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5 Tips from NHL Player-Turned CEO Mike McKee

“I am a huge believer in modeling inside and outside of the workplace. I strongly believe in the expression, “actions speak louder than words”. I have tried to lead by example and model values around honesty, hard work, loyalty, fairness, and transparency in everything I do.”
I had the pleasure of interviewing , CEO of ObserveIT, a rapidly growing software company with offices in Boston and Tel Aviv. Prior to spending the last 20 years in technology, Mike was a professional hockey player in the National Hockey League, scoring his first career goal against Wayne Gretzky and the LA Kings in front of national TV audiences in the US and Canada on American Thanksgiving, 1993.

Yitzi: Thank you so much for doing this with us! What is your “backstory”?

I am not sure that I have an inspirational or aspirational backstory, but there are some recurring themes throughout my life which relate to the desire to compete, learn and create an energizing and fulfilling work environment for people.

From a very young age, I loved competing in sports. Sports provided me with the opportunity to learn, work with others, and compete in a unique way — until I had my first experience running a business in college. While at Princeton, I took over the student agency that made and delivered pizzas to students. After analyzing the competition, lining up new food suppliers, hiring new employees and designing a brand new pizza making process, I vividly remember the first night we sold 100 pizzas (historically the business sold 100 pizzas a week). It was the first time outside of sports I experienced an incredible adrenaline rush and sense of accomplishment. It was that experience that showed me how fulfilling it is to assemble a great group of people, get them aligned around a specific goal, and watch everyone grow and execute well together. “Work” could be fun and I realized I wanted to create similar work environments in the future.

Yitzi: Can you share the funniest or most interesting story that happened to you since you began leading your company?

Attention to detail was not the forte of many of the managers that were in place before I started at ObserveIT. I found a typo on a piece of sales collateral referencing an email address, “,” as opposed to “” If you look closely, an extra “t” in the first email address changes the meaning in quite a significant and embarrassing way. What was incredible to me was that people in the organization continued to use this piece of collateral despite the non-minor typo. It’s all “part of the journey,” as we like to say now.

Yitzi: So what exactly does your company do?

ObserveIT is a “people-focused” cybersecurity solution that helps organizations detect insider threats, decrease investigation time and prevent data exfiltration, e.g. make sure employees and contractors don’t intentionally or accidentally send confidential information outside of an organization.

Yitzi: What do you think makes your company stand out? Can you share a story?

One of our core values at ObserveIT is “Customer Centric”. While lots of organizations have a customer-oriented value like this, we truly live it. We want to understand how our customers use our software products and we want to make sure we are developing our products in a way that allows our customers to decrease their overall cybersecurity risk. At a recent Customer Advisory Board meeting, we had each of the ~12 participants introduce themselves and start talking about ways in which they use our products. The “introductions” lasted almost four hours and most of the attendees, ObserveIT customers and employees, said the meeting was one of the most valuable customer workshops in which they had ever participated.

Yitzi: None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are?

Without a doubt, my wife. There is no doubt she has more confidence in my abilities as I CEO than I do. When I played in the National Hockey League, most of the time I was marveling at the fact that I had made it to the top level and I was happy just to be there as opposed to having the full confidence I belonged there, that I was as good as the people around me, and that I was going to stay for a long time. I regret not being more confident in my athletic ability at that time. In business, my wife has given me great confidence that I should be a CEO, that I am an effective CEO and that I will be a CEO for a long time, if I want to be. I genuinely hope she is right because I absolutely love the challenge of building a business — especially the aspect of putting together a great group of people who believe in what they are doing and want to compete, learn, and work together to build a successful business that truly helps customers.

Yitzi: How have you used your success to bring goodness to the world?

I am a huge believer in modeling inside and outside of the workplace. I strongly believe in the expression, “actions speak louder than words”. I have tried to lead by example and model values around honesty, hard work, loyalty, fairness, and transparency in everything I do. I also try to share my work experiences and learnings through writing and public speaking — something I wish I had the opportunity to do more often.

Yitzi: What are your “5 Things I Wish Someone Told Me Before I Became CEO” and why.

Finding and hiring great people takes a long time and is a never-ending process. When I took over at ObserveIT, pretty much every senior management position had to be filled. I approached the challenge thinking it was a serial exercise and once I went down the list and filled every position, I would be all set. Little did I realize not everyone would work out and that the needs of a company are constantly changing as are the people within the organization.

You can never get close enough to the customer. While I have always been wired around ensuring customers are successful and get value from their investments, I have learned that staying close to customers and prospects through a sales cycle is the best way to fully understand their pain points, how your organization can help them and what competitors are out there. A customer or prospect cutting a check for something is the truest way of knowing what you are selling has value.

It is incredibly important to say, “I don’t know.” Fortunately, I learned this lesson in my first month as CEO. I remember calling an Executive Coach and asking him if it was “okay” to say, “I don’t know”. He gave me the great advice that not only is it okay, but it is a good thing because it sends the message that everyone needs to be constantly learning and that everyone will make mistakes. Saying “I don’t know” and asking what I fear are “dumb” questions, which usually don’t turn out to be dumb, is one of the things I have done best since taking this position.

Get your doors blown off! Establish a peer group of CEOs who will “blow your doors off” and give you really harsh and blunt feedback. Once again, I was given this advice soon after taking the CEO position and it has been incredibly valuable. Once a quarter, I participate in a two-day offsite with a group of eight other CEOs of similar-sized technology companies. Every time, I have gotten my doors blown off and learned many ways to be a better CEO, all while interacting with an incredibly high quality and well intentioned group of people. The forum has become two of my favorite days of the quarter.

Emerging companies are like adolescents: they are highly prone to wide mood swings. I vividly remember beating our forecast in Q3’16 when a big deal came in the last hour of the quarter. This was my second full quarter in the business and came on the heels of missing our number in Q2 and a lot of tough personnel changes that summer. The Boston office thus felt great and went out to celebrate the accomplishment. For the next two weeks, I was travelling to conferences and our Tel Aviv office. I came back and the Boston office was a train wreck: people weren’t excited to be there and there was very little leadership. Fortunately, the mood swung back in a better direction, but I realized how important it is to be on the lookout for these mood swings and address issues in their infancy.

Yitzi: Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US whom you would love to have a private breakfast or lunch with, and why? He or she might just see this ☺

I was fortunate enough to see Nelson Mandela speak at the Harvard commencement. The aspect of his speech that stuck in my head was the concept of leading from behind. He talked about great leaders being able to move a large group of people in a single direction with everyone thinking it was their own idea to go that direction; sort of like a flock of sheep heading in a single direction with the leader at the back. I would love to have had the opportunity to understand this concept more deeply and see how it could be applied to many aspects of life.