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Thank you to the 1,400 leaders who’ve generously done the 7 questions!
I hope reading

7 Questions with Jesse Hillman

helps you in your leadership.



Jonno White

7 Questions with Jesse Hillman

Name: Jesse Hillman

Current title: Vice President & Chief Information Officer

Current organisation: Tessco Technologies

Jesse Hillman joined Tessco in April of 2021 as Chief Information Officer. Mr. Hillman has held multiple leadership roles throughout his career, such as Vice President of Information Technology at LightBox Holdings, where he was responsible for security, compliance, risk, and privacy, and as Chief Information Officer Digital Advisory Practice at Pan American Enterprise Solutions. Before that, Mr. Hillman held Chief Information Officer and Global Director roles at firms including Imperial Irrigation and the Walt Disney Company.

Mr. Hillman holds a Bachelor of Business Management from California Lutheran University, a Master of Business Administration from University of the Incarnate Word, and is currently working to complete his dissertation to meet the requirements for his Doctor of Business Administration at Toulouse Business School.

7 Questions with Jesse Hillman


1. What have you found most challenging as a CEO or executive of a large enterprise?

In recent times, dealing with the varying attitudes at both the executive and staff levels regarding the efficacy of COVID 19. Because it was made so political in the media, many are reluctant to voice opinions or their true feelings and this makes for a passively aggressive workplace as we return.

2. How did you become a CEO or executive of a large enterprise? Can you please briefly tell the story?

I took a less than traditional approach, beginning my management career as first a non-commissioned, then commissioned officer in the US Navy. I then moved into a series of more senior roles in both consulting and corporate IT.

3. How do you structure your work days from waking up to going to sleep?

I have a pretty regimented approach to schedule management. I rise with the sun in order to allow myself time to begin my day without feeling rushed. I'm typically in my office 60-90 minutes before the first arrivals begin trickling in. This allows me to prepare for the day without distractions. I will typically remain in the office for an hour or two after my staff leave to recap the day, and catch up on the tasks that there simply isn't time for due to meetings etc.

4. What's the most recent significant leadership lesson you've learned?

Having worked in both consulting and executive roles, I have had the benefit of being able to watch several CIO lifecycles from beginning to end. Several have been almost surreal, almost like slow motion train wrecks. Learning from others' mistakes (as well as my own) in understanding the human dynamics of leadership has been a significant boost to my success.

5. What's one book that has had a profound impact on your leadership so far? Can you please briefly tell the story of how that book impacted your leadership?

Danial Goleman's "Emotional Intelligence". We read it during my graduate studies and it made a profound impression on me and what I had already discovered to be a large gap in most management models.

6. How do you build leadership capacity in a large enterprise?

I believe you build leadership capacity in an organization through the development and execution of empowerment and delegation. Both require self confidence in your personal judgement and trust in your staff. This provides a significant opportunity to identify and leverage teaching moments as areas requiring additional training or coaching are identified.

7. What is one meaningful story that comes to mind from your time as a CEO or executive of a large enterprise so far?

Leadership is often taken for granted. When this is the case, organizational morale is typically the first casualty. Having entered into many organizations as a turn around CIO, the first thing I assess is the organizational culture, who the informal leaders are and who maintains the artifact of that culture. This allows me to rapidly understand the source of many issues and to be able to tap into the unspoken issues and fears that are prevalent when new leadership arrives.

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