Learning How to Delegate as a Leader

Avoid “I’ll Just Do This Myself” and Other Management Mistakes

“The worst delegators are those who are afraid,” says Lorraine A. Moore, whose Accelerate Success Group specializes in leadership resilience and business transformation.

The most common fears, she points out, are near-opposites of one another.

Learn to Let Go

All of the attitudes expressed here have one thing in common: the manager isn’t willing to let go. Unless you work alone, at some point you have to trust other people—and, often, that means demonstrating trust before the other person “earned it.”

If you try to control everything, ultimately you control nothing.

Moore cites an example that illustrates the debacles that can ensue. A CEO of a manufacturing company had prior experience in leading global, wide-scale engineering projects, she says. The new CEO did not fully delegate the overall project management for large projects. Instead, he prepared his own project reporting, he talked to the project staff without senior project managers present, he regularly asked for updates, and so on. Two very experienced project managers resigned in frustration. The projects were negatively impacted by this turnover.

Since the CEO’s time was taken up with the details, Moore says, he did not spend sufficient time on other responsibilities, such as dealing with regulatory risks or getting input from the CIO. He neglected key customers, leaving those meetings to his business development team and regional vice presidents. The CEO had a wake-up call when one of the company’s largest customers canceled, citing in part its perceived lack of relationship with and trust in the CEO.

“We worked together for several months,” says Moore. “During that time we identified which items he had overall accountability for, and which he should delegate to responsible leaders. We ensured that each of his direct reports were given clearly defined goals and metrics so they would know what was expected and how performance would be measured.” Doing so also enabled the CEO to gain confidence that his direct reports knew what success looked like, with input from regular meetings in which they discussed goals, metrics, and results. “We also scheduled meetings with all key customers so that he developed relationships with existing and prospective clients,” she adds. “The CEO agreed to not respond to staff issues from people who did not report directly to him until he had first spoken to his direct report.”

Realize You Aren’t the Only One Who Can Do the Job Properly

One emotional reason it’s hard to let go is the inner certainty that the team member won’t do the job the same way you would. That’s true. You have to come to terms with the idea that “different from how I would do it” is not the same as “wrong.”

“We all have our preferred way of doing things, but they are exactly that: our way,” says Bill Sanders, managing director of Roebling Strauss, an operational strategy consultancy. “Getting things done doesn’t disqualify a different way if it produces the same result.” Focus on the result. “It requires much more energy and time to evaluate how someone does a job as opposed to the quality of the work they produce,” Sanders adds.

“Accept a new ‘perfect,’” advises Moore. “If it does not look exactly like it would if you completed it, think carefully: does it matter?”

When you’re new to managing, it certainly seems as though it matters. “When I was first in business, I just yelled,” says Francine Hardaway, advisor to entrepreneurs through Stealthmode Partners. “Most of the startups we deal with face this problem and create turnover in staff by being too critical. As a leader, it is better to create a culture of overall excellence and make people reach for it than to belittle them for not being you. Even you are not always you.”

There’s another side effect of a manager holding the reins too tightly: you reduce the team members’ capacity to add their own selves to the project vision, to point at some piece of it and say, “That’s mine! I helped make that happen!”

You want everyone to buy into the project’s mission. To succeed, you need to let them contribute to the vision, not follow it blindly due to a “because I said so” decree.

This is an important lesson, especially for managers and CEOs whose organizations grew rapidly after beginning with a few ideas scribbled on the back of a napkin. You might start a company with a vision in your head, and then hire people you hope can make your vision happen. If the staff doesn’t exactly match your image of success, you see it, and them, as a failure.

“There are two reasons CEOs do anything: vision and/or pain,” says Kisgen. “When they have a clear vision, they make decisions that help them reach it. When there is pain, they problem-solve to alleviate it.”

Imagine a CEO who expects everything to be done his way, and meddles in the staff’s work even when they have more expertise in their domain (e.g., web design or trade show best practices). The CEO should step back and contemplate the company’s vision. “Does he always want to be the main guy running everything? Or does he want to evolve into a true visionary with a talented team that helps him reach his vision?” asks Kisgen. “Does he want to scale his business or constantly be knee-deep in the weeds of what is going on?”

If the CEO wants to always be “the guy” doing everything, then he will never retain great talent, says Kisgen. “Unless he wants to endure the pain of constant staff turnover, he needs to either hire lower-level talent or learn how to let go in order to retain higher-level talent.”

Neither choice is a bad decision, Kisgen points out. But it is a critical decision every business owner (and team lead) should make: what
kind of company does he want to build? “Some owners want to be small mom-and-pop shops that afford a nice living,” says Kisgen. “They like calling all the shots and usually aren’t visionary enough to scale. Top talent will not stay long in businesses like this. Other owners want to build an empire. And the only way to do this is to attract top talent: get them to buy into the mission, vision, and values of the company—and then get out of their way so they can execute on what they do best.”

Understand That Delegating Is the Opposite of Micromanaging

The worst form of delegation is micromanagement: when the manager joggles the elbows of the team member and tries to control everything.

Delegating should not involve you explaining every step to the person. If it does, then you are actually training them. And while training is necessary and valuable, it’s really supposed to happen only once.

For example, one manager assigned an employee to write a report, then described in minute detail how to do every single step. “He went into so much detail that the telling took longer than the task itself,” Macdonald says. This frustrated the employee, too. By going into so much detail, the manager implied that the person wasn’t capable of doing the task unsupervised.

“Micromanaging is worse than not managing at all,” says Stealthmode’s Hardaway. She knows this because in her youth, she admits, “I was a micromanager. I made every employee miserable. They left, and either went to work for someone who wasn’t such a bitch or they became my competition.”

Micromanagement is readily recognized by employees, but most micromanagers don’t think of themselves as micromanagers. The manager sees the actions as a mark of seriousness and doing the job right, often operating with a belief that, “If you want something done well, you’ve got to do it yourself.”

But you weren’t hired to do that task yourself. Someone else was. The secretary for a middle school’s music department complains about one teacher who wants to do everything himself.

“I have gone from feeling like a treasured part of the music staff to an extra person,” the secretary says. How long do you think that person will stick around?

Micromanaging is giving orders without giving up control, whether the practice is motivated by pride, ego, insecurity, or fear. Even if the well-meant intention is to make sure everything is done right, it has a terrible effect on the team members, ranging from one’s own burnout to employees who give up any pretense of taking initiative, since they know the manager will override them anyway.

Delegating is the opposite of micromanaging, points out Miki, an executive coach. Delegating is based on trust. With micromanagement, workers bring their knowledge, skills, and experience to the organization and see it not being used. Or they have amazing potential, but the micromanager fails to reward it with training and promotion opportunities.

Recalibrate Your Mindset: Let Others Do the Work

Not delegating hurts the manager, too. “Leaders who do not delegate become stuck,” says Moore. “They are not readily promoted, as they do not develop successors; they do not learn how to develop and mentor others; and they do not accomplish as much as those who delegate.”

When delegation is done well, it helps develop the employee (who gains skills, confidence, or both), and it also eases pressure on the manager.

Sarah, a director of tech operations, has been managing five team members. Among the lessons she’s learned is to stop feeling guilty about giving out the less desirable jobs. “I learned to give out more work so I can focus on boss stuff (budget, forward-thinking projects, etc.) that might get me further in my career,” she says.

No matter how you get there, eventually, you know it’s time to delegate when you can no longer handle the work. Either there’s too much for you to do, or getting it done becomes too complicated.

Which leads us to actually assigning the work to your team members.

Define the Task

Once you’ve given yourself permission to “let go” and to allow other people to help, the question of “What do I delegate?” usually isn’t that difficult. You probably have a strong sense of what needs to be done. You know which tasks make you feel inept, overwhelm you with their complexity, or simply never get done.

One useful way to categorize tasks is the Eisenhower Matrix. US President Dwight Eisenhower was well known for his organizational skills, which he based on a simple strategy. Everything falls into four buckets:

Urgent and important

Do these tasks immediately.

Important, but not urgent

Schedule these tasks to do later.

Urgent, but not important

Delegate these tasks to someone else.

Neither urgent nor important

Eliminate these tasks.

You can use this matrix to clarify where to focus your energies. If you have urgent “not important” tasks that you never seem to keep up with, bring in someone to take care of it.

Also consider how much knowledge a task requires. If you lack the skills for an urgent task (whether that’s coping with a legal matter or adding ecommerce functionality to a website), find an expert for whom this work is appropriate—and who probably can do it faster and better than you would.

In general, if you can delegate it, you should delegate it. “We are naturally drawn toward our strengths,” Kisgen says. “However, almost every position has tasks or projects that are out of alignment with what we do best.” Learn to identify the people who possess the talent that you lack, and assign them these tasks or projects. “This is incredibly valuable if the goal is to scale a business,” says Kisgen. “It also ensures that I am working on the highest-level projects that bring the greatest returns for my time.”

Often, though, managers wait until an “urgent” task has gone critical before they delegate the work—which can cause even more problems.

“For most people, the first hire is someone who can do something they’re weak at,” says Stealthmode’s Hardaway. “My first hire was a bookkeeper. Many technical founders hire a marketing person.”

That first hire is critical, though often wrong. “It’s probably a function of lack of funding,” Hardaway says. “You hire too late, you’re already overburdened, and then you don’t have the money to hire experienced people, so you hire a friend or a relative. It almost never works out.”

There are some things you should never delegate, however. According to Bernard Marr, CEO of the Advanced Performance Institute, handing off these tasks or roles removes you from your team, opens you up for criticism, and ultimately paints you in a bad light. In short: don’t assign to someone else the “vision stuff” and team building you’re expected to supply.

The never-delegate-these list includes:

• Core functions or responsibilities

• Praise and discipline

• Team building and talent nurturing

• Fundraising and investor relations

• Mission, vision, and company culture

• Crisis management

• Traditions and etiquette

Whatever it is you choose to delegate, be very clear in your mind about the task and its scope. “A task can be delegated, but responsibility for the task or delegated authority cannot,” says Macdonald.

Assess Your Team

After you identify which tasks to assign, the next step is to find someone to give them to. For simple tasks, maybe you can get away with choosing by looking around the office and pouncing on whoever appears to have time on his hands.

But for most business situations, it behooves you to make a conscious choice rather than dumping a to-do item on a random victim. Understanding the team members’ knowledge, skill, and experience lets you factor into the “Now who gets this?” choice the amount of guidance or coaching the individual needs. For example, when time is critical (yours or the project’s), choose a team member who’s done this task before; if the schedule has more slack, view it as an opportunity to train someone in a new-to-her skill.

In some ways, delegation works the same way without regard to the team you’re leading. In every case, it’s important to be clear about what needs to be done, for instance. But there are critical differences in the manner in which you delegate—and manage, in general—based on the team’s makeup and the organization as a whole.

For instance, the manager of a fast food restaurant where workers are paid minimum wage probably doesn’t expect the staff to buy into a corporate vision or to invest themselves in an attitude of personal responsibility for the company’s success. The team members generally are unskilled (at least in the efficiencies of burger flipping), so assigning them a new task requires training, explanatory hand holding, and dedicated oversight. Nobody, least of all the burger flipper, is surprised or dismayed when you watch him like a (hungry) hawk.

But when you hire industry professionals, you and they begin with different assumptions about the workers’ existing knowledge. There are plenty of variations therein—a marketing intern doesn’t know as much as someone with five years of experience—but you sure don’t hover over the professional watching her dot every i and cross every t. Not twice, anyway.

So before you begin to consider to which individual you’ll assign a task, think about the makeup of your team and the manner in which that delegation should be given. That’s part of your decision process, particularly since people either behave according to how they are treated or they resent being treated inappropriately (and then they leave).

You can make that assessment based on a seat-of-the-pants judgment, and many people do. However, some management experts have worked out various scales to help understand team members’ needs and expectations. And naturally, when managers’ and workers’ expectations regularly are met, everyone is happier.

For example, Jurgen Appelo, author of Management 3.0: Leading Agile Developers, Developing Agile Leaders (Addison-Wesley Professional, 2010) organizes managerial delegation into seven levels to enable and grow trust:

Tell

The manager makes the decision. She may explain her motivation, or perhaps not. A discussion about it is neither desired nor assumed.

Sell

The manager makes the decision, and tries to convince the other people that it was the right choice. She helps them feel involved.

Consult

The manager asks for input first, which she takes into consideration before making a decision. That decision respects people’s opinions, but it’s the manager’s call.

Agree

The manager enters into a discussion with everyone involved. The goal is to reach consensus as a group.

Advise

The manager offers opinions and hopes the team listens to her wise words. But it’s the team members’ decision, not hers.

Inquire

The manager leaves the decision to the team, and afterward asks them to convince her of the wisdom of their decision.

Delegate

The manager leaves the decision up to the team. They are the experts and professionals with in-depth knowledge, so they have the decision power. The manager waits for team members to update her about the decision and the reasons why.

Thus, at one end of the scale, if you are the manager of a fast food joint, it’s appropriate to tell the new worker what to do, with a lot of persnickety detail and feedback. A teenage burger flipper knows he doesn’t know how to do the task the right way, and he expects to be taught. In fact, if the manager didn’t show him how to do the job, the worker would be upset about the lack of training.

Yet, at the other extreme, imagine a manufacturing company CEO who hires a web developer with 15 years of experience. The “tell” methodology doesn’t work at all. If the CEO instructs the developer about which algorithms to use and hovers behind her while she writes code, the developer would be upset—particularly if both the CEO and developer are aware that the CEO has never written a line of code.

But not every team member is truly an expert—even when he thinks he is. The manager is still responsible for guiding the staff to get the work done just right.

For example, Story teaches “The Five Levels of High Impact Delegation,” in which the default state is Level 3 until the person can be trusted to move to a higher level of delegation. (It also dovetails nicely with Appelo’s delegation levels.) Here’s the worker’s viewpoint at each level:

Level 1: Wait until told

There’s no worker growth and development because the manager is doing all of the thinking. The manager is responsible for determining what’s next.

Level 2: Ask what’s next

The manager still has the responsibility to determine what’s next. A worker who finishes a task won’t go on to the next thing until he asks for instruction.

Level 3: Recommend a course of action

Everything changes at this level. The worker now has the responsibility for thinking and recommending a course of action. The manager learns how the worker thinks and can steer and guide using questions, but never directions. (Directions are given at Levels 1 and 2 only.)

Level 4: Do it and report immediately

More responsibility is given to the worker, but it isn’t unlimited. The manager must be informed every step of the way.

Level 5: Do it and report routinely

This is full high-impact delegation. When there is full trust, the worker is completely responsible and reports to the manager at predetermined intervals—weekly, monthly, or only when necessary.

“A person may be at different levels relative to different areas of responsibility,” cautions Story.

Empower Team Members

The premise behind these delegation levels is that the manager aims to help the team member grow, both in technical skills (such as choosing a programming algorithm) and business expertise (including confidence in making one’s own choices or himself learning to delegate). The goal is to create a collaborative environment in which everyone joyously feels responsible for the results.

“In such an environment, delegation is not really needed!” says Steve Ray, senior associate at Groupwork Institute of Australia. “Think about it: if you feel responsible for achieving great things in an organization, you want to see it through, to make sure it gets done! That’s the environment a manager needs to create: one where people feel responsible for the work (or parts of it) so the discussion shifts from, ‘I want you to do this work’ to ‘What can I do to help you do your work better?’”

Collaborative managers rarely need to tell people to do anything, says Ray. Instead, these managers ask lots of questions.

“When people ask these managers for help,” he says, “the managers are ready to support them. But when people ask, ‘How should I do this?’ the manager keeps asking questions, such as ‘Where have you got to so far? You’re the expert, but I’m happy to be a pair of impartial eyes that may see something you haven’t yet.’”

That’s a great goal, but it assumes that both manager and team member are working on the same expectations, particularly in regard to the amount of guidance needed. For instance, it’d be unwise (and likely offensive) for a new orchestra leader to tell someone who’s been playing violin professionally for 20 years how to tune the instrument. That’d be seen as micromanagement, rightfully so. But if you’re leading a junior high orchestra, the still-feeling-helpless student would expect explicit suggestions.

Absolutely, you should work to empower the team so that they share the project’s goals. It’s better (and more fun!) to manage a collaborative team than one that requires orders. But, as Story suggests, start by recommending and adjust as necessary. It’s just as wrong to assume that people are equipped to be self-starters as it is to assume they need to be told every detail.

For example, one software engineer responded to a query about effective delegation by saying, “Don’t delegate. Delegation is antithetical to effective management. Delegation is a push system and works very poorly. It relies on an uninformed person or system to decide when someone or something downstream should work on something. This results in a lack of flow, bottlenecks, multitasking, and many other issues.”

All of which is true—except it has its own possibly mistaken assumptions. If the team doesn’t feel as though they have the power, knowledge, and authority to make good decisions, the manager saying, “You figure it out! It’s your job!” causes resentment, not heightened self-sufficiency. A well-meant intention to encourage the team member to think for himself may be perceived as, “She doesn’t even care what I do!”

That’s one reason executive coach Miki gives all employees, including senior staff, a single, written page that delineates the scope of their responsibility and authority within the company. It defines what the individual is supposed to do; what authority he has to get it done; from whom he needs approval or agreement; and the parameters within which to do it.

This is drawn as a box or bulls-eye diagram, because it shows the employee’s scope of responsibility.

“Inside the box is the employee’s turf; she can do anything she wants to do, including make mistakes,” Miki says. “Mistakes are key to growth.”

The manager must respect the perimeter. “The manager can act inside the box only if the employee requests it,” Miki says. “By stepping in, the manager signals that he doesn’t believe the employee can handle the situation. At that point the employee will assume that (whatever) is no longer her responsibility. The number and severity of mistakes allowed are up to the manager. It is better for the person to realize the error and correct it, or ask for assistance, than for the manager to point it out.”

At a junior level, that process works relatively smoothly. However, the more senior the employee, the bigger impact mistakes have on the company. Take that into account when deciding whether and when to intervene.

By providing an inviolate box for each employee, no matter their function, the company can speed up individual growth and enhance productivity, says Miki.

“The box is discussed, defined, and agreed upon by the manager and the individual,” says Miki. “The box increases or decreases in size as the employee’s skills and abilities change. It is better to make the initial box a bit too large and then shrink it as needed; however, all changes should be discussed and agreed upon. Changes can be initiated by the individual as well as by the manager.”

Choose the Right Person for the Job

Quite often, the team members’ existing responsibilities make it clear who should be given a task. The marketing manager gives SEO-related work to the SEO specialist and assigns a Twitter chat to the social media pro. Or that’s the case most of the time.

Even when a manager knows the team members’ strengths and weaknesses, there are still choices to make. “Delegation is not a one-size-fits-all approach,” says executive coach Dooley. “The level of detail, context, and monitoring required has to be tailor-made for the person you are delegating to. Competence, confidence, previous experience, contextual understanding, networks, and even personality all have to be taken into account to effectively delegate a task or project to a specific individual.”

Sarah often needs to choose which person on her team to tap. When she delegates, she looks first at the timeline. If it needs to be done quickly, she gives the task to an expert. If the priority is lower, she uses the opportunity for training, and assigns to a lesser expert. She also considers, “What’s going on with my staff? Are they bored? Need more sense of satisfaction? I need to give them something juicy.” Sarah uses Agile retrospectives to determine what would fire up the team, sometimes pulling a lower-priority but higher-satisfaction item from the backlog and giving it to a pair of programmers to tackle.

Sometimes, it’s best to assign a task to the person who wants it. “You can either choose the person with the best strengths for the task, or choose the person who wants to do it the most,” says Stealthmode’s Hardaway. “I always try to find the person who volunteers to do a task, because that would motivate the person to extend herself again and again.”

That’s particularly so when you’re offloading work that you don’t want to do personally. “Pick someone who is better at or likes a particular type of work as much or, ideally, even more than you,” says Accelerate Success Group’s Moore. “This could be creating a presentation, analyzing data, completing research, creating a spreadsheet, calling customers, or writing a speech.”

If you are lucky enough to work with a collaborative team, you can let its members choose tasks by making the work visible. During team meetings, prioritize work by stack ranking, usually sorted by most to least valuable; invite the team members to pull work from the top of the list. Get yourself out of their way, except to ask how you can remove obstacles from their path, so they can get work done.

But even that has its challenges, because some team members would never take on a task that they don’t know how to do—and it keeps them from stretching themselves. One of your managerial responsibilities is to help your team members grow, after all.

So before you assign a task to the usual suspects, offer subordinates the opportunity to spend some of their time doing something different. Be careful that you don’t surprise the usual team member by giving away “his” work, or he will wonder how he offended you. For example, in your one-on-one meeting, point out that last week he said he was overloaded, so you are thinking of giving this additional task to another team member who could stand to learn about this related area.

“Explaining the purpose of the delegation can reinforce that this is part of the employee’s skill development plan or perhaps acknowledge the expertise of a team member,” says Macdonald. If you miss this step, the team members may feel they are being taken advantage of, or that their manager is dumping her work onto them.

And keep in mind that not everybody is interested in a new challenge, so always make it an offer. Not everyone is ready for a next step, or maybe the current workload is plenty. And some are terrified when they are directed to the deep end of the pool and told to dive in. How much management oversight and direction are you ready to provide?

“I was coaching the CFO at a private equity firm who had delegated a significant quarterly financial report to his second-in-charge,” says Addam Marcotte, VP of Operations and Organization Development for FMG Leading. “This person had the interest and willingness to take on the task, but had never done it before. However, the executive initially overlooked this, assuming that the employee would ‘figure it out,’ when in reality, it terrified the employee and she froze.”

The employee didn’t want to tell her boss she didn’t know how to do the task because she was afraid she never would be asked again. Although the executive was more than willing to teach the employee, he never checked it out before formally delegating the task.

“The result was a poorly executed report that came from a failed attempt at Googling ‘how to create quarterly financial reports’ and an executive who felt he couldn’t trust his employee to deliver,” says Marcotte.

As Marcotte points out, the situation could have been avoided with a brief conversation before the executive handed off the baton. Even though the boss had delegated other reports to this employee, he didn’t realize that each situation was unique based on her previous experience and skill set.

Delegate Objectives, Not Procedures

With some “just follow orders” teams, it’s OK to tell people what to do without asking them to buy into the bigger picture. For instance, once you train those burger flippers in the proper hamburger-making procedures, delegation doesn’t require much more than, “Barbara, you’re working the lunch shift on Tuesday.”

For nearly everybody else—anyone who aspires to leadership—it behooves both manager and team to understand the short- and long-term goals. Find people who hold themselves accountable, then give them a clear goal and broad discretion in how to achieve it.

Explain why the job is important, says leadership coach Karen Schmidt. “When people understand where their tasks fit into the bigger picture, they start to feel their work matters,” she says. It also helps them make better decisions and recognize when it’s time to raise issues with the manager.

That doesn’t need to be a big mission statement; sharing the context helps even the lowest-ranking employee feel he is contributing. So, Schmidt suggests, instead of saying, “Can you photocopy this?” tell the team member, “We need this photocopied to help us win an important client contract.”

Explaining why makes sense even with employees who are just climbing onto the first rung of the career ladder. Case in point: Kimberly Davis, who teaches leadership programs, has worked with an international restaurant chain. The company invested a tremendous amount of time and resources to identify the best way for servers to approach restaurant guests when they’re first seated; it developed detailed scripts for servers to follow. “When new servers are trained, they are given the scripts to follow, but oftentimes they don’t use them,” says Davis. “They think the scripts sound ‘canned’ and feel uncomfortable saying them, so they don’t. Their results suffer and the restaurant’s results suffer.” However, if a thoughtful general manager takes the time to explain the reasoning behind the script from a customer’s standpoint—the why—the servers embrace the greeting ritual and make it their own. “The server is set up for success, the guest is happy, and the restaurant tends to be more successful,” says Davis.

Talk in terms of results rather than instructions, advises Schmidt.

“Show them a sample of a finished item if it is a task involving repetition, or refer to a previous job that is similar,” she says. The results include some kind of metric for “done.” Results could be about quality, wastage, appearance, or how people will feel, she says.

When we delegate methods, we remain responsible, adds Story. When we delegate results, we allow others to become responsible.

“Leaders of people delegate results,” he says. “Managers of people delegate methods.”

In Behind the Cloud (Jossey-Bass, 2009), Salesforce.com’s CEO Marc Benioff describes his planning process, which applies to any new initiative and guides existing ones. V2MOM represents vision, values, methods, obstacles, and metrics:

Vision

What do you want? What’s the big picture?

Values

What’s important about it? How does it help the company?

Methods

How do you get it? What specific tactics lead to the desired goals?

Obstacles

What prevents you from getting it? What works against success?

Measures

How do you know when you succeed? What are the key performance indicators (KPIs)?

V2MOM is used to align the entire organization, from the company mission to the projects and tasks and individuals. If a team member knows the company and project vision, it’s a lot easier to see where her task du jour fits in and gives her permission to innovate in accordance with the objectives.

Sharing the goal is more than a one-way communication. It helps the worker recognize how a process can be improved or responded to. For example, system administrator David is frustrated when he isn’t empowered to alter a process to better achieve the goals. He might be (and was!) told, “I need Classroom 5 wired for audiovisual components ASAP. Call everyone in Networking until someone comes here and does it.” But David knows the task doesn’t truly need to be done for three days because he’s familiar with the project. “Harassing the networking department staff (and trying to circumvent their support/request procedure) does more harm than good both for the task and the long-term relationship,” he points out. It would be far better for the manager to explain what needs to be in place, when, and why—particularly if there truly is a reason it needs to be set up sooner than the three days David assumes.

Provide Complete Job Instructions

Any delegation needs the basic facts, what journalists call the Five Ws and One H: who, when, where, what, why, and how. We’ve already addressed the importance of emphasizing “why” in any task assignment, and if you work with capable team members, they already know “how.” But that doesn’t mean you should ignore the other Ws!

Specify the task’s objective, the scope of work, the lines of authority and accountability, and the deadline for the project, says Fred Schebesta, CEO of a financial comparison website. Don’t give a vague arm wave. “The consequences of not taking the time to delegate properly can be miscommunication, a missed deadline, lower staff morale, and lower productivity,” points out Schebesta.

Clearly communicate your desired results with metrics: how many, by when, and so on, says Accelerate Success Group’s Moore. If you define the result, you don’t need to worry so much about how the team member approaches the task. “Let the person shine using their own methods that may be faster, quicker, easier, or more effective than yours,” says Moore.

It’s the manager’s job to set up the team member for success. So in your instructions, clearly articulate expectations, deliverables, and timeframes. Also ensure that in delegating the task you give the team member appropriate resources, information, and training—particularly when he is new to the topic or to working with you.

Commonly, a critical criterion is timing: this task must be done by the end of the day, or the team has until year end to complete the project. But don’t just give people a deadline, says Schmidt; that is an
easy way to create conflict, particularly when the team members have a better understanding of how long it takes to do the job.

“Instead, get their input on a realistic timeframe,” she says. “Take into account other work they have and leave room for the unexpected. It is always better to set a longer deadline and encourage them to finish early than to rush the process.”

Clarify Expectations

Establish your workflow when you make the assignment, such as measurable milestones. “Let your people know how much detail you will need as they go along,” says Rick Maurer, author of Beyond the Wall of Resistance (Bard Press, 1996) and an advisor to leaders in large organizations on ways to build support for change and other new ideas. “Some leaders want to be in the loop every step of the way, while others prefer minimal updates. Make sure these leaders know what you want.”

Make sure the team member understands the assignment. Don’t ask, “Do you have any questions?” suggests Mark Goulston, author of Talking to Crazy: How to Deal with the Irrational and Impossible People in Your Life (Amacom, 2015). “Instead, say, ‘To make sure I have been clear, please tell me exactly what I told you to do, by when, and why it’s important to what we are trying to accomplish.’” Doing so shows respect to the individual, says Goulston, instead of treating him as only a function.

That conversation might include an explanation of why you asked this team member to take on the project. One of Davis’s clients was scheduled to give a presentation to the C-suite, but he was pressed for time, so he decided to assign it to a smart, capable direct report. The manager saw this as an opportunity to give the team member exposure to the senior team so she would be set up for future growth opportunities. But he failed to tell her so.

“The presentation required a great deal of additional work,” says Davis. The team member wasn’t very confident in herself, and she spent days agonizing over the content, during which she grew to resent being chosen. “During her next one-on-one with my client, after she survived the presentation, he told her, ‘I’m so proud of you! I knew you would do a great job, which was why I chose you to do this. I wanted my boss to see how great you are!’”

Her response came as a total surprise to the manager. She told him, “You’ve got to be kidding me! I thought you were trying to sabotage me! I wish you had told me that. I was ready to quit!” Had the manager told her why he chose her for the presentation, says Davis, he would have bridged her confidence, transformed her entire experience, and set her up for success. By not doing so, he almost lost a valuable employee.

Learn to tap into what might make someone want to do the task at hand, says Davis. What might they learn from doing the delegated task? How might it impact their ability to get their job done? Their visibility within an organization? Why might the delegated task matter to the manager, to the team, to the organization, or to the clients? Why should the employee care about the delegated task? “Taking a few minutes to think about these things and communicating them will make all the difference in a manager’s results,” says Davis.

Allocate the Necessary Resources

What does the employee need to meet the targets you set? Some part of the answer should come from the team member, but if you have more experience with the knowledge domain, you may be in a better position to guide the conversation.

Maurer suggests that managers consider these issues:

People

Who do they need to be successful? Perhaps the team members need access to an engineer in another location, or a stakeholder whose time is limited. How much of that engineer’s time is available? How can you, as manager, arrange to get the individual’s attention?

Money

What’s the budget for their portion of the project? Is that enough? If not, what has to happen to ensure adequate funding? What happens to the project if it can’t be acquired?

Access to you

Discuss the best ways for you to stay in touch. Tell them the best way to contact you when they have an urgent question.

As part of the delegation process, give the team members workable parameters. “Let them know about what they can and can’t do,” says Schmidt. For example: how much money they can spend, who can assist them, which suppliers they should use (or refrain from using), equipment they can access, or commitments they can make on behalf of the organization. Decide how to do the job within those parameters.

Another resource is time. Delegating a task to a subordinate who is already overloaded and serving many masters may put him in the position of being unable to deliver to someone else, points out Goulston. Disappointing someone else can cause undue stress to that individual, not to mention other people in the organization. Suggests Goulston, “To counter that, ask your subordinate, ‘Is there anyone for whom you’re doing something whom I can call, to free up some of your time to get this done? I will work things out with them.’ Doing this will make you a legend to your subordinates, and they will love you.”

Communicate and Support

Quite often, problems do not result from the act of delegation done poorly. It’s that managers fail to pay attention to the task’s progress, and they miss danger signs.

It’s easy to see how overworked managers can delegate and then assume everything’s taken care of. Startup founders often turn a task over to someone and don’t follow up to see if it is done correctly, or done at all, says Stealthmode’s Hardaway. In one case, she says, “The company grew so quickly that tasks were delegated to people who didn’t have insurance certifications, and the founder even found a way to try to get around compliance.”

Doing so hurts the project, sure, but it also keeps the team from coalescing into a more functional group. One benefit of deliberate follow-up is that it creates trust between the manager and staff.

“I would delegate a task and monitor how effectively it was done,” says serial entrepreneur Kisgen. “Then I would keep delegating tasks and evaluating the results until a consistent pattern was established. Once proper execution was proven, I would continue to let go. Eventually, with the right people in the right seats, I would know the outcome before I delegated the task.”

This approach might help you avoid the situation Katherine encountered when she delegated a task to a young intern and then got busy with her own work. “Turns out that he mostly played video games. It was not the normal employee behavior, so I was unprepared and didn’t have adequate checks,” she sighs, 20 years later.

One step in the delegation process—during the conversation when you say, “You’re in charge of getting this done”—is to agree on a time for a check-in. “That way you can answer any questions or identify any mistakes, without the feeling you are checking up on them,” says Schmidt. “‘Call me if you have any issues’ is often said in such a way that the person feels like he failed if he needs to.”

You can do a formal check-in for each project (Tuesday is Project A, and Wednesday is Project B) if it’s complex enough. In many cases, you can solicit status updates in the course of established team meetings (such as a daily Scrum) and one-on-one meetings. That’s also the right time for you to share information downstream when it affects the work to be done, such as when funding is pulled, the schedule is adjusted, or you decide after the fact that the task should be done another way (one hopes it is for a good reason).

Ask questions that don’t have yes-or-no answers. For instance, don’t ask, “How’s that product analysis going?” (“Just fine!” Even though I haven’t opened the box…) Instead, ask, “Did you encounter any problems with installing the software?” (“Um, well, actually…”)

The project check-ins are bound to reveal problems. That’s fine. It’s why you’re doing them!

Encourage an attitude (in yourself and the team) of “fail fast,” so you can course-correct early, says Belen Tokarski, senior VP of Operations at insurance company Insureon. That’s not to suggest it’s easy. “I have to let go early enough to allow them to fail,” she says. “If I stay on top of them too much, then it ends up being my project and not theirs. When that happens, they never learn and get better.”

Sometimes, you find that the staff member simply needs a bit of managerial support. “Your job is to ‘provide air cover’ if they encounter roadblocks from other senior leaders,” says Maurer.

In other situations, it’s a stumble on the part of the team member. That calls for actual management on your part.

For example, business advisor Karl Sakas has sometimes assumed that people understand how their work impacts others. “They don’t have my bigger-picture perspective on how everything fits together,” he says. “When they’ve missed deadlines, it’s delayed others’ work. Now, I make sure to highlight when one deliverable impacts another deliverable. I also preschedule check-ins midway through the assignment; it’s not micromanagement if it’s a prescheduled check-in.”

Make It Easy to Ask for Help

Maurer spoke with an engineer who described a major enterprise resource planning (ERP) initiative that was sure to fail. “They had spent months and a lot of money on the project, and most people knew that it wouldn’t work,” Maurer says. “I asked if the leaders knew. He said no. It was too risky to tell them the truth.”

When someone asks for help or shares a problem, appreciate it. It’s a sign that the team member wants to do the job right and relies on you for guidance. Ideally, the team member proposes a solution (“I was thinking we could rewrite that module…”) instead of asking for more instructions (“What do I do?! I’m lost!”). But you should expect to encounter all sorts of feedback requests.

In fact, that’s far better than the alternative. Many people are afraid to talk back, to question, and to ask for help, particularly if they’ve had bad experiences in the past.

Make it safe for the team member to tell you about issues, or he is apt to wait until the problem blows up. Goulston suggests that part of the task delegation process is to say explicitly when and how you want to hear about progress or lack thereof. For example, say, “The shortest distance between two points and between what I told you and you’re doing it is a straight line, but that goes against human nature. What that means is that it is normal and human for you to slightly veer off course, the same way as a plane does when flying to its destination. When that happens, the sooner you bring it to my attention, the sooner we can make a course correction, and the better for you and me and our group. If you’re feeling too embarrassed or uptight because you hit a bump, you’ll just delay bringing it to my attention and that will make matters worse.” He stresses asking for buy-in explicitly, adding, “So can I count on you to commit to letting me (or someone else in the group) know when you’ve hit a bump or veered off course and you’re unable to get back on course using everything you know or have?”

This is also a good time to ask the team member the best way for you to provide feedback, particularly when it’s critical. “To seal the deal and make future confrontations easier when your subordinate has not followed through, focus on the future that he or she has not messed up yet,” says Goulston. This avoids or lessens awkward confrontations after someone hasn’t followed through.

To do this, Goulston suggests, say, “In the event that for any reason you are not able to do what I asked and you have agreed to: how do you want me to be with you if my sole goal is not to be critical or punitive, but to get you back on track as soon as possible? For instance, should I tell you politely, should I yell at you to get your attention, should I do it in person? Or what other way works best for you?” Most people do know how they respond to criticism, but even when they don’t, they appreciate the sensitivity of a manager trying to work with them.

After they tell you how to best confront them, Goulston suggests, say, “This is too important for me to not get exactly what you told me, so what I heard you say is (repeat exactly what they said). Is that correct?” Then wait for them to tweak it or to confirm that you got it right, which he says deepens their commitment. “The best part of this approach is that you will be able to bring up this conversation when you need to confront your subordinate by saying, ‘If you’ll remember, we had a conversation where you told me the best way to bring something up to you when you haven’t followed through is (what they said), which I need to do now, because I need to get you back on track.’”

That benefits your own comfort level with giving negative feedback, too. “Having a way to confront people will cause you to do it sooner rather than delaying,” he says.

Effective and honest feedback means that managers need to develop good listening skills. “This includes what we call the ‘three curiosity skills’ of being present to absorb what is said in the dialogue; listening with an open, nonjudging approach, focused on what the person is saying about how they will complete the delegated work; and asking open questions to gain clarity and support the other person so there is mutual understanding about the work to be undertaken,” says executive coach Kathy Taberner, coauthor of The Power of Curiosity: How to Have Real Conversations That Create Collaboration, Innovation, and Understanding (Morgan James, 2015). That lets the manager feel more comfortable about relinquishing control and trusting the worker. “This approach shifts the responsibility and accountability to the delegatee, supports their learning, and messages that the delegator believes in them and their abilities,” she says, “all of which supports employee development, resilience, and engagement, as it messages that the delegator believes in the delegatee.”

Overcome the Insecurity of Ignorance

There’s a certain kind of altitude when a manager delegates tasks to people in the same knowledge domain. A programming team lead almost certainly spent some years as a programmer before she was promoted into management. She understands what junior team members are going through, including the questions a programmer hasn’t thought to ask yet. And because team members start with an assumption that the boss knows more than they do, it is easier to give and get feedback. At a minimum, everyone shares a common language to describe problems and solutions.

It’s not always that easy.

One thorny issue is how to supervise someone who knows more about the topic than you do. Perhaps you’re a hardware expert and you hired a software consultant. Maybe you’re the CEO of a manufacturing business, and you brought in a social media director. Or you’re a marketing expert who needs someone on the software development team to add just one tiny little feature to the company website; that should be easy, right?

It’s really difficult to assign tasks to people who are more expert than you are—in part because you have to trust that they do know more than you do, and you feel powerless to judge their expertise. If you personally have never written a line of code, you honestly don’t know if the web developer you hired has the skill to do the job. (Maybe that one little thing is easy; maybe it isn’t. How do you know?) He may say he is an accomplished developer—he may even believe it—but it’s difficult to trust that you’ll get the result you want when you aren’t even sure how to articulate your needs. The all-too-common result is micromanagement, in which you oversee every little thing in order to measure the results against your (often unspoken) internal vision.

That’s the wrong way to go about it, in part because it starts with the assumption that your inexpert vision is better than what your true subject matter expert can make possible. (There’s an entire blog collecting “client from hell” experiences illustrating what can go wrong.)

Instead, refer to the seven levels of delegation described earlier. When you hire someone for expertise you lack, take a deep breath and—provisionally—decide to trust that she has that expertise. Do your very best to convey the overall goals, purposes, and limitations, and then get out of her way.

That is bound to make you nervous, especially when—as with many tasks—it seems like nothing is happening for a while. So it’s appropriate and useful for both of you to schedule frequent check-ins. During those meetings, ask about the project status just as you would with a team member whose work you understand, and then perhaps go a little further. Ask the expert to explain what she’s doing and to show how it contributes to the goal. It’s OK to say that this doesn’t match your initial vision, but don’t infer or imply that the expert is wrong. If she chose a path that doesn’t match your internal vision, share your viewpoint and ask her to educate you.

Operating on a “tell them what to do” philosophy (suitable for the burger flipper) with an expert is likely to offend her. Plus, if she follows your advice to “do it this way,” you prevent her from demonstrating the expertise you wanted. “I feel as though he hired a three-star Michelin chef and then told me to make peanut butter and jelly sandwiches,” complains one content marketing expert. “Then he was disappointed that the sandwiches weren’t special. Worse, he never even saw what I could do for him.”

So how do you know if the expert is good? Depend on metrics to find out if the team member’s expertise really is as good as promised.

Or, spend a lot of money.

In John Molloy’s original edition of The Women’s Dress for Success Book (New Win Publications, 1977), Molloy addressed women who were conscious that they didn’t have good taste and were unlikely to choose the best haircut for their professional needs. (He didn’t offer the same advice in the men’s book because men’s fashions, in everything from suits to hair, were more constrained and easier to judge scientifically.) Molloy’s advice to women was to go to Pierre the Expensive and to put themselves in his hands, saying, “Choose the right hairstyle for me.” Then, Molloy suggested, take a lot of photos of that haircut. Bring the pictures to the more affordable salon and say, “Duplicate that.” That method was more limiting, but it was a “known good solution” appropriate for the need, and thus a useful choice.

So if you know you aren’t capable of judging the expertise of someone who works for you, as staff or a consultant, rely on others’ judgment of what’s best. That is, dig into your pocket for the expensive, in-demand supplier, and put yourself in their hands. Their reputation—as measured by their hourly rate—should reassure you that someone thinks they’re worth the money.

“Once you give someone authority,” says Miki, “you can offer suggestions, forward pertinent articles, discuss the task, even recommend against their directions, but it is still their decision.” However, adds Miki, referring to the “box” of authority and control, the person can invite the boss into his box and ask for help in an area in which the boss has authority without incurring any negative effect on the future. That’s especially so in these circumstances.

First, Say Thank You

In nearly every situation, your team member worked hard on the task you assigned. The outcome might not match your expectation or his, but it’s important to acknowledge the individual’s effort. Take the time to say so with sincerity, because this is a moment when your leadership matters.

“It’s very important to express gratitude,” says Diane Dye Hansen, chief inspiration officer at What Works Coaching. “Often, I just get so caught up in the day-to-day I forget to say thank you.”

Always point out something you particularly liked, no matter how hard you have to work to find it. Sensitive team members, such as nervous interns, are terrified of criticism (even well-meant constructive feedback), so you need to give them a positive to hang onto, even if it’s, “What nice text formatting!” Try to give the individual a full paragraph’s worth of praise, particularly if you’re going to follow with a long list of things to improve.

If nothing else, tell the team member, “I see how hard you worked on this.” Which is not necessarily praise, though it is likely to be received as such by the less competent.

Acknowledge Success

Do a debrief, urges Schmidt. After the task is successfully completed, talk to the team member about what he learned as well as any way the process could be improved. “By getting them involved, you are showing you care about their opinion,” she says. “You can also check if they are keen to do more of this type of work.”

There are at least two elements in a debrief, however: the task and the person who completed it.

That is, does the result match what you asked for, without regard to the who-did-it? Does the finished product match the specifications you included when you first delegated the task? If it does, hurrah. If not, consider—together with the team member or by yourself—what kept the result from meeting the quality, budget, time, or other defined spec.

And ask yourself: when the completed task isn’t what you expected, is that failure?

A manager has to determine in advance what outcome or product is needed, says Billie Blair, an organizational psychologist and CEO of the international management consulting firm Change Strategists. “Then,” she says, “no matter how the work was done, if the outcome was achieved, the work was ‘good.’”

Blair counsels that you should look first at your own skills. “If the outcome is not reached, then likely there was a flaw in the choice of the person to do the work,” she says. “Notice I didn’t say that there was a flaw in the person doing the work, just that the manager’s choice was incorrect. It takes a bit of refining of one’s perceptions as manager to learn how to make good choices. But the biggest hurdle is always in turning loose the reins of control and accepting that one will learn to ‘live with’ the product, if it meets the predetermined specifications.”

Don’t look for perfection. If the team member did what you asked, celebrate. If he did more and better than expected, celebrate louder.

Take Advantage of Mentoring Moments

Usually, the more valuable part of the debrief is in its mentoring opportunities. It’s a time for you to pass on your own skills.

“Delegation is not just about getting work done: it is more critically about developing your people and building capability across your team,” says Dooley. “This approach ensures that you don’t suffer from ‘key person risk,’ where you pour your efforts into a high performer, who then walks out the door, leaving you woefully exposed.” Instead, deliberately and strategically train your entire team to support each other’s work and to grow their own professional skills and expertise.

That applies to learning delegating skills, too. Shadow a manager whom you admire, says Blair, and watch how he does delegation, such as how he chooses what work to delegate and what he keeps for himself. “Debrief after each shadowing session and ask him how he selected people to whom he delegated,” she suggests. “Then study your own people very well; get to know their specific skills and attributes. And when there is work that needs delegating, select the best person for the task based on your in-depth knowledge. After that, it’s a learning experience of trial, error, correction.”

Cope with Failure

So what do you do when the results are disappointing? Determine the source of the failure and what it takes to prevent that from occurring again.

Mistakes can provide a powerful source of development if you can focus on the lessons rather than allocating blame, says Dooley.

Start by evaluating what you personally did and didn’t do. “Rule number one: if the person you delegated work to fails, it’s probably because you forgot to tell them something important!” says Jennifer Hancock, who teaches humanistic business management.

After all, you’re the person in charge; you’re supposed to know how to lead people. Consider your own credibility with the staff. Do you delegate at the last minute? Are you perceived as lazy? Is it always urgent? Is it your job? Ideally, after reading through this document, you have identified your own weaknesses, and are already in a better position to delegate more effectively in the future.

Sometimes, the issue is with the person to whom you delegated the task. “The problem is when you have people who fail to hold themselves accountable. They usually blame the process or the organization or such,” sighs one manager. “This usually requires transitioning those people out of the organization or into roles in which they have a micromanager to keep them responsible.”

“Good delegation always seems to go along with a good flow of authority and accountability,” says an IT manager at a large university. “You cannot delegate well when you don’t hand off an equal portion of both. Too much authority and the employee can take an unforced error; too much accountability without the authority frustrates the employee and sets up a forced error.”

Delegating is an important and powerful tool, says Barak, a VP of software engineering. By doing so deftly, he says, “you can really create a multiplication effect. By delegating the right things in the right way, both you and the delegated party achieve more than before.”

And then: rinse and repeat. Because there is always more work to do and more tasks to delegate!