Why Aren’t I Better at Delegating?

All leaders—from new managers to seasoned executives—must delegate tasks to free up time and attention for the big-picture work their more-senior roles demand. This is an axiom; indeed, delegation is one of the first skills typically required of new managers. But both my experience and my research show that leaders too often find themselves mired in the details of their teams’ efforts, with debilitating consequences for their organizations. Failure to delegate well produces three bad outcomes. First, a relatively expensive employee (you) is doing work that could be done more cost effectively and probably better by a lower-paid team member who is closer to the customer or the operations. Second, your team is likely to become frustrated at micromanagement, and stagnant from the lack of real responsibility, undermining your leadership pipeline. And, finally, you stay mired in your old work, which prevents you from focusing on the critical strategic planning, cross-functional networking, people management, and self-development work your organization needs you to do to stay ahead of the competition. Being less effective at these vital parts of your job will almost certainly limit your chances to advance as a leader—and will make it less likely that you’ll succeed in your current role. For example, one CEO—formerly the CTO of his company—continued to give his old engineering team detailed instructions about how to improve the user experience on its app long after he had been promoted. His successor as CTO, who was now closer to the latest usage data, often had to push back on the CEO’s instructions, wasting everyone’s time (problem #1). The CEO also continued to prioritize the software engineers’ tasks—for example, asking for fixes to small issues on the landing page ahead of more-fundamental back-end bugs—which further irritated the team (problem #2). Lastly, he couldn’t then find enough time to do his new job—communicating the strategy to the wider company and meeting and developing his new leadership team—which meant its members couldn’t make effective decisions about their own priorities without his continued involvement (problem #3). Most leaders I work with understand that they need to delegate, but they don’t always know how to distinguish between the work they should be doing and the work they should be handing off. And even when they get that determination right, they often fail to follow through. Consider, for example, the thousands of managers who have taken my leadership development programs at London Business School and the MIT Sloan School of Management. They leave these programs committed to delegating more, but when my team and I follow up with them six months later, about a third admit to still being bogged down in lower-level tasks. Recently, we surveyed this group to find out what was tripping them up. From their stories, we realized that many needed a refresher on which tasks to retain and which to give to others. A how-to on that is outlined below. But we also identified four challenges that stop even those who know how to delegate from doing it successfully: an addiction to the dopamine hit of easy productivity, a disinclination to reject requests for help, a desire to meet their own bosses’ or clients’ unmanaged expectations, and a misunderstanding of what “work” should mean for a manager. Drawing on research and my own two decades of experience advising senior leaders, I’ve developed concrete recommendations for overcoming each challenge. Deciding What to Delegate Before you can successfully delegate, you need to learn to differentiate between the work you should keep—and, indeed, do more of—and the work that is better left to a team member. My advice is simple: When considering any meeting, task, or responsibility, always ask yourself, “Am I the best and cheapest person to get this done?” If the answer is no, delegate the work and give the person you’re handing it to the context needed to succeed. Context-setting includes explaining why the work needs to be done (following an organizational strategy, entering a new market, onboarding a client, or investing in a project, for example); the results the person or group is expected to deliver; the deadline for the work; and how people should behave (with one another, other colleagues, clients, and others) to get it done. By contrast, activity-based work—including making decisions about what work to do to achieve the company’s or team’s goals—should be your team members’ responsibility. That’s because their time costs less than yours, they typically have more on-the-ground insight to drive good choices, and they’ll be motivated to do the job well when given autonomy and accountability. Case study research I conducted from 2011 to 2013 showed that leaders’ strategic initiatives were more likely to succeed when they made the desired outcomes clear but left the execution decisions to their teams. When a managing director in a large global bank I worked with used this “best, cheapest” test to consider her portfolio of work, she ended up ceding 40% of her meetings and 25% of her tasks to the directors and VPs who reported to her. She found that everyone was happier: clients, because her team was just as strong as her on most issues and more responsive than she had been; her employees, because they enjoyed the exposure, development, and career progression; and the managing director herself, because she could reflect, learn, and ultimately contribute to a high-visibility strategy project that she hadn’t previously had time for. Overcoming the Four Challenges Even leaders who understand what work to delegate and how to hand it off with skill still struggle against four challenges. 1. The dopamine hit of personal productivity. MRI brain scans show that when humans accomplish something, our brains release a tiny hit of dopamine that produces feelings of pleasure, motivating us to take on and complete difficult tasks. Unfortunately, activity-based work offers more-regular dopamine hits than context-setting does. Many leaders in our study said that they miss having lists of discrete to-dos to check off each day. What’s more, context-setting is cognitively taxing, especially for those new to it, creating a dopamine deficit. So managers just learning to delegate will feel a craving for those old hits. Ultimately, leaders need to accept that their work will yield fewer and less frequent chemical rewards associated with productivity. But there are ways to avoid feeling their absence so strongly: Create different types of checklists. Activity-based work might be easier to break down into to-dos, but it’s possible to do the same for your context-setting work so you can get dopamine hits there, too. For example, during each internal meeting or client onboarding, track that you’ve (1) explained why you’re having it, (2) outlined what those assembled need to achieve, and (3) described the behaviors that will help you meet that collective goal. You can also make lists of tasks to delegate and tick those off one by one. Routinize good practices. Putting routines in place with others can make the work of managing, including delegating, easier. For example, you might structure all of your one-on-ones around a list of questions, such as, What is your most pressing challenge right now? What steps are you taking to overcome it? What’s one thing I can do to support you? In group meetings, make a habit of asking every person attending to give an opinion so you have a window into how each might contribute to the work at hand. Reframe your purpose. Instead of chasing quick dopamine hits, train your focus on longer-term goals. Remind yourself that you are helping your organization to scale by staying out of activity-based work, and you’re encouraging your employees to grow by giving them more responsibility. Léonie Després I once coached a junior partner at a law firm whose senior leaders wanted her to manage more and larger transactions. But she struggled to do so, admitting that she preferred “the short-term deal deadlines, ‘urgent’ client calls, and ‘emergencies’ where [she] could put out fires and be a bit of a heroine.” After adding context-setting checklists to her routine, creating a system to let junior members make more and better contributions to client meetings, and reminding herself that it was their time to shine, she was able to embrace her managerial role and delegate more often and more successfully. 2. Employees’ requests for help. Some leaders embrace context- setting but get derailed when team members come to them asking for assistance or buy-in for their decisions. Questions like “What should we be working on?” and “What’s the priority client this month?” drag managers back into the activity zone. Of course, you shouldn’t just turn employees away. But you need to redefine how you help by limiting yourself to the right kind of guidance and involvement. Follow these steps: Re-explain the context. Prompt your team member to recall the key points of context. “Let’s remember why we’re doing this, what outcomes we need to deliver, and how we need to show up differently.” Give the work back. Refrain from giving explicit advice: “So given that context, what do you think the priority is?” Teach with examples, not answers. If the response shows that your team member lacks the knowledge or experience to make a good decision, explain how you made similar decisions in the past and what you learned. Then prompt your team member to think about how those lessons might apply in this situation. Establish accountability and support. End the conversation with, “Let me know how that goes and when you’d like to check in with me again.” Your team may not respond well to this approach right away. Some people will not yet trust that you want them making all the activity-based work decisions and so may be reticent to take them. But if you keep at it, over time you’ll discover who is willing and able to exercise good judgment and who isn’t. Consider a tech company senior manager whom I recently coached. In the weeks following her promotion, members of her team still came to her with questions, pulling her back into the work she’d tried to delegate. But once she learned to recognize these as requests for activity-based help and responded appropriately, her employees learned to take more responsibility. She recounted the story of one direct report who asked which project to prioritize that month: onboarding a recent acquisition onto the group reporting system or improving the working capital cycle. “In the past I would have given him my answer,” she said, “but instead, I reminded him why we were working on these projects and the outcomes each one needed to deliver.” Although he was initially surprised that she didn’t just tell him what to do, he made his own decision—to focus on the onboarding, because it was part of the critical path for the project, and other people could handle improving the working capital cycle. Both were happy with the decision. As she consistently declined to join her team’s activity zone, the stronger players stepped up to take on more work, and even the more reticent ones started trying harder to make better decisions without additional input. 3. The boss’s or client’s expectations. Some leaders are pulled back into the activity zone not by the people below them in the org chart but by those above. It’s not unusual to have a boss (or a client) who expects you to know every detail about the work being done on a project. My research finds that this is a particular challenge in sectors where the consequences of failure are high (such as public utilities, mining companies, and hospitals). Combating this challenge is also difficult in organizations that are culturally hierarchical, where pushing back on the boss isn’t acceptable. But all leaders need to manage up. You can take steps to ask your boss to hold you accountable for outcomes rather than expecting you to be involved in all the activities that will deliver them. Here’s how: Start small. First, choose the outcomes that are most likely to be achieved and seek permission to fully delegate those activities. For example, one director of a research lab told her boss she planned to provide oversight but not dig into the details of work in the area she had previously run because she already had a good understanding of what her team could do without her and of the risks involved. When she delivered well on those goals, her boss began to trust her decisions to delegate elsewhere. Be accountable. Encourage your boss to hold you to your promised outcomes. As one leader in our survey explained, “I made it clear [my manager] could fire me if I didn’t deliver….Before that conversation, I think he felt like it was all on him, whereas now he realized it was all on me, and we were both happy with that.” Give visibility to team members. Bring your direct reports into as many senior-level conversations as possible so that your boss or client sees that they have a strong command of the details. For example, a senior lawyer I worked with always gave her team members key roles in client meetings. As a result, her clients grew more comfortable not having her on routine calls. Over time, target the more complex work. Finally, wean your boss from dictating your level of involvement in the details of larger projects. As the head of operations in a major public utility put it: “I couldn’t have started with the big, complex stuff. But now, with my team established and the trust built, I have more credibility when I say, ‘They’ve got this.’” 4. A limited definition of “work.” Ultimately, what derails many leaders from effectively delegating is their belief that real work is activity-based. For example, a star lawyer who had been appointed head of his firm’s M&A practice described how doing deals for clients still felt more meaningful to him than managing his team to do the same. This challenge is especially problematic for people who are skilled at highly technical work that constitutes a part of their identity. My research found that lawyers, surgeons, research scientists, and salespeople have the most trouble delegating, in part because they’d achieved seniority through their individual subject matter expertise and activity-based work—rather than their ability to lead teams and delegate. Training yourself to place more value on managerial work, including handing off key tasks, can be hard. But a few approaches can help: Recognize your limits. There is only so much work you can personally produce. A surgeon, for example, can perform a finite number of operations a day. If she is to treat more patients and make more money, she must coach and teach others to operate at her standard in her stead. The same scaling principle applies in many other functions from sales to R&D to marketing. The biggest successes are accomplished by teams, not individuals. Decide if you really want to manage. Global business culture glorifies leadership, but if you love doing, managing others might not be right for you. Coming to terms with this can be difficult but rewarding. For example, even as the newly appointed head of the M&A practice worked to learn new skills in delegating and leading teams, he realized he still preferred doing deals, and so he suggested that leadership consider making a change. The firm—which had simply promoted its best M&A lawyer to be practice head—gave the role to a lawyer who wasn’t as prolific a dealmaker but who actually wanted to manage. The law firm let its star go back to what he loved doing and was best at, and celebrated him for it. Spread the mindset. Encourage others in your organization to buy into the value of context-setting work as well. If you’re a middle manager, be proactive about not just delegating to your reports but also volunteering to take work that you know you can do off your boss’s plate. If you’re a senior leader, help your peers understand that managers doing less activity work and more context-setting is the best way for all of you to deliver at scale. And use your position to build systems that reward people for this kind of contribution. The C-suite executives at an insurance broker I know realized that their long-term success depended not on hiring more brokers at ever-increasing salaries but on developing leaders of brokers, who could teach their direct reports to improve and build teams. To do this, the company began to reward senior brokers who demonstrated collaboration and coaching skills. In part because of this approach, the business units that adopted it boasted year-on-year organic growth rates that surpassed those of their competitors. Be Patient Even for leaders with the best of intentions, overcoming these challenges will take time. When you’re new to context-setting, you will crave the dopamine that activity-based work has long provided you. Team members will invariably ask questions, and some will struggle to stop themselves from frequently checking in or resisting when you hand decisions back to them. Bosses and clients may question how much you delegate until you’ve proven your decisions are sound. And your own beliefs about the value you bring to your organization will be tricky to shift. However, effective delegation is one of the most important skills for any leader to learn. If you stick with it, you’ll get so much more out of your team members—and yourself, as a developer of talent and as a big-picture, strategic thinker.

Why Aren’t I Better at Delegating?

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