Leading the Unleadable

by Alan Willett

  The most fundamental problem of leading leaders is that they can be unleadable too and in whole new ways. As one CEO told me, “The higher up a manager is in the organization, the more fog there is around that manager’s performance. It is very hard to judge how well they are doing.”

  The problem with the fog is it takes longer to see if the leader is the root cause of the problem.

  The Case of the New Leader as a Maverick

  Sarah was the division leader of a growing $100 million business. Her division employed about 500 people. She hired Tom as one of her leaders after an extensive search to find the right skill set. Tom had lots of ideas that fit what Sarah wanted for the business. She knew that with his ideas and experience he would help take the company to the growth she envisioned.

  Over the initial weeks, Sarah noticed significant indicators of trouble.

  She noticed that people came out of meetings that Tom ran looking dejected, not excited.

  She overheard a loud discussion between Tom and one of the people who worked directly for him. The loudness did not bother her, as she had engaged in many passionate debates herself. The tone seemed wrong, however, and she did not hear anyone else being that loud, just Tom.

  She had an instinct that the energy level of her team was getting lower. She could not yet quite articulate why she felt this way, but she knew to listen to her inner wisdom.

  Sarah knew that she had to act. The question before her was what specific actions to take and how to take them. Leading leaders is not a lot different from leading individual team members, but there are enough differences that the whole topic deserves special consideration. Sarah became worried that Tom fit the model from the taxonomy of trouble called the maverick.

  The Special Challenge of Leading Leaders

  Leading a team where everyone works with you personally has many challenges. Typically, the ability to lead people personally and directly will begin to rapidly diminish at X number of people. The X number will vary with the leader, the people, and the situation. I have not personally seen that number exceed thirty people.

  Note that I am not talking specifically about how many people are directly reporting to a manager on an organization chart. That situation does apply here; however, I am talking more broadly. For example, there are people with very few others directly reporting or even none reporting to them on an organization chart. Yet, often these leaders are responsible for initiatives that involve over 1,000 people.

  Thus, there are many situations where a leader will be leading a very large body of people. These people may include individual contributors, team members, and leaders.

  In many situations, you may be leading leaders of leaders.

  Although there are many similarities between leading leaders and leading individual contributors, there are significant differences that deserve consideration. The following are the key differences.

  1. There is increased distance between you and much of the work. Thus, you will often be one or more levels removed from where the trouble is and even distant from the indicators of trouble. There could be troublesome projects or people who could be a risk for your whole organization. The good news for you is that the leaders you are leading should take care of it without needing your intervention. The question is whether they are doing so fast enough. If the leader is not dealing with the trouble, or dealing with it incorrectly, how would you know? And what actions should you be taking, if any?

  2. You do not know how the work is actually done. The skills that are involved in large initiatives are very diverse. Good leaders may actually know the names of even a thousand people who work for them. However, they will not know all of their backgrounds, nor will they know the details of how the work should be done.

  3. Troublesome leaders have a large impact. If a leader is the one creating trouble, the depth and breadth of the impact of the trouble grow significantly. The impact of that problem is amplified in a number of ways. First, it is likely that the trouble is affecting significantly more people than when it is caused by an individual contributor. Second, the impact lasts much longer. A leader always has an impact on the people he leads. The impact lasts longer than the tenure the leader has with those individuals. What lessons have the leader’s followers learned? Are those lessons good for the organization?

  4. Your breadth of responsibility increases. Many good managers find that they are like the legendary vaudeville act of the plate-spinning madman. That person gets plates spinning on a tall stick and then runs from stick to stick to get and keep more and more plates spinning until many crash, with much laughter from the audience. The same happens to many leaders without the laughter around them.

  5. With great power comes great . . . pressure. The more you are responsible for in leadership, the more intense the pressure most people feel. More and more people are looking for you to make decisions. This includes the people you are leading, the people who sponsor you as a leader, and your peers as well. The impact of these decisions is greater. It is likely that if you are leading leaders, you do feel that pressure. Remember that the leaders you lead also are feeling their own.

  6. There is increased need for autonomy among the people whom you are leading. This is true when you are “simply” leading team members. It is even greater when you are leading leaders. The more responsibility they have, the more autonomy those leaders require and should have. People need the space and capacity to make their own decisions, to make their own mistakes, and to complete excellent work, with a sense of great personal satisfaction that “I did it all by myself.”

  Set Your Specific Expectations for Leadership Excellence

  In many organizations, it is obvious to almost anyone when there are troubles in the ranks of leadership. One example of an obvious symptom of trouble is destructive conflict among leaders that leads to conflicts between the teams that they lead. Another symptom often seen is where individuals who work in a matrix organization get different priorities and directions from the different leaders they work with.

  In the organizations where there is a significant issue in the leadership, the most common root cause is that the leader of the leaders has not clearly thought about the expectations for how the leaders working for them should lead. If they have thought about those expectations, they are not acting upon those thoughts. Even if there is a strong idea, it has not been clearly articulated. This is the most important preventive measure in ensuring that the leaders you lead will more likely be tremendous than trouble.

  Some leaders think that their expectations should be obvious, but unfortunately they are not obvious. There is a great diversity of ways to lead. This is one of the reasons why there are so many books about leadership! Also, within that diversity of ways to lead, exceptional leaders know that different circumstances call for different styles of leadership. The key is to make your expectations of leadership known.

  What follows are my personal expectations of leadership excellence. It is fine if you wish to start with my list, but the most effective expectations are those that are specific and personal to you.

  1. Make the noble purpose of the organization your own. In Lisa McLeod’s book Selling with Noble Purpose, she shows with stories and hard data that organizations that clearly articulate not just their purpose, but also purpose that has meaning to the customers, do better in the marketplace. What truly motivates people is typically not money. It is critical for the leaders to engage each other in conversations about the purpose of their organization and of each of the projects that make up their mutual success.

  For example, in the medical device industry there is considerable work in the best organizations to ensure that everyone knows that the primary concern is to treat patients expertly and safely with the equipment they create. They are aware that the customers of their systems could very well be themselves or their children.

  2. Take the long view. As a leader of leaders, you must have a longer view than any of the leaders working for y
ou. The CEOs of larger organizations must be focused on creating next year’s business while other leaders focus on delivering today’s products, services, and promises. To be clear, I expect everyone to be engaged in thinking about the long-term success of the organization. Each leader must be able to articulate the direction the company is going in and how the success of today contributes to longer-term potential. The ability to provide services to customers is constantly changing in all industries. Besides being focused on satisfying today’s customers, leaders must be looking to the distant horizon.

  3. Your job as a leader is to grow the talent of the organization. John Wooden won a thus far unmatched ten NCAA basketball championships as a coach. Whenever he was asked what was the most important factor, he replied without hesitation, “having the most talented players.” Hidden behind that short quote are very important concepts. The first is that you want to recruit and acquire talent. That is obvious. The more important concept is that it is your job as a leader to grow the talent of each individual whom you lead. It is your job to provide each person you lead with inspiration, guidance, discipline, correction, training, and, most of all, the opportunity to make mistakes and to excel.

  4. Expect the leaders who work for you to challenge you. If I am making decisions about our direction that you disagree with I would expect you to challenge me. I prefer you challenge me politely and be able to back it with facts. If you can’t do that, and you only have an emotional gut feel, I still expect the challenge. Further, if I ask a leader to deliver a project with a key set of attributes by a specific date and that leader doesn’t challenge me, that leader has made a commitment.

  5. I do not expect that we will always have harmony. I expect constructive, collaborative conflict. Each of you who are leaders has significant talent and ambition. I expect each of you to have more ideas than we could possibly accomplish. I expect my leaders to be competing for the rare top talent performer positions in our organization. I do not expect harmony. However, I will not tolerate destructive conflict. We will argue our positions with data, facts, and intuition. I expect that some of the discussions could be loud and emotional. We will stay focused on our common goals. We will make decisions through a process that strengthens our relationships and trust in each other.

  6. Get things done. You are still responsible for the ultimate success or failure of the overall group and initiative. Is that enough said? As an individual contributor, you are responsible for getting your stuff done. As a leader of individuals, you are responsible for getting stuff done through the people you lead. As a leader of leaders, you are absolutely still responsible for the success and failure of each of the leaders you are responsible for. I challenge each leader to get things done while growing the talent of his or her teams and collaborating with his or her peers. It is a high bar of excellence. I expect nothing less.

  The most critical part is that exceptional leaders know what they expect, and they let the leaders they lead know what those expectations are.

  Trouble Spotting: The First 100 Days

  Setting clear expectations of leadership excellence clears much of the fog that obscures your view of a leader’s performance. This, of course, is not the whole story. The next step is to follow through on those expectations in a way that ensures that your expectations are being met and, better yet, exceeded.

  There are two distinct phases of spotting trouble with the leaders you lead. The first phase is when they have just come under your leadership. Many people consider the “first 100 days” to be the most critical. I believe that number varies considerably with the pace and stress of your own organization. The second phase is, naturally, the ongoing work of leadership.

  The following are techniques for spotting potential trouble in the first phase of a leader joining your organization.

  Ask them to report on the strengths and weaknesses in the organization that they are joining.

  When a new leader joins you, I would recommend you set the leader on a mission to interview as many people as is rational in both the team of people they will be leading and across the whole organization. This provides a unique opportunity to do multiple things.

  First, you can get a fresh perspective on how the organization is performing. Second, you will be able to quickly judge much of the leader’s character and how she thinks about things from the report she provides you. Third, you are providing the new leader a rapid socialization into the organization. Fourth, you are setting the expectation clearly and strongly that you listen to the people she is leading and working with.

  I would do this even with people who were already in the organization and are being promoted to new positions. It is perhaps even more important in these situations. They will think they already know about the organization. Taking this listening tour will provide each of them with a whole new perspective. Moreover, people who have been promoted often have a hard time getting other employees to think about them as having this new role in leadership. The listening tour rapidly changes that perspective.

  Start the leader with a difficult challenge.

  I encourage you to give new leaders difficult immediate challenges with clear sets of expectations and deadlines. I also prefer that they will need more than the team that they are leading and have to collaborate with others within and even external to the organization in order to meet the challenges.

  You may consider this “throwing someone in the deep end to see if he can swim.” You would be correct. The timing for doing this is perfect at the beginning. Typically, when you bring a new person to work for you as a leader, this is the time when you can provide the most attention to him. The more important thing is that you really do want to know not just if he can swim but how he swims and if there are any troublesome attributes. This approach will help you see any of those troubles and see them early.

  Engage them in conversations about the most difficult challenges they are most likely to face while leading in your organization.

  If you have been leading the overall organization for any length of time, you will most likely know where the trouble spots are and what issues are almost certain to arise. Provide possible scenarios to new leaders and ask them how they would respond to the situations if they do arise. Provide examples of what has happened in the past.

  These conversations are fascinating. You will learn a considerable amount about how these new-to-you leaders think. You will learn about how they are likely to handle situations. Also, your conversations will be active opportunities to model how your working relationships will be. The way you provide guidance here will be a model for how you will provide guidance later.

  Each of these techniques helps prevent trouble and identify trouble spots early.

  Trouble Spotting: Ongoing Leadership

  After the initial new-to-the-organization phase, a pattern for how you work together will be established. As the leader of leaders, you will of course have many things to do. You won’t have the time even if you had the desire to be constantly investigating whether your leaders are doing a great job. In fact, you are expecting it.

  However, as discussed in Chapter 4, you still want to be continually honing your trouble-shooting radar. All the techniques in that chapter still apply. You want to be able to see trouble coming and be able to deal with it before it is obvious. It is obvious you have trouble when you repeatedly have issues with on-time, quality deliverables. It is obvious when the top talent in the organization is complaining about a leader, and even worse when these talents are fleeing the organization to find better leadership.

  Here are a few specific ways to determine whether there is trouble before it has greatly impacted your organization.

  The leader’s negative attitude days are noticeable.

  Consider the impact when one of your leaders is cutting off other leaders or their own team members in conversations. Consider how it reflects on you if a leader you are responsible for is dismissing other people’s ideas or concerns with no con
versation.

  It is amazing to me how many leaders tolerate leaders who work for them and display such negative attitudes. I know there are reasons to be cynical or sarcastic. I know that some days are worse than others. I know that sometimes, one can feel like a victim and just need a minute or two to whine that it is unfair that some negative thing happened.

  Do not tolerate this as a daily habit, nor even a weekly habit. If leaders are acting that way with you or in the meetings you are leading, it is likely to be happening even more in situations with the people they lead.

  The energy levels of the teams they lead are lower than the rest of the organization.

  It is important to watch the energy levels of your leaders and of those whom they lead. As I noted in a previous chapter, it is important to walk around and talk to people. You can also notice the energy levels. Be careful not to react to a single set of events or days but do watch the trends over time. If a set of people seems demoralized, it is almost certain to be that they are, and it is their leader’s responsibility to address the situation. Circumstances do not make up the motivation level of the team. It is always the leader.

  Engage in a listening campaign.

  Ask team members how it is going and then listen. It is surprising to me how many organizations have situations where leaders feel it is inappropriate to walk around and ask about how projects are going. They do not want to undercut their leaders. I understand that, but you are not undercutting anyone if you are giving advice or direction. It is your responsibility to understand how your organization is working. It is actually fine to ask people directly how well a leader is performing. If you have concerns, ask before they are in your office telling you why they are quitting.