Ameesh Divatia, co-founder and CEO of Silicon Valley data security specialist Baffle, thinks that the world of startups is lonely. Fortunately, he also benefitted from years of mentoring, and is now dedicated to “paying it forward” by advising young tech professionals on how to navigate the turbulent waters of the tech startup scene. 

From his perspective, a mentor is someone who allows young professionals to talk about their fears and work through them, giving them the confidence to be prepared when the market changes—which Divatia says it always does.

“The environment that a tech startup grows up in is extremely dynamic. It’s very likely that a young person going into a startup has not seen the downtimes, and if you haven’t seen that, you don’t appreciate what to do in the good times,” he said. “The one thing they absolutely need to be aware of is that things will change, and they have to be open to change. You can’t get set in your ways.” 

When Mentoring, Always Make Things Relevant

Divatia thinks it’s important for mentors to provide their mentees with examples drawn from the world the mentee is familiar with—using learning lessons from the software space if that’s their focus.

“The last thing you want to hear as a mentee is an example that is irrelevant to your experience,” he cautioned. “You want to have a relatable example. Draw lessons from history, but don’t dwell so much on the past.” 

Constant contact is another critical component when building a good mentor/mentee relationship, something that video conferencing and social networking sites have helped with tremendously. 

“I have a mentee who happens to be in Boston: I would never have been able to pull that off without communications technology—and I would never have even taken it on, because staying in touch was so hard,” he said. 

The Furthest Reach

James Lloyd, co-founder and chief technology officer for Madison, Wisc.-based healthcare API developer Redox, has come to believe that, between the professional mentoring relationships he’s developed through Plato (an organization helping connect product engineers) and more informal relationships, the process is a two-way street where he can advise and learn simultaneously. 

“One thing that I always keep in front of my mind, is that as a person just hearing about these situations once a month, it’s very rare that I’d have a direct answer to a problem—it’s more about providing resources or support,” he said. “Not being the know-it-all, but trying to get them to think about tough decisions, asking questions to get them to step out and look at the overall outcome—that’s a useful structure within which to work.” 

Lloyd rarely conducts in-person meetings with his mentees, but technology has nonetheless made it possible for him to participate in a mentoring network that spans the country.

“The pace at which tech is evolving and changing means it doesn’t matter how smart you are, you can’t keep up with everything,” he explained. “The ability to learn through others—by being a mentor—there’s a lot more in it now because I can seek out people in [a] space that I don’t know much about, to mentor them and learn something new at the same time.” 

It’s the development of personal relationships through tools such as Slack or video conferencing that will make the difference in helping today’s young tech pros solve tomorrow’s problems. “There’s a ton of online courses and everything like that, but the gap mentorship fills is the situational awareness—when it comes to figuring out how to do something, and the team isn’t responding the way the course said they should, there isn’t a resource for that context-specific situation,” he added. “That’s going to be more of the domain of mentoring if you really want to hone a particular skill.” 

Focus on a Project Together

Tom Pageler, CSO of digital asset trust company BitGo, explained how his mentoring period began in 2013, when he was working for DocuSign (then a startup with 200 employees that needed help building a security team). 

He’s been teaching future CSOs and CROs at Carnegie Mellon University for six years, and simultaneously expanding his role as a mentor through BitGo’s internship program. 

“I’m a builder—it’s important to build the team and make sure there’s someone who can take over when you leave,” he said. “It’s important to have a really strong network and look for opportunities for people on your team, even if it means sending them elsewhere.”

His approach to mentoring is to pick a project and give the mentee oversight, acting as a sounding board but ultimately letting them make the decisions.

“They might not make the decision you agree with, but it’s an OK decision. By letting them present it to upper management, they understand how it all works, with you as a safety net,” he said. “Then when you’re not there, it makes them much more confident. That’s the way I was mentored.”

Paegler explains that managing a team and having a strategic vision are areas where people need mentorship. They can be guided through the process of weighing vulnerabilities and impact, making informed decisions, and making sure that they’re strategically thinking about the grand scheme.

“That’s why mentorships are needed,” he added. “It’s showing people that it’s OK to ask questions, it’s OK to bounce ideas off other people. Whether that’s having a mentorship available from a security-specific angle, or help with executive decision-making, or just looking at something from a different angle—I think that’s really important.”

Listening is Key

For Kristala Prather, Arthur D. Little Professor of Chemical Engineering at MIT (and instructor of the MIT professional education course Fermentation Technology), returning to her alma materafter years at Merck Research Labs was a decision she made in part because she wanted more opportunities to mentor young people.

Her mentor during her years at MIT as a student, Professor Daniel Wong, is now her co-instructor in the Fermentation Technology course. He played a major role in bringing her back to MIT in a professional capacity. 

Wang also helped get Prather involved with MIT Professional Education, offering her additional opportunities to have an impact through courses for people who are currently working in industry.

“If you’re a young person interested in any area in the tech space, mentors are especially helpful in using our collective experiences—and individual experiences—in helping them navigate through the excess of information the digital age has brought,” she said. “There’s so much information today that we’re almost in information paralysis mode unless you have someone else to help guide you.”

Part of an effective mentoring relationship means there needs to be space for the mentee to say: “No, that’s not what I need.”

“There has to be enough exposure that the two individuals can understand each other and be comfortable and clear in what it is that they need,” Prather said. “Part of it is having a commitment on the mentor side and recognizing that if I am making this commitment, it requires a time investment.”

That goes equally for the mentee, as well, which means those seeking Prather’s advice can expect homework assignments and other information-gathering tasks: “That helps establish what the needs are, and what I like about giving homework assignments is it emphasizes the fact that mentorships take work.”

The results of building a relationship: A long-tail impact that extends beyond the mentee’s years in academia or initial period in the marketplace. 

“If you talk to a lot of effective mentors, you’ll find we all still continue to have great mentors,” she said. “It’s important to help young people get established, but those relationships don’t need to be restricted to just those years—they can be lifelong relationships and be very beneficial and rewarding for all parties involved.”