An Airplane Wi-Fi Exec, Restaurant Chain Leader and Health Care Venture Capitalist Walk Into a Room …

From left: Rock Health's Halle Tecco, Roti Mediterranean Grill's Carl Segal and Gogo's Michael Small chat with moderator Michael Arndt from Crain's Chicago Business. Photo courtesy of Chicago Ideas Week

The cliché goes: It’s lonely at the top — but it doesn’t have to be.

At the fifth-annual Chicago Ideas Week in a panel discussion called “Executives Uncensored,” Roti Mediterranean Grill’s CEO, Carl Segal; Gogo’s president and CEO, Michael Small; and Rock Health’s founder and managing director, Halle Tecco, got together to discuss work-related problems.

Uncensored might be a bit of a stretch, but it did produce some interesting discussions.

Like you and me, these executives have problems big and small in their companies, but the panelists seemed intrigued about getting feedback from some unconventional sources.

Gogo as you might know provides Wi-Fi service on airplanes, but there are limitations. Ya can’t access Netflix, for example, on Gogo.

As Small said, “Our biggest problem is we are a victim of our own success.” Translation: The service can be slow because so many people are using it during a flight, and the price has gone up over the years. There definitely can be sticker shock, especially for infrequent travelers used to getting free Wi-Fi who have to pay $16 for an all-day pass on Gogo.

The key, according to the panel, is communicating with customers about why it costs so much to provide Wi-Fi at 30,000 feet and why the strength of the signal isn’t always the best. Of course, this is not something Small hasn’t thought about before. He responded that he’s all for “brutal transparency” when it comes to communicating service issues and constraints. Of interest to business travelers, he said that Gogo would be rolling out its 2Ku technology in the next year or two, which, he said, will improve the quality of the signal on planes. Let’s hope it’s five bars or bust.

Roti’s Segal quipped that, if all else fails, “blame the airlines.”

The group also offered another solution: Why not give travelers the opportunity to pay more to get better service at the expense of the Wi-Fi experience of other passengers. This idea didn’t seem foreign to Small, who said it has come up, but the company is focused on bringing a high-quality Wi-Fi signal to all passengers. Thank goodness; elitist Wi-Fi should be a nonstarter.

For Roti, the challenge is competing and growing in the competitive “fast casual” restaurant space. The relatively new company has about 20 locations in three areas right now: Chicago, New York and Washington, D.C. The company caters to a healthier fast-food audience with its hummus, falafel and shawarma offerings. If I had the opportunity, I would have asked him about the mechanical slicing devices the locations I’ve been to use to cut meat from skewers. I’m fascinated by the efficiency and am curious if he has stats on how much quicker a sandwich can be prepared with auto-slicing.

Interestingly, Segal said he gets together with CEOs from other fast-casual restaurants in the Chicago market where Roti is based to discuss common challenges. This seems like a great idea to me. Why spend time and money fighting competitors when you can work together, solve problems and help both companies grow?

It sounds Utopian, but it might be crazy enough to work!

As a consumer, Tecco said her concern with huge growth for the restaurant would be “consistency.” With expansion, will future restaurants be able to maintain the same quality and four-star Yelp ratings as the original locations or will the tables go unattended for long stretches after customers leave?

Speaking of Tecco, she is one of the few female venture capitalists around. According to TechCrunch, women make up as little as 4 percent of venture capitalists in Silicon Valley. Her San Francisco-based company invests in digital health care, a relatively young but growing field. And not surprisingly with a company that deals in health care, even though it’s from an investor’s point of view, she cited policy as a big problem.

“We see the headaches of bad policy all the time,” she said, citing telemedicine as an example. By law, you have to be in the state where you practice medicine, so a telemedicine company has to have a doctor in each state it wants to do business in. Why can’t a doctor, say, in California see a patient in another state? she asked.

Good question.

While I don’t think solving health care’s many problems were on the table at this particular discussion, it was interesting to think about how many players are actually in wellness fields, even if it’s tangentially. Is Roti, or other Mediterranean restaurants for that matter, considered to be in the wellness realm because they serve what is considered healthier foods?

You don’t get that type of discussion in the boardroom.

Bouncing ideas off the usual suspects tends to produce the usual solutions. It makes sense to look elsewhere for answers, and that’s why this panel was quite enjoyable to listen to even if it didn’t have all the answers.

Consider giving it a try yourself.

And if bouncing ideas off people in other fields or even competitors doesn’t help you solve your problems, just blame the airlines.