Coaching Entrepreneurs

For successful entrepreneurs, coaching is an incredibly valuable tool. Coaches help you uncover blind spots, maintain accountability, and find new solutions to previously insurmountable challenges. What follows are brief accounts of ways that three of my clients used coaching to help them find the paths they were always meant to be on. (All names have been changed to preserve confidentiality.)

Marco was laid off from his job managing a high-profile NYC restaurant group. After the initial shock, he realized it was a blessing to be leaving an environment that he characterized as ‘toxic at best. Marco wanted to accurately assess why he found himself in his current situation, so he reached out to me for executive coaching.

Through coaching, we were able to gain insight into Marco’s behavioral patterns. We employed a technique I call The Crossroads. We looked at the times in Marco’s life when he had found himself at a crossroads, and discussed the reasons behind his choice- making. Marco realized he could not stop looking in the rear-view mirror of his professional life. He had a debilitating fear of making mistakes.

At one point early in his career, Marco had an opportunity to make an investment in anew business. Though the opportunity was exciting to him, Marco couldn’t make up his mind and the opportunity slipped through his fingers. Later, when the business ended upfolding, he counted himself lucky to not have acted. But, we discovered that Marco’s habit of over-analyzing was only heightened by this experience. And he found himself unable to act for fear of failure.

But, every bad habit is created for a reason. At one time, that habit did serve you. So, Marco acknowledged where his bad habit had come from, and he gave value to why it had been created. I asked Marco to then thank the habit for the ways that it had served him, but then asked him to release it. This process was extraordinarily cathartic. Eventually Marco could make peace with his hesitant nature and boldly make new choices.

Ultimately, he decided to pursue his own venture and to use his skills to actualize a new service in the area of hospitality management. His new venture is an incredible success and he now considers being laid off as one of the best days of his life.

Jennifer was the executive director of an exclusive prep school in Brooklyn. She had an uncanny ability to hire exceptional staff, but recently she had noticed an underlying tremor in her professional life. There was no specific eruption that signaled any seismic shift, but she could feel that her joy in her work had waned, and she was rightly concerned by the departure of two of her senior staff within six months of one another.One of the texts we focused on was Marshall Goldsmith’s What Got You Here Won't Get You There: How Successful People Become Even More Successful! 1 We knew that Jennifer was adept at finding talent, but she was increasingly aware that she was having a hard time hanging on to that talent. In coaching, Jennifer came to see that she was micro- managing all aspects of her school. She was unable to delegate, had an incredible backlog of work, and her staff felt disempowered and disenchanted.

Using a technique, I call Practicing Small, we found that Jennifer was most comfortable beginning to work on her challenges of delegation at home. By simply asking herhusband and children to help her with some of the many household obligations that she’d always clung to as her exclusive province, she realized how much time and space she could free up for herself. Jennifer learned to trust and include, and her new ability to delegate spread quickly into her work life as well.

She was so enamored of the discoveries she’d made that she pushed her CFO for a coaching program for her entire staff. Now, as she prepares for her own transition out of her role as director, she is pursuing work in organizational psychology so she can start her own educational consulting company.

Deidre was about to re-enter the workforce after taking two years away from it to have her first child. As a well-known designer, she was concerned that her absence now put her at a disadvantage. She wanted to pursue a new facet of her work, but was consumed with her previous standing and felt any variation from her previous work would signal a failure.

Deidre sought out coaching to help smooth her reentry. As a jumping off point, we looked at a piece about Elon Musk from the popular blog The piece explores the necessity of constantly adjusting your goals to reflect your new aspirations. From there, we did an exercise I call All Things Under the Sun, where the client allows herself the space and time to truly envision all the things that she would like to pursue.This exercise allows clients to dream without the shackles of ‘reality.’ And more often than not, given this freedom, we all realize that what we truly want is more easily within our grasp than we’d previously thought.

Through this exercise, Deirdre was able to embrace this shift in her desires. She began to explore opportunities she had not previously imagined. She decided to join the board of a local non-profit whose mission was close to her heart. And she decided on a new position with her previous employer; one that made her happy while allowing her time to help her community.

For all my clients, executive coaching helped them to find more authentic versions of themselves. Coaching gave them the tools necessary to break through barriers and tackle their own self-limiting beliefs. Each one was then able to uncover the goals and pursuits that they found most engaging. They found a new path, and that made all the difference.

Alexandra Phillips