Few things can help an individual more than to place responsibility on him, and to let him know that you trust him.¹

—Booker T. Washington (emphasis added)

Mateo is a leader ready to move to the next level in his career. He had been very successful where he was for quite a long time. He knew how he was viewed in his division but not across his global organization. He wanted to know what others with whom he had interacted throughout the years outside of his immediate division thought of him. Mateo gave me a list of key leaders he wanted to work for in other parts of the company so that I could find out how they viewed his leadership potential.

To start the process, I crafted several questions to understand better how they perceived leadership and how they perceived Mateo. The questions I used were as follows:

1. What does it take to be a successful leader on your team/in your organization?
2. From your experience or from what you’ve observed, what do you believe are the leadership strengths Mateo would likely bring to your team/organization?
3. From your experience or from what you’ve observed, what do you believe are the areas in which Mateo would struggle or needs further development if he moved to your team/organization?
4. What additional insight or information do you have that would help Mateo continue to grow as a leader?
5. On a scale of 1 to 5, with 1 being “no way” and 5 being “without question,” would you hire Mateo to lead in your organization?

Overwhelmingly, the leaders I spoke with agreed that Mateo was a superstar. They knew he was capable of much more than what he was doing, and they all agreed it was time for him to make a major career move. In terms of specific feedback, Mateo was most interested in knowing what one key leader (we’ll call him Peter) had said when asked, “Would you hire Mateo to lead in your organization?” Peter was a leader Mateo worked with often and respected more than anyone else. Peter agreed with the others that he would hire Mateo but not for a more senior role. He said he would likely transfer Mateo to his department in a lateral position, rather than a promotion. When I asked him to explain this more, he said that he wasn’t sure Mateo delegated and developed his people to the level that he would want a more senior leader in his organization to do. In fact, I knew from interviewing Mateo’s team that this was true.

When asked to rate how well Mateo clearly and comfortably delegates both routine and important tasks and decisions, his team rated him a 3 when all other competencies rated were at 4 and 5 consistently. When I asked Peter to tell me how he knew that Mateo struggled with delegating and developing his people, he told me that whenever there was a problem and he needed Mateo’s team to solve it, he would hear directly from Mateo and only Mateo. Peter felt that if Mateo were leveraging his team more effectively, he would be including them in high-stakes problem solving and giving them outside exposure. Peter acknowledged that Mateo might be doing a better job of delegating to his team when working with other groups, but he wasn’t doing so with his.

When I shared this information with Mateo, he was disappointed but he didn’t disagree. He said he knew he struggled with delegating to others. He said he felt like he could do it better than anyone else on his team. He feared that giving responsibility to others who could fail put his reputation at high risk, so he didn’t delegate. Unfortunately, Mateo’s choice not to delegate became the reason he would not be considered for a promotion by one of his most respected leaders.

At Personify Leadership, we define delegation as “sharing authority and responsibility with a delegate.” We define the delegate as “someone who is authorized to represent the leader.” For most leaders, these definitions cause an instant jab of pain right to the gut. Giving others power, giving others control, and giving others a chance to do what we do so well is risky. Very risky. Who in his right mind wants to take a risk when he can quickly maintain status quo by doing the job himself and ensure his reputation stays intact? Delegating to others requires a word we haven’t explored much yet: vulnerability.

Dr. Brené Brown is a research professor at the University of Houston Graduate College of Social Work and best-selling author. She has spent the past twelve years studying vulnerability, courage, and worthiness. During an interview with Dan Schawbel in Forbes, Brown described the power of vulnerability this way: “When you shut down vulnerability, you shut down opportunity.”²

These words could not be truer than when you apply them to delegation. Mateo lacked the willingness to fail or have others fail. In other words, he lacked the willingness to be vulnerable. The consequence of not being vulnerable was that he was unable to exercise an opportunity for growth and advancement. From my experience in working with leaders all over the world, this is true in general. It’s a small minority who learn to overcome what we at Personify Leadership refer to as the Delegation Doom Loop (Figure 6.1).

The Delegation Doom Loop looks something like this: I don’t delegate because the (potential) delegate is unskilled. Why is the delegate unskilled? Because I don’t delegate. I continue not delegating to this person, and therefore, the team member remains unskilled. And round and round it goes. As a result, we continue to do the work ourselves, and the other individual never develops new skills. Here are some of the most common responses to why leaders don’t delegate:

• Delegation takes too much time.
• I feel guilty giving my team more work.
• I like being the superstar.
• I am afraid my people won’t do it as well as I would.
• My customer wants only me.
• I don’t have the people to delegate to.

A survey of 332 companies found that 46 percent of companies have a “somewhat high” or “high” level of concern about their workers’ delegation skills,³ which means that just slightly less than half of leaders commonly fall into the Delegation Doom Loop. Most of us don’t need a research study to tell us this; it’s a familiar experience. But the question on everyone’s mind is “Why?” If we know we are perpetuating a cycle that will not produce good results, why do we continue to do it? The answer goes back to our fundamental understanding of courage. We believe the pain associated with delegating is worse than the pain of doing the work ourselves. If you recall from “The Courage to Get Unstuck,” the pain of change is part of the pain of delegation. We don’t want to traverse our way through the cold and hungry part of change to get to a more sustainable and productive place of warm and full, so we stay in warm and hungry. It isn’t until we are overlooked for promotions or find ourselves unable to scale our business to the size the market demands that we begin to realize warm and hungry is no longer an option. It’s hard; I get it. But is the alternative—stuck in the Doom Loop with limited opportunities—worth it to you? Do you want to end up a delegation statistic, or do you want to do something different?

Leveraging the other facets of courage we’ve discussed so far, consider what you already know to help you get there.

• Consider “The Courage to Take a Stand”—what does it say about what we value if we do all the work and save the best, most visible projects for ourselves?
• Consider “The Courage to Get Unstuck”—similar to Mateo, do we want to be somewhere else? Are we holding ourselves or others back?
• Consider “The Courage to Be Humble”—what does it say about us if our egos can’t let go of responsibility and authority? What does it say about us if we think we’re the only ones who can do it right?
• Consider “The Courage to Be Confident”—what does it say about our confidence in others if we don’t trust them to fail temporarily so that they can grow long term? What does it say about our own self-confidence if we don’t trust ourselves to fail temporarily so that we can grow long term? Let’s end the Delegation Doom Loop by making a declaration to be and do something different:

I am a leader who delegates authority and responsibility (value) so that others and I can grow (get unstuck) and contribute amazing things to my team and organization (humility and confidence).

Now, let’s look at the obstacles to delegation one by one and discuss how to look at them differently so that we can live this declaration in our daily life.

Delegation Takes Too Much Time

I’ll start by asking this question “How much time have you spent in the Doom Loop?” Chances are months, maybe even years. Nothing can be more of a waste of time than repeating the same behaviors over and over expecting a change. That’s the definition of insanity.

Brooke was recently promoted to project director, which meant she was no longer responsible for managing the day-to-day of the projects with her team but instead overseeing the entire project team with no involvement in project management. She had a team of five. However, two of her team positions were open with no qualified candidates to fill them, one employee on a leave of absence, and another on a performance improvement plan, leaving only three employees who were really capable of carrying the workload. We agreed the most important thing she could do would be to hire two qualified team members and manage the performance of the lower performer. Unfortunately, Brooke could not pull herself out of her daily tasks long enough to do either. I asked her why she wasn’t delegating more to her team so that she could focus her energy on her priorities. She said it was just faster if she did it herself. A year went by and Brooke hired another individual, but unfortunately, it was not a good hire and that employee left within two months. The employee on leave came back, but the employee on the performance improvement plan was let go from the organization. All in all, she was in just about the same position as a year before.

What’s even more unfortunate for Brooke was that, as a result of not delegating, she didn’t do that great a job at the project director level, and she was eventually demoted.

The magic question is “How do I create time for myself to delegate when the thing that will create time is delegation?” Regrettably, I don’t have a magic answer. But I do have some suggestions:

1. 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.
2. Look at ways to streamline your day so that you are always focusing your energy on your top two or three priorities.
3. Change expectations of outcomes. If you don’t have the right team in place with the right skill level to manage a traditional workload, maybe it’s time to change the workload temporarily. We don’t always have control over this, but we can influence others who do. The goal here is to buy you time to use delegation as a developmental process.
4. Manage your 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).
5. As requests for your time come in, practice asking, “Why this task and why me and my team?” rather than “When do you want it done?”

The most important thing to know about creating time for yourself and your team is that you have more control to do this than you think. If you read this list of suggestions and mentally said, “That will never work,” then you’ve already lost the battle. You can do much to influence the way work gets done for you and your team.

I Feel Guilty Giving My Team More Work

It’s not uncommon to feel guilty delegating more work to someone who already has a lot on his or her plate. However, when we don’t delegate, we aren’t doing our part as leaders to provide opportunities for others to develop. Instead of thinking about how you are increasing someone’s workload, think about how you are using delegation to help him or her grow. In this way, we can reframe our guilt—or shift our thinking about delegation. To delegate well as a developmental process means being thoughtful about the assignments, projects, or tasks we hand over to our team members. It’s not something we do in haste. Ask your team member what it is he or she is doing that he or she can give to someone else (or stop doing) that frees up time and what is it he or she wants to do that you’re doing. See where the conversation goes from there.

It’s also important to remember as you are delegating that you count too. If you are not delegating what you need to because others are not prepared to handle it, you’re not making your needs equally as important as others’ needs. It’s true that leaders rarely get to put their needs above their team’s. But they need to manage their energy boundaries, or they’ll be of no use to their organization or their team as a long-term, sustainable resource. Leaders also need to be able to scale their role so that they can scale the organization. It’s nearly impossible to be strategic when you’re stuck in the weeds.

Finally, consider that part of your role as a leader is to allow others to struggle to some extent before stepping in to lighten their load, however counterintuitive that might seem. Teaching my kids to read has been a very challenging endeavor for me for exactly this reason. My natural inclination is to step in and solve the problem. My very tenacious daughter, whose first phrase was “all by myself,” said to me at bedtime one night, “Ugh, Mom, stop trying to help me. I’m reading the book, not you!” That was the goal, but I kept butting in with my insatiable need to move things along. Coaching employees isn’t far off. When we step in before they struggle a little, we rob them of the opportunity to learn for themselves. Let them see how far they can go.

In the best-selling book Living with a SEAL, author Jesse Itzler writes about David Goggins and the Navy SEALs’ 40 Percent Rule, which basically states: “When you think you are finished, you still have 40 percent left.” Think about marathoners, for example. Most marathoners complete the race even when they feel like they’ve hit the wall. That’s because when the racer feels the pain of being depleted, it’s an indication he or she has 40 percent in reserves left to go. Likewise, letting our people carry their workload and more gives them an opportunity to see how far they can go. It allows them to tap into their reserves and challenge themselves to achieve more.⁴

I Love Doing It All—or at Least Being the Superstar

Andy is a superstar. Just ask any of his clients. At a moment’s notice, he will jump on a plane and land where the nearest crisis exists and put out the fire. He thrives on the adrenaline of swooping in and saving the day. He admitted to me that it would be hard for him to give up that part of his job—ever. On the other hand, Andy is struggling with delegation. It’s hard for his team to get the direction and development they need from him when he is traveling all over the continent solving problems. During our discussions, he said he believes he is actually a better leader because he is willing to do the hard work. I told him that may not necessarily be true. To offer a different perspective, I shared with him Mateo’s story and how being the superstar limited his potential for being considered for a promotion. This made Andy stop and think.

Like Andy, there are ways to still be a superstar and delegate and develop others well. It starts with reframing how you see your role as a superstar. If you believe superstar is only about doing the work, eventually you’ll have to decide whether you want to be a fantastic, over-the-top individual contributor or you want to be a leader. If your choice is leadership, consider a superstar leader as being an exceptional developer of people.

I learned this lesson the hard way, and I would say it represents one of my most humbling experiences. At one point in my career, I went from a department of one to a department of four. I had been the superstar individual contributor for a couple of years, but as the team expanded, other talent emerged. I had one exceptional team member we’ll call Tracey. Tracey had great potential. Even though I wanted her to succeed, I wasn’t ready to share the spotlight with her. I was relishing it myself. It didn’t occur to me that it was much of an issue until the CEO, a man I respected and trusted, shared some tough feedback. I had just finished presenting and leading a formal executive leadership event where Tracey sat watching. He said to me, “Angela, Tracey will never shine in your shadow.” He didn’t provide any specifics. I guess he figured his feedback was obvious enough to understand, and if I didn’t get it, there was a much larger problem at hand. But I did get it. His words humbled me. I realized I had hoarded opportunities for myself and limited hers. It was a lesson I’ll never forget.

Superstar individual contributors are naturally blind to the need for them to shift to becoming exceptional developers of people. Everything the superstar has learned so far in his or her career rewards his or her superior performance, not others’. When they are promoted to leadership positions, most superstars, unfortunately, never get the appropriate support to help them make the transition. This leads them to rely on the tools they already have—not the ones they have yet to develop. Learning to be an exceptional developer of people is a transition and does not happen overnight. If you find yourself here, find a superstar developer of people to learn from. If you’ve been the superstar individual contributor turned developer of people, offer your guidance to those who can learn from you.

Don’t underestimate the beauty in this transition. Giving others the spotlight can be incredibly rewarding. No matter where your people go, even if they shine so brightly that they are promoted outside your team or outside the organization, they will always be a reflection of you.

I Am Afraid My People Won’t Do It as Well as I Would

How many of you have said to yourself or out loud to others, “I don’t delegate because I’m afraid my people won’t do it as well as I would”? Okay, I have some validating words to share. You are right. They won’t do it better than you, at least not at first. But they may be able to do it better in the long run. Or they may do it differently and unexpectedly add innovation and creativity to your team.

Part of what makes it tough to let others struggle, get it wrong, learn from it, and finally do it as well as, if not better than, you is that most organizations don’t embrace failure as a learning tool. Creating tolerance for failure is a number one priority for the leader who needs to delegate. Of course, when you begin talking about creating a tolerance for failure, you start hearing whispers about simultaneously creating a culture without accountability. But the two can be mutually exclusive. If you want to remove fear of failure but maintain accountability, consider how you are managing failure in your organization today. Does every failure have the same consequence? Does the intention of the team member factor into your decision? What about the reason for failure?

Amy Edmondson, a professor at Harvard, believes widely held beliefs about failure in the workplace are misguided. Failure can be bad, it can be inevitable, and it can be good. In a Harvard Business Review article titled “Strategies for Learning from Failure,” she describes preventable failures in a predictable operation as different from unavoidable failures in a complex system and intelligent failures on the frontier as different from both the preventable and the unavoidable.⁵

What exactly is an intelligent failure? Duke University professor of management Sim Sitkin coined the phrase “intelligent failure” as a way to describe a process for proactively creating an environment in which people can experiment, be creative, practice, and learn from failures. If we consider developing our people as an intelligent step toward expanding the frontier of our team’s capacity and, as a result, our organization’s capacity, then intelligent failure is the way to go.⁶

To better understand intelligent failure, let’s look at some examples. While attending my kid’s school play, I found myself sitting next to an irritated dad. He was distracted, and visibly upset, checking his phone every few seconds. I asked him what was going on, and he shared with me frustrations he had with his sales manager. A multimillion-dollar deal was on the table, and without any preparation on the proposal, his sales manager had decided to meet with the client. Things did not go well. The salesperson did not understand some of the nuances of the proposal and did not have an adequate understanding of the history of the relationship to the client. Needless to say, there was cause for concern. This was the kind of failure that could have been prevented.

On the other hand, Colin Powell shares a story of a team’s intelligent failure in his book It Worked for Me: In Life and Leadership⁷. Instead of providing a security briefing to the president directly, he chose to delegate it to his team. The team was very excited about the opportunity and did everything they could to prepare. Powell also informed the president that the briefing would be led by his team to ensure the president supported this attempt at delegation, even if there was some level of failure. As it turns out, the team did an excellent job, impressing the president and Powell. However, Powell explains that, had the briefing gone poorly, he knew this would have been informative for him. If his team had not been able to brief the president adequately, he would’ve gained valuable insight into their capabilities. This is an example of intelligent failure, failure that brings about needed information to grow and develop people and the organization.

Personify Leadership’s entire first year in the market was one failure after another, some intelligent, some not. There were some successes sprinkled in there as well. We’ve lived to tell the tale. My business partner and I had designed the Personify Leadership program after first being experts in our individual fields, and second, being business entrepreneurs. To let go and give others authority and responsibility of our baby (not to mention our life savings) was a radical shift for both of us. As the principals behind the work, it made the most sense that together, we would keep delivering our program to our customers and leading our certification courses for other facilitators. Until one day it just didn’t make sense anymore. Our calendars were so busy working in the organization that we couldn’t work on the organization. After relatively static growth between year one and year two, we decided we would have to delegate to take our organization to the next level. We trained other facilitators to work with us and, eventually, in place of us. The result was evident by year three, when we grew by 125 percent. Looking back, it was the smartest thing we ever did for our organization.

My Customer Wants Only Me

Rachel was promoted with increasing responsibility because of her stellar reputation and work ethic. In addition, Rachel inherited a very capable and motivated team, who accepted responsibility and authority. However, even though Rachel wanted to delegate and step into her new role, her customer was reluctant. He liked working with Rachel and Rachel only.

Rachel decided the way to change this without alienating the client would be to get the client involved in the delegation process. She began by briefing the customer on her developmental goals in her new position as well as her new responsibilities. She shared how important it was to her to succeed in this new role and at the same time make a successful transition for her client and her team. She explained the benefits of the transition to the client. With Rachel working at a more strategic level, she would have the opportunity to help the client take a longer-term view of their partnership while bringing someone with new and creative ideas to work in her place. The client expressed concerns about the learning curve, and together they agreed on how they would work with the new team member to shorten the curve. Rachel made the client a partner in the delegation process to ensure a win-win for everyone.

Samuel had a different challenge. Every time he introduced himself to a new client as the face of his team, the client was reluctant to work with anyone else. Samuel realized he had to find ways to remove himself from the front-end client relationship-building phase and allow his clients to connect with other team members before he stepped in. Otherwise, he would forever be doing the work once the contract was signed. He also learned that if he did choose to be a part of the front-end client relationship-building phase, he would have to be firm about when his role ended and where other team members’ roles began. Like Andy and me, Samuel liked being the superstar, so before he could change the dynamic with the customer, he had to change how he viewed his role as the leader.

I Don’t Have People to Delegate to

Maybe you’re reading this chapter thinking to yourself, None of this applies to me because I don’t have direct reports. I’m a department of one. Or maybe you’re a project manager responsible for getting projects done without a team. If so, you’re not alone. This is what we call in Personify Leadership the new delegation paradigm. If we describe a paradigm as “a way of thinking, or a way of viewing something,” we can define a paradigm shift as “a fundamental change in your viewpoint, or your perspective.” Our fundamental thinking about delegation has been the traditional top-down model. If you report to me, I’m authorized to give you work and you’re required to do it. However, this model has not evolved much as organizations have shifted how they operate. Rarely do we just have a direct-line manager up top; we usually have a dotted-line leader as well. In addition, we have responsibilities to create and lead change throughout the organization with no direct reports and no direct authority. This changes how we approach delegation and how we think about delegation. This requires a new delegation paradigm that represents a matrix organization.

In this new paradigm, getting work done through others who don’t report to us may seem more difficult, but in reality, it’s not much different from the top-down model. We are fooling ourselves as leaders if we believe we have complete authority over people just because they report to us. Our people still have the ability to veto us; they just don’t always say it aloud. Instead, the veto comes in the form of subtle and sometimes outright sabotage. The sabotage can show up as resistance, negative watercooler talk, missed work, and low performance and effort. The solution to sabotage is to treat your delegates as individuals with voice and choice, able to share their thoughts and feedback and say no if they don’t agree with your delegated request. Working without direct reports requires building relationships with your potential delegates, allowing them to share their voices, and giving them choices. In this way, the skills a leader learns delegating to nondirect reports prepares them to be exceptional delegators when they have their own direct-report teams.

Delegating in the new paradigm also means a leader needs to manage up, across, and down in the organization. The first step is partnering up front with peers, the boss, and the boss’s peers about the work initiatives they represent and how they will work together to meet one another’s expectations. The role of delegation in the new paradigm is as much about interpersonal savvy and political savvy as it is about developing others. Let’s look at an example of a leader who does this well.

Sasha is a vice president of talent development for a privately held transportation company in the North Pacific. Like many companies suffering from the flood of baby boomers retiring, her company is losing top talent rapidly. To adjust the trajectory of this path, Sasha was hired to create an enterprise-wide talent development strategy. The strategy includes sharing talent across six organizations that operate completely independently of one another. As part of this process, Sasha has lofty goals, a decent budget, and limited head count. What she needs to accomplish enterprise wide will happen only if she leverages the human resources directors and their teams at each company.

To get buy-in and support up front, Sasha invited all the company HR members to the enterprise headquarters for a team meeting. She began the meeting by giving each team the opportunity to share what their group does, what they are proud of, and what they feel are their challenges. During the meeting, they learned a lot about one another and gained an appreciation for one another’s expertise and goals. Sasha also shared the enterprise vision, which included leveraging each of them and their teams. She also invited the enterprise CEO to speak at the meeting, reinforcing Sasha’s vision for the team. Sasha then invited her delegates to define their own level of commitment to the enterprise strategy and the timeline in which they would be able to execute their commitments. By the time the meetings wrapped up and everyone was on the way back home, Sasha had successfully created a team of delegates who did not work directly for her but were ready to do the work needed to make things happen. Over time, there have inevitably been struggles and setbacks, but the focus and commitment have not wavered.

Breaking out of the Delegation Doom Loop requires time management, being willing to let your team struggle a little, stepping out of the spotlight, creating a culture of intelligent failure, involving the customer in the delegation process, and navigating a new paradigm. It takes courage, but it is possible. You just have to be willing to stick it out past warm and hungry to warm and full.