The Executives' Club Of Chicago

Member Spotlight: Peter Diamond


After years spent working in business and advertising, Peter Diamond started his own executive coaching practice, and has been at it for almost nine years. Peter initially sought out The Club seeking new networking opportunities, but quickly found that he’d find a place for himself within the mentorship program as well as LEAD. In reflecting in his time with The Club, he shared that these two initiatives provide an exceptional way to connect with professionals at all levels and keep pace with the ever-changing corporate landscape. We are proud to have Peter on board as a member of The Club, and appreciate his dedicated involvement in mentorship and LEAD.

What about your work, company or role makes you most proud?

I experience day-to-day satisfaction working with leaders and teams as they raise to the next level and amplify their success. I’m proud of having built sustainable relationships with a cadre of long-term clients.

What is your favorite binge-worthy show or podcast?

I’m embarrassed to say, I have too many that run the gamut from the salacious Succession to the sweet Great British Baking Show. Right now, I’m knee deep in the dark and disturbing world of Ozark.

What was your first job? What lesson did you learn that you will carry with you?

My father passed away when I was fourteen. By fifteen with a work permit in hand, I got my first job at Dino’s Pizza. It was a small carry-out operation. I quickly learned about responsibility and the value of dollar. I learned how to balance work with school, sports and student council. I learned about working as a team and keeping the peace in a small space with a blazing hot 450-degree oven. Most important, I learned how to toss and stretch pizza dough.

Who was the best boss you ever had and why?

Currently, I have the best boss, but he can be chintzy with bonuses. All kidding aside, it was when I joined Leo Burnett as a client service associate in 1990. I had many great bosses. Besides being whip smart they all believed in the importance of growing and nurturing talent -teaching skills best learned on the job like critical thinking, creative problem solving and presence. Thankfully for me, they took as much pride in their talent as in creating world class advertising. Many of them are still among my close friends.

Can you share a time when you had to reinvent yourself, your product/service or your brand?

I’ve had a couple of reinventions. The most significant was pivoting from my first career in corporate accounting and finance to advertising. Initially, I was met with a lot of resistance. “How can an accountant be creative?” Once I wedged my foot in the door, that question was put to bed. Twenty-one years later, I made my next transition to executive coach. Do I have one more reinvention in me? Stay tuned.

What’s your best “work from home” life hack?

I group similar activities together such as emails, invoicing or special requests like this one and block out time on my calendar to do them. This keeps me focused on one thing at a time and I maintain structure over my days. It was quite liberating to free myself from having to reply immediately to emails. Thankfully, there aren’t a lot of urgent coaching emergencies.

What drew you to Chicago as a business or personal home?

In 1988 my company transferred me to Chicago. I packed up my Mazda 626 and with my hometown of Detroit fading in the rearview mirror, I set my sights on the Windy City. As soon as I saw the Hancock building looming large along Michigan Avenue I knew this was the place I would call home. I’m still in awe of the city every time I motor along Lake Shore Drive. It’s the best skyline in the world.

Among the people you work with, who inspires you and why?

I get inspired by my clients who are engaged and curious about themselves and how they can grow and develop as leaders and citizens.

Peter highlighted techniques to stay focused, prioritize tasks and create structure to the work day. We would love to hear from you and highlight your achievements and tips in our member spotlight. To be featured or to recommend another member of The Executives’ Club to share a spotlight, please contact our team at