Why do mentors offer up their time and energy just to boost a stranger’s career? And what do they get in return for such an investment?
Earlier this week we brought you an interview with Kendra Ott, a first-time Everwise protege, who gave mentorship a shot despite a few initial reservations. Her progress since the program ended has been impressive; Kendra left a comfortable, but stagnant role at a non-profit and leapt into the unknown, only to find herself in a different role at a new organization, with plenty of room to grow. Today we bring you another perspective on that same story, the perspective of her mentor, Chris Crosby, a seasoned entrepreneur and current CEO of xaqt.
Chris’s calm, thoughtful demeanor is a welcome contradiction to the typical founder/CEO stereotype of a loud, impulsive adrenaline junkie. And maybe that’s partly because he didn’t set out to build companies. Chris ran call centers for over a decade before he caught the entrepreneurship bug from his mentors and started launching startups in the early 2000s. Over the course of his career so far, he’s ventured into identity theft prevention, reputation management, predictive analytics, and IRT analytics. In addition to offering his time and energy as a two-time Everwise mentor, Chris recently joined us for an interview and gave us a peek at how he approaches each mentorship, what he and his proteges talk about in their meetings, and how his experiences on both sides of mentorships have shaped his career.
Have you ever had a mentor yourself?
Yes. Back before I was starting companies, I ran call centers, where I had two really good mentors who helped shape my trajectory from a business perspective.
What were you hoping to get out of mentoring?
For me, I was at a point in my career where I wanted to give back a little bit and I remembered how important it was having a mentor, particularly in that mid-to-late twenties spread. It was a very rewarding experience because I got to go on a kind of journey with the mentees, and sort of learn more about my own career development through that mentoring.
What were your biggest career influences during that turning point around your late twenties to early thirties?
I left corporate America to start my own company and my mentors were both entrepreneurs who had built and sold companies. So from an early age, I was around the entrepreneurial environment. They have this attitude: Now go build something. You don’t have to excel at it, just go create something, build it. I took that with me when I left and started my own company.
You’ve mentored with Everwise twice. Were your two Everwise proteges, Rob and Kendra, in similar places when you started mentoring them?
Rob was in a familiar situation to Kendra, where he was looking to take the next step and wanted some guidance around finding an ideal role for himself.
What did you discover during the mentorships?
That the process is ongoing. Careers change and the challenges don’t stop — it’s a cycle. Whether you’re twenty, thirty, or forty, staying focused on a growth trajectory really matters.
What was the first meeting with Kendra like? Was it awkward at all?
I wouldn’t say it was awkward because we were both there for a purpose, which was to dive in and understand what Kendra wanted to accomplish and how I could help. Everwise did that first introductory call. It’s a great process, I think — the way Everwise matches up the mentors and mentees, and the way that initial call is set up.
What were your first impressions of Kendra and her situation?
I saw someone with this tremendous amount of talent who was looking for a transformation in her career and her trajectory. She was looking at starting her own company and didn’t know what that would look like. She was looking at other career opportunities but again didn’t know what they would look like, so it was really around setting up a discovery process for Kendra to figure out what her values were and what was most important to her in that myriad of options available to her.
She mentioned that she was really impressed with the assignments you gave her. Do you remember any of that homework?
Yeah vaguely. We talked about making a decision tree of her options. She was thinking about starting a company, so I told her to look at the different options for creating a company and plot out where each path ultimately led.
Were you pulling for her to make one decision or another?
No, I don’t think that’s my job. I don’t think a mentor should push one way or the other. My job is to give them the tools to make those decisions.
And what did she decide on?
We ended our cycle of mentorship right before she made a decision. We spent a couple of months meeting together and then lost touch right at the decision point. She made a lot of progress and considered a lot of options in that time. A year later I reached out to her and she told me she had quit her job. I congratulated her on ignoring some of my advice and taking a leap anyway.
Did Kendra and Rob require different approaches?
I think their communication styles were different. Rob and I did a lot on the phone and Kendra liked to send me updates by email. Kendra did a lot more with career development on her own. She would go out and get involved with things that she wanted to learn, whereas Rob’s task was more to get out and not meet a lot of people to figure out what the next career move was.
How did things work out with Rob?
I talked to him maybe six months ago and he’s doing great. When we started he he liked a lot of different things about different job roles and so we were trying to figure out how to find him a creative role somewhere that brought together the best elements of what he wanted to do, as opposed to going to work at a big company where the roles were more narrow and defined.
And did he find that role?
Yes. He went to work for an early stage company. By moving into more of an earlier stage startup he was able to take on a lot of responsibility and wear more hats.
Any pieces of advice that you gave to both of them? Kendra mentioned you encouraged her to slow down and think more carefully.
I wouldn’t say it was about slowing down, necessarily, as much as applying some critical analysis around: what are the high-value activities for your time? If you’re planning to quit your job, make sure you’re approaching the decision from all angles. I didn’t help her make a budget but I said, “You need to sit down and put together what will it take for you to quit your job from a financial perspective.” And even Rob, he was thinking about talking about taking HTML classes and I said well if you can hire a web developer on ODesk for $15 an hour, why would you go back to school for $15 an hour job? I would say that advice was universal between the two of them.
And have you found these mentorship experiences changing how you think or interact?
Everwise recommends reading a book together and discussing it and I think that type of tool is valuable because it gives you a common framework for discussion. You can each talk about how you approach things differently. I’ve used that outside of Everwise.
Now that you’ve gone through the whole cycle a couple of times, what’s been the biggest takeaway for you?
That mentorship can be more formalized. My mentorships never had any formal script around them, so the Everwise experience put that framework in place.
Were there any mentors or mentor like figures that you keep in touch with today?
Yep. I keep in touch with a few folks — I would say Ron Heifetz’s work on the adaptive leadership construct has really stuck with me and I’ve brought that concept into everything I do in mentorship or career development. Whenever I’m setting up conversations with people, I draw on experiences from the Harvard Kennedy school.
Do you have any advice for prospective mentors?
It’s important to remain objective. I identified with both of the mentees, because they are both great people, but it’s important to be able to provide an outside perspective that’s more career focused. I think a mentor’s role is not necessarily to be a big brother, but to be focused on that career trajectory.
If you were to recommend a few books to anyone early on in their career what would they be?
Well, in keeping with the Kennedy School theme let’s say, Leadership on the Line by Ron Heifetz; and The Alchemist — which is one that I actually had Rob read.
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