CHAPTER 9

recognizing coachable moments

seize the opportunity

Fall had arrived. The air was cool and crisp, and the trees were turning from green to bright yellow, orange, and red. For Ray Lewis, however, this fall was more than just a change of season; it was also a time of transition in his life. Ray had decided to embark on an educational and personal development journey that would prepare him for the next big step in his career—to assume greater responsibility in his family’s business.

That path had been laid out for Ray for many years. Already he was serving as corporate accounts manager for the company his family founded in 1989 to provide planned and emergency response services, including spill cleanup, environmental remediation, and transportation of waste. Ray’s father was part owner of the company, and he’d long been grooming Ray to play a more prominent role.

Not only was Ray’s professional future laid out for him, certain aspects of his personal future had been prescribed as well. For example, when the family decided to sell the home where Ray and his siblings had spent their childhood, they convinced Ray to help keep it in the family by buying it and investing money in its needed renovation.

All of this would have been fine—except that deep down, Ray knew he wanted something else, although he didn’t know exactly what that was. Fortunately, the executive MBA program in which Ray had enrolled, which included personal coaching, was designed to help him reflect on and articulate a personal vision for his future.

When Ray began working with his coach, he admitted that advancing in the family business felt flat and somewhat constraining. Yet the coach saw that Ray still seemed willing to fulfill the career path that had been carefully crafted for him (with loving intentions) by others. The “ought” self can be especially powerful when family relationships get mixed with professional work. Although he was eager to learn and grow, Ray hadn’t fully appreciated the power of identifying and pursuing his true passion.

That is the essence of what we call a coachable moment. For the coach, manager, teacher, or other helper, identifying a coachable moment comprises two aspects: (1) observing a critical situation or learning opportunity that the individual may or may not be aware of; and (2) correctly perceiving that the individual is open and ready for reflection and learning around that opportunity.

In this chapter, we’ll look at more examples of coachable moments and then how to determine if a person is actually ready to be coached. We’ll provide a practical guide for creating a safe space for reflection and openness, and we’ll discuss typical “tough” coaching cases and how the techniques of coaching with compassion can help.

coachable moments all around us

Ray’s situation came to light within a formal coaching relationship, but when we pay attention, we can see coachable moments in many scenarios around us. The senior leader who has been “invited” to take a promotion that will mean he’ll be traveling three out of four weeks every month and who is concerned about the toll that will take on his relationships with his wife and kids. The friend who feels a calling to start a nonprofit organization to help disadvantaged high-school students gain access to higher education—but who’s reluctant to quit her lucrative corporate career to pursue that calling. The employee struggling in his new supervisory role who now realizes he accepted the promotion primarily because of his family’s ideas about “career advancement.” The diabetic patient who refuses to adhere to his treatment protocol even though he knows there will be dire health consequences. The high-school senior who’s been accepted at several top universities, but who is unsure about what she wants to do in life and is thinking of taking a gap year and traveling around Europe before starting college. Or any one of the many professional women who left the workforce to raise children and years later feel lost as to how to jumpstart the return to a career.

But there are other key moments too. One major time when people are open to coaching and help is when they’re taking on a new position, according to research by our friend and colleague Claudio Fernández-Aráoz. He found that the first two years in the job is a critical time to help someone be more effective.¹ Claudio is tapping into a more general category of coachable moments—times of life or career transition. Additional examples of coachable moments might include an upcoming graduation, new job, first home purchase, getting married, having or adopting a baby, being laid off or fired, hitting the lottery, getting an inheritance, or being diagnosed with a lifelong or terminal illness. There may be other transition moments that might not seem as earthshaking as the above list, but they are all opportunities for individuals to rethink their personal dreams and visions for the future. In an earlier chapter, we referred to life and career cycles that also create such moments.

When we fail to recognize coachable moments, we miss the chance to help others. We don’t do this intentionally, of course; in the midst of our own hectic schedules and daily stresses, it’s easy to miss key moments in a colleague’s or family member’s life. Or perhaps we feel that we can’t be helpful because we haven’t experienced what the person is going through and don’t have suggestions to offer. Even if we recognize a coachable moment, however, we’ll likely fall short of truly helping the individual if we don’t respond to it effectively. And, as with many things in life, sometimes timing and readiness are key.

recognizing readiness

Whether a coachable moment is associated with a broader, long-term change effort or a more narrowly defined issue or opportunity an individual is facing, the person needs to be ready to be coached or else the impact will be far less meaningful. Bruce Avolio and Sean Hannah have studied readiness in the field of leadership development, which we can apply to coaching readiness as well. They found that when companies target employees for leadership, sometimes they need to assess and enhance, if necessary, the developmental readiness of those individuals.² Likewise, before trying to help someone through a coachable moment, coaches or other helpers should assess and if possible, enhance, the coaching readiness of the individual.³

The model of change developed by James Prochaska and his colleagues stresses the importance of readiness to an individual’s change efforts. This model has been widely adopted in the fields of psychotherapy and executive coaching and consists of five stages, the first three of which (pre-contemplation, contemplation, and preparation) describe levels of readiness.

In the pre-contemplation stage, individuals are clearly not yet ready to change; the need or desire to change is not even on their radar. In the contemplation stage, they still aren’t quite ready to change, but they are at least thinking about it and trying to get themselves ready to do so. It is not until they reach the preparation stage that they are truly ready to change, however. Until individuals reach this stage of readiness, they are unable to effectively move on to the action and maintenance stages of change (the fourth and fifth stages in the model, where change is actually made and sustained).⁴

responding to a coachable moment

We sometimes respond to coachable moments by treating them as problems to be solved. As a result, we offer advice or solutions rather than coaching. While this may seem to be an effective way of helping at that time, it is less likely to lead to learning and growth for the individual involved. It is just not sustainable. The difference between advice and coaching is nicely expressed by the aphorism, “Feed a man a fish so that he can eat today; teach him to fish so that he can eat for a lifetime.” Another example is that of a teenager who has just been told a valuable “life lesson” from his parents—but he promptly forgets because he hasn’t experienced the situation himself.

As coaches and professors who advise PhD students who are typically in their thirties, we can add that when we give in to the urge to offer advice, the advisee sometimes (if not often) ignores it. But when we’re able to recognize and take advantage of coachable moments in ways that inspire a student’s growth and curiosity, that’s when we, as advisers, truly become coaches.

Coaching with compassion is how we help a person frame the situation or opportunity in the context of who she wants to be as a person and what she would like to achieve in her ideal future. Such broad framing helps the person draw on the inner resources most likely to enable her to learn, change, or grow in meaningful and sustained ways as she works through that situation, whatever it may be.

Remember too that coachable moments may also take the form of something smaller in scale that doesn’t necessarily involve a career or life decision. (See the sidebar “Recognizing Micro-Coachable Moments.”)

challenging coaching cases

As we have discussed throughout this book, coaching with compassion generally leaves the person being coached feeling excited, energized, and ready and able to pursue sustained change. Most people welcome the opportunity to be coached in this way. After all, who wouldn’t want someone to help them articulate and then pursue their dreams of an ideal future? However, sometimes helping someone can be difficult, even when you are coaching with compassion. Next, we explore five typically challenging kinds of coaching situations. Although the examples we offer here are all from professional coaching cases, the lessons are the same for anyone—managers, teachers, parents, and so on—trying to help another person change. Reviewing these cases should better enable you to handle them, or similar cases, should you encounter them.

satisfied with life just as it is

Many years ago, when Melvin was just starting out as a coach using intentional change theory and the coaching with compassion approach, he ran into a case that really stumped him. In the short time he’d been coaching with compassion, he’d come to think of it as “liberation coaching.” He was amazed at how freeing it was for individuals to frame the coaching engagement, and what they hoped to get out of it, in the context of what they truly wanted to do with the rest of their lives. Tapping into their passions, dreams, and deepest aspirations as the overarching frame for their desired change efforts was transformative for many individuals. And even in the cases where it wasn’t necessarily transformational, it seemed to at least be an energizing, positive emotional experience for almost everyone he coached in this way—at least, until he met Anjit Singh (not his real name).

At fifty-three years old, Anjit had successfully moved through significant positions in quality control, manufacturing operations, and IT in a major US chemical company. Anjit and his wife Indira, to whom he had been married more than thirty years, had three children who were now grown, successfully building careers and lives of their own.

While most people Melvin coached found it fun and exciting to reflect on exercises designed to help them craft their ideal self and personal vision, Anjit found the exercises difficult and of limited value. From his perspective, he had a job that he loved, and he had a wife, family, and overall life that he loved even more. What was there to dream about? There was really nothing in his life that he wanted to change.

Having coached some individuals who were initially hesitant to allow themselves to dream about an ideal future in an unconstrained fashion, Melvin kept encouraging Anjit to allow himself to think about an ideal view of the next phase of his life—even if he was incredibly happy with where things were today. Still no movement from Anjit. He saw no value in envisioning something else other than what he was currently experiencing.

Melvin was puzzled and wondered if he were doing something wrong. Why couldn’t he find the “magic questions” to open Anjit up to the exciting possibility of envisioning even more for his life than he’d already experienced?

That’s when Melvin asked his mentor Richard for help; surely, he had the silver bullet that would open Anjit up to some desired change he wished to make in his life. But what Richard said surprised him: for some individuals, the ICT process is not about making a desired change to achieve an ideal self. Instead, for some it is about sustaining or maintaining an ideal self already achieved. That was an enlightening moment for Melvin as a coach: the ICT process does not always have to be about making change. If someone has already achieved a desirable life, unless and until that image of his ideal self changes, the process can be more about doing things that will support and maintain that ideal life.

Melvin shifted his approach with Anjit, and it clicked. Now Anjit could embrace the intentional change process as something more than just an exercise that had no real value to him. Instead he could begin to envision ways to solidify and sustain the wonderful life that he had already created. He was able to articulate a vision and develop a plan to ensure that he was prepared to deal with any potential factors that could impact his ability to sustain the ideal life he had achieved.

living in a repressive or oppressive environment

In 1996, the Weatherhead School of Management received a grant to offer top executives from a number of Russian companies advanced techniques and ideas in modern management and leadership. One participant in the six-week program was Julia (not her real name), the CFO of one of the largest engineering manufacturing organizations in Russia. Richard was her coach in the program.

Walking into the management building on the third morning of the program, Richard saw Julia and smiled, asking how she was doing.

She grimaced and said, “Awful. I was so upset that I could not sleep.” Richard said he was sorry to hear that and asked what had upset her. She turned to him and said, “You!”

Richard, who thought that the seminar and discussions had gone well, was shocked. He asked, “What was it I said or did that was so upsetting?” By then, they had reached the lobby and Richard suggested they get a coffee and talk.

When they sat down with their coffee, Julia explained:

At this point, Julia was hanging her head. Richard waited before she added, “It feels like such a waste of talent—all those years and decades. I don’t know if I can change sufficiently to even create a personal vision.”

Although Julia’s example was extreme, there are many refugees fleeing countries under conditions of war or religious, economic, political, or psychological oppression who have trouble once free. In his classic analysis, Viktor Frankl documented how he and many Holocaust escapees and survivors had difficulty for years in their new home countries because their existence was entirely focused on surviving or their family surviving. During the process, many lost hope repeatedly.⁵

In Julia’s case, she would be leaving the program to return to a dramatically changed environment but with her old beliefs and ways of dealing with management issues. The way to handle this coachable moment, then, was to reduce her anxiety and focus on what kind of person she wanted to be. By helping her focus less on what she hoped to do and more on her values—who she wanted to be and how she acted with others—Richard was able to help Julia focus on something within her control. Julia’s values were uniquely her own; reflecting on them allowed her to return to her authentic self, which was both grounding and liberating.

When working with people whose environments are restrictive, the best approach is to focus on their core values—those beliefs about what is right, good, true—which are fundamental to being, living, and if appropriate, leading authentically. From that foundation, they can often consider behaviors and actions that can be seen, altered, and experimented with day-to-day in support of their values. That is often more feasible than framing a ten- to fifteen-year personal vision.

torn between equally attractive and mutually exclusive ideals

Joseph (not his real name) had just gotten his dream job as CEO of a midsized company. He wanted to advance even further, however, so he was completing a doctorate at the same time. He had used visioning and planning his whole life and had even taught the process as an adjunct professor to MBA students. Joseph had outlined stages in his coming years with the priorities shifting at each stage. In his current stage, he wanted to be a better father and husband, as well as a better human being to everyone with whom he interacted in contributing to his community. He wanted less stress in his life and to be more mindful.

Joseph had three dreams. One was to build the company and show how effective leadership can work. The second was to lead a more balanced life and spend quality time with his family, friends, and others. His third dream was to write, publish, teach, and be a public speaker who motivated others to reach for their dreams.

The dilemma was that he could not feasibly accomplish all of those at the same time. The time and energy demands of running and growing a business were, on the whole, incompatible with a more balanced, less-stressful lifestyle. His coach tried the one thing that often works with people with multiple dreams, some of which appear to be incompatible. The coach asked Joseph to prioritize his dreams—literally, to rank order them. “If you could only do one of these, which one would you want to do the most?” Joseph knew that it was to be with his family more. But he had led a driven life and work style. So the coach asked, “Which of the other two could allow you to spend more time with your family than you do now and still pursue that work dream?”

Like getting hit by a bolt of lightning, it became clear to Joseph that he needed to make a specific plan to transfer leadership of the company within two years. Before that happened, he was able to begin publishing and giving lectures at various universities. He tried to include his family on more of his work trips, planned more vacation and relaxation time with them, and promised that after the CEO job was finished, he would devote a great deal of his time to his wife and children. Within two years, as he completed his doctorate, he had transferred ownership of the consulting company and explored faculty positions. He was hired as a tenure-track professor at a university that emphasized teaching and not the publish-or-perish race he wanted to avoid and that would threaten progress on his other ideal—spending time with his family. Today, a number of years have passed, and Joseph reports he has succeeded. But he could not have gotten to this point without confronting and reprioritizing his aspirations.

too much invested in the current path to change direction now

Gabriela (not her real name) was a prosecutor in a midsized US city. She was intrigued with how coaching might work and agreed to meet with a personal coach—but that was about the limit of her willingness to explore possibilities.

When the coach asked her about her dreams of a perfect life, she looked at her watch and said, “This is too self-serving.” The coach understood that she didn’t feel positive about her future possibilities, but what he didn’t know was just how hesitant that made her about even talking about it. The coach asked about her ideal image of work. Her response focused on resolving present workload issues. He asked about her dream of an ideal personal life. She said she didn’t have time for one.

Gabriela had come from a working-class family and was the first to go to college. She was also the first to attend graduate school and become a professional. With a highly prestigious government job, Gabriela had achieved more than she had ever thought possible as a young woman. She did it by working harder than anyone else around her. She had sacrificed when friends were having fun. She had devoted herself to her work in ways that others thought a bit single-minded.

But she had made it. Gabriela was now middle-aged and knew she’d paid a price for her success: she had missed out on having a family and enjoying the kinds of personal relaxation she knew others had. This wasn’t intentional. It had just happened that way. She had always focused on her career and hadn’t put the same focus and energy into dating and activities outside of work. Yet she felt comforted by the knowledge that none of her friends had gotten as far as she had, both professionally and socially.

Her coach tried many different approaches to get her to consider what she wanted out of life and to explore possibilities for the future. All she could see was the present. Although at some level, she may have felt trapped, she literally did not allow herself to think about it. It had taken too much to get to this point, and she was not going to give it up! For Gabriela, the coaching did not translate into new learning, new insights, or new behaviors. Perhaps at some point in the future, she’ll have an awakening of some kind, after a crisis or other kind of transition, and be ready to engage in the process. But this was clearly not that time for her.

Another variation of someone not ready or willing to be coached is when the person goes along to “play the game.” This happened to one of our colleagues, who tried to help a former coachee, Franklin (not his real name), who had just been released from prison and was out on parole. Although they had an engaging initial conversation, Franklin’s coach walked away unsure anything would happen as a result. With a history of multiple convictions and even more arrests, Franklin’s past did not offer a lot of hope. But his coach knew he’d started a driving service, and he’d gotten a job as caretaker for a local community center—so he had at least a fighting chance to succeed this time.

The challenge was that Franklin couldn’t see anything beyond his current tasks. He had not a long-range dream but rather a short-term plan—staying out of jail and having some form of legal employment. While the typical “coaching to a long-range vision” method did not seem to help or even engage him, he at least was willing to discuss his steps and intention of staying compliant with the conditions of his parole and making a life for himself.

That’s when his coach shifted his focus from the future to the present. “How do you wish to be acting and to be seen by others now—this week, next month?” the coach asked. That engaged Franklin. Like many people with biochemical or behavioral habits that are addictive and that simply recreate the conditions that got them in trouble, people in these situations are fighting against the odds of recidivism and their own past. By focusing on the present, Franklin was able to work with the coach to find new social groups and develop a new identity to make a sustainable change in his life. Besides building his new business, he wanted to be seen as someone who was trustworthy, reliable, and approachable. Reflecting with his coach on this identity he desired gave his life new meaning.

trapped in an “ought” self

Recall our opening story of Ray Lewis. He proved to be a challenging case for his coach. Here was a situation where the coachee knew that he wanted to do something other than what he was doing currently. But he was having a hard time envisioning and articulating what that might be, and an even harder time imagining how he could possibly pull away from the path that had been so clearly established for him.

Ray’s coach, however, could almost see another version of Ray, inside of a shell trying to break out—but that shell of his “ought” self was seemingly impenetrable. His coach tried a number of ways to help Ray imagine what a self-defined view of his ideal future might look like, but Ray was so clear on what his father wanted for him that he couldn’t craft his own vision. And because he loved his father dearly and didn’t want to disappoint him, Ray felt truly trapped.

Throughout their relationship, Ray’s coach continued to challenge him to examine and then follow his heart. Eventually, Ray decided that it was time to take a bit of a leap. He could no longer suppress the desire he felt to explore a life of his own choosing. Ray took a leave of absence from work and spent some time traveling the world. During his travels, he reflected on who he wanted to be and what he really wanted to do with his career and life. It was during these travels that things finally clicked for Ray: he knew what he wanted to do and how he was going to go about doing it.

Sometime after his return, Ray attended an executive MBA alumni function. He immediately approached his coach and confidently shook his hand, saying, “Hi. Meet Ray Lewis.” Ray had finally found himself. He had discovered his ideal self and, with it, the passion and confidence to pursue it. He now knew in his heart what he wanted for his future. With his newfound passion and confidence, Ray soon left the family business and cofounded a small business of his own. Since that moment when he was able to escape the grip of what felt like a constraining “ought” self to pursue his own ideal vision, Ray has flourished both personally and professionally. His relationship with his father (who eventually understood and respected Ray’s decision) is as strong as ever, and he is living life with a newly found sense of joy and adventure.

Recognizing coachable moments so that we can effectively capitalize on them and being able to handle challenging cases in addition to the “easy” ones are important for coaches, managers, and anyone else trying to help another person. Our approach of coaching with compassion, and the various nuances we have discussed in this book, should equip you to do both of these things well. In chapter 10, we offer final words of inspiration to prepare you to go forth and, we hope, apply the things you have learned in this book as you help others through coaching conversations that inspire them.

key learning points

1. A coachable moment involves a potentially critical situation or learning opportunity of which the person to be coached may or may not be fully aware, and the coach correctly perceives that the individual is both open and ready for reflection and learning around that situation or opportunity.
2. Capitalizing on coachable moments often involves assessing and potentially enhancing the readiness of the individual to be coached. If an individual is not ready to be coached, the extent of their coaching-facilitated change is likely to be limited.

reflection and application exercises

1. Think about the last time you encountered someone who was in the midst of what we have described in this chapter as a coachable moment. Did you recognize and treat it as a coachable moment? How did the person respond? Was she ready to be coached? Is there anything that you would have or could have done differently in your handling of the situation to be most helpful?
2. What are some of the more challenging cases that you have encountered as a coach, manager, teacher, parent, cleric, or other person who was trying to help someone? How might you apply some of the lessons learned from this book to help you in the future more effectively deal with those situations?

conversation guide

1. What ideas or techniques from this book are you eagerly looking forward to trying and developing further?
2. Are you finding coachable moments in one aspect of your life and work, but not others? How can you become sensitive to such moments in the other aspects of your life?