The Art of Leadership: A Candid Discussion with NAI Global President & CEO Jay Olshonsky

As President & CEO of NAI Global, Jay Olshonsky, CCIM, FRICS, SIOR, values leadership, courage, coaching, listening and actively encouraging all to express their points-of-view and take on projects without fear of failure.

Jay began his real estate career in Washington DC in 1982 as an office-leasing agent and spent 15 years in leadership at CBRE in the Washington DC area before joining NAI Global. In 2020, Jay was recognized by as one of The Best Bosses in Commercial Real Estate.

We sat down with Jay for National Leadership Day, for a candid discussion on leadership.


What is your definition of a successful leader?

A leader is someone that people respect, they listen to, and seek out when they need advice. Respect goes a long way when it comes to working together effectively to find a path toward solutions. Advice could be in the form of a direct ask, such as “I would like your advice on something,” but sometimes we don’t ask for advice, per se, especially when we talk to our respected colleagues and peers. Rather, it’s a little less direct – like guidance. It’s a great feature of good management, because it includes an element of vulnerability, and the spirit of this style of advice – both seeking and giving, is helpful in nature.

What are the top 3 qualities of a successful leader?

To me, a successful leader is always engaged in listening, exhibits responsiveness, and is visible among their staff, teams and clients. I find responsiveness to be especially important. Your employees want to be heard and guided, so responding promptly and clearly shows that you care and that they matter. Can you share a lesson you learned that changed how you lead your team?

I have learned that if it is important to your team, it must be important to you. You need to set your team up for success by finding out and providing what motivates them and what their priorities are.

In a previous role, I had an employee come into my office and ask me to go over the details of the annual holiday party. I was skeptical. I had just planned a bar mitzvah at home and didn’t want to go into party planning mode again. But she insisted. She didn’t want to spend a hefty chunk of change on a huge and important event without my input.

She didn’t ask me because she wanted my opinion on linen colors. She asked me because it was important to her and it was important to the financial health of the company. In order for her to do her job effectively, I had to care about what she cared about.


If you were to write a book, what would be the title, and which the first chapter be about?

“Go Forward: The Past Matters Much Less Than You Think”

The first chapter would focus on getting people, and leaders in particular, to move away from the notion that “we have always done it that way”. You have to have protocols in place, of course, and general management principles, yet too often people tend to rely on their past experiences. Those experiences matter, but one should always look for new and better ways to do things.