Swimming with The Sharks

From Therapist to Executive Coach

Magazine Issue
November/December 2012
Placeholder Image for psychotherapynetworker.org

My body knew it before my mind caught on. For a long time, I’d been growing antsy and having trouble sitting in my chair for the full hour of therapy. Too often, I watched the hands of the clock tick by in slow motion and thought about how many more clients I still had to see that day. I knew it was time to move on with a midlife career change, but what would I do?

For most of my life, the world of business seemed off-limits to me. I’d grown up in Detroit, the home of the automobile industry and a place where conflict between labor and management was the norm. From my father, I’d absorbed the unquestioned assumption that businesses were run by blustering bullies out to exploit their workers. When I entered the therapy world itself, I encountered much the same belief: that unenlightened materialism and cutthroat competition were the prime forces driving the business world.

But in the late ’80s and early ’90s, as I began to look at the impact of cultural definitions of masculinity on the men in my practice, I began to see how even business leaders were influenced by broader social forces. Despite being treated as superheroes in the office, they were “lost in space” at home–estranged from their wives and children, struggling with partnerships and friendships strained to the breaking point, chronically stressed out, and in ill-health. The lives of these presumably privileged people were severely out of balance.

I began to think about how I might work with corporations and business leaders to make work settings more humane and bring more balance to the lives of the decision-makers who shaped the work environments in which most people earned their livings. Eventually, I decided to switch my focus from doing individual and family therapy to consulting to business leaders on how to be more self-aware and compassionate. Although I was only dimly conscious of the emerging professional discipline of executive coaching when I started off, I became intrigued by the idea of applying my therapy skills to help business executives not only gain deeper insights about themselves, but learn methods for creating a more positive work environment for their employees.

Selling My Services (Hopefully, not My Soul)

The trouble was I knew little about how business worked. I had no clear idea of what made a successful company or a successful executive. I couldn’t read a balance sheet, and I was clueless about the specialized language and acronyms of the business world, like ROI (return on investment). It became immediately apparent that to survive in my new enterprise, I’d have to learn how to run a business myself. Sure, I’d run a successful therapy practice for more than 20 years, but I’d relied mainly on word-of-mouth referrals to find “new business” and didn’t need advanced financial knowhow to balance my books each month. Now I faced the challenge of moving into a field that required the mastery of more-advanced business skills, including sales, marketing, and contracting.

One of the most useful things I did early on was to enroll in a six-month training program in sales. I was intrigued to discover how much of the model for understanding sales and marketing had been drawn from psychology. Probably the most useful concept I learned was the idea of “pain points”: businesses understand that reducing pain is the most direct motivation for someone to buy a product or service. The omega-3 in fish oil may offer vast benefits for your mood and your heart, but you don’t rush out in the middle of the night when you run out of it; however, if you have a bad headache, you might well go out at 1 a.m. to a 24-hour drugstore that sells aspirin. Likewise, most people are likelier to buy services to relieve their immediate pain than to invest in their long-term growth or development. Accordingly, I learned to develop an “elevator pitch” that spoke to the prospective client’s immediate pain points. Instead of saying “I’m an executive coach who helps leaders grow and become better at running their company,” I discovered I got a much more enthusiastic reception when I said, “I’m an executive coach who helps business people face their toughest challenges and handle difficult situations.”

Early Missteps

My midlife career shift was far from an instant success. Within a month of launching my website, I received a telephone request for a consultation from Fred, a young man working for a large corporation on the East Coast. “How cool is this,” I told myself. “I’m talking from home, being well-paid, and doing work that I love.” The only trouble was, I realized after a few telephone sessions that I wasn’t at all prepared to help this young man tackle the challenge he was facing. After Fred’s company had been taken over by a larger corporation, he’d discovered some irregularities in the finance department where he worked. Should he be a whistleblower? Should he cover his own behind and ignore things? Should he look for a new job?

I quickly realized that I was in over my head. These were complex issues, for which I didn’t have adequate training. Furthermore, even though I’ve been told that coaching often was conducted over the telephone, I missed having face-to-face contact with Fred. I just couldn’t read his nonverbal cues, and I was easily distracted on the phone. I knew I needed to bring in other resources. After directing him to talk to a lawyer, I arranged for him to consult a more-seasoned executive coach, who could help him navigate the complex human resource issues involved in this problem.

From this early experience, I learned to be much more careful about contracting with clients. I had to be clear about what they needed and whether I could supply it. Furthermore, I recognized that, although telephone coaching seemed attractive, it wasn’t for me. As a matter of personal style and preference, I needed to see my clients face-to-face. Today, I do have some telephone sessions, but only after I’ve met with clients and arranged to see them regularly, in addition to the phone sessions.

After a few more years of training in leadership development, mentoring by other executive coaches, and successes with corporate clients, I was ready to make the transition from part-time therapist and part-time executive coach to full-time executive coach. I’d realized I couldn’t straddle these worlds and be successful in either, and I wasn’t doing my clinical clients any favors by sticking with my limited practice when my heart was in the exciting new possibilities that executive coaching promised.

What’s an Executive Coach?

In the dozen years since then, I’ve had the opportunity to face the full range of challenges that executive coaching offers. My work as an executive coach falls into several major categories:

  • Leadership skills
  • Career changes and/or transitions
  • Making tough decisions

Leadership Skills

The commonest requests for coaching come in the midst of difficulties within an organization’s hierarchy or within an executive team. Someone, typically the chief executive, recognizes a problem in how the team is functioning and typically suspects that the problem could be with one individual, who needs coaching to learn to interact differently. When an individual feels that he or she is being forced into coaching, the initial response is likely to be anger and anxiety about the job. I call this “remedial coaching,” and have found that it’s frequently unsuccessful.

The second type of request comes when an executive believes that coaching might make him or her a better leader. This type of coaching, which I call “leadership coaching,” is usually more productive. The contract might be to work on an individual basis with the executive, or to work with the executive and his or her team–which is my sweet spot.

Alysha found me through my website. She was acting vice president of the small computer-supply company that her father had started 30 years earlier. Trained as a lawyer, she had little business experience. After some discussion to clarify her goals and our working arrangement, we agreed upon a six-month contract, during which I’d help her become a better leader within the company.

As I typically do, I used some standardized assessments to help give Alysha a clearer picture of how she was functioning as a leader and how others perceived her. Most people assume that executive coaching focuses on correcting weaknesses, but I find people are already all too aware of their weaknesses. I like to use an approach, based in Positive Psychology, that focuses on identifying strengths, rather than shortcomings. It’s far more productive to teach leaders how to leverage their strengths, so that they can more effectively collaborate with others on their team whose strengths complement their own.

The initial self-report assessment I used with Alysha, based on the “Strength Finder Profile” in the book Now, Discover Your Strengths by Marcus Buckingham of the Gallup Organization, indicated that she was strongest in the consistency and collaboration aspects of business. This suggested that, if she were to think systemically about what her business needed, she might look for collaborators who were strong on the competitive and creative aspects of business development. I coached her on how to find and work with these types of people.

To learn more about herself from the perspective of others, I used an exercise called “The Reflected Best Self Exercise” developed at the University of Michigan. Alysha sent out 20 e-mails to friends, family, and coworkers, explaining that she’d started a leadership development program focused on expanding her strengths. She requested that they e-mail her feedback on what they perceived as her most positive attributes, as well as a brief story of a time they saw her functioning at her very best. Alysha was delighted by the supportive, confidence-boosting feedback she received.

A key characteristic of effective leadership is the ability to choose the right people to be on one’s team and to be sure that they’re in the right positions. One of the members of Alysha’s team proved to be a pivotal challenge for her. Sue was supposed to be specializing in developing new business, but she was actually much more interested in running the internal operations of the company. The problem was that someone else was in charge of operations. After several coaching sessions with Alysha and Sue, it became clear that Sue didn’t want the role she’d been hired to do. Alysha’s dilemma was that she liked Sue and was reluctant to give her the bad news.

Like so many executives with whom I’ve worked, Alysha preferred to avoid conflict at all costs. But the situation with Sue had reached the point where the future welfare of the company was at stake. Here, I had to use my familiar clinical skills to explore with Alysha why she was fearful of conflict. Together, we reviewed how her upbringing had influenced her to avoid conflict. She’d been raised in a culture where women were supposed to be “seen and not heard,” so to engage in conflict was seen as a breach of her culture’s norm of what it meant to be “a good girl.” Furthermore, as a female vice president in a male-dominated tech world, she felt unprepared to confront men who were far more experienced and adept.

I suggested she read Difficult Conversations by Douglas Stone and his colleagues, which explains how best to manage conflict. Through these explorations and readings, she learned how to resolve the situation with Sue. Through my coaching, she was able to reach an agreement that Sue would leave, with the understanding that she’d receive a positive recommendation for a more suitable job.

The next step of the coaching process was the most difficult and the one in which my family-therapy skills proved most relevant. Even though she’d been running the company for 10 years, Alysha was still officially only the vice president and hadn’t yet discussed a transition plan with her aging father. What made the situation particularly difficult was that, as a Muslim woman, she had to risk the disapproval of other family members if she were to take on the position of running the business, because men were the ones who were supposed to be business executives.

I was able to coach Alysha through a series of conversations with her father about her desire to run, and eventually, own the business. She discovered that her father hoped to be able to retire and wanted her to succeed him, but he was worried about treating his other children unfairly. Together, we planned a series of negotiations with her father and then processed how they’d gone. She found the negotiations emotionally draining, but was able to hang in with her father until they’d reached a mutually agreeable resolution. She was pleasantly surprised that her mother strongly supported her assumption of the role as the company’s top administrator.

Today, Alysha is the CEO of her company, which has doubled in size and employs more than 20 people, mostly women. She’s on extremely good terms with her father and her extended family. Seven years later, I continue to consult with her every month.

Career Changes and/or Transitions

A major part of my work as an executive coach is helping people confront the ambivalence and ambiguities of career transitions and changes. In this capacity, I work with a wide variety of people, from students trying to find their first job to midlevel executives who feel that it’s time to move on, within or outside the company, people who enjoy what they’re doing but wish to leave a toxic work environment, and older people who are considering cutting back or retiring.

With these clients, I like to draw four intersecting circles. In the first circle, I ask: Are you passionate about what you’re doing? In the second circle, I ask: Are you using your unique talents to the fullest of their potential? In the third circle, I ask: Does the community value what you’re doing, and are you working in a healthy work place? In the fourth circle, I ask: Are people willing to pay adequately for what you do? The intersection of these four circles is what I call someone’s “occupational sweet spot.” This is the kind of position and work environment I try to help them identify and achieve.

Recently, I’ve been working with a lot of executives in their sixties who are trying to figure out what to do about their careers. Most don’t want to retire, but also don’t want to continue in their current role. I’ve formed a group of six to eight business administrators that meets monthly to discuss how to transition from a key leadership role or business ownership to some other, less demanding role that still meets their needs.

One member of the group is 71-year-old David, who wanted to consult about whether to keep his 40-year-old speech-therapy software business going or to shut it down. As we talked about his situation, I jotted the four circles on a piece of paper and asked him to consider the key questions:

Is he passionate about his business?

“Absolutely, I love what I’m doing. I love helping families and kids. I love the challenges of the complex programming for a very large application.”

Is he using his talents to the fullest?

“Yes, I love programming. I love the marketing aspects of my business. Every day, I feel challenged and fully engaged on an intellectual and emotional basis.”

Does society value what you do?

“Decidedly, I help children with special needs, and now I’m able to offer my product to autistic children and others with speech problems.”

Are you working in a healthy work culture?

“Yes, I’ve been working with my partners for more than 20 years, and we get along extremely well. I enjoy myself and feel like I’m part of a great community.”

Are people willing to pay for your services and product?

“This is the problem. Our sales are way down, and we’re having a tough time meeting expenses.”

Additionally, since Dave was thinking of retiring, I asked “Do you have the energy, health, and family support to do the job?”

“Most of the time,” he replied, “but I’d like to be able to work fewer hours and take more time off.”

From this analysis, we determined that while the major problem was the lack of revenue for their product, Dave and his partners had other sources of income, and they didn’t really need much from the company. Furthermore, Dave had the flexibility to work as much or as little as he chose. The nature of the work didn’t require him to be in the office, or even on the computer, an intolerable amount of time.

I asked him where he could use his unique talents if he were to give up the business. “I guess I could stay home and work on my property, cut the lawn, and manage investments” he said. “I don’t know where I could use my talents. I could expand my role as a volunteer ESL tutor, which is related to my work.”

Where would he find a community like the one he’d built with the people he’d worked with for 40 years? “I don’t know. I’m kind of an isolated person, and it’d be hard for me to make new friends,” he said.

So why was he considering leaving the business? “It’s just not making any money. I hate going out this way. I want the software application to be of service, and I feel like a failure, even though I know we’ve had success for many years.”

Together, we developed a new plan. Dave would consider giving away the home version of the software to families who could use it, while still selling the professional version. Through parent endorsements, he might be able to raise more money to cover his operating costs. Since he didn’t have to make any more money on it, all he needed to do was generate enough money to pay expenses. Dave happily went off to talk to his partners about this approach. At this point, he’s still mulling over his options.

Making Tough Decisions

Fifteen years ago, Roger, a lipid biochemist by training and the codiscoverer of a highly successful cardiovascular drug, had left the large pharmaceutical company where he’d worked for many years to create his own biotech company. Now, he was striving to lead the company that he’d established as it developed a medication to raise HDL, the “good” cholesterol.

When Roger hired me as his executive coach, he was concerned that he didn’t have the right people on his team for his company to succeed. But as we worked together, he was surprised to discover that he, himself, needed to make changes.

He’d hired Tim, a very effective CFO/COO, to take charge of corporate finances and run operations, while Roger functioned as the CEO, president, and chief scientific officer. However, since both Tim and Roger were responsible for securing financing for the company, they were struggling over their respective roles. To help them gain clarity about their responsibilities, we did an exercise I’ve developed called “My Job, Not My Job,” which proved to be a breakthrough for their working relationship, allowing them to stop competing and leverage their respective strengths.

For the next two years, through monthly meetings focusing on communication and relationships, I worked with Roger and his executive team to create alignment and accountability. Then, Roger faced an excruciating decision. It had become clear that if everything remained the same, his company would run out of money before it could take its drug through clinical trials. The choice was clear: cut expenses. The best way to do this was to lay off staff. The problem was that Roger had a deep sense of commitment to his employees, so this choice was anathema to him. He felt that to lay them off would betray the trust they’d displayed in him and the company.

I facilitated meetings in which the executive team debated long and hard about what to do. After many sleepless nights, Roger realized that, as a CEO, his primary responsibility had to be not only to his employees, but to the company’s investors, the scientists who’d developed the drug, and the heart patients who needed it. When it came to laying off employees, he had to think about the good of the many, rather than the welfare of the few. This was a key leadership lesson for him.

Once Roger made the decision, I had to help him deal with his guilt and the sense that he hadn’t been able to uphold his core values. I worked with him and the executive team to insure that the layoffs were conducted as painlessly as possible. We spent considerable time discussing how to help those who were laid off find new jobs. I encouraged the executives to focus on working with the employees who remained so they’d stay engaged and productive. I helped them plan a meeting of the entire staff in which the leaders explained in detail why the layoffs had to happen–that reducing staff had ensured that the company had enough capital to survive until the end of the clinical trials.

In retrospect, the layoffs were the right decision for the company, which was able to meet its financial and scientific goals. After the clinical trials proved successful, several pharmaceutical companies tried to buy or invest in Roger’s company. While he tried to find a way to keep the company independent, the realities of drug development prohibited such a small organization from being able to complete the drug-development process.

It became obvious that Roger needed to sell the company to whichever of the larger corporations made the best bid. Ironically, the purchaser was the same company that Roger had left a few years earlier. The sale of this company was one of the largest in the state’s history, and was the entrepreneurial success story of the decade.


After 15 years of experience as an executive coach, I feel more passionate about my work than ever. Among many satisfactions as an executive coach, I can draw on all my psychology skills. I use behavior therapy to help people set goals and achieve results, cognitive therapy to help clients recognize how their thought patterns might be getting in the way of their leadership, and family-of-origin training to help clients recognize how they’re playing out family scripts in work environments. Drawing on my community-psychology perspective, I help companies design large-scale culture change. With my background in cultural and gender studies, I help leaders recognize the importance of diversity in the workplace.

An unexpected dividend of my career shift is how valued I’ve found my work to be by the general public. This was reinforced to me the other day when some people at a party asked me what I do for a living. When I told them I was an executive coach who helps organizations overcome negative practices, one man said, “Boy, could my boss use your services!” A woman engineer told me, “I need to meet with you tomorrow to help me deal with a difficult coworker.” In contrast, I remember the days when I told people that I was a psychologist and they backed away as if I represented a direct threat to their well-being.

I suspect that even my dad, with his strongly held antibusiness worldview, would wish me well. He’d be happy to know that I’m working to help companies, even large ones, become more sensitive to the needs and feelings of their employees. He’d probably say, “You mean you can make those bastards into nicer people? Good work!”


Photo © PBNJ Productions / Getty Images

Rob Pasick

Rob Pasick, PhD, a psychologist and executive coach, is the author of Balanced Leadership in Unbalanced Times and Conversations with My Old Dog.