Boss of me: 3 CEOs dish on their favorite former bosses

by Kelly O'Halloran
August 31, 2017

Great bosses can leave a lasting impact. Recently, leaders at Umbel, Headspring and Invenio Solutions spoke with Built In Austin about their favorite previous bosses. As you'll see, this group of CEOs borrowed a few moves from their favorite leaders’ playbooks, proving once again that imitation is the sincerest form of leadership greatness. 

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2017_LisaPearson_square-thegem-person.jpgPrior to becoming a CEO herself, Umbel’s CEO Lisa Pearson reported to seven different bosses. Fortunately for her, she said many of these executives were amazing to work with, making it impossible to select just one that has inspired her leadership approach today.

Could you describe some of your favorite bosses?

There have been bosses that stretched me to develop. Ones who have given me autonomy to run with ideas and created a safety net so I felt comfortable taking risks. I've had a boss whose optimism and big thinking was so contagious you couldn’t help but want to be a part of what they are doing. I had a boss that always emphasized generosity and took a lot of time to know me as a person. The human side of business always came first. I had a boss who encouraged me to think bigger for my own career, pointing out areas I needed to shore up and helping me find a way to do so.

When did you realize they were amazing bosses?

As a new-in-the-seat CEO at Umbel, I have new appreciation for the demands of the role. It’s harder than anyone would ever anticipate. I can look back at decisions my previous bosses made that I didn't fully understand at the time, but now I do. I have greater empathy for the way the role is taxing and how essential it is to surround yourself with a team you trust and respect.

How have they influenced your management style today?

Their influence shows in my commitment to try to be humble and transparent in how I communicate to build credibility with employees and other stakeholders. I care about the people I work with and try to connect with them as humans first. I’ve learned to push employees to think bigger about the business, but also about their own career opportunities. I'm by no means perfect at any of this, but have tried hard to follow the good examples set by my previous bosses.

 

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Unlike some seasoned tech leaders, who have had many bosses, Headspring President and CEO Dustin Wells has only had one. And his name was Greg. Wells said Greg regularly brought him books, tapes and other programs to work on his professional development on his own time. This interest in his personal growth spurred both positive and negative effects on his current approach to leadership.

When did you realize Greg was an amazing boss?

I knew when we first started working together. He took an immediate interest in my growth and took time to understand my goals in the bigger picture. He was supportive of my path and gave me the resources to grow my skills and myself.

How has Greg influenced your management style today?

In a positive way, I try to be supportive of others’ paths, even if that means they will not be with Headspring long term. I am supportive of entrepreneurial paths especially and am excited when someone leaves Headspring with the skills and passion to launch their own business.

On the negative side, I was always grateful for the resources Greg provided me, but I took it upon myself to apply those resources and really get the most from them. Today, I am quick to provide a great deal of resources for the learning and growth of my team, but I expect them to make the personal investment to use and apply them for their learning.

Sometimes the pressure on my team to invest their personal time is not realistic given their other commitments, which puts unnecessary strain on them.

 

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John_Grady_thumb.jpgJohn Grady, CEO of Invenio Solutions, recognized Neil Hand as his favorite boss. Grady said he appreciated Hand’s management style, which prioritized autonomy as well as their mutual distaste for the corporate workplace.  

When did you realize Neil was an amazing boss?

When he started giving me the teams and individuals who were deemed lost or not recoverable. I started to build a track record of getting these folks back on track towards agreed upon goals and deliverables.

How has he influenced your management style today?

Neil helped me see that teams and people are not usually the issue. The issue, usually, is that what they are being asked to do — and the support/training/guidance that they are getting — is murky or nonexistent. Providing clear and measurable guidance along with training and regular reviews make a world of difference.


 

Images provided by social media and company websites.

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