My Biggest Leadership Blindspot, and the Moment it was Exposed

Imagine you employed a team of six strength coaches, and rather unexpectedly, three of them left to start a competing business…

This is the game we played at Cressey Sports Performance - Massachusetts (CSP) during the second half of 2017. As you might imagine, it was a time of turmoil in a business that was just passing its ten-year anniversary of operations. There were challenging transitions in our business that followed, and so many valuable lessons learned that my business partner Eric and I could probably write a book about the experience.

Today, it appears we’ve righted the ship, having positioned ourselves to make an honest run at CSP’s best year ever just 16 months removed from the third and final employee defection. It is important to note that we absolutely, positively, did not do this ourselves. Eric and I have leaned heavily on spouses, incredibly motivated and talented employees, and each other along the way.

As the dust continues to settle on a tumultuous period in our entrepreneurial journey, there is one lesson that stands above the rest in my own personal adjustment. I’m sharing it with you now because I’m certain that any gym owner who reads my material is either dealing with challenging times, or vulnerable to them in the not so distant future.

The lesson I learned was not an instantaneous one, but instead a necessary adjustment that took place over time. It was during recent a transatlantic flight that I stumbled upon a quote that made this experience all seem so simple and obvious in hindsight. And as they say, this hindsight stuff is always 20/20. 

The quote read as follows:

“No one yet has managed to figure out how to manage people effectively into battle; they must be led.”

Quote pulled from this bad boy. Great read.

Quote pulled from this bad boy. Great read.

Competing with former colleagues is a business battle of sorts, and I was fully aware of this reality in 2017 as we worked to rebuild our team while taking care of existing clients. I was not aware, however, that my efforts to manage the situation would be unproductive if I continued to misconstrue micromanagement for leadership. I’d somehow convinced myself that the things we needed were limited to tighter systems and as much structure as I could possibly throw at my organization.

I wasn’t wrong that these needs existed. 

I was, however, wrong to assume that my time was best spent being the person to deliver change on this front. As it turns out, an intelligent and detail-oriented employee was perfectly capable of dealing with the complexities of management, while only I was truly in a position to handle the biggest responsibility of leading us through a period of change.

Employees wanted clarity on the direction we would be moving with the structure of our staff. They also wanted to know that there were strategic objectives in place for retaining existing business and repositioning ourselves to generate new leads. At the time, I was capable of creating a strategy to address these factors, but too bogged down in the mechanics of managing to find time to share the message of where Eric and I saw us to be headed.

I needed a manager to assume control of all things relating to staff coaching assignments, continuing education calendars for the team, and so much more. The man for that job was (and continues to be) John O’Neil. 

While John was the first coaching hire we made following this staff shake up, it was nearly eight months before we realized that I needed a Chief of Staff, of sorts.

Today, John serves in a Director roll, and has assumed what I would call a leader-manager identity at CSP. He deftly handles the surprisingly complex logistics of delivering a quality semi-private training experience in an operation that averaged 102 athlete training sessions daily during the month of June (a 25-session/day increase from where we were at when the wheels came off in 2017). He also serves as the unofficial voice of the team, helping me to stay better in-tune with the collective attitude of our staff at any given moment in time.


I, in turn, am now able to spend more time behind closed doors discussing strategy with each of my employees. I am also given the opportunity to address circumstances of employee dissatisfaction in something closer to an immediate style, as opposed to in a retroactive format as was my habit in years past. Lastly, and arguably most importantly, this newfound freedom from the technical process of managing helped to free up time to drive more business through the doors. 

In short, I got my head out of my ass, stopped confusing a busy spreadsheet and calendar-management life with productivity, and got back to allowing my employees to see me as someone willing to lead.

Want to know the best part, outside of the revenue growth? John is better than me at every single task he inherited. Feels good to put that out there.

Does this sound like you?

Identifying and addressing our blindspots is hard as hell. Thing is, you’re probably already loosely aware of those blindspots, and just not willing to acknowledge them. Do yourself a favor, and empower an ambitious employee to assume some control of your operation. Shell out a few additional dollars in conjunction with a promotion in title, and use your newfound time to generate business that will far outperform the resulting increases in payroll commitment. 

The minute you stop trying to manage your team into battle, and instead start leading, you can expect to start winning.


My business partner Eric and I are going to spend Monday, September 23rd digging deep into everything from lead generation, to pricing strategy, gym design, and everything in between. If you’re interested in learning exactly how we’ve attacked building and maintaining the model we’ve had in action since 2007, this packed day of information is for you.

*** Take note that this registration includes complimentary attendance to the CSP Fall Seminar which is set to take place during the two days before our mentorship event. This one will be a good bang for your buck continuing education opportunity.

Check out all of the details HERE, and make sure to shoot me an email ( if you have follow-up questions.