Why Delegation is So Hard (And What to Do About It)

“Just delegate more.” That trope doesn’t help—you already know you’re ‘supposed’ to delegate, but it’s hard to actually do it.

Today, we’ll look at why delegation is hard (hint: it’s actually 15+ unique steps), where agency leaders get stuck, and what you can do about it—including tips to overcome 12 common delegation obstacles.

From my agency coaching experience, this advice might eventually save you 3-15 hours a week, especially if you’re getting sucked into doing too much client-facing work. Imagine what you could do with an extra 150 to 700 hours a year!

Taking 4 hours vs. 20 minutes

A few years ago, an agency owner told me that he was frustrated that his junior developers would take 4 hours to complete a set of tasks he could do in 20 minutes.

As we dug into the problem during our coaching call, I learned that his devs were recent graduates, that he hadn’t dedicated time to train them, that he’d been doing the particular work for nearly a decade, and that he hadn’t told them they were supposed to get it done faster.

In short, his employees were new to the work, didn’t know his shortcuts, and didn’t know they were taking 12X as long as his benchmark. No wonder he was frustrated about delegation!

Your team is unlikely to go from 4 hours to 20 minutes overnight—but you can get them from 4 hours to 3 hours, and 3 hours to 2 hours. Even if they still take 1 hour to complete something that you can do in 20 minutes, it means you’re not having to do the work yourself.

As the agency owner, your job is to primarily do the “$ 1,000/hour” activities that only you can do as the owner—things like setting the long-term vision and strategy, managing your direct reports, building referral partnerships, and (to a point) recruiting key employees.

Excuses about delegation

Do these “don’t delegate” excuses sound familiar?

• “It’s faster just to do it myself.”
• “Other people can’t do it as well as I do.”
• “I don’t have anyone else available to do it.”

Those are each sometimes true—but together, they’re hurting your ability to focus on the $ 1,000/hour activities.

When you waste your time on low-value activities, you’re making life harder for yourself—you get stressed, you risk burnout, and you’re hurting your agency’s potential to scale.

Why delegation is hard

Delegation is hard because it requires trusting others. Trust doesn’t come naturally to everyone, and it’s hard to build trust when you’re overloaded already.

It’s not just trust—delegation is hard from a technical standpoint. That is to say, delegation is complicated—it requires practice, and access to resources.

How complicated? Based on my analysis as an agency consultant, delegation requires at least 15 steps.

You won’t do every step every time—for instance, once you have a freelancer under contract, you don’t need to renegotiate the contract each time you request help. But the 15+ steps need to be in place; missing even one step can stop or otherwise ‘break’ the process.

Yes, delegation requires 15+ steps!

It’s not just you—if you break delegation into each relevant step, it’s actually at least 15 different things.

Let’s say you want to delegate pre-screening sales prospects—that is, they’ll ask initial qualifying questions, and pass prospects to you for followup sales conversations.

Here’s the list of 15+ delegation steps I’ve identified, if you’re the delegator as an agency leader:

1. Recognize that you can’t do the task yourself—or shouldn’t do it.
2. Consider the components of what to delegate to someone else, so you can hand the task to someone else.
3. Identify how you’ll later integrate their deliverable(s) into your own workflow, if applicable.
4. Identify the skillset(s) required, to define the role(s).
5. Find and hire the person (or people) who can do the work.
   • Decide whether this should be an employee, an individual contractor, or another firm.
   • Identify prospective candidates who can do the work.
   • Interview the candidates to assess their competence.
   • Make an offer to the finalist.
   • Negotiate rates—including hourly rate, salary, or project-based fees.
   • Get them under contract.
6. Decide how you’ll communicate tasks to people helping.
7. Identify who’s competent to handle a particular task.
8. See if they’re available on your timeline / budget / other specs.
9. Transfer knowledge to them about the goals and specs to consider, including sharing access to relevant resources.
10. Pre-schedule a check-in with them at an appropriate time, to review before the deadline (especially if this is a new relationship or a new task).
11. Do the mid-way check-in.
12. Share constructive guidance as appropriate.
13. Get the final deliverable.
14. Confirm QA on the deliverable.
15. Integrate the deliverable into your workflow, if needed.

That’s a lot of moving parts! For clarity, I’ve consolidated the “hire someone” into a single step, but that technically adds at least six sub-steps when you don’t have someone on-board already.

Fortunately, you don’t have to do all 15 (or 21) steps each time!

Delegation gets easier with time, practice, and staffing…

In practice, delegation is more straightforward once you have the people on board. For instance, it might be roughly three touchpoints, where I’d say:

1. “Diane, could you draft a v2 of ABC client’s new XYZ deliverable? The v1 is in their shared folder.” [She confirms, and asks any clarifying questions.]
2. “It would help to talk through a few points by phone; can we review tomorrow afternoon? I posted a few followup questions in Trello.” [She confirms, reviews the questions, and finds a time to speak.]
3. “Your updates make sense, with the edits we discussed to Part 2. ABC sent me a new update this morning, which I just forwarded to you. Please revise the deliverable based on their latest changes. Once that’s complete, you’re all-clear to send <ClientName> the XYZ.” [She takes action.]

…but beware the hidden assumptions!

Three steps seems easy—but there are at least 7 ‘hidden’ assumptions behind those my three hypothetical comments to Diane:

1. I’d already hired Diane; we didn’t need to renegotiate fees.
2. I know she is competent to do the work; I just needed to clarify her availability and turnaround timeline.
3. Beyond overall competence, Diane is generally familiar with the specific client’s history and goals.
4. I sometimes need to clarify a change in priorities, if my new request means she’d need to pre-empt an earlier assignment.
5. Diane knows about each client’s shared folder in Google Drive, and she has access to the folders and other resources.
6. We already have a software system and process for assigning tasks.
7. We had enough time to complete the process before any client-facing deadlines.

The next time someone says “just delegate,” you can see how it’s not as easy as they seem to think. (And it’s why team retention is so important, so you don’t have to re-explain everything every time.)

12 solutions: How to make delegation easier

If you’re new to delegation—or it’s not your favorite thing—that’s OK; I’m here to help!

Here are potential solutions to 12 common problems in delegation—including the common excuses I listed at the beginning.

1. If you don’t have someone to do the work: Weigh whether to hire an employee, hire a freelancer, or hire an outside vendor. For instance, light bookkeeping might work best with a freelancer or outside accounting firm—whereas someone doing client-facing project management needs to be an employee (or perhaps a guaranteed-hours freelancer) if it’s early.
2. If you can’t afford help: That’s a tough situation. You might temporarily ask a current team member to help with this. You might also find a freelancer to help, if it’s a low-hours recurring task. You can sometimes use #12 below—just stop doing it, if it’s not important.
3. If your team isn’t competent: You need to help them become more competent. Assuming they have the potential, this might involve your training them (block-in the time; it’s worth it!), pointing them to online training resources, or recruiting an external trainer to get people up to speed.
4. If you have to keep redoing the work: Are you clear on the definition of success for each thing you delegate? When I assign something, I’ll frequently be explicit about that: “The ideal outcome is v1 strategy that <ClientName> can review, for us to create a v2.”
5. If your clients expect you to do it all yourself: That’s a challenge—especially when your team doesn’t have the background knowledge of the relationship—but you can eventually delegate clients to your team. It takes time—so the sooner you start, the sooner you can get things off your plate.
6. If you still don’t trust others to do the work: Ask yourself whether this is about competence—it might be—or about something deeper that’s specific to you. If your team is competent and trustworthy, you might need to work through this with your therapist.
7. If you don’t want to make time to delegate: Your team can’t magically read your mind—you need to explain what you’re trying to accomplish. (If it’s a matter of not wanting to type up the request, you can delegate via phone call or in-person conversation. But if you do that, I recommend having the delegate recap the assignment to you, to ensure they understand it correctly. And an interim check-in is especially important.)
8. If you don’t have time to delegate the work: Recognize that delegation always takes more time the first time—but then you start seeing significant efficiencies. The second time, you might answer a couple questions. The third time, you might recommend a couple tweaks. After that, you might not need to answer questions or review things at all. Imagine the time you’ll have saved the 20th or 100th time someone else did what you used to do!
9. If you have trouble communicating the steps to follow: Don’t focus on the steps—focus on the outcome you want, and on providing access people need. (For instance, you can’t say, “Figure it out” if they don’t have a login to the system.) Usually, the delegate can figure out the steps… or ask you for help when they get stuck.
10. If you like doing certain things yourself: That’s fine; you can keep doing them. But be clear with yourself that you’re making a tradeoff that may cause problems elsewhere.
11. If you don’t have PM software to make this easier: Get the process down first—you don’t want to automate a bad process. Then, review my list of PM software for agencies. There’s likely something in the list that’ll be a fit for you. (Unfortunately, the list is approaching 70+ options… but you can delegate software selection!)
12. If you’re not sure anyone really needs to do the task: Stop doing it! Manager Tools calls this “delegation to the floor.”

If you’re on the fence, know that delegation pays off—it frees you to do higher-value work as you run your agency.

Question: Where do you get stuck when it comes to delegation at your agency?

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