Tent Talks Featuring Kara Fitzpatrick: Tools, Trust, and Transformation: A Guide to Modern Mentorship

[00:00:33] Chicago Camps: You’ve mentioned having a perspective on structured versus unstructured mentoring. Can you break down the key differences and share why structured can be such a game changer for both mentors and mentees?

[00:00:46] Kara Fitzpatrick: Over the years, I’ve been a mentor. I’ve been mentored. And a lot of the observations I’ve made are there’s basically three kinds of mentorship.

There’s, Hey, let’s grab a coffee. And there’s the middle one where let’s meet X number of times a month or X number of times over the next six months. And then the kind that I’ve grown into and created my own flavor for over the years, my own process is a really structured mentorship where you start off with a meeting, getting to know each other, getting to know goals and objectives, and really setting goals for the time together while being a little flexible in a few ways.

But I think those are the big three. And for me personally, if I’m going to invest my time in you and you’re going to invest your time and effort and learning, I really want to make sure we’re both getting out of it something that’s going to be great for both of us.

[00:01:35] Chicago Camps: In your experience, where do people trip up when starting a mentorship relationship and what can they do to ensure a productive partnership?

[00:01:43] Kara Fitzpatrick: It’s a great question. I find that people are complex humans full of feelings. And where people trip up the most is they get their feelings hurt because they haven’t set up from the beginning what their expectations are, right? And again, I think at the beginning, the most important thing you can do is set expectations and really laying out what both of you expect to get out of this and then getting it written down.

So that’s one of the things in the very first meeting, it’s get to know you. And the questions I usually ask are, What do you love to do? And then I ask, what can I learn from you? And then I asked, how can I help you? And so those three questions really just, they really take up the first half hour in a nice, authentic way that gets to know each other as a human.

Usually I’ll send them out with homework. And for the second session, it’s come back with answer these two questions. What does success look like? And what problems are resolving for and those problems end up becoming the goals. And I try to limit it to two to three goals for our time together.

Usually it’s a three month mentorship or a six month. We meet every two to three weeks, but we’ve got it all written down, and then we’re aligned before we even start the formal mentoring and the formal feedback loops. Those are where I see it set up best and avoiding tripping over themselves because inevitably, you’ve got the Brene Brown story, I’m telling myself where I might have to miss a meeting as your mentor, but what really you might be telling yourself the story, oh, she doesn’t like me or she doesn’t value us or she doesn’t want to be doing this anymore. And the reality is I had to run to the ER because my dog got sick, but you’ve built up this story in your head.

So by writing everything down, we get aligned on what that looks like. And there’s some roles that we can put in place together as the person being mentored and the mentor. Is it okay if we check in that morning and if both of us are swamped or one of us is swamped? Do we both feel like it’s okay for us to cancel or shift or move to another day?

And again, just encouraging that open communication from the beginning gets rid of most of the problems with people’s feelings, getting hurt or misunderstandings happening and getting bigger than they need to be. That’s also a giving them permission. Because there’s often a power dynamic in a mentor mentee relationship and the person might not feel like they can come to you with something that’s a difficult conversation.

So again, setting up those ground rules of “if you have a question, don’t let it fester and let’s get it out of the way.”

[00:04:04] Chicago Camps: What tools, practices or frameworks have you found most effective for creating meaningful and lasting mentorship experiences?

[00:04:12] Kara Fitzpatrick: In preparation for this interview, I went out and I’m like, what do the formal people say about mentorship?

And guess what? None of it’s formalized. There’s the three C’s of mentorship. There’s the five C’s. There’s the four A’s, which is, listen, my background, my undergrad was theater and English. My grad degree is in training, design and development. So teaching adults.

I’ve also spent years and years coaching and producing and directing. And so we all actually are doing mentor or mentee all the time. We’re always teaching somebody something we’re always learning. And so I think, you know, is there a formal way to do it? What I found that works for me is really, that’s the best way you can do it.

Figure out what works for you. Go do the research if you want. But what I found in my coaching, literally as a soccer coach and in my mentoring is just start with a Word doc. It can be a Google doc, Word doc, write down all the questions that you want them to answer. It can be ahead of your first meeting.

What does success look like and what problem are we solving for? Success look like gives you a nice true north for your time together. I had one person that I was coaching and she was trying to move up a step on the ladder. I had another person who didn’t feel like she could speak up in meetings. And so a lot of the assignments in between was to give you an example, a concrete example.

In another meeting where you’re comfortable with your peers, I want you to interject with an idea between now and three weeks from now. It could be I want you to go to your boss for the proposal, but we work together in a way that they feel comfortable and confident. So I’m not going to give somebody an assignment or a stretch goal in between our sessions or from session one to session six, whatever it is that makes them really uncomfortable because there is far too much in this world, Russ, that make people feel less than, and I’m not going to be one of them.

So I will push, but I’m not going to push them over the ledge. Right? I’ll have them inch a little closer, but not go over. So WordDoc is great, and then it was really sweet. One of my folks I was mentoring, at the end, they put together a PowerPoint deck.

And it was like six slides. Here’s the problem we were solving for. And then each slide touched on all four of those things. And at the end, there was just a general slide that said how they felt. It’s about both the journey and who they were at the beginning versus the end. It’s a concrete accomplishment.

It’s a certificate of completion. It’s a, look how far you’ve come in our time together. I’m so proud of you. And so I, part of it is the tools we literally use. And part of it is your job is to be a professional hype person. I’ll never forget one of my first mentorship roles where I was the mentor. Cause again, the age and stuff, it’s weird.

Your mentor can be older than you. Your mentor can be younger than you. As long as your mentor is somebody you want to learn from, it doesn’t matter if they’re older or younger or anything. But I remember I was at a conference in Seattle and it was called OS and Feels (Open Source & Feelings – osfeels.com). It was the intersection of humanity and technology.

And this person just walks up to me and asked me what I did and where I worked. And I happened to be at the white house at the time. And he said, I want you to be my mentor. And I was like, great, here’s what it looks like. Here’s the expectations. And he looks at my list and this is a fair thing for people to consider.

And he just looked at that yeah, no, that’s too much work. I just want to be your friend. And we’ve been friends for eight years now. And he’s one of my best friends. Part of it is also that, who do you go up to and how do you ask? And bless his heart, he just walked up and he’s, hi, we’re going to do this.

The coffee mentorship might be right for people. It’s not right for how I view my mentorships, but just because it’s right for me, doesn’t mean that you shouldn’t try to have a mentor relationship just because you only want to get coffee or whatever works for you. So that goes back to that first meeting of setting expectations, setting an agreement, making sure you’re both aligned on what this process is going to look like, because I’ve had other people are like, Oh, really? A phone call won’t work for me. I need FaceTime. And I’m like, okay, it’s going to go longer than we agreed. And then it goes back to let’s revisit the agreement.

That’s another thing too, as far as like processes and tools. Yes, there’s the once every two or three weeks meeting, but then there’s also the like midpoint check in. I want folks to reflect, because if you pause and reflect in the middle, of the relationship, then it gives you the opportunity to course correct.

Because you don’t, both of you don’t want to be spending time doing something that really doesn’t benefit what the, the person being mentored wants to get out of it. So I find that midpoint check in is a nice time to just have an honest conversation and then you can both shift here and there as needed to make it better for everybody.

[00:08:41] Chicago Camps: Mentorship can happen beyond the workplace, and you’ve done pro bono work, you’ve taught in rural India, and you’ve supported micro entrepreneurs. How do mentorship principles shift when you apply those in a community focused setting?

[00:08:56] Kara Fitzpatrick: When we were in government together, we had a saying. One was go where you’re wanted, right?

And another one was be adaptable and meet people where they’re at. And so a lot of these principles may work in a corporate environment or they may work in government. But the story I’ll share about Indian microentrepreneurs was we were over there figuring out how can we help them through the use of technology to run their small businesses more efficiently.

And these are micro businesses. These are cake designers and bakers. These are jewelry makers. I’ll never forget, we went out and did some follow-me-homes where we go out to their place of business and we just watch them work for a couple hours and take notes and ask questions at the end.

And I remember we thought our answer was to give them financial software. We were so confident that they just used financial software their lives would be so much easier. And I remember about 20 minutes into the observation period, I looked over and there was three large books with a computer monitor on top and a keyboard was on the floor with the CPU and it was unplugged.

And I said, why is that unplugged? Tell me more. What’s the story here? And he said, Oh, that old thing. We can’t use computers. We lose power every two hours in our town. And so if I haven’t backed up everything, then I’ve lost all of it. And he pulls out a ledger, probably about say 18 inches by 30 inches.

Pulls out his paper ledger and he said, this is the most efficient way to do my business. And so it was such a humbling moment of when we come in with, Oh, this is the person I’m mentoring and this is the process I’m going to use and these are the tools and this is what they’re going to get out of it by the end. 

That inflexibility is not going to work for people. And so really it’s about, again, spend that first meeting, getting to know them as people, what is their currency, meaning what’s important to them, how do they want to succeed and why, who do they want to impress, who do they go to for advice and feedback? And most importantly, how do they like feedback? Because your how, or a president might be different than your how for an executive assistant that you’re working with, or a mid level designer.

And so really, the most important tool you have as a mentor is adaptability and empathy.

[00:11:08] Chicago Camps: Your career spans tech innovation, public service, leadership at iconic organizations. Even being on the field or on the stage for a lot of really cool things. How has mentorship played a role in your own growth and how do you approach coaching others to navigate major career pivots?

[00:11:27] Kara Fitzpatrick: Thanks for that question. It’s such a weird space to be in having worked in sports and entertainment and government. And when people come to me and say, Oh, what is your career path or how did you get there? And I’m like, I wish I had an honest, awesome answer for you. It just all happened. Something showed up in front of me and I thought, that sounds cool.

And then I went and got the role. I was fortunate to get picked for a lot of cool things. The funny thing about me saying that sounds cool is I actually have a monthly check in with a friend. And the title of the check in is, That Sounds Cool, because she was one of the first ones to come to me and say, How did you do all this?

And the cool thing about the check in is that’s not actually when we talk or meet. That is when we text each other to say, What day looks good for you this week? And then that’s the day we meet because that’s rule one of mentoring. If you set a day and then one of you can’t make it, what usually happens is it just gets punted to the next check in.

So instead, having a time where you actually check in to say, What’s a good time this week? And that was what I learned from one of my first mentors. Was go ahead and set the thing, but then be flexible. And if I look at my whole career, that’s my whole career. I tell people all the time, I’m a kid from Jersey who was supposed to be a high school English teacher and coach soccer.

That has not been my life, but if I had stuck to that, so rigidly, I wouldn’t have experienced all these beautiful things. And so that was what my one mentor taught me is be open to things that come your way because, as she said, your life can be so much more spectacular than you could ever have dreamed. I had another mentor who, and this was as a former government official and a private sector employee, I had another mentor who said vacation time is all made up and there’s no rules, right?

And this was when I was working in pro sports and you would show up on game day, let’s say it was a two o’clock kickoff. You show up at the stadium at 6am and you’re not leaving until 11 o’clock at night. And so her thing was take as much time as you need. Cause the lesson with her was at the end of the day, we will get more hours out of you than 40 hours a week over the course of your career with us.

So you take as much time as you need to relax. And I try to pay that back with my teams where don’t you dare ever put in time for going to the dentist office. I know you worked five extra hours last week to get something out the door to our customers or to people in America. And I’d say the last role when you and I were in the Obama administration, the thing I learned from President Obama and Vice President Biden, the number one thing is you can be kind and still get shit done.

And that’s another thing too, is as a mentor, it’s the direct relationship you have with the person, but also paying attention to the rest of what they have going on. And how might you influence their career for the better? So you and I have a shared value that if somebody has a training budget, they should use it.

And I think we’ve both gone after our teams and yelled at them as the year and gets closer because why aren’t they using it? And so that’s things where I’ve also looked at as a mentor. What’s the bigger picture that might be affecting the person that I’m working with and how might I affect that in positive ways?