4 Ways to Escape the Delegation Roller Coaster

“The best executive is the one who has sense enough to pick good [people] to do what [they want] done, and self-restraint to keep from meddling with them while they do it.” – Theodore Roosevelt

 Delegation is one of the most valuable management tools at our disposal. Properly deployed, it empowers employees to feel ownership and personal satisfaction in their roles and, statistically, makes organizations more productive and successful.

A Gallup poll found that companies led by CEOs with high delegator talent posted higher growth rates, greater revenue, and more jobs created than those run by CEOs with limited or low delegation abilities.

But learning to strike an effective balance when delegating is easier said than done. For many, delegation feels like a wild roller coaster ride with a peak and two deep valleys on either side.

Productive delegation occurs at the peak, where leaders balance between the two valleys. 

On one side is the valley of micromanagement, where leaders frustrate their teams by meddling, over-directing, and questioning their decisions and actions. On the other is the valley of abdication, where leaders throw projects and tasks at their team and assume things will get done without meaningful oversight or follow-up.

Micromanaging results in a non-scalable, unhealthy codependency between a leader and their team. This results in what I call the “genius with a thousand arms and legs” or hub-and-spoke organization structure, where the leader is like a puppeteer and employees essentially do their boss’s bidding. This structure repels top performers and is frustrating to everyone involved, including the leader!

Abdication, on the other hand, produces inconsistent execution, erratic work quality, and an inability to predictably achieve performance targets. You can’t assume that because you’ve asked someone–even a top performer–to do something, it’s going to magically be done correctly and on time!

It’s critical to overcome whatever prevents you from finding the balance point on the delegation roller coaster, lest you resign yourself to a frustrating, less profitable road ahead. 

Here are four common obstacles that prevent entrepreneurs and leaders from getting out of the delegation dips—and four solutions to find and stay at the balance point.

The Obstacles

Obstacle #1: You Enjoy Doing Shallow Work

Although shallow work—writing reports, creating spreadsheets, organizing calendars, making phone calls—is ripe for delegation, we often shy away from handing it off because it’s comfortable and easy.

In his book, Deep Work: Rules for Focused Success in a Distracted World,  author Cal Newport defines shallow workas tasks that are logistical and not cognitively demanding. To our detriment, shallow work is often at the bullseye of our comfort zone. These tasks can be quite seductive because they make us feel like we’re accomplishing things! In reality, they pull us away from more strategic, more cognitively demanding, more important work that advances the firm.

Obstacle #2: You Don’t Do the Math

Have you ever refrained from delegating a task because the upfront time commitment to show or teach someone how to do something seemed too high? If so, you’re a victim of a psychological concept called “hyperbolic discounting.”

In short, our brains are wired to value short-term rewards over long term gains. It’s the reason we choose a cookie today over a beach body three months from now. 

The same thinking affects your leadership! Sure, you could spend an hour teaching someone how to complete a report—OR you could do it yourself in 15 minutes. But the long-term math on a scenario like this rarely results in any gain!

Let’s imagine the report needs to be completed once per week, and now let’s do the math.

While investing an hour in training someone seems costly in the present, you’ll break even on your time investment in three more weeks and then gain 15 minutes per week in perpetuity. And that’s just from delegating one report!

Obstacle #3: You’re Afraid

Fear is often a primary factor preventing leaders from escaping the valleys of the delegation roller coaster, and it frequently results in overcompensation. 

If you’re afraid of being perceived as a micromanager—perhaps because you worked for one in the past—you’ll either not delegate as much as you should or not follow up appropriately and dive into the valley of abdication.

I’ve found this to be a very common scenario. When I speak about Creating a Culture of Accountability—in particular,  how to use the building blocks of accountability—I’m routinely asked, quite specifically, how to avoid veering into micromanager territory.

Creating accountability without micromanaging is quite straightforward, but if you’re focused on the fear of being perceived as a micromanager, you’re prevented from doing even reasonable things that are part of delegating and following up properly.

At the other end of the spectrum, you might have a fear of letting go. For example, if you’re afraid a team member isn’t going to perform a task as well as you can, it could prevent you from delegating. Ironically, that team member doesn’t necessarily HAVE to perform the task as well as you do in order to be effective, but that’s a difficult barrier for leaders to overcome.

Obstacle #4: You’ve Hired Poorly

Poor hiring is the last of the four obstacles for a reason. There’s a tendency for leaders to blame people first when examining delegation roadblocks. But if you’ve examined the first three obstacles within yourself and your organization and you still have an issue delegating, the root cause may be a people problem.

The wrong people are those who can’t—or won’t—learn, who ask the same questions repeatedly, and who make the same mistakes over and over again. I learned this lesson the hard way as a coach: You cannot coach or train people who have no desire or capacity to learn and change.

The Solutions

Solution #1: Invest Time and Energy

You can’t reasonably expect a return in the absence of an investment.  

When it comes to delegation, your investment consists of time and energy. You have to make sure that the people to whom you’re delegating have the context, knowledge, and capacity to execute what you need them to do the way you need them to do it. Your investment ensures that happens.

It also prevents the “genius with a thousand arms and legs” organizational structure I mentioned earlier, where the leader is the only person who understands the context and process of certain tasks.

Consider investing in your team the same way you might justify the purchase of a tool or piece of equipment that automates something to be faster and more reliable. There’s always an up-front cost, but the payback over time makes it worthwhile. Do the math by asking: How will my up-front investment of time and energy pay off in the future?

Solution #2: Create More Staff Independence and Autonomy

In his book Turn The Ship Around, David Marquet outlines a series of statements called the “Ladder of Leadership” that evolves from “Tell me what to do” (which is what employees expect from leaders who have the answers) through seven incremental steps to “Here’s what I’ve been doing” (which is how highly empowered employees communicate to leadership). This tool helps to engage your team more deeply in what they’re doing and take more ownership of the process and the outcomes.

The trick is to learn how to answer a question with a question before simply providing an answer.

For example, when a team member asks you some version of “what should I do?” respond with:

“What do you think you should do?”

This type of interaction creates learning, and as that learning progresses, it builds autonomy.

Not getting this right is definitely an obstacle to finding the balance point on delegation, because it’s frustrating to have people constantly asking how they should do their job. But consider: The reason they keep asking is because you keep giving them answers! Indeed, even with good intentions, we can create our own monsters.

To be clear, I’m not suggesting that you stop answering questions. It’s also unfair to assume that 100 percent of the time your staff will know the right answer. But if employees are never in a position where they’re challenged to figure something out on their own, they’ll continue to depend on you for solutions.

Solution #3: Delegate Using The Building Blocks of Accountability

The three building blocks of accountability—expectations, context, and attention—help business leaders find the delegation balance point and gain traction via more accountability from their team.

When delegating something, first communicate your belief in that person or team. The simplest way to say it is “I believe in you,” but you can use any number of variations: “I know this project is a stretch, but you’re more than capable of meeting the challenge,” or “I have no doubt you’re ready to take this on.”

Then, communicate WHY the task is important. Context is a critical component of accountability because it provides important information that helps your team appreciate the bigger picture beyond the work on their desk. Take the time to explain why a role or assignment matters to the firm, to the team, and even to you personally as the leader.

Finally, ensure they know you’re paying attention. Although attention might seem like the most difficult step to implement because it’s more abstract and ongoing than the first two, it doesn’t have to be. It can be a repeatable process, like a three-minute weekly sync, or a quick question/comment in the hallway: “How’s that report coming along? I’ll have it on my desk by Thursday, right?”

By establishing clear, high expectations (I believe in you), thoroughly explaining the context (This is important to me), and paying attention over time (I’m watching), you’ll find the balance point on the delegation roller coaster.

Solution #4: Create Frequent Checkpoints

If you’re still a little nervous about delegation, a good way to combat that anxiety is to create  frequent checkpoints early in the process.

For example, if you’re delegating a 30-day project to someone, you might choose to schedule a check-in after two days where the employee will present their thinking and plan for how they’re going to execute the project.

This interaction will allow you to gain an early understanding of whether they “get it” and are on the right track. It’s also an opportunity for you to offer course correction as warranted, before they are actually off course!

If the early checkpoint goes well, you could choose to schedule the next checkpoint a week later. If, on the other hand, your team member is off the mark, perhaps you could aim to regroup in another day or two after they’ve incorporated your feedback.

Consider these more frequent, early checkpoints an investment, because it’s likely your employee won’t need as much up-front guidance and structure the next time you delegate a similar project.


“If you really want to grow as an entrepreneur, you’ve got to learn to delegate.” — Richard Branson

As you reflect on the four obstacles and the four solutions I’ve provided, it’s important to note that, like relationship statuses on Facebook, delegation is sometimes “complicated.”

Although you might not necessarily experience any one of these obstacles in the extreme, it’s very likely you face two or three of them at a low level. It’s when they act in concert with each other that  you’re unable to escape the dips in the delegation roller coaster.

Take time to consider:

  • Where are you micromanaging and afraid to relinquish control?
  • Where are you abdicating your responsibilities to put structure in place and follow up?
  • Where aren’t you doing the math and thinking like an investor?
  • Where are you creating an unhealthy codependency?

After you identify the obstacles in your way and as you begin to implement the solutions, you’ll escape the delegation valleys and appreciate a more pleasant, less stressful, more profitable view from the peak. 

Importantly, your team will appreciate it too!


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