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October 15, 2020 47 min

Diane Hessan is successful entrepreneur, CEO, author and has been highly recognized for the broad range of impactful work she has done.  And she has served on virtually every type of company board and seen the work of the board from many perspectives.  In the fascinating conversation, she shares her insight and opinion on the experience of running and serving on a board.


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First Board Experience

My first board experience was very hands on.  It was a real passion project because we all were completely dedicated to the mission.  I started by spending way too much time on operating issues and eventually sat back and became more strategic.


I thought it would be great for my family and my job and my learning, to broaden my horizons and to learn how to do some other things. I had a conversation with a friend of mine who was on a whole bunch of boards, and I just said to him, I feel like I want to do something bigger. I feel like I want to give back and not focus on myself so much and yeah, he said, what are you passionate about? I said, I'm passionate about kids. I'm passionate about antiviolence, I'm passionate about homelessness.

He was just like "Diane. I have a great organization for you and they really need marketing help" because that was why people wanted me on their boards at the time. It really was a great fit and I basically got it by talking to somebody who had already been there.


There were times when I would say something and I learned to say, “is this a board issue or is this not a board issue?” I mean, I was just very explicit about it. 



Changes in the Boardroom because of Covid

Every organization that I'm on the board of no matter whether they're for profit, nonprofit, et cetera, have had talks about the impact of COVID on how their employees are working, how they're building culture, how they're recruiting, retaining, onboarding, what the impact is on people working from home, when they should open up again, whether they should give their employees free stuff to be able to be more effective at home, how they handle the huge challenges of employees who are parents and how to make everyone feel fairly treated there.


(Companies are) Looking for shifts in customer behavior and customer requirements is also a really interesting topic.  Most of these companies have new go to market strategies, new strategic partnerships, interesting new acquisitions, and I think in general, new ways of actually reaching out into the marketplace and building strategy around that.


And for me it's meant much more time on my boards of just doing my homework and reaching out and try to see what other companies are doing and just generally getting educated so that I can be as helpful as possible.


What makes an effective board meeting?

I think the great board meetings are when the CEO says, “here's your deck or here's three pages about what's happening in the business. I have three issues that are keeping me awake at night, and I really want your help on them. Here they are. A, B and C.  Please come prepared to help.”  Spending a board meeting with four hours of PowerPoint is the worst most boring thing in the world.  And it really doesn't help.



Big Ideas/Thoughts


Learned about being a Board member from being a CEO

Number one, when your business is going well, you want your board to just ask questions and beat you up and challenge all of your assumptions.  You're energized.  You're doing well.  You want a board that gives you watch outs and says, well, what about this? And could we grow this faster?


When a business is not going well, you don't really, as a CEO, want to get beat up. So, when things weren't good, I really appreciated board members that were supportive, that helped me look on the bright side that shared with me information about how other companies were also struggling.  So, when things are good, you want to tough board when things are bad, you want a board that walks in your shoes and also knows how to be supportive.


I learned how sometimes asking questions is more valuable than giving advice to the CEO.


One of the things that I learned from being a CEO, but also from being a board member.  Guess what: the board meeting is not just about the CEO making the board happy. The board meeting is also about making the board members feel that they're contributing.

One of the things that I've done in one of my boards…. We're going to talk about this for the next hour and a half.  I'm going to leave the last half hour of this conversation to just go around. I'm going to give each one of you a chance to just do two to three minutes more of final thoughts on this issue….Sometimes you're in a big room, you got a lot of people talking. You feel like you can't get a word in edgewise. I know I feel that sometimes and if you're an introvert, and some of my best board members have been introverts, they just give up, they just don't want to interrupt and jump in and say, I have something.

So if people know that they'll have their say at the end, because you're going to go around the room and give everyone a chance to talk, you sometimes get extraordinary advice from people who otherwise just would have given up on participating… and after a while you get really good at packing your 120 seconds with everything you wanted to know. 

We all as board members want to feel that we're adding value and we can't do that unless the board process works really, really well


On the broad range of company boards

I wanted to broaden the industries in which I work and it is particularly fun as a board member to just dive into an industry where you've never really looked at financials before.  You've never really thought about how they make any money.  And you have to learn an entirely new language. It's just a great stretch experience


Term Limits

I don't love term limits, but I love bringing fresh faces onto a board.  In some industries that's more valuable than others. If you're in an industry, banking is an example, sometimes business knowledge, knowledge of the industry and knowledge of the company and its functions has an outsized impact on your ability to be successful on the board. And year after year, the more you learn, the more valuable you become.  You get to the point where you have somebody that's been on the board for 10 or 15 years and they are outrageously valuable. They have the history, they still are full of impact, et cetera, and it's hard to say goodbye to those people.  But every time you bring on a new, extraordinary board member it changes the conversation. It opens up the possibilities. It brings in all kinds of perspectives that you thought you never had before, and I think that's really valuable. Especially now that the world's changing so fast. As the world changes, the skills that we need and the perspectives that we need are also changing. 


Boston as a collaborative investment community

Boston is an extremely collaborative community, so that whereas other ecosystems like San Francisco or New York have a reputation for being competitive - you know:  My fundraising is bigger than yours. My product is better than yours. My app is cooler than yours. My black turtleneck is blacker than yours, - in Boston I really believe that the biggest question that you get asked when you're trying to build a company is “what I can I do to help you?”

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