Why Executive Coaching?

One of the most frequent questions I field is a variation on one of the following themes: why did you get into executive coaching? When did you know it was time to leave corporate America? What is it about business coaching that draws you? How did you make the leap into entrepreneurship? 

Here’s the blunt answer as to when I knew it was time to leave my role as a corporate executive without a crystal clear vision of what was next: 100 hours. That’s how many hours I spent in a room, on a call, or on video with my boss in 2017 absent any purpose other than for him to hold court. On the surface that’s a remarkable investment of time, made more so when considering there were productive meeting commitments, too: project meetings, team meetings, one-on-one meetings with my direct reports, skip-level meetings, and so on. 

This is not to say that I had a tick-sheet with a threshold that, once achieved, was my indicator to exit, stage left. It was more the headline that summed up a tumultuous relationship – one that so many people can relate to in some form or fashion having had their own experience working for “that guy”.

My Own Executive Coaching

The neon, blinking headline of 100 hours is the clearest symptom of what can only be described as a dearth of leadership acumen, skill, proficiency, and accountability in many offices all over America. And that painful experience working for an organization I deeply admired, doing noble work with a team I adored, yet a boss that struggled with integrity and accountability planted the seeds for what would sprout into my own executive coaching, team effectiveness, and EOS® implementation business. My core values of Kindness, Clarity, and Accountability brought to life through Challenge, Evolution, and Opportunity in my own business were borne of the fire that comes from working in an atmosphere of acknowledged incompetence. That was a profound insight gained during my farewell tour during my final eight weeks of employment; a myriad of commentary from leaders ranging from front-line to senior-level – acknowledging my boss’ limitations, leadership struggles, and lack of effectiveness.

If I were speaking these words you would hear no vitriolic tone, no affront, not a stitch of grievance, but rather a cogent after-action report. What you should also know is that I had my own accountability to confront – all of the things I did not say to the people that needed the information, so that they could have made better decisions about our leadership structure. What does that mean? It means that the boss’ leader met with me quarterly and asked three questions: who’s in your way, what resources do you need, and how can I help? You’ll notice I referred to her as a leader because those are the kind of questions leaders ask. Unfortunately, my answers were not equal to her leadership. I said nothing. I did not provide her with the facts (those 100 hours and other particulars) that would have told her that the grass appears green, but there was a septic tank brewing underneath.

Helping Leaders Become Stronger

After I left, cleared my head, and got real with myself, the future became clear. I would dedicate myself to helping leaders become stronger versions of themselves, build better relationships with their teams and customers, and create a future for their business that they truly looked forward to. 

Why would I tell you a story sharing what I did *not* do correctly rather than persuade you with a story of having slayed a mighty dragon, stormed the castle, and rescued the innocent villagers? Because that isn’t real life and that’s not how I learn – nor does anyone else. We do learn through successes when we can discern between skill and luck. We also learn by screwing up, owning up, speaking up, and then standing up to move forward, and to challenge ourselves to then go further, faster. This is what executive and business coaching is all about. Insight. Objective observation. Real conversations where we courageously interrogate reality. It can be a challenge. We then get real about what must change and evolve. And ultimately we reap the fruits of our effort with the inevitable opportunity springing from this type of deep work.

Reflecting on that experience and asking myself how I was showing up if I was able to deliver my best work, and most of all, whether or not I was happy led me to a place where I once again work for an extraordinary company (my own), serve amazing people (clients that are CEOs, business owners, and executive leaders), and deliver with kindness, clarity, and accountability. What could be better?

Check Out More Articles From Our Blog

Skip to content