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.


What advice do you have for young professionals aspiring to leadership roles?

Take risks. There is no way to win without innovation and doing things your competitors may not. Hence, a calculated risk here and there should be in the playbook.


How do you foster collaboration and teamwork among your team members to achieve shared goals?

Get the team and staff together and make suggestions, then get them engaged in the decision-making process and foremost, have them develop options and solutions. Foster an environment that is open to all opinions and ideas.


When have you had to make difficult strategic decisions that significantly impacted the company? 

Over the years, I’ve had to make hard people-decisions that led others to step up. Sometimes that has meant asking a colleague or employee to resign, consider a bigger role in the company, or worst case, employment termination. Fortunately, I have been lucky to have had strong supporting teammates and we have gotten better at making good hiring decisions, and for the most part, our people have succeeded.


How do you establish and maintain strong connections with clients, partners, and stakeholders?

By visiting with them often. Phone is good, Zoom is helpful, email is necessary, but nothing beats being in person. There’s so much nuance to in-person visits. You build trust. There’s potential for discovery. But also, there’s the element that shows you care.


Where do you see the commercial real estate industry headed this year?

Flat at best. Let’s face it, 2023 was light on transaction volume because of the rise in interest rates and general fear in the business community. With the amount of distress in the system, it’s going to take some time to work out, so this year and probably 2025, are likely to be challenging.


How has mentorship played a role in your journey, and how do you pay it forward in mentoring others?

My best mentors are younger and smarter than I am. I make myself available to everyone as they need. I hope they learn something from me that enhances their career development, but I can say unequivocally, I always learn something from younger people that I manage and from colleagues and clients that have had fewer years in the business than me. The industry and the world are rapidly and constantly evolving and the people with the most pertinent skills and knowledge often come after me.