IT mentors: How to make the most of this win-win relationship

IT mentoring gives leaders a satisfying way to pay it forward. It also offers a way to engage star talent, learn about new tech, and relate to younger workers. Here's how both sides can make it work best
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The Mentor CIO

When I talk to people who’ve never engaged in either side of a mentoring relationship, what I hear most is, “How do you even start one? How do you find someone? Are there regular meetings? Homework assignments? How do you know when you’re done?”

Mentoring can seem like a strange bridge to cross, but it’s really not that difficult. 

Mentoring is one of the most important things a leader can do, and not just for altruistic reasons.

Mentoring is one of the most important things a leader can do, and not just in the altruistic sense of helping develop the next generation of leaders. While that’s extremely valuable, there are other important reasons leaders should mentor. It also helps IT teams increase engagement and retention of their best talent, and it helps the mentors themselves stay abreast of changes in technology and the expectations of younger workers.

“I feel a need for a next generation of leaders who can take us further in today’s massive, ongoing tech transformation. And when I’m mentoring someone a generation or more behind me, I’m definitely going to learn from them about their perspective and what’s motivating them,”  Dollar Bank CIO Bill Fortwangler recently told me. He is both a sponsor and participant in the Pittsburgh TechLX mentoring program I help run. 

Here’s what I’ve learned from my experience as a mentee, a mentor, and someone who helps run mentoring programs.

How do I find a mentor?

A mentoring relationship can happen organically: A worker sees a leader he admires and asks for some advice. Or the leader notices a junior staffer who’s struggling, or has great promise, and reaches out. Many people tell me it would be awkward to take the first step on either side of that equation, and I always tell them to think it through. If someone came up to you and expressed admiration and a desire to learn from you, wouldn’t you be flattered? If a senior leader in your organization said she sees such potential in you and that she wants to coach you to the next level, would you be upset? Of course not.

If someone came up to you and expressed admiration and a desire to learn from you, wouldn’t you be flattered?

Sure, once you get into the initial conversation, you may find that you and this other person don’t align well. “My schedule won’t let me make as much time as you need,” or “I don’t think I have the right experience to help you with the issues you’ve identified.” No harm in that, and it may lead to a better outcome: “But you know who’d be perfect for you to talk to …”

Many larger companies offer formal mentoring programs that make it even easier to connect to someone in your organization. My company has been putting on regional leadership TechLX development programs for years, and mentoring is one of the pillars of the program (along with leadership assessments and workshops, and peer learning). Such efforts give mentors and mentees from different companies and industries the chance to connect, using a little bit of matchmaking and suggesting just a bit of formal structure to get the relationships off the ground.

Andy Bonelli, a senior IT manager who has worked with both his in-house program at PPG and our Pittsburgh TechLX group, sees the value of a structured program.

“I think there definitely needs to be kind of an enablement between the two parties,” he says. “A little structure around the pairing process, providing biographies and helping take away the uneasy introduction part of it is definitely helpful.”

In PPG’s program, Andy has been both a mentor and mentee. Recently with the Pittsburgh TechLX group, Andy was paired up as a mentee with Bill, the CIO at Dollar Bank. I asked Bill how he knows when a mentee is right for him.

“In Andy’s case, I just started talking about personal things, what he likes to do, what motivates him, his family situation, just to get a feel for what drives his personality,” Bill says. “From there, I always ask about what a person wants to focus on. Often, they may not know. But Andy knew, and I saw the potential to help him achieve his goals.”

Andy says he wanted to get a perspective outside PPG’s manufacturing realm. He saw that Bill was in financial services, yet had a similar enough background that he’d understand Andy’s journey so far. And someone in his TechLX group worked at Dollar Bank and spoke highly of Bill. “So I went ahead and reached out, and we took it forward on an ad hoc basis, about once a month for a few months.”

Let mentees drive the agenda

Structuring the relationship after that initial meeting presents more challenges. My work has me on the road two weeks per month, which means a lot of my mentoring conversations take place over the phone, and at irregular times, rather than a “lunch every second Wednesday” cadence. It’s whatever works for the two people in the relationship. Depending on the immediate needs and the learning style of the mentee, more frequent meetings or in-person conversations might be better. Other folks just need someone to check in with when a thorny challenge presents itself.

[ Read more by Dan Roberts: Goodbye soft skills, hello core skills: Why IT must rebrand this critical competency. ]

As both a mentor and mentee, Andy has seen that the junior partner must take the initiative.

“The mentee really has to drive the structure and cadence,” he says. “First, it makes it easier for the mentor because they're offering up a lot of valuable input, and second, the relationship wouldn’t be as productive if the mentor were driving the conversation topics and meeting times.”

“The success of the relationship depends so much on what the mentees put into it,” Bill agrees. “They have to make the effort around getting things scheduled, working through agendas, coming prepared. They have to be able to talk about where they feel insecure or feel like they’re failing, because those are the discussion points we can put some plan of action around.” 


Dan Roberts
Dan Roberts is CEO of Ouellette & Associates Consulting. In this role, Dan leads the firm that has been known since 1984 for “Developing the Human Side of Technology.” His team has helped more than 3,500 IT organizations build a world class culture, a high-performing workforce and a differentiated talent brand.