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7 Questions on Leadership with Mary Olson

Name: Mary Olson

Title: Industry Executive Director | Education & Research

Organisation: Oracle

Mary Olson is the Industry Executive Director for Oracle Education & Research market segment. She has an extensive background in technology & innovation. Prior to joining Oracle, Mary spent 30 years with IBM leading Education for North America; expanding global markets; enabling the high-volume business partner channel; and executing programs to grow market share.

In addition, Mary has spoken at industry conferences on the topics of education and economic development. She is the co-author of “Education and Economic Development: A new approach for jobs and growth.” Published in Smarter Cities for a Bright Sustainable Future: A Global Perspective.

Mary has been a keynote presenter at multiple education conferences on the topics of Personalized Learning, Education & Economic Development, and Financial Literacy. She has also presented to the American Council on Education (ACE), The Association of Governing Boards (AGB), and Leadership Texas.

Mary was Chair of the University of Montana Foundation Board and served as a Trustee for 12 years. During her tenure, the foundation embarked upon an IT modernization effort and dramatically enhanced cyber security for all systems. Mary was also chair of the Montana Council for Economic Education (MCEE) focused on improving High School economics curriculum and financial literacy.

Thank you to the 2,000 leaders who’ve generously done the 7 Questions on Leadership!

I hope Mary's answers will encourage you in your leadership journey. Enjoy!


Jonno White

1. What have you found most challenging as a leader?

Continuous change is one of my biggest challenges as a leader. The technology field is in a state of hyper accelerated growth. I need to keep up with the new developments and lead people to help them keep up. It isn’t comfortable for some people to adapt.

2. How did you become a leader? Can you please briefly tell the story?

I took my first steps as a leader in high school. I was very involved in 4-H and it gave me the opportunity to develop leadership skills that I carried into my career. It also enabled me to realize that leadership is a characteristic in a person, and not specific to a job. Some people equate leadership with management, and they are not the same. I’ve worked for over 40 different managers in my professional life and a select handful were true leaders.

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

On weekdays when I am not traveling I have a solid pattern to my day. I wake up about 6:30, do my work out and get ready for the office. I’m normally in my home office about 8. My days are filled with zoom meetings, learning, writing, researching industry trends, and engaging Higher Education customers virtually as much as possible. And I hate to say that email takes a significant chunk of the work day …… that is one thing I would most like to change about my day. At 5 my husband and I fix dinner and have time together in the kitchen, my favorite place to be after work! Evenings I like to relax, reading, watch a little TV, possibly go to our local university for a lecture or get out to meet friends. I typically get to bed early for a good night sleep, about 10:30. When I read that it sounds very routine, and it really is. I like the structure. There are occasions when I am up against a tight deadline at work, and I’ll need to go back into the office for a few hours after dinner, but that is the exception, not the rule. When I am traveling for work, which is approximately once a month, my days are very different. I’m on the go from early morning breakfast meetings and as many customer and partner meetings as I can get in until late in the day. Often my travel involves conferences where I present or host panel discussions. These engagements require a lot of preparation and energy. After travel weeks, I do my best to take a free weekend to recharge. Hiking, skiing, or something outdoors always centers me.

4. What's a recent leadership lesson you've learned for the first time or been reminded of?

Recently I have become aware of how important self-awareness is for a leader. I’ve observed the difficulty that some have in knowing how they are perceived by the people they lead and the negative affect this has on teams. As a result, I’ve raised my sensitivity and have actively sought feedback on how my personal style affects others. I don’t believe we can ever truly see ourselves as others do, so my advice is to listen to the people around you and build a trusted network who will let you know if you have gone off the rails.

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?

Elizabeth I CEO: Strategic Lessons from the Leader Who Built an Empire by Alan Axelrod. It was a fascinating account of her decades ruling the empire where the sun never sets. Admittedly she was born into her leadership role, but she took it in directions that were not expected, encouraged, or welcome by many around her. She was charismatic and had the ability to build intense loyalty which helped her survive, thrive and held her nation together. The impact the book had on me was a realization that everyone leads in their own way. Observe and learn from others, but develop and nurture your own brand of leadership.

6. If you could only give one piece of advice to a young leader, what would you say to them?

Pay close attention to core values. Know what you believe is right and wrong, and always stay on the right side. Making tough decisions is easier when you ground them in your core values. Difficult choices you are required to make will be the right ones and easier to live with when grounded in your values. Authenticity is a foundational building block of being a good leader, so make sure that any company or group you work with allows you to be yourself, and that includes adhering to your core values.

7. What is one meaningful story that comes to mind from your time as a leader, so far?

I had to fire someone once for poor character. It was an agonizing decision because he was getting top results. I worked with him, coaching, doing my best for 6 months to get him to change. I really believed that if he could just see how much more impactful he would be if he treated other employees better, that he would change and we would have the benefit of his performance and a better work environment. There would be brief periods of improvement, but they were not sustained. His character and the way he treated others was detrimental to the organization as a whole. The only choice was to remove him from the role. It wasn’t easy, but I knew it was the right thing to do. After he was removed it took months to undo the damage he had done. The lesson for me is to listen to my gut, and make the hard decisions sooner. In hind sight, the months I spent coaching and trying to get him to change would have been better spent moving the entire organization forward. I see that my months of coaching and misplaced optimism were really me avoiding a painful action.

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