “hire a person,” and it’s not always “automate it.” 

Most of the time, the answer depends on the task itself:

So today, we’re going to walk through a framework for deciding where the work goes based on what the work actually is, and how often you need it.

Before you decide the right solution for a task, you need to determine what kind of need it is:

Those three buckets will lead you to three different solutions.

For example, if a task happens every week and you never want to do it again, you’re looking for a permanent solution. “I don’t want to pay my bills and run payroll.” “I don’t want to close my books every month.” Those are recurring business functions, and you want someone or something that can own them on a regular basis.

Then there are (sometimes intense) temporary needs, and they might even be the tasks you hate most. An easy example is events. If you have two or three events a year, and there are six things you dread every time, you can hand those off without turning yourself into an events company. You just need the right kind of support at the right time.

And if you want to delegate work that is still in flux, you’re solving for the next few months while you learn what the business actually needs. That means you may need to engage in some good ol’ fashioned trial-and-(hopefully minimal) error, while your long-term support requirements become more clear. 

This step does a lot of the work for you. Once you know how much help you need and how often, the “who” becomes much easier to find.

Once you’ve labeled the work as permanent, temporary, or in flux, the next question is who or what is the right answer.

Sometimes the right answer is a human.

Sometimes the right answer is technology. 

Both will need systems and SOPs that tell them how to do the job that you’re carrying around in your head. 

Here’s the simplest way to think about it:

Of course, you can only delegate something to technology once you actually understand how you do it. If every time you touch the task you have to intervene and make a new decision, you’re not ready to hand it to a tool yet.

Meaning, if you can describe the process clearly and it can run on its own most of the time, you’re looking at technology. But if you still need someone to think, choose, and troubleshoot, you’re looking at people. Those people may be assisted by technology tools, but the tools can’t DIY.

This is also where you have to be honest about your own operating style.

If you lean on gut feelings and improvisations, it’s going to be harder to delegate. Processes and people both need consistency.

Sometimes you look at a task and you just know: this isn’t a technology problem. This is something that needs a human. 

So, now it’s time to figure out: what kind of human do you need?

Option 1: Employee

Most of you would say this was not the first option, but most of you are swimming in dangerous employment law waters. Control comes at a price. If you want to dictate exactly how work is done, when it’s done, where it’s done, and how much you pay, you’re looking at a W-2 employee. That can be full-time, part-time, temporary, intern, seasonal. 

Option 2: Consultant or vendor

Again, we apply the Pretty Woman test. Does the person you’re hiring get to say when, where, and how much? Then you can use a consultant or vendor. 

Bookkeeping and closing books is the easiest example. You agree on the deadline, and they complete the work within their own processes and schedule. 

This is also where you need to respect the limitation. Consultants are not obligated in the same way employees are. There will be moments when you want someone to act like a focused-only-on-you-at-all-times employee. But a consultant can say, “I’m not available that day,” “That’s not in our scope,” or “I don’t do that,” and you have to respect it. 

Option 3: Professional partner

While professional partners (e.g., CPAs, lawyers, financial planners) may look like contractors, they’re also important members of your extended management team. 

This is who you hire when you need someone for their credentials and domain experience. You can hire them for a one-off project or for recurring needs.

Just like you warm up before exercise, you should ease into delegation. And it’s a skill muscle you can (and should) develop over time. 

You don’t delegate one big thing, and instantly get to throw your hands up and stop managing. 

For example, if you delegate a task that takes three hours, you might still need to do an hour of oversight. But two hours back in your day is still a win. And if you continue to delegate that task, that process will become more efficient over time.

So start with something finite, low-risk, and achievable so you can get a clean win. Calendar help. Bookkeeping. Basic admin. Graphics. Lots of people can do those well, and they can guide you in how to work with them. Build from there.

Ready to get started? Great, here’s what you do:

Need a sounding board for evaluating your work? Book a free 20-minute strategy session.

SORRY FOR THE CAPS BUT OMG, PROCRASTINATORS, HELP ME HELP YOU. If you are filing by mail, take it to the counter and ask for it to be hand-cancelled. The USPS does not postmark in real-time anymore. Finish your online transactions and print/PDF your confirmations.

A quick reminder, the personal retirement contribution deadline cannot be extended. The business contribution deadline can. And any ticking clocks stop on the day you file your taxes.

Predatory business credit. Since November, I’ve had daily offers to lend me money, ranging from vendors we use like Stripe and American Express to some very spammy daily emails. For the latter, it’s often a merchant cash advance (MCA) vendor and using it can lead to some astronomical balance payments and even having your bank accounts frozen. If you’re a bit short on cash for your tax payments, do yourself a favor and take an IRS payment plan, not an MCA. 

Income inequality. The Fed released new data that shows wealth inequality is at the highest level since they started tracking it, in 1989. We’ve out-Gekko’d “Greed is Good” Gordon. The top 1% of Americans hold the same amount of wealth as the bottom 90%: $55 trillion. In other news, an Amazon worker narrated burning down a warehouse over low wages. Separately, a man threw Molotov cocktails at OpenAI head Sam Altman’s house, leading Altman to publish a 13-page response in which he supported basic universal income. 

Small businesses eating bigger ones. Joe Procopio published a piece this week about the death of large tech companies at the hands of smaller companies developing niche products. Considering what comes next? This is a solid thought-starter.

ICYMI, here are resources you should know about:

Now for a little bit of good news… 

Rory McIlroy became the fourth golfer ever to win back-to-back at The Masters this past weekend. Now, does Rory have a bit of a reputation for ups and downs in his performance? Sure. He can look unstoppable on Thursday and erratic on Friday. But his win is a good reminder to us regular humans that even the best, most repeatable, trained people have bad swings every round. As much as we attach winning to practice and skill, it also takes mindset, persistence, and resilience. Plus, who doesn’t love a good comeback story? Sometimes a win is only so sweet because you got knocked down and chose to get back up again. Even when the odds were stacked against you.