Charting the Course to Smoother Sailing

It’s lucky that Amy Gleklen’s father was a doctor. He had taught her the Heimlich Maneuver when she was young, and the lesson stuck. One sunny day years later, Amy was hosting a pool party for her daughter, when one of the little girls began to choke. “A piece of watermelon lodged in her throat and she couldn’t breathe,” Amy recalls. “Everyone else just sat there. The girl’s mother rushed over but didn’t know what to do, so I took over and tried the maneuver. I thought, not on my watch! My friends remarked how I had gone into action, and I realized that, yes, that is how I’m wired—quickly jumping to action to solve the problem before me.”

Whether I’m helping people make better choices, navigate a career move, overcome an obstructive behavior, or solve a business dilemma, it’s always about following their energy, exploring choices, and charting the best course forward to a better future.”

Amy has always been equal parts visionary, mapping out the future, and activator, making things happen. From the time she was young, she eagerly explored different paths to discover what could be, never content to pick the safe or comfortable option for herself. And as she navigated through various roles, she cultivated a deep understanding of all aspects of business, including sales, marketing, finance, budgeting, and operations. She ultimately came to find that her own circuitous route was the powerful delineator that allowed her to understand diverse contexts, experiences, and possibilities, building just the insight that today’s leaders need most when facing their toughest challenges. “Executive coaching is my purpose and passion,” she says. ”And thanks to my own career trajectory, I can understand my client’s context and offer a business perspective. Whether I’m helping people make better choices, navigate a career move, overcome an obstructive behavior, or solve a business dilemma, it’s always about following their energy, exploring choices, and charting the best course forward to a better future.”

Today, Amy puts this gift to work as a Chair for Vistage Worldwide, leading two peer advisory boards for CEOs in the DC metropolitan area, and as Founder and CEO of Next Game Plan, Inc. She launched Next Game Plan in 2008 and grew it through a combination of executive coaching, leadership development training, and career coaching services. “My clients are diverse but have one thing in common: they’re stuck and want clarity,” Amy explains. “Sometimes our work is spurred by feedback from co-workers, and sometimes it’s self-motivated. They need a trained coach to ask good questions, help them understand the problem more fully, make connections, and see choices and possibilities. Once we do that, then I help them commit to new actions to lead to desired results.” Amy loved this work, but something was missing. “As a solo practitioner and executive coach, my clients are my community,” she recounts. “But most clients engage for only six months or a year to tackle specific coaching goals. I missed being part of a larger, more enduring community.”

In 2014, when Amy learned about Vistage, she knew it was just what she wanted. Not only could she be part of an outstanding worldwide organization with over 22,000 members in 22 countries, but she could also be responsible for building her own community through her advisory groups as a Chair. Each individual Vistage Chair builds his or her own independent boards, each structured to accommodate the specific and local needs of its executives.

The combination of individual coaching, group mentoring, and community building was perfect for Amy. Her first group launched with thirteen members, including several CEOs from larger businesses that faced challenges unique to their situations. Within the same year, she decided to build another group targeted to more experienced CEOs, all while continuing her private coaching work at Next Game Plan.

Balancing these demands has been exhausting but incredibly rewarding. She received a “Rookie of the Year” award in 2017 for her work at Vistage, but her proudest moments always come when a client tells her that the work they did together made a difference. “It’s the emails I receive years later,” she affirms. “For instance, I was at an event the other day, and one of the caterers notice my name tag. She told me I worked with her son, and it had changed his life. At the end of the day, I really do what I do because I know I’m making a difference.”

For Amy, then, success is the joy her clients feel when their issues are resolved, measured against the frustration or sadness her clients feel, visible in a client’s face in that first session or Vistage meeting. “Through that process, we become like a family,” she remarks. “Over the course of my coaching career, I started working with senior management in organizations and found they don’t often have people or colleagues in their lives who they can trust fully and who will hold confidentiality. Now, when I work with a client, I feel like their best friend because I have no hidden agenda and have only their best interests at heart. I feel humbled to be that person for my clients at a time when they need it the most, and the honor of helping others be happier is a great joy in my life.”

In reflecting on her path, where seemingly disparate experiences and talents brought her to a place she never imagined but fits perfectly, Amy often refers to a Steve Jobs quote that reads, “You can’t connect the dots looking forward; you can only connect them looking backwards.” Her work, in turn, is about connecting other people’s dots, helping them figure out where they need to go next. It embraces a philosophy of forward momentum that avoids getting stuck in the present—a mindset that served her well through her own childhood spent shuttling across countries and cultures at a young age.

Amy’s father, whose own father was German and mother had fled the Russian Revolution, was born in Switzerland and met Amy’s mother while attending New York University. They moved to Dayton, Ohio, where he opened a successful private practice as a physician. Within a few years of Amy’s birth, he grew restless and dreamed of moving to Israel. At the age of five, Amy was heading overseas with her parents, two older brothers, and three dogs, with her father’s Airstream trailer and beloved boat in tow.

Amy’s father was promised a job there that never transpired, and for a time, the whole family lived crammed in their little trailer. Then they got a small house, and Amy was sent to an Israeli school for kindergarten, where she stuck out like a sore thumb as the only American. “I didn’t know Hebrew at the time,” she recounts. “I felt like an alien. The kids had never met an American before. I made up a language that was some combination of English and Hebrew, and somehow the other kids eventually started to understand me. But I cried myself to sleep a lot. Going to school was pretty hard for me.”

The following year, in 1966, Amy’s parents decided to head back to the States, but not to Ohio. Her father wanted to be somewhere he could use his boat and be near friends. They parked their trailer in a trailer park in Homestead, Florida, and once again, Amy felt like something of an oddity. “Even the Southern accent was different from what I was used to,” she laughs. “I went to first grade there, and then we moved to Maryland, leaving the trailer in Homestead. We’d go back three times a year, and I continued my friendships with people from the trailer park, which had a huge impact on me.”

In first grade, Amy hadn’t noticed much difference between herself and the other kids in the trailer park. But as she grew older, and her doctor father drove the family down in their Cadillac for visits, she began to see that she had significant privilege compared to the other children. “My life was so different from theirs, but I was still one of their best friends,” she recalls. “They nicknamed me the Psychologist because I was the person everyone came to for advice.”

She loved to talk—a trait she got from her father, a deep thinker and great pontificator who studied art, history, and politics. Family dinner conversations were his chosen medium for expressing his thoughts and ideas, cultivating Amy’s own analytical abilities and inspiring in her the same strong work ethic. Amy’s mother, meanwhile, has been her lifelong support system and confidant.

Amy grew up a natural extrovert always eager to perform—early expressions of the creativity and freedom of spirit that she uses to serve her clients today. “I’ve always been a ham, and I’m not afraid to make a fool of myself in front of a crowd,” she says. “Having fun, letting loose, and being creative is an important part of helping clients come up with creative solutions of their own.” As a kid, she was also a tomboy who spent a lot of time outdoors, climbing trees and playing with animals. She loved to talk—a trait she got from her father, a deep thinker and great pontificator who studied art, history, and politics. Family dinner conversations were his chosen medium for expressing his thoughts and ideas, cultivating Amy’s own analytical abilities and inspiring in her the same strong work ethic. Amy’s mother, meanwhile, has been her lifelong support system and confidant. “Now 91, she’s still my first phone call in times of trouble,” Amy says. “I learned compassion and unconditional love from her, and it was a great source of strength to know she was always there for me.”

After the family’s move to Maryland, Amy finally settled into a less transient lifestyle. In middle school, she remembers standing up for her best friend when a group of girls began bullying her. After that, she felt more socially isolated, but Amy was glad she had done the right thing and opposed injustice. In high school, she made plenty of new friends, was involved in musical theater, played the drums for several bands, and became a leader in her local Jewish youth group, United Synagogue Youth. She spent time demonstrating for social justice, focused significant energy on community service, and was also chosen out of thousands of people to receive a regional leadership award, marking an important milestone for her.

Upon graduating from high school, Amy enrolled at the University of Pennsylvania, where her father encouraged her to pursue medicine. She had worked part-time in his medical office from the age of thirteen, but she was reluctant to commit so much time to school and initially planned on becoming a nurse instead. But in her freshman year, a traumatic experience led her to change her mind. “A couple of years prior, I had been the last person to see my grandfather in his hospital bed before he passed away,” she recounts. “Then when I was eighteen, the rest of my family was out of town when my grandmother had a heart attack. I was the only one there with her telling her she was going to be okay, and I was the one there when she flatlined. I had completed one semester of nursing school, but I decided the profession was too hard, so thought I should pursue social work.”

But Amy’s father wasn’t a fan of her new career idea. “We were in a recession at the time,” she remembers. “He was worried about my job prospects, so I started looking through the course catalogue and came across Wharton School. He thought that was a great idea.” To submatriculate into the business school, Amy had to achieve a 3.5 GPA in her second semester. She dedicated herself to hitting the mark and was admitted to Wharton the following year as a marketing major.

In 1981, Amy graduated and landed her first advertising job, only to realize that advertising wasn’t her thing. She soon transitioned to Booz Allen Hamilton, where she had a much better experience as an internal consultant helping a partner run a 70-person practice. Her mentor there advised her to get an MBA if she wanted to gain any real traction in the business world, so she headed back to Wharton, where she also struck up a greater interest in public policy. She worked on the Hill between the first and second years of the program, but ultimately decided to accept a job offer from Merrill Lynch because it was the most coveted option at the time. “I ended up in healthcare finance on Wall Street,” she recalls. “It was pivotal for me because it was just not a good fit. It felt too empty, and I didn’t feel like I was really impacting anything. I would go home and fantasize about winning the lottery to help me escape my situation. At some point, I finally worked up the courage to leave. My boss thought I would regret it, but I never did.”

After Merrill Lynch, Amy was open to something new and different, and she didn’t have to wait long. Interested in getting involved in politics, she booked a train from New York City to Washington, D.C., and happened to sit next to a financial consultant to Joe Biden’s Presidential campaign. They conversed on the ride, and within a couple weeks, she was heading to Wilmington, Delaware, to accept a position as the National Budget Director for the campaign. “It was a great job,” she says. “I had a financial role with spreadsheets and budgets, but there was a purpose behind them. I cared so much more about what we were trying to accomplish.”

Also on that campaign, Amy met her husband, Jonathan. Jon was an intern, still in college and several years younger, who jokes that he was the “First Budget Director” on the campaign. The two hit it off, and at their wedding, Joe Biden commented that the pair was the best thing to come out of his campaign. The couple relocated to Chicago while Jon obtained his law degree, and then to DC, where he was hired by the law firm of Arnold & Porter. “The next ten years were kind of a blur!” Amy says. “I had a bucket list of career interests, which included television production. Then, around the time my third child was born, I went back to my roots and decided to get a Master’s in Counseling at John’s Hopkins.” Before she could put her new degree to work, however, fate intervened. A friend from Wharton was volunteering with an organization called Compass, and thought Amy might be a good fit for the Executive Director position. “I thought it sounded really fun because the goal was bringing together MBAs from top business schools to help other non-profits,” she says. “Up to that point, my career path didn’t seem cohesive, but Compass put all the pieces together. They happened to be piloting executive coaching for non-profit leaders through a one-on-one program, and the field seemed perfect for me, utilizing my MBA, my counseling background, and my yearning to connect deeper with people.”

Amy kept the idea of executive coaching in the back of her mind, ultimately deciding to enroll in an intensive 6-month Executive Leadership Coaching Certification program at Georgetown. “The girl who didn’t want to become a doctor because it was too many years of school, ended up getting two Master’s Degrees and a Certification,” she laughs. “It turns out I do love learning. I’m learning all the time, and I’m hugely passionate about it because I get to apply my knowledge and breadth of experience to help my clients move forward.”

Through it all, Jon has been a partner and support system in every way. “He helps me think through my own issues, especially the curves and moments of inflection I’ve experienced along the way,” she reflects. “He’s worked at one law firm his entire career, but he’s always been supportive of my bucket list and my interest in trying new things.” Their four children—2 boys and 2 girls— are now happy and healthy at 24, 22, 20 and 16. “I am so grateful for my beautiful family. I am very lucky.”

As a leader, Amy focuses on inspiration and collaboration. “You have to both see the big picture and set the course, and you have to invite others to help and participate,” she says. She keeps in her mind life’s inverted truth—its fragility and unpredictability, as hammered home when her son, Ryan, grew a tumor between his eye and nose at only nine months old. “Instead of freaking out, my reaction was, what’s the big picture and what’s the next step?” she remembers. “What’s really going on and what are our choices for moving forward? It’s the same way I coach my clients. If you only have one life to live, it’s important to think about how you want to live it and the imprint you’re making.”

In advising young people entering the working world today, Amy underscores the importance of continued learning and growth, because we’ll never have all the answers. “Know how you got to where you are, because there are plenty of lessons to learn,” she says. “Once that’s clear, you can get some sense of where you might want to go. Start to think not in terms of the present, but the future. It’s easy to get stuck in the present, and that’s when people become unhappy, seeing what is and not what could be.”

Beyond that, Amy encourages everyone to seek out the energy in life that speaks to them— that which is both profound and peaceful, like water is to her. “Like my father, I’ve always found being on the water to be a source of serenity,” she says. “It’s also a place where things can go terribly wrong, like when my son almost drowned. On the water, we’ve been both powerful and powerless. But with the right tools, the right mindset, and the right help by your side, there’s always a way to chart the course to smoother sailing.”

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