Kendra Ott wasn’t exactly sold on Everwise. “I thought it was going to be a little bit surface-y and not all that useful, to be honest,” she says. But she gave it a try anyway because she was weighing some heavy career decisions. After four and a half years at the same organization, Kendra had grown out of her role and was ready to take on something new. But without a clear concept of the right role and a real plan to get it, she knew she was just going to keep treading water unless she tried something new.
If Colin Schiller (President and Co-Founder of Everwise) hadn’t asked Kendra outright if she wanted to try Everwise, she might not have given mentorship a shot. Though she’d certainly had bosses and professors who’d taken an interest in her career development in the past, she’d never actually had a formal mentor before. “Sure,” she said, “Can’t hurt, right?”
Through Everwise, Kendra was matched with Chris Crosby, an entrepreneur out of Dallas with an impressive background as a Founder and CEO, with over 20 years of experience and several successful companies under his belt. Kendra was considering pivoting away from nonprofit work, towards something more entrepreneurial, something closer to what Chris had spent the last two decades doing. They met over the phone every three weeks for five months, working through her obstacles and formulating a plan. Looking back at the experience now she says, “The Everwise mentorship was a big part of my process of moving beyond that in-between phase.”
But what does an Everwise mentorship look like, exactly? How can a handful of calls translate into real career development? And isn’t it blind-date-level awkward at first?
Now that it’s been almost exactly a year since Everwise’s mentorship officially ended, we caught up with Kendra to ask how the mentorship impacted those big decisions, how her career has developed, and what advice has stuck with her since.
Do you remember that first meeting?
I do. Someone from Everwise lead the call and introduced us, then Chris and I caught up afterwards and followed the guided questions that we were given.That first meeting was structured and formal, it was like, “Who are you? Who am I? What are we here to do? How are we going to communicate?” We were sort of setting up our baseline, which is really important, but our relationship ended up being a bit more casual and consultative than our first call was.
Going into that first meeting, did you already have a clear idea of what you wanted to work on?
Not really. I was sort of pie in the sky. I also had a different experience than I think a lot of Everwise mentees do because I wasn’t given an Everwise seat by my company, and I wasn’t trying to move up in my company. I was interested in exploring my career more broadly. I didn’t have a super clear idea, I just knew that I was ready for a change and that I was ready to talk to someone outside of my immediate network.
You said that the relationship evolved to be a little bit more casual. Did it evolve really quickly or did that take some time?
No, it evolved pretty quickly. I think we maybe even got there on the first call, because we really got along. We had a great conversation. I wasn’t quite sure what magic algorithm put us together, but it didn’t take very long for me to see why we’d been put together. Chris had done all kinds of cool things in the world that I was really interested in joining. It just sort of flowed really naturally from there.
What kind of surprises did you encounter?
I had little experience with career coaching. I was just floored with how helpful it was. I was also surprised at how seriously Chris took it. He had tools for me to use and structured ways to think about what I wanted. It wasn’t just him saying, “Here’s my experience, here’s how I did it, here’s how you do it.” He was really listening to me and thinking with me about my situation in a way that wasn’t simply helping me mirror him. From the few meetings we had, I took away some real nuggets that I still think about today.
How minute and practical were his initial suggestions? Or were they big and theoretical?
His suggestions were practical, which I needed. He was like, “Sit down for an hour and make a decision tree of your different options. Really think through each branch, think about what leads to what leads to what.” We talked a lot about budgeting too, because I was ready to leave my job without another job.
Was that your primary goal for the mentorship? To find a new position?
Yes, my goal was to get a new job. I was vague about what that was going to be. Chris slowed me down a little bit and made it more serious, gave me some serious things to consider before I made a hasty decision.
Where did he challenge you the most?
I remember talking a lot about calculated risks. I was ready to be really risky, and he pushed back on that a little bit, forced me to really think through some things and make sure it was going to work out. He encouraged me not to quit my job without another job, which is really good advice. I did it anyway, but it was so helpful to have another person seriously considering my situation with me. I thought long and hard about his advice, it was up there with my parents and my husband.
Which pieces of advice have stuck with you the strongest?
When I told him what I wanted to do next it was fairly vague and I was unsure that it was even possible. I was approaching it in more as wishful thinking, but he was very much like, “You can do that. You should do that. You will do that.” That assurance was so interesting given how little we knew of each other. It was such a source of strength for me then, such a force at my back like, “Oh, yeah. I am going to do that.” That feeling stuck with me.
Have you noticed a lasting impact in either your professional or personal life?
Since then, I’ve had conversations with other people going through the same thing and I have found myself deferring to his advice more than once — which is funny because it’s not necessarily my natural advice. I often think about how much weight someone puts on another person’s advice. That certainly affects how I’ve been interacting with people since.
Have you considered mentoring yourself?
I get to mentor often in an informal way. For example, I belong to a women’s group and every once in a while, someone will reach out and ask, “Hey, would you mind grabbing a glass of wine? I want to pick your brain.” I’m always really happy to do that, but I haven’t considered formal mentoring yet. I’d like to do it a bit further down the line so I don’t lead anyone astray!
When you decided to leave your job, how did Chris help you clarify your next steps?
He told me, “Schedule meetings, schedule coffee, schedule lunches. You’ve got to talk to everyone you know.” I remember sending him a lengthy list of people I promised I was going to talk to. He encouraged me to network and get out there and talk to people about what I wanted to do, and to have really good questions prepared going into the meetings. I ended up spending three or four months networking every day.
Are you still in contact?
Chris emailed me recently, a year after the mentorship ended to ask how things were going, how it had all turned out for me. I thought it was so cool that I was on his radar that day. We had another really nice exchange. We live in different cities, so I’ve never met him in person, but it was really nice to connect with someone who I felt really got it, really got me, and was really thoughtful and cared a lot about my circumstance.
What did you talk about when he reached out?
We updated each other – we’ve both had big years. And I recommended a book to him.
It’s awesome. It’s called The Crossroads Between Should and Must by Elle Luna. It’s very San Francisco, heed-your-calling type stuff. It’s a fun read.
When he got in contact with you, did you find yourself with any different perspectives on the time?
Well, I went back and read some of our emails. It was funny to see small threads from a year ago that have really come to life and turned into big threads for me. It wasn’t all peaches and cream to get here, but it was fun to revisit what we were talking about a year and a half ago and to see some of that coming alive. Definitely.