Diane Hessan Seeks Common Ground in Era of Fake News and Facebook

When I sit down with Diane Hessan for a recent conversation, the entrepreneur, startup investor, and budding political researcher is nothing but hearty laughs, cool optimism, and earnest passion about her work.

That’s despite having spent the past year and a half corresponding with hundreds of American voters on a weekly basis, during one of the more polarizing periods in U.S. history. Lately, the voters are feeling burned out from the constant political bickering on Capitol Hill and the divisive nature of much of our discourse in the online corridors of Facebook and Twitter, on TV, at the dinner table, and elsewhere. But it seems Hessan’s conversations with voters have energized her and infused her with more hope about America and its people.

“We are so much less divided than people think we are,” she says, as we chat in a conference room in the Boston offices of C Space, the market research and consulting firm she co-founded in 1999 and now chairs.

In the summer of 2016, Hessan (pictured above) left her job as CEO of Startup Institute to consult for Hillary Clinton’s presidential campaign. She was tasked with finding undecided voters in swing states and gathering insights that might help Clinton’s team better understand them. Hessan drew from skills and experience gained through running C Space (formerly called Communispace) for about 14 years, and she found that she enjoyed and was fascinated by talking with voters. After Donald Trump won the election, Hessan decided to continue having regular conversations with voters and self-fund the project.

She says she recruited a new group of about 450 voters—45 percent Republicans, 45 percent Democrats, and 10 percent independents. They correspond weekly, mostly through e-mail, Hessan says. She usually poses a question for them to answer, like how they’re doing lately, or perhaps she’ll ask them to do something creative, like fill out a “Mad Libs” word game, she says. She will have occasional phone calls for “really meaty issues,” she says. (She pens columns for the Boston Globe about what she learns.)

“My agenda is I’m trying to understand, I’m trying to find common ground, I’m trying to see if there’s any way that we can move forward together,” Hessan says. “And I’m also trying to just educate everybody about what’s going on on the other side.”

I wanted to speak with Hessan to hear more about her foray into politics and to find out whether her conversations with voters hold any lessons for the tech industry. After all, politics and technology are frequently colliding these days, from fake news spreading through social media to rising concerns about online privacy and cybersecurity. In a wide-ranging discussion, we explored some of these topics, as well as Hessan’s thoughts on improving diversity in tech and the venture capital industry, the challenges around retraining workers for an evolving economy, her prescription for fighting fake news and social media’s ills (it’s not all Mark Zuckerberg’s fault), and one of her (many) new startup ideas.

Here are the highlights of our conversation:

Xconomy: Your most recent column talked about burnout among American voters. Do you feel like people have reached their breaking point? And if they have, what follows?

Diane Hessan: Well, look, what follows burnout? It either gets worse and people totally freak out, or somebody makes change, or there are enough people who are fed up that something productive comes out of it.

I see one outcome of people being so exhausted is that they are more open to compromise in the name of progress. If they understand other people, they’re a little more open to shifting their views—not necessarily radically, but enough to be able to say, “OK, so now that I understand what’s going on for you, I think I see a way through the madness.”

X: How will that sentiment that you’re seeing among the voters manifest in Washington? Do you think it will lead to more moderates in Congress?

DH: I don’t know. … I’d bet that we’d have more moderates. But it’s hard for moderates to win in primaries because the extremes all come out passionately and vote for what they care about. But yeah, I think this is the time for moderates. I think Mitt Romney is going to win in a landslide, whether he’s in Utah or elsewhere.

There are Democratic voters that admire Susan Collins more than they admire Elizabeth Warren. There are Republican voters that admire Lindsey Graham more than they admire Ted Cruz or the like. I think it’ll be a really interesting time.

X: What are some of your takeaways from talking to voters every week?

DH: If I get out of Massachusetts and I talk to my voters, I think people know that I’m not a Trump supporter, and yet I’ve got a lot of voters that I talk to on a weekly basis who love Trump. After talking to those people every week for 18 months, I’ve come to have huge respect for and admiration for many of those people, independent of who they voted for. So, I’ve been able to kind of separate how I feel about the president from how I feel about the people who support him.

I’ve really gotten to understand their lives. I will tell you, a 55-year-old, unemployed coal miner is not going to learn to code. And what happens is you get all these politicians up there screaming, “Retraining the workforce, retraining the workforce, retraining the workforce.” We need to really get very, very concrete about what the opportunities are going to be for people who are further along in their careers.

Go to Milwaukee. Look at people who are unemployed there.

Look at people who have lost their jobs in the automobile industry. Will some of them learn to code? Sure. But it’s going to be a small fraction. And so, what I’m really interested in is who’s putting together a jobs policy for the future that really makes sense. Where’s the plan for our workforce when the economy changes all over the place? I think that’s a really interesting area. I’ve got a lot of energy for that.

X: Something Xconomy focused on in interviews at the end of 2017 was what we and others have called a tech backlash because of a confluence of issues: fake news, Russian interference in the presidential election, social media companies not having the best response to those issues, sexual harassment allegations at tech companies, and the growing concentration of power in just a few companies. Does any of that come up in your conversations with voters?

DH: It comes up a little, although I must say I think that’s a really interesting issue, and I could [discuss it] a little bit more with my voters. I think it’d be interesting to see what they’d say about that.

They’re all upset about the media. They’re all upset about fake news, across the spectrum. I think Facebook and Twitter have done an absolutely horrific job of handling the problem.

Where they have missed is they haven’t said, “Look, we are really surprised about this. We’ve got to own up to this. We’ve got a 25-part plan. Now, in the meantime and forever, here’s what all of you need to do that we cannot control. Every American citizen who is on Facebook needs to do the following things: one, two, three. Here’s how you need to change the way you’re consuming news. We’re going to work on getting our house in order. But you guys have to step up to the plate.” … Ask not what Facebook can do for you, ask what you can do for Facebook. We can all help.

It’s the de-compartmentalization of our issues. In business, one of the most important things I had to do as a CEO—I learned this from Gail Goodman, who’s a good friend of mine who started Constant Contact. Gail used to say to me, “The key thing you’ve got to do is you’ve got to hold people accountable. You have to have one throat to choke.”

In business, we have a very high need to identify one person, make them accountable, and that’s where we go if we’re not making the [target] number.

I think in terms of these more complex issues, you can’t go, “You know what, at the end of the day, my one person who I’m holding accountable is Mark Zuckerberg. He is at the core of this. If this fake news thing keeps going on, and we’re still reading stuff produced by Russian bots, I’m looking to him.” I don’t think that’s the way we make this kind of institutional change happen across our country. I think he’s got to be accountable for some stuff, but I think we all have our own accountability.

Since I have learned about Russia’s impact on the election, I read things differently. I’m incredibly skeptical of any Facebook group that is political, for instance. I have my guidelines; they’re not super sophisticated. But we all need to jump in, as opposed to going, “You know what, I’m doing nothing because Mark Zuckerberg is my one throat to choke.”

X: Will you ever run a company again?

DH: I don’t know. I still get a bunch of phone calls, which makes me feel good, I must admit. You do worry that when you change careers and you shift, everybody’s going to say, “OK, Diane’s retired.”

I will tell you right now I’m having a great time. I’m on seven boards, and I spend a lot of time working with startups. I have two goals: I talk to five startups a week … and I also try to speak with five women founders every week just because I kind of know what it’s like in their shoes.

And then I have all this political stuff, which is very, very inspirational to me to play in a different kind of arena. My life is great now because every day is a new adventure.

I would run another company if I fell madly in love with what it was doing. I’m not going to start something, even though I have a million ideas.

X: What’s one you’d be willing to share?

DH: [Laughs.] If you said to me today you have to start a business right now, I would basically do Geek Squad 2.0. When I say to people, “How much time do you spend talking to your parents on the phone helping them with their technology?”, people start laughing or groaning. People really understand this is an enormous problem. And you would never say to your parents, “Why don’t you call Best Buy and have a Geek Squad guy come out?” Because sometimes they’re just trying to make an attachment work. I think that there is a great business for helping people on a weekly basis with their technology.

I have the whole thing laid out in my mind. I have the pricing. I have the name. I have the entire thing all ready to go. I just need somebody to do it—take it forward and run it.

X: How long do you want to do this work with the voters?

DH: I’m going to do it until it’s not interesting anymore. My mission is to find common ground. And my mission is to do in our political arena what C Space did in the business arena. What we were about in our first five years was helping companies understand that if they’d just shut up and listen to their customers, that they could generate innovation and growth beyond anything that they had ever imagined. And this was in an age when all marketing departments were doing was just blah blah blah blah blah, “I’m going to talk to you on TV, I’m going to talk to you on the radio, I’m going to talk to you online, I’m going to interrupt, I’m going to bombard you with messages all day long.” Taking a chunk of that budget and turning it around to try to walk in the shoes of your customers was breakthrough for so many brands.

That’s what I’m really trying to do here, which is just to say, what if the people who are responsible for running our country just stopped making speeches and really tried to understand what’s going on? What could that be?

We have so much more common ground than people think. We are so much less divided than people think we are. I’m passionate about that right now.

X: What’s it going to take to boost diversity in the tech industry?

DH: I think it’s kind of like that Facebook thing we were talking about before. I don’t think that fixing the diversity problem is about going, “You know what the problem is? The problem is that the VCs only fund people who look like them.” Or, “The problem is in eighth grade, little girls get told that they should major in art, music, and English.” That’s what we do. We go, “Where’s that throat to choke that’s going to fix my diversity problem?”

I think that every sector of our economy needs to work on this. One of the things that’s going on now is we are starting to get a critical mass of organizations that think about diversity. There are bootcamps at Startup Institute that for a while have given scholarships to people of color or to women, to come in and learn technical skills. We have a lot of learning institutions, both for-profit and nonprofit, in Boston working on that.

We have an incredible research project that gets done every year by The Boston Club on gender diversity that literally takes every company in Massachusetts and rates them based on how many women are in senior management and how many women are on their boards. And that data works because if you are a “no-no” company—meaning you don’t have any women in senior management and you don’t have any women on your board—it’s bad reputationally. And there are a lot of tech companies that show up there. Those companies should be embarrassed. [According to The Boston Club’s website, the study Hessan referenced covers the 100 largest public companies in Massachusetts; a second report looks at the state’s largest nonprofits.—Eds.]

And now, there are organizations, there are women’s groups, for instance, that call up those tech companies and say, “Aren’t you embarrassed to be on this list? I know it’s probably difficult to find qualified women for your board, but we actually have a list of five women. You should talk to them.”

X: Do you see the #MeToo movement as giving more momentum to the effort to increase diversity and talk about some of these issues in tech and VC?

DH: It helps, and it hurts. I’ve had male friends say to me, “I’m done. I’m not going to take any of my women executives out to dinner anymore. I’m just not doing it.”

That’s one person saying that to me, but if that is how all male executives are thinking, that’s a really negative impact for me. I’ve had some of my career development conversations sitting over dinner with a male board member or a male boss saying to me, “Let’s talk a little bit about your career and what’s possible and what do you need to develop.” And getting out of the office and hanging out with somebody who can really help your career is a hugely important thing for women. And if men are going to walk away from those sorts of things … just because they’re worried, I think that’s bad. So, there are negative things that come out of it.

But again, it’s not just about what those men decide to do. I think what women also need to do is step forward and say, “I really need some help. Can we do breakfast, lunch, dinner, drinks, anything?” Everybody has a responsibility to figure out how to take all of this stuff and turn it into something that’s positive and motivating.

X: Are you optimistic that’s going to happen?

DH: I’m super optimistic it will happen in Boston. I’ll just say that Boston tech is filled with phenomenal male executives and investors who want nothing more than to help their women colleagues and friends. They really do. They’re not jerks who are hanging out in locker rooms saying, “I wish I never had to hire another woman again.” It’s just not the case.

There are a few bad eggs here. But I think we have a critical mass of really phenomenal male leaders in tech who want to do the right thing. They will all figure it out. And they’ll figure it out more if the women and the people of color can just come in and help them—call them on their issues, make suggestions, have a voice. Say, “Hey, I know you’re trying to work on this. I have two ideas. Do you have five minutes?” All of that helps. I think there are a lot of guys who are really willing to listen.

And I’ve had more men call me on the phone and say, “Diane, let me just check here, have I ever done anything inappropriate with you?” Which is a great thing to do. And the guys who call you up on the phone and ask you that are never the ones who are guilty.

There are other men in this city who will be called out. It’s hard because I can tell you that when you have an incident and you’re a woman, there are a million reasons that women don’t talk. But one of them is you think you’re the only one. If you think you’re the only one that’s ever had a guy do that, you start saying, “OK, so, maybe it was my fault. Maybe I was too flirtatious. Maybe I interpreted it the wrong way. Maybe I didn’t say no loudly enough. Or, or, or.” What happens is then you find a whole bunch of other women who have the same story, and you go, “Yeah, it wasn’t me doing the wrong thing.”

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