Women Making History Today: Diane Hessan

Diane Hessan is a dynamic business woman, author, influencer, and angel investor who I had the pleasure of meeting at a networking event in Boston many years ago. I remember very clearly how funny and personable she was, in addition to being quite accomplished. Since that time, she’s been an unofficial mentor for me, as well as an ongoing inspiration to women in tech and highly regarded Boston business leader. She sits on the Boards of numerous companies, including Panera Bread, and is currently CEO of Salient Ventures and is engaged in a wide-ranging longitudinal study of the American voter as a columnist for The Boston Globe.

She is also Chairman of C Space (formerly Communispace), where she was previously CEO and founder.

And with that, I share my interview with her. Thank you, Diane!

Was there an “Aha Moment” that led to your current career path?

My professional life has been a series of serendipitous “aha” moments. Although I never really knew what I wanted to be when I grew up, I was confident that opportunities would come my way -- and that I needed to be open to trying new things.  I started my own company when a boss told me that my desire to be CEO of his was far in the future; I started doing my political research because of one phone call from a friend where I said yes and totally changed my career; I changed my company strategy based on one meeting with one client in Kansas City, and so on.  Training myself to notice those moments has made life much more interesting!

You and I met at a Boston tech networking event back in the day when people could see each other :) I remember we both had on pink and were the only women in the room with color on. Further, it’s been reported that women carry different character traits at work than men but sometimes try to downplay them. For example, Pew Research reported that women are more compassionate and empathetic than men, which actually helps them  to work out compromises. Do you think that women have become more comfortable acting and dressing like women in business vs. trying to fit the mold of how men act and dress? Why is this important?

Definitely women are more comfortable.  In the beginning of my career, I remember that women would not only wear suits, but we wore bowties.  It was insane. Now, it’s not controversial to wear pink.  Having said that, I am wary of stereotypes that say women are more compassionate and better at relationships because there is this undertone that therefore we aren’t tough, we can’t do deals, we can’t run the numbers and so on.  We can!  And there are certain things that I find women doing that we need to get better at; we need to stop apologizing all the time, we need to net things out, and so on.

It’s been quite a year! The world has seen a lot of political and social unrest. How has the last year changed you, if at all?

I have changed in many ways!  For instance, I have learned to appreciate quiet time and not always running from event to event, I’ve become a better writer and listener, I’m much more fit, I appreciate my closest friends and family more -- and I know them better.

Resilience is a key topic here and one that we are all facing as we come out of this pandemic. What makes you resilient?

My father always used to say, “It’s not how far you fall -- it’s how high you bounce.”  I think I learned resilience when I was in a sales job because it was a constant exercise in handling rejection and I built up thick skin, which has served me well.  When you have thick skin, people are willing to give you tough feedback and help you improve.  And, when you are resilient, you are much more willing to try new things because, well, What’s the Worst Thing that Happens?  You feel bad, and  you move on.

You were kind enough to serve as informal mentor for me when I approached you several years ago as I was starting my first software company. You are also an active board member and angel investor. What inspires you to do this sort of work and how important do you think it is for women to mentor women?

So many people helped me as I was building my career, and so now, I feel an obligation to do it for the next generation.  I think we need to put a small M on mentoring.  If you gave me a choice between one major mentor and a network of people who were willing to help and advise me, I would pick the latter.  The challenges we have these days are so varied, and so I love having dozens of people who are willing to take my call for help.

What’s one piece of technology you can’t live without?

My Dyson Hair Dryer.

Can you tell us more about your engagement in the wide-ranging longitudinal study of the American voter as a columnist for The Boston Globe? What is your long term goal?

Since 2016, via a panel I created, I have been engaged in a longitudinal study of American voters.  On a weekly basis, I have been in conversation with 500 people and I have a massive amount of data about where we agree and not, why people feel the way they do, and so on.  Whenever I learn something new, I have written about it for the Boston Globe, and I’ve done about 50 Op-eds.  Now I am finishing up a book about it all!  It’s called Our Common Ground:  Insights From Four Years of Listening to American Voters -- and it will be out in June. I’m excited.

What have you been doing to keep yourself mentally stimulated during the COVID lockdowns?

Above and beyond the voter research project, I have an angel investing company called Salient Ventures where I invest in and coach startups.  And, I’m on 8 boards, including 4 corporate and 4 nonprofit boards.  I love the challenges and variety in my board work.  So, I’ve been busy, and all of this has been pretty easy to do remotely.  Thank goodness for Zoom.

I understand you founded The Sound Bytes, an a cappella group that sings about business. What inspired you to do this and where can people catch your performances (are they online now, where did you perform before COVID, etc.)

I love to sing, and although I don’t have a great voice, I have a good ear and can do harmonies.  And I love writing rhymes.  So, our group sang songs about business that were familiar tunes, with the lyrics customized to the business situation.  We had a gig over several years at one conference where we’d go and sing before every general session, and we sang to introduce everyone from Jack Welch to Tom Peters.  It was a blast.  We don’t really perform any more because we lost one member of the group tragically, and we all have day jobs, but it was thrilling and an absolute blast for many years.

What other hidden talents or passions do you have?

I love baseball and I have a large collection of baseball cards and signed balls. And I love playing piano and golf.  And my big passion is my family, including my 2-year-old grandson.

You authored the book “Customer-Centered Growth: Five Strategies for Building Competitive Advantage, which was a Business Week best-seller, and published in 11 languages… so inspiring. Will you be writing other books?

See above!

What’s one piece of advice you would give young girls today? 

Life is long!  When I was younger, I was in such a rush to figure things out and I thought everyone else was so much clearer.  As it turns out, we are all searching. We have so many chapters in life.  So: try new things.  Find a great boss who develops you. Find friends who support you.  Stay close to your family.  Try to get experience in something that will be important in the future like cybersecurity or AI or telehealth. Travel. Work harder than everyone else because it will be noticed. Ask for feedback. Get your nails done.

Where can people stay in touch?

 Find me on LinkedIn or on Twitter at @DianeHessan