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4 Reasons Delegation Fails and How to Fix It in Your Business

Every successful business owner requires a well-appointed toolkit of useful skills. One of those skills is effective delegation. Dustin discovered that the hard way when he arrived at a job site after a lengthy call with his very unhappy client.

Dustin’s client had requested a new roof with right-angled, wood-colored shingles. The crew had arrived early, while the homeowner was preparing for work. Everything was going according to plan—until the homeowner stepped out of their home and looked up to see how the job was progressing.

The shingles were triangular, not square. Worse, they were green! That’s when the client pulled out their phone.

“I get a wonderful call,” said Dustin—chuckling as he recalled the incident with the benefit of distance—“just a wonderful call from a client who loves Jesus but, once they realized what was going on, decided to look up four-letter words in the dictionary and share all of them with me at once.”

For the client, the problem was Dustin’s crew installing the wrong roof. For Dustin, the problem was ineffective delegation.

Delegation is essential to successfully and sustainably scaling your business. It’s one of the only ways you can both multiply your skillset and expand it without having to develop those skills yourself.

But here’s the catch: When I talk to busy entrepreneurs and executives, the one area they struggle with more consistently than any other is effective delegation. Incredibly successful business leaders run aground here all the time.

Using Dustin’s story, let’s talk about four struggle points when it comes to delegation. If you’ve ever had difficulty delegating, chances are good at least one of these will apply to you. Then, along with diagnosing the problem, let’s explore solutions so you can turn it around and become a master delegator.

1. Identifying High-Leverage Work

The first struggle point leaders usually face with delegation is identifying their highest-leverage work. Most of the time, they haven’t done it. And that means they end up holding onto work they shouldn’t. Their to-do lists are full of work that others on their team can do better, work that others enjoy more than they do, and work that others could do less expensively.

I always go back to this quote from Navigators founder Dawson Trotman: “I purposed never to do anything that others could or would do when there was so much of importance to be done but others could or would not do.”

When an entrepreneur builds a business from scratch or an executive climbs through the ranks, they do so by learning skills and gaining abilities. But their current role is not the same as their preceding roles.

Leaders often think—usually unconsciously—that their current role is just all their prior roles combined. But that’s a major mistake. They must now lead people who do those prior tasks, reserving for themselves those tasks that add the greatest value to their company: the stuff of importance that others cannot do. That’s high-leverage work.

In our business-owner coaching program, BusinessAccelerator®, we teach our clients to identify their highest-leverage work using a tool we call the Freedom Compass. You can also find out more about this tool in my book, Free to Focus.

The big idea is as simple as this: Given your unique set of skills, insights, and abilities, you should focus your efforts on work you have the greatest passion and proficiency for. We call that the Desire Zone, and it’s exactly opposite to the work you loathe and aren’t much good at—what we call the Drudgery Zone.

Why passion and proficiency? If the work doesn’t energize and excite you, you won’t bring your best. And if you’re not proficient, it won’t add value to your customers—to the marketplace. When you combine these two qualifiers, you get the best criteria for high-leverage work.

To his credit, Dustin was clear on this point. “My Drudgery Zone activity would have been ordering materials for job sites,” he told me when recounting his client misadventures. “It was a pain. It was a waste of time for me. And I just hated doing it.”

If you’ve got tasks like that still on your to-do list, you need to offload them. If it’s not high-leverage, and you can’t eliminate it or automate it, you need to delegate it. The Freedom Compass is the best tool to help identify these sorts of tasks—high leverage and low—but all you need to get started is to ask, Where do my passion and proficiency converge? You need to do more of that and less of everything else.

Based on his telling of the events, where Dustin went wrong is everything past this point. See if you can relate.

2. Selecting the Best Delegates

People make their highest and best contribution when they’re working as close to their Desire Zone as possible. That’s true for leaders—and the people they lead.

That means you should delegate tasks to people who have proficiency and passion for the work, if possible. Of course, it’s not always possible. Sometimes we and our teams have to press on with tasks in which our passion and proficiency are suboptimal. Welcome to life.

But if you want to become a master delegator, you not only have to identify your highest-leverage work, you also have to select the best delegates. And that’s another struggle point for a lot of leaders: They delegate to whoever is available and unreasonably expect results beyond the person’s expertise.

Dustin fell into this trap. Early in his business, he gutted out the materials ordering and similar back-office functions. He hated it and knew he needed to get someone to take it off his plate.

“I finally got to the place where I was ready to hire somebody to delegate really anything to,” he told me. But was it the right person? Was the person chosen because they had passion and proficiency in areas that Dustin didn’t? Not really.

“One of the things that I expected and tasked this individual with doing—who, mind you, has zero roofing experience—was to call in our work orders,” Dustin admitted.

If you’re offloading Drudgery Zone activity, you want to find someone who has more passion and proficiency for that activity than you do. Otherwise, you’re just multiplying your own frustration and setting someone else up to fail.

I see this time and again with the business owners I coach. It may not be green shingles instead of brown, triangles instead of squares. But they end up with something they didn’t intend. They realize they need to delegate. They even hire to do so. But they delegate to the wrong person—whether it’s because they’re underqualified or suited for different work entirely.

When delegating, we must ensure we’re delegating to the best people for the work whenever possible.

Even then, we’re not out of the woods. Sometimes I find, when working with clients, that they’ve selected the right person but haven’t properly equipped them. That was also a factor in Dustin’s situation, and it’s also the next sticking point in effective delegation.

3. Empowering Delegates to Win

Assuming you’ve got the right delegate, you can still go wrong if you don’t equip and empower them to win. By that I mean you’ve got to:

  • define the deliverable;
  • define the scope of their responsibility; and
  • provide the resources (and/or the authority) they need to succeed.

It’s fair saying that Dustin hit this sticking point hard. He recognized that his highest-leverage work didn’t include ordering materials. He saw he needed to hire someone to take that over. He stumbled there. But here is where he really got hung up.

“I trained her up,” he admitted about his hire. “And by trained her up, I mean, I told her once ‘this is what I expect’ and gave her nothing written down.” In other words, Dustin’s delegate was more or less on her own to figure out the job.

Unfortunately, he complicated that as well. “I had enough awareness to say, if I’m going to ask this person who has no roofing experience to order roofing materials, I should probably have a form for that,” he said.

The problem was, it was a terrible form. As Dustin explained,

It is the most complex order form in the history of the universe. And if the multiverse is real, it includes the multiverse. So imagine infinite universes. If I were to enter this document into the most complex contest, it would win in a landslide. And keep in mind, I’m using this form to delegate to somebody who has no clue what they’re looking at.

It’s no surprise the client ended up with the wrong materials. Worse, the job site was also missing materials. Dustin knew all sorts of information about the job he never wrote down and didn’t include in his form.

This is called the curse of knowledge, and business owners fall into this trap all the time. We know something about the work we do and assume that others ought to know it too. Everything is obvious once you know the answer. The problem for our delegates is that the answers are usually locked in our heads.

“Me being a roofer, I knew that certain things like nails, if there’s 20 squares, that’s one box of nails,” Dustin said. “So I just knew those things and never wrote any of those things down. I would just get on the fly when I call in the orders.”

The problem for his delegate was that she didn’t have any of that information. So she didn’t order the nails or several other items the crew needed to finish the project.

When Dustin arrived at the job site, he had to calm down his client, figure out what went wrong, purchase the right materials—all of them, this time—and return the unneeded materials. I’d say it was a costly mistake, but it was more like many costly mistakes all rolled into one.

“It was a glorious disaster,” Dustin admitted, “a massive failure of delegation.” At Full Focus, we use a tool called the Vision Caster to clarify expectations and empower delegates to win. It’s a simple way to detail the deliverable so the delegate can reliably deliver it.

But there’s still one more delegation sticking point worth considering. If Dustin got this next one right, he might have prevented that glorious disaster.

4. Following Up as Needed

Nobody likes seagull management, when a business owner or executive flies in, squawks, makes a mess, and flies away. Master-level delegation is all about maintaining connection to the result. That means appropriate follow-up—providing feedback, checking in as necessary.

Dustin passed off the order and assumed it would be done as he wanted—done as he imagined. He didn’t delegate to the right person. He didn’t empower them to succeed. And he would have known that, had he followed up on the work being done before it was too late.

Delegation is all about results—getting better results than a leader could manage if they did it on their own. That’s true in both the positive sense—the delegate is better at the delegated work—and in the negative sense—the delegator has better things to do with their available time.

But if you’re concerned about results, you have to stay focused on them. When leaders delegate and fail to follow up, they’re not taking responsibility for the result.

I’m not talking about overmanaging someone, leaning over their shoulder. The “as needed” qualifier above is important, because some delegates require very little direct supervision. They’re hyper-qualified, super responsible, and fully equipped to execute the task.

Follow-up is a shared responsibility. You may task your delegate to report back to you on their progress. In fact, I recommend that. Our Vision Caster indicates four levels of delegation to get aligned on those responsibilities when assigning work. If Dustin had that baked into his workflow, he would have experienced better results.

That’s true for any of us regularly delegating. When we task our delegates with work but leave them unequipped to win and don’t properly follow up along the way, we’re almost guaranteeing results we don’t desire.

“After I got back to the office,” said Dustin about his employee, “she was super upset about it. She thought she had failed me. But the truth of the matter was, it was an example of maybe the worst delegation in the history of the universe.”

Looking back at our four sticking points, Dustin had identified his highest-leverage work and chose to delegate the rest. That was excellent. Many leaders struggle here. But he failed to select the best delegate, failed to properly empower them, and also failed to follow up as necessary.

“As you can expect,” he said sarcastically, “the desired result was great.”

If we want truly great results as business owners and executives, we have to become master delegators. Thankfully, familiarity with these sticking points can expose where we’re likely to go wrong. And using tools like the Freedom Compass and Vision Caster can ensure we get the results we desire.

Disclosure of Material Connection: Some of the links in the post above are “affiliate links.” This means if you click on the link and purchase the item, we will receive an affiliate commission. Regardless, we only recommend products or services we use and believe will add value to our readers. We are disclosing this in accordance with the Federal Trade Commission’s 16 CFR, Part 255: “Guides Concerning the Use of Endorsements and Testimonials in Advertising.

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