Leading the Unleadable

A SoundView BEST Business Book of 2017

Sample Chapter

Chapter 5 Take Action: Transforming the Troublesome

“Thought provoking and to the point, Alan Willett’s LEADING THE UNLEADABLE transformed how I handle difficult situations.” — Rob Snyder


Once you spot trouble, how will you deal with it?

The trouble can be a conflict brewing, a conflict in progress, a quality issue, a scheduling issue, or any issue that puts the group and mission at risk.

There is a choice to be made by the leader. If action is not taken, it is possible that things just might get better. However, it is more likely that if action is not taken things will get worse, and often in unpredictable ways. It can get worse in big ways, such as larger conflicts or schedule delays. Often, these situations get worse, instead, in small ways, such as a lethargy overtaking the team as team members become apathetic about the mission. If the leader does not care, why should the other people in the organization?

If improper action is taken, it can make things worse faster. For example, consider a leader who suddenly delivers a lengthy monologue at full volume to a troublesome person in a public situation. This leader had waited for things to get better and had let her own anger build until it escaped. This incident led to significant attrition of the team over the next weeks and to those within and outside of that leader’s organization to actively avoid her.

It is best to take proper action. To take proper action, proper preparation is required.

This chapter provides the general framework and mindset for working with people who, to put it mildly, are out of compliance with your expectations. The framework is an orderly set of action steps with compassion at its heart.

These steps will help you focus on the person at the center of the trouble and learn how to take action that leads to a positive difference. This framework is effective regardless of the type of situation that arises. You should, however, always use your experience and judgment to adjust to the exact situation with which you are dealing.

The Case of the Team Slacker

When reading the steps for preparation, action, and follow through, consider the following situation that team leader Alison faced.

Alison works for a company located in the northeastern United States that has grown to more than 100,000 employees and has a long history of innovation. Alison aspires to grow her role in the company.

The project Alison was leading was what was known in our organization as a “bright lights project,” as it had intense importance to all the executives, including the CEO. The company was counting on it, but there was trouble brewing. The project was getting significantly behind, and the team was blaming Carl.

Carl was showing up late but not very late. He was at all the meetings that he was needed at but didn’t seem engaged. These were trouble indicators enough but, in addition, his work was behind schedule and, even worse, it was sloppy.

The pressure and Carl’s lack of energy were starting to affect the team. Some members were getting angry. Others were starting to show up late too. The high team energy from project kickoff was fast dissipating.

Alison should have spotted the trouble earlier and acted earlier, but in this situation, she didn’t. She realized she needed to act now.

Prepare for Proper Action

As a leader, you have seen situations where it was clear that if issues weren’t already apparent, they soon would be apparent to everyone and that they should be addressed quickly. Your ability to handle such situations is greatly amplified if you can first clearly hear your own inner voice. Understand why the situation at hand is important to you and to the group and why it is important that it be resolved.

Mastering this ability to hear and understand your emotions and what is behind them will help you immensely in taking proper action. Four steps are needed to prepare for proper action.

Understand What Emotions You Are Feeling and Why

What emotions are you feeling and why? It is really important to listen to your inner wisdom. If you are frustrated or angry with someone, it is important to stop and ask yourself why. Is the behavior simply annoying or will the behavior negatively impact the organization? Your answers are likely an important part of the discussion you need to have.

Having to deal with situations like the one in the case study is often very upsetting to a leader. There are many reasons why:

• Leaders already have too much to do. Thus, it is upsetting when some unexpected trouble occurs, but more than unexpected, the trouble often feels like it is a pointless, irritating distraction.

• Sometimes it seems that the greater the pressure the project and the leader are under, the greater the level of difficulty of the situations that arise. Often, it is just that the impact of ordinary trouble escalates if the project is already under pressure.

• Troublesome situations almost always stir up strong emotions. The fog the drama creates makes it more difficult to see the real problems. This is true for the people around the situation and for the leader.

• Confronting people with performance issues is difficult. Talking to people about what they are doing wrong evokes the feeling of being in conflict. Leaders, too, are susceptible to the fight or flight syndrome.

Any of these root causes by themselves can cause upset. When other problems join in, as tends to happen, it can be magnified into a worst-case scenario, adding to the stress level. The typical reactions to these difficult situations are the classics of denial, bargaining, anger, and depression.

For example, Alison had a combination of emotions. She was angry that the project and her own future could be jeopardized if the project failed to deliver on its promises. Further, she felt betrayed by Carl. There was also a feeling of shame that she was letting the overall team down that was counting on her leadership.

Emotions cloak the real problems in a fog that the leader must work to clear away. It takes practice for people to listen to their inner music and learn what their emotions are telling them. Two methods that are useful for this are:

1. Talk to a trusted peer. The trusted peer must understand that your goal is to sort out the emotions from the real risks of the situation. A good peer can ask questions and make observations that help you find the core of the issue.

2. Write down your emotions. Write down what you see as the root causes of those emotions. Write down likely risks and impacts. You may have other methods that work well for you. The important thing is to get clear about what the issue is for you.

Alison thought about her emotions after talking to a trusted peer and wrote down the reasons she was angry:

• Carl’s teammates felt betrayed and had additional unreasonable stress put on them.
• In spite of her extreme efforts to make a rational plan, and many difficult conversations with upper management, the project was now significantly behind.
• The project was very important to the future of the company.
• She personally felt embarrassed about the situation.
• Carl was causing her to fail her team, her upper management, and the future of the company. Her feelings were amplified because she had experienced a similar situation on a previous team that she had failed to handle.

When Alison wrote down these reasons she was able to separate her emotions from the real problem: Carl was not performing well. The team project was behind and Carl was the center of that problem. She also realized that the situation was not as bad as it felt. This situation could be improved and perhaps completely recovered.

Move Past Negative Judgments and Assumptions

Most of the time we really do not know why individuals behave in problematic ways.

While driving, my wife and I were just starting up a hill with a “no passing” line dividing the road. It was truly a do not pass situation. A car going outrageously fast came up from behind and passed us. I was immediately furious at the danger that driver put my family in. I assumed that the driver was evil incarnate. My words reflected my anger. We crested the hill to see the car screeching to a halt in the entry to a hospital’s emergency room with medics running toward the car. My assumptions changed and my anger was replaced with embarrassment and empathy.

Why do people act in ways that are disruptive to the team, the project, and the organization? In many work situations, leaders have discovered surprising reasons for the behavior of their troublesome team members. Many times, they learn that the troublesome people did not realize the negative impact they were having on the group.

When talking with a peer or writing things down, work to ascertain what facts and assumptions you have about the situation. The key is to truly realize that many of what you think of as facts are actually assumptions. You most likely do not know the reasons the situations are occurring. You may have a hypothesis, and you may even be right. Write your hypothesis down if you have one. However, it is rare in these situations that you really know why.

After Alison had written down the reasons for her anger, she was able to think more clearly. She considered her assumptions about Carl. On reflection, she realized that Carl’s past performance was not just good, but excellent. So, she quickly removed “incompetence” and “lack of talent,” which were judgments she didn’t even realize she was holding in her mind. She did note that it could be a lack of skill in that specific technology in which he was working. However, if it was that, why wasn’t he asking for help?

It was at this point that all the judgmental feelings and anger she had toward Carl dissipated. Alison realized she simply had to understand what was going on for Carl.

Prepare Your Clear, Short (Two Minutes or Less),
Judgment-Free Message

It is critical to make your message very concise. You want the key message to be heard. You want it to have impact. You want it to lead to positive change. Longer messages always consist of belabored points, emotions rising, and negative judgments creeping in. The person you are working with will then begin to wander in his thinking or interrupt you, and likely start disagreeing.

This is why the two-minute or less rule is critical. Although many people think this is too short, it is actually a bit too long. With practice, most leaders can reduce the clear message to about one minute or less.

If you read the following example feedback out loud you will see that it takes less than thirty seconds to deliver the message.

“Carl, I am concerned. We made a clear plan together and agreed to clear goals and a timeline. I know you are very capable of meeting these goals; however, for the last few weeks you have not met any of your commitments. This project is very important not just to me but also to your teammates and the organization. And your current shortfalls are having a negative impact on your teammates and the rest of the organization. I am concerned about you. I am concerned about the group. Can you explain what is happening?”

Set Aside Time with the Individual to Focus on This One Topic

It is best that you and the person receiving the feedback meet privately. Do not add other topics to this meeting. It is critical that you focus on your key message.

Also set aside thirty minutes to one hour so that time is there if needed. Most of the feedback sessions I have given, however, have taken less than fifteen minutes with positive outcomes.

The time set aside is to give both yourself and those you are talking with the sense that there is plenty of time to work this out.

Alison had her message prepared. She had removed negative judgments. She had time scheduled with Carl. She was ready.

Take Proper Action

Proper action is the center of your lever for change. With preparation on one end and follow through on the other end, proper action is the fulcrum, the critical leverage point to success. This is where you talk with the troublesome person, or even a troublesome group.

Follow these steps when taking proper action:

1. Meet in a private space. If necessary, this can be via videoconference or telephone, as is often required in our networked world. However, do not use email or other written correspondence, as the most likely outcome is to make the circumstance worse.

2. Deliver your key message. Do not start with small talk. Take time so everyone is properly situated, but there is no reason to delay. Delay will make the other person nervous and, even worse, it can make you nervous. You prepared by removing judgment and having clarity about the good the person is doing. Deliver your key concern with respect and empathy toward the other person. Do so concisely and without judgment.

3. Wait patiently and quietly for a response. Often you may have to wait a few minutes, or longer, for a response. The key is to be patient and wait for the individual to talk. If you have to wait longer, the response is often an unexpected set of events you did not know about.

4. Be in the moment. The best way to prepare for the response is not to anticipate what it will be. Sometimes the response is a complete surprise: a litany of the hard things going on in the person’s life. Sometimes the response is quick and easy. Once the response I received was “Alan, I have been falling short of my own standards and yours. I will fix it.” Given that you really do not know the response you will get, just be in the moment and listen.

5. Listen to understand. Stay focused on what the speaker is saying and how he is saying it. If there are parts you don’t understand just keep listening until the person is done speaking.

6. Reflect. Tell the person what you heard to make sure you did understand. Reflect both on the facts and the emotions. This is not a place to argue. For example, if the person is saying that you gave him bad guidance, the proper reflection is “You are saying that the guidance I gave you was not helpful. Can you elaborate on that?”

7. Discuss. It is fine to ask questions. It is fine to bring up things you are wondering about. The discussion part should not be long. It is just for you to make sure you understand the situation and the other person understands the impact his behavior is having.

8. Set expectations. The meeting must provide clarity on what your expectations are. This is the part of the meeting for the other person to listen and understand. Make your expectations clear. Test understanding such that you really do trust that he understands.

9. Ask for action steps. It is best if you set up a second meeting for the person to be able to take time to internalize what he heard. He will also have time to build a proper set of actions for moving forward. That is the simplest, minimal action item that should be taken during this meeting. If it went easy and fast, feel free to record the key other actions the person will take to remedy the situation.

10. Summarize. Conclude the meeting with a summary. There are a variety of responses that you would expect when delivering the difficult message that a person is falling short of expectations. You might expect to see anger or rationalizations or many forms of excuses. If you are centered and in the moment, you should focus on listening and also keeping clear in your own mind your expectations of excellence. The concern you started the meeting with was based on those expectations.

The meeting should also conclude with that clarity. The fact is that, overwhelmingly, people do have good intentions and are working to achieve the best results they can. Treating people with love and respect for their inner strength is the greatest part of the feedback you can provide. When you do so, they will most often rise to the challenge and improve the situation.

Alison Takes Action

Alison sat down with Carl. She gave the key message in less than one minute and then asked a question.

The message was simply the fact that the project was behind and the key reason was that the work that Carl had committed to do was not getting done. Alison also noted that Carl was not working in the way she had observed on previous projects. She told him the project needed his top performance, but she was more worried about him than she was about the project.

She asked the question, “It seems to me something has changed. What is going on?”

Her tone was calm and relaxed. Carl reported later to me that she was genuinely concerned about him. She waited in silence for about five minutes before Carl spoke. With tears he explained that he and his wife had decided to divorce. He was trying to keep it completely separate from his work life, but he saw now that he had failed.

He was then quiet again. After another minute he said, “I have to apologize to the team for my behavior. Also, you know I love this work. I will get back to my prior performance, but I will need help. Can you help?”

Follow Through

After the meeting, Carl walked into a room where the team had just gathered. He apologized and explained his situation. After he and the team talked, the whole team rallied around Carl and offered not just help with work but also various other kinds of support for his unwelcome life transition.

Alison also followed through by talking with Carl’s teammates and ensuring that a proper recovery plan was made.

The whole team rallied and delivered a very successful project.

Carl’s team members looked back to when Carl asked for help as the point of project turnaround. Most of the team members were unaware of Alison’s talk with Carl. Carl’s act was courageous.

He thanked Alison for her courage in being the catalyst for his change and the subsequent success.

Work Toward Mastery of Delivering Feedback That Makes a Positive Difference

A few months after I drafted this chapter and shared it with a client, he decided to use the techniques in a situation he was having. He had an employee who was constantly coming across as angry to all the people who worked for her and around her.

My client took a few days to prepare. He had one short talk with the disruptive employee on a Friday and, like magic, the employee had a new positive attitude on the following Monday.

Now months later, my client and the employee are still doing great. The formerly angry employee recently thanked her manager.

After the talk she was quite upset but realized first, that her manager was really concerned for her and her future, and, second, that her own attitude problem wasn’t about work, but about other things.

She resolved to change her attitude at work and at home. She did. And things at work and home improved. The first time the team leader employed these actions it took a few days to prepare. With practice he has decreased his preparation time to less than one day. Often he finds he moves through his emotions and past his judgments almost on the spot. Further, the speed of success of the people he provides feedback to is also improving. This is a journey of mastery.

As a leader, it is important to listen to your inner wisdom.

If something is upsetting you, it is almost certainly upsetting others. It is a problem to your group. It is your obligation to the greater good of the organization to listen to your inner music and take the actions that lead to a positive difference.


Reflect back on times that you received feedback that you needed to improve.

1. What was an example of useful feedback you received that made a positive impact on you?

2. What was an example of feedback you received that was a negative experience and essentially did no good for you, the group, or the leader?

3. What were the essential differences between those two experiences?

4. Repeat these questions for the times you have given feedback both well and poorly. What was the essential difference in how you did it?


If You Don’t Schedule Time for Maintenance, Downtime will be Scheduled for You

I saw a sign that read, “if you don’t schedule time for maintenance, downtime will be scheduled for you.” This phrase had such ancient wisdom it made me wonder if Socrates said it first. Following are some of the thoughts the sign brought up for me.

Look Under the Surface to Find Reality

When looking at new projects, we need to look under the surface of our ideas from two angles.

Create a Frame for People to be Heroes

The way we frame our challenges can have a huge impact on our outcomes.

Base your Body of Work on Making a Positive Difference

Following are five principles I use to guide the creation of my body of work.

Focus on the Big, Scary, Long Term Goals

Despite how much we complain, there is a joy to working on urgent items. They give us a ready excuse for not working on the hard things.

Everyone Makes Mistakes

About 23 years ago, I did a course in software development where I tracked every mistake I made. It was shocking and disheartening. I made too many mistakes. And I found that those mistakes were costing me too much time.

Are You Prepared

Last night, it snowed about 7 inches. The snow was not a surprise, and we were prepared. I was out at daybreak, clearing pathways for all to enjoy.

Mindful Enjoyment of the Holidays

December can be a busy time of celebrations, as well as a time of closing out one year and ushering in the new.

Do You Have a Powerful Personal Support System?

One of the most powerful things we can do for ourselves is to make a conscious effort to create, sustain, and grow our personal support systems.

Thank Some Engineers

This Thursday in the United States is our Thanksgiving holiday. This holiday means many things for many people. For me, this is a week of conscious gratitude.

“Whether you’re new to leadership ranks, a veteran, or recently promoted from one leadership role to another, Alan Willett’s Unleadable will lead you through the quagmire of difficult issues in turbulent times.  Alan gives you the courage and skills to lead in tough situations, with tough people, in a tough environment.  

Alan Weiss, PhD

Author, Public Speaker, Entrepreneur

 “Alan’s book is timely, topical and extremely valuable. Alan’s “out of the box” thinking is refreshing, challenging, wise and always useful. I highly recommend this book to leaders, potential leaders and the unleadable.

Barry Dwolatzky

Director, Director, Joburg Centre for Software Engineering (JCSE) Wits University, Johannesburg, South Africa


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