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The Art of Delegating: What and How to Delegate to Your Directs

When done right, delegation means everyone on your team wins

Kathleen McAuliffe
Kathleen McAuliffe / July 6, 2017

Surprise! Pushing your unwanted projects onto someone else actually increases productivity for everyone. For the overworked manager juggling their business development duties with supervisory activities, delegating sounds like a gift from beyond.

Okay, thoughtlessly shoving your spreadsheets onto your intern won’t produce the same benefits as a carefully planned project, but the point remains: successful delegation works. Not only does delegation enable managers to swap their time-wasting activities for top-priority strategic initiatives, it gives your junior employees an opportunity to take on stretch projects and hone their skills.

But delegation is a delicate dance. You need to foist extra work onto someone—and frame it as a growth opportunity. You need to respect each employee's time and autonomy while supporting them when problems arise. You need to maintain accountability for the overall outcome, but distance yourself from the details.

Oversee the process too heavily and you’re micromanaging. Back off entirely and you’ll be accused of abdicating responsibility and abusing your employees. By operating between those two extremes, you can free up your schedule, develop your employees, and improve the bottom line.

What’s Stopping You From Delegating?

Done well, delegation presents a win-win situation for all involved. But most leaders don’t delegate well—or at all.

A 2007 study on time management found that close to half of the 332 companies surveyed were concerned about their employees’ delegation skills. At the same time, only 28 percent of those companies offered any training on the topic. And in an executive leadership study by Stanford University, 72 percent of chief executives said that they either need to improve or are working on improving their delegation skills. For middle managers who need to answer to senior leadership that number is likely higher.

Hesitation stems from personal insecurity—whether it’s fear of losing time, control, credit, or delegating yourself out of a job. But because delegation only succeeds when you can surrender control of the details and decision making process to your colleagues, you need to recognize and address those concerns before assigning tasks.

You don't have enough time to delegate

"That extra hour you spend training your colleague on a new software or process could grant you an extra three hours for a higher-value project"

Between explaining the tasks to employees, following up, addressing questions and problems, and providing feedback, delegation can occupy a lot of time. At that point, it may seem more efficient to do the work yourself, even if it steals time from something more valuable. True, you might complete your presentation in less time than your subordinate. But instead of considering the time differential, consider opportunity cost. As a manager, you likely have more pressing business-enhancing projects on your plate than your junior employee. So that extra hour you spend training your colleague on a new software or process could grant you an extra three hours for a higher-value project.

Also, not having enough time to delegate is the surest sign that you need to delegate something out of your schedule. But time crunches place managers in a vicious cycle. How do you create time to delegate when delegation is what creates time? In The Courageous Leader: How to Face Any Challenge and Lead Your Team to Success, Angela Sebaly recommends simple ways for managers to make time to delegate:

Assess what is on your plate that can be postponed or dropped. Not everything we do is necessary. Some of what we do is because we’ve always done it, the person before us in the role always did it, and the person before them, and so on.

Manage energy in other parts of your life so that you can temporarily do more of the strategic stuff at work that gets you unstuck (like hiring a qualified team).

As requests for your team come in, practice asking, "Why this task?" and "Why me and my team?" rather than "When do you want it done?"

Delegating yourself out a job

Although this is a possibility, realize that when your direct reports create value for others, their competence will reflect positively on your management, even though you’re not directly involved in driving those results.

Consider the alternatives, too. To take a less optimistic perspective: their failures will reflect poorly on your leadership. Though you could hoard the work for yourself, under-prioritizing strategic imperatives for busywork or burning yourself out will be counterproductive.

What Should You Delegate?

what to delegate

Although we managers fiercely protect our right to make our own choices, we tend to shy away from decisions that carry negative consequences.

This pattern holds even when stakes are low: In a study published in Organizational Behavior and Human Decision Processes, participants tasked with choosing a restaurant were two to three times more likely to delegate the choice to someone else if it negatively impacted others or if the options were unappealing. According to the investigators, they outsourced their choice to avoid feelings of responsibility or blame for their decision. If a hypothetical dinner decision can provoke this anxiety, imagine the choices that managers face daily: Firings, business mergers, or other major consequences.

But rather than giving those tough or politically sensitive decisions to someone else, managers need to devote more time for those higher-level strategic tasks.

Instead, delegate out problems that prevent you from enhancing your business. On Entrepreneur, Matthew Levey, owner of Field Trip Beef Jerky, recommends low-value, time-intensive activities for managers to shift elsewhere, including:

Tasks that keep you from growing your business

Banish the busywork. For example, a standalone editor at a rapidly growing media company who spends hours proofreading freelance submissions might be better served hiring a copyeditor. Free from micro-analyzing every comma and period, she can devote more time to setting content strategy or forging partnerships with sponsors.

Areas that are out of your wheelhouse

Once again, think about opportunity cost. The more time and energy you spend trying to make sense of that complicated financial report, the more resources you’re diverting from other projects. If the buck stops with you, it’s worth the sacrifice. But if one of your direct reports can figure it out in five minutes? It’ll save time—and once you factor in your hourly pay—money, as well.

Anything you want your team to learn

Allowing workers to take ownership of tasks helps them truly absorb lessons and skills, as Bob Marsh, CEO of a motivational software called Level-Eleven, discusses in the Entrepreneur article. If you’ve been meaning to teach your team SEO optimization or a new software, a hands-on project will go a longer way than just about anything else.

How Should You Delegate?

how to delegate

Much has been written about the importance of delegation, but one reason many leaders don't delegate is they're not sure the best way to go about delegating—and making sure the job is done right. Here, in a nutshell are the most important things you should consider before handing over a task or project.

Choose the right people to delegate to

Match activities to your employees’ activities. This will help minimize the chances of unduly burdening someone with a task that’s completely outside their capabilities. For example, offload your editing to the detail-oriented wordsmith in your group, the client check-ins to your charismatic salesman, and your budget reports to the math whiz.

But equally, if not more important, is spreading the load evenly throughout your team. Researchers from North Carolina State University emphasize the importance of fairness in delegation as well:

Some of your team members may feel that they are already putting in extra time for your team’s project. This may be true, so make sure that you are fairly dividing tasks between yourself and all of your team members. If everyone feels overworked, you will have to explain that in order to get the job done, everyone needs to put forth the extra effort.

Especially after a missed deadline or a blown deal, it’s understandable to avoid the people who burned you in the past. But constantly saddling your most dependable employees with time-consuming tasks will only invite resentment and accusations of favoritism. Lean too heavily on a few stars and you’ll lose them. Instead, identify the weak links in your department and decide whether to train them or replace them with more reliable people.

Cultivate a culture of trust

Remember those team-building exercises where you close your eyes, cross your arms, and let yourself fall into someone else’s arms? Delegation is the workplace equivalent of the falling tests: You’re betting your work product and reputation on your coworkers’ work, thus revealing the trust level between you and your team members.

Nobody will want to pick up your work if they don’t believe that you have good intention. For many business leaders, that poses a problem: in Edelman’s Trust Barometer, one in three workers said that they did not trust their employers. Also, most considered a fellow worker’s voice more credible than that of their CEO.

Even if you think your direct reports trust you, realize that your mannerisms and offhanded comments could subtly undercut your credibility. Carefully word your ask and avoid these common pitfalls, which Gwen Moran presents on Fast Company:

One way to damage your credibility is to offer a “non-apology apology” when you owe an authentic one, says Michael Maslansky, CEO of Maslansky + Partners and coauthor of The Language of Trust: Selling Ideas in a World of Skeptics.

When you apologize for occupying a worker’s time, don’t couch your mea culpa with qualifiers. Just own up to it and move on.

While sometimes situations require consequences, such as for carelessness or bad actions, publicly making someone else a scapegoat is just going to make people wonder about how much you can be trusted.

Classic social psychology research confirms that we learn just as much from observing other’s experiences as we do from our own. Scapegoating prevents people from taking the risk to take on new projects, so avoid that if you want to create a culture of trust.

Address your staff’s concerns

Sure, sometimes your employee doesn’t want to pick up a new project at 4pm on a Friday. But when your direct reports resist an extra assignment, don’t assume that they want to slack. In fact, their biggest concerns mirror those of their managers.

Frustrating as it may be to meet resistance from your team members, realize that their hesitance could stem from their own fears. North Carolina State University presents the most common barriers for employees, including:

  • Not enough time
  • Not enough experience
  • Fear of failure
  • Fear of being a scapegoat
  • Not their responsibility
  • Reaction from other team members

Unless they’re obviously slacking off, hear them out. Once you understand why they’re really wavering, you can meaningfully respond to those barriers. Encourage and use open communication to air out and alleviate out minor problems before they balloon into major issues.

Follow the Acceptance Theory of Authority

No matter how politely you ask your assistant to pull performance data from the last five years, there’s no getting around the underlying message that, "My time is more valuable than yours.” So approach the ask delicately and if possible, create some buy-in for them. The process will be much more pleasant if your subordinate sees some personal value in their end product.

So how can you exert authority while empowering your employee? Follow management theorist Chester Barnard’s “Acceptance Theory of Authority,” which outlines the four conditions employees need to meet before accepting a task. Incorporating these conditions into your ask will encourage you employee to take, if not embrace, the extra work.

What your directs need from you:

1. They need to comprehend the assignment

Clearly articulate the desired outcome. Begin with the end in mind and specify the desired results. If necessary, spell out necessary steps and “signs” of adequate progress, so they’ll be able to catch themselves in a mistake before involving you.
But after describing the non-negotiable aspects of the project, leave the process up to them. This recognizes your employee’s autonomy to work according to their own style.

To Heather Herndon Wright, senior director of alliance relationships at the Women’s Business Enterprise National Council in Dallas, Texas, this is the secret to successful delegation:

I frequently use the analogy, "Here we are, and there is the Emerald City. Build me a yellow brick road. It must be made of brick and they must be yellow, but I don’t mind if it’s curvy, straight, or triple decked, as long as it’s completed on time and meets the requirements I laid out."

2. They must consider the assignment to be related to the organisation’s mission

Basically, you need to convince your direct report that their sacrifice will serve a purpose beyond giving you time to hit the slopes this week. So during your ask, clearly connect the assigned task to business goals. Will it expose your company to new fundraisers, stakeholders, or customers? Will it enable you to recruit and hire the talent you need to improve your department? Will it help your company provide services for others?

Tying their work to a broader mission that they believe in encourages employees to take ownership of their work, according to research by Teresa Amabile and Steve Kramer.

Why is meaning so important? Because when people find meaning in the work, they also feel a sense of ownership. The work means something to them personally. And as Keller describes, when people take ownership of the work, they are more committed to it, more intrinsically motivated, more engaged. And that makes for better performance on all dimensions.

3. The assignment must be consistent with their professional goals

That said, people also respond to more obvious, immediately gratifying motivation. So give your employees tasks that improve their skills and make them more valuable. This sends the message that you’re as equally vested in their advancement and progress as you are in your own work and convenience.

Since nobody considers spreadsheet formatting instrumental to their professional future, achieving personal buy-in isn’t always possible. But if you’ve built a track record for prioritizing your employee’s personal and professional development, they’ll be more likely to cut you some slack when you do give them a thankless task.

4. They must be have the skills and knowledge necessary to complete the assignment

Obviously, you shouldn’t hand off client meetings to the new intern and hope everything works out.

But unless they’re at your side from 9 to 5, your subordinates probably don’t know all of the resources you have in your arsenal. They also won’t automatically know what level of initiative is expected of them or whose inboxes they can spam with questions and requests. Especially if they’re several rungs below you on the organizational ladder, they’ll likely err on the side of being conservative. Without full knowledge of their authority, they’ll fear overstepping their bounds—and keep asking you questions.

Streamline the process as much as possible on the front end by telling them exactly what permissions—and resources—they have, from your valuable contacts to that spreadsheet hack that saves you hours every time. Dr. Scott Williams, a professor at Wright State University’s Raj School of Business, outlines other questions that managers should address upfront:

Can subordinates assign tasks to their peers or other personnel not in their line of authority? What workspace and equipment can subordinates use? Can subordinates have a budget for the project? Can subordinates hire assistants or temporary help? These are the types of questions that should be addressed when delegating.

If this seems too exhaustive, remember that one face-to-face conversation now can save you an annoying email thread later on. Not only will the preparation ease your employee’s burden, but it’ll prevent them from “reverse delegating” the task back to you. Remember that the point of delegation is to create more time for yourself to take on strategic tasks. If you don’t prepare your employee to fully own the project, and you’re forced to assist them, your delegation will result in extra work for you. You’ll find yourself split between your new higher-value projects and the ones you offloaded before.

After You Delegate

after you delegate

Once you've handed off a task, you're all set, right? Not so fast. You'll need to follow up to see how the task was performed.

Inform others of the tasks and projects you've delegated

Separating yourself from a project is hard enough without being pinged every five minutes for permissions to documents or fielding questions from clients wondering why you suddenly disappeared. Avoid logistical headaches for you, your subordinate, and other stakeholders by informing everyone affected by the project that you’ve shifted responsibilities and permissions from yourself to your direct.

If you’ve granted your employee access to confidential documents or databases, let the relevant IT representatives know. If you’ve told your employee to contact outside clients, give them a courtesy heads-up or even better, facilitate a virtual introduction between the two parties. This not only enables your employee to assume their authority, but it lets you fully disengage from the nitty-gritty details of the job.

Set a schedule for checking in

Your project’s out of sight, but it’s not out of mind. Even the most meticulous planning and check-in process can’t completely erase the uncertainty—or the resulting stress of handing over work. But if you interrupt your employees' process, you’ll not only undercut their autonomy, you’ll subtly encourage them to refer problems related the project back to you. This both prevents your employee from testing and improving their skills and keeps you from progressing on higher priority jobs, thus rendering the entire exercise useless. Worse, it forces you to split your resources between the assignment that you outsourced and the extra one that you picked up.

Although you remain responsible for the project’s final outcome, accept that you’ve surrendered control over most of its execution. And be flexible: Because your subordinate has less familiarity with the project than you, they’re unlikely to perform as effortlessly, efficiently, or quickly as you might like.

As a compromise, set up a collaborative Google doc or Slack channel for the project. With real-time progress updates and a clear line of communication, you keep the door open without barging through it every ten seconds. (But if you find yourself refreshing the page every 20 minutes, go cold turkey.) Establish a set routine for checking in and discussing issues, such as a standing weekly meeting. Once you’ve determined a specific day and time to meet, leave it alone.

Conduct a mutual review

Nobody delegates perfectly and, as mentioned above, few managers even do it well. So when you review your employee’s performance, don’t forget to solicit feedback from them as well.

As Amy Gallo writes on The Harvard Business Review Why Aren't You Delegating? - Harvard Business Review,

Give your direct reports permission to call you out when you haven’t delegated something you should. Remember that it’s never easy to give your boss feedback, so be crystal clear that you are open to and expect this kind of input. Also, let them know that they’re responsible for their own growth and if they see a project they want to take on, they should ask for it.

If you completely micromanaged your employee or abandoned them during a critical moment, that knowledge will help avoid those mistakes and improve your working relationship in the future. Beyond that, your openness to criticism will do wonders for your credibility.


Although it eliminates something from your schedule, delegation still requires work. But it's worth the effort! When done right, delegation means increased productivity and progress for everyone on your team. As John C. Maxwell wrote in Developing the Leaders Around You: “If you want to do a few small things right, do them yourself. If you want to do great things and make a big impact, learn to delegate.”

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