Building a Successful Career Mentorship - Real Creative Leadership

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Building a Successful Career Mentorship

March 24, 2022 Brand Leadership Business Growth Career Growth Creative Agency Design Leadership Mentorship Strategy

Guest Speaker

Jess Kessler

Head of Content and Creator Marketing, Audible

Jess Kessler is the Head of Content and Creator Marketing for Audible. As a creative and data-driven marketer with 15+ years of experience, she has led and managed across companies and platforms including Cinedigm Digital and Nickelodeon. She is also a published journalist, mentor, mentee, loyal Miami Hurricane, and mom of two.

Guest Speaker

Ashley Walsh-Lopez

Paid Search Manager, Reprise Digital

Ashley Walsh-Lopez is a Paid Search Manager at Reprise Digital. She has worked with communications teams on local, state, and national elections as well as with data-based optimizations across digital media suites. She has a BA in Political Science from Eckerd College.

Make mentorship matter.

The best kind of mentorship is a win for both parties. As a mentor, you get to give back in ways that reflect the values you care about most. And as a mentee, you get to benefit from another’s hard-won knowledge in the creative industry. But as you move through the mentorship process, it turns out there’s space for both of you to do some learning along the way.

In this episode of Real Creative Leadership, real-life mentor/mentee Jess Kessler of Audible and Ashley Walsh-Lopez of Reprise Digital talk to us about how asking the right questions, listening intently, and having ongoing flexibility made their mentorship a meaningful — and enjoyable — experience.

Listen now to learn more about the give and take of a successful mentoring relationship.

Watch this episode to discover:

Where to look for mentor/mentee opportunities
What kind of groundwork can help you in your role
The intangible benefits of a mentoring relationship
How to make a mentorship the right level of personal

mentioned in this show:

Adam Morgan

Creative Leader and RCL Host

The Stoke Group

Digital Marketing and Full-Service Content Agency

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RCL Episode Season 3, Episode 3
Mentorship – Guest Show
Jess Kessler and Ashley Walsh Lopez

Building a successful career mentorship

with Jess Kessler and Ashley Walsh Lopez

Opening Quote (27:29)

“It’s really about creating a safe space and a place of trust where someone can come to you and confide or ask a question that may have some negative connotation to it if it were asked in a broader group. So I think that’s really valuable as people try to navigate their way through their careers.”

Transcript

Adam Morgan:

Hello and welcome back to Real Creative Leadership. This is season three, episode three. And our topic today is on mentorship.

Now this is an important topic because every time we reach out and ask people, “What do you want to hear about, what do you want to talk about?” inevitably, the question of how do I get a mentor comes up. And it’s always top of mind.

So we’re going to be doing, we have a solo session, we’re going to go through a lot of research on, and my personal experience on mentorship. But today we have two special guests and we’re going to get their lived experience on how they’ve been both sides of the fence, on both being a mentor and a mentee in different situations. So we’re going to get some great information from them.

So our first guess is Jess Kessler. She’s the head of Content and Creative Marketing for Audible. Welcome to the show, Jess.

Jess Kessler:

Hi, Adam. Thanks for having me.

Adam Morgan:

Excellent. And our second guess is Ashley Walsh Lopez. And she is the Page Search Manager at Reprise Digital. Ashley, thanks for joining us.

Ashley Walsh Lopez:

Thanks for having me.

Adam Morgan:

Let me tell you a little bit about where we met. So I went to Content Marketing World and there was a special session on this formal program that CMI had set up for mentors. And both of them were a part of this awesome program. We talked afterwards. And of course they were the perfect people to come on the show and talk about mentors. So let’s get going into this.

First let’s start with Jess, and then we’ll move over to Ashley. Jess, give us a background, a brief introduction of your career, where you are, who you are, so we know a little bit about you and then we can move on to the topic.

Jess Kessler:

Great. Well, I’ve loved storytelling since I can remember. And so I actually started my career as a journalist. And then I slowly learned after being exposed to additional industries that I could tell stories through marketing. And so I moved over into the marketing space where I worked for companies like Nickelodeon and where I also did film and television distribution and marketing for indie films, like Tribeca Film Festival, or Sundance, and where I also worked with some TV networks. And then that led me to Audible, And now I get to tell stories through marketing, but I also get to listen to great stories every day. So it’s really a dream come true.

Adam Morgan:

Well, excellent. Now, Ashley, let’s hear a little bit about your background.

Ashley Walsh Lopez:

Yeah, so my background is actually, I got started working in politics and on elections all over the country. I worked in communications teams and field teams at more junior levels. But the really great thing about working on political elections is that everyone needs to pitch in, and there’s just so many opportunities to learn. And so I really got to get started that way as a marketing generalist. And while I didn’t stay in politics, because with the demands of the industry, I did float around with tech and travel for a long time. And now I’m actually going to be working at an agency, Reprise Digital, which I just got started with recently, and it’s exciting. And I’ve kind of come from being a marketing generalist. I’ve specialized myself in the paid search marketing industry. So that’s what I do now. I work with Google ads, Bing ads, all paid search.

Adam Morgan:

Well, that’s awesome. Thank you both for sharing your background. Well, let’s dig into it. So let’s hear the backstory. How did you two get connected? First, let’s talk about the CMI program. And then I want to ask some other questions about those other programs you’re in, but first let’s start with CMI. Jess, if you want to give us an intro of the whole situation.

Jess Kessler:

It was really amazing how we got connected. The Content Marketing Institute I think is just a really amazing experience for people. It’s an educational tool, but it’s more than that. It’s about building and creating relationships, and transferring information and knowledge, and making content marketing as a whole, just a more established and fulfilling journey for a lot of us.

And so I volunteered to be a mentor, and they paired me directly with Ashley. It was their inaugural mentorship program. So first year out of the gate, they were so prepared. They had everything buttoned up, and Ashley and I got our kickoff and they said, “Hey, you know what, meet at least three times over the next three months, but take it as you guys will. It’s really what you make it.” And so Ashley and I kicked it off, and then we’ve been in touch ever since. And that program, I think I want to say started sometime mid-2021. So it really turned into a lovely relationship.

Adam Morgan:

Oh, excellent. And that’s just great to hear, because a lot of people who ask and ask questions about how do I get a mentor, they’re usually looking for an informal, just one-on-one relationship. And I’m glad that yours could move beyond just the formal program, which is awesome. Ashley, how about you? How did you find this program? What were you looking for? How did you get involved?

Ashley Walsh Lopez:

Yeah. So the funny thing about finding this program was, I actually had another mentor through a coding bootcamp I was doing at the time to brush up on some ad operations skills that have been really helpful for what I do. And my mentor there actually recommended look into Content Marketing Institute.

So I got into that, and I actually saw this more formal mentorship program than what I had with my instructor. And I thought, this has been so good for me so far, I’d love to go into a more formal mentorship program, and see who I can meet and what I can get out of that, and what I can learn.

And Jess is just absolutely the best possible outcome. Kind of what she was saying, our relationship really has been able to continue. And the mentorship, while we got so many great things out of it, was almost just a kickstart to what our relationship has become. So it’s been really lovely.

Adam Morgan:

And I want to dig in a little bit more onto why you joined, Jess, this program, because if you think about having a mentor, a lot of people think it’s going to be a silver bullet. It’s going to solve all of their career problems and this person will have every answer, but I really feel like there’s just few things that you should hope to get out of it. Like building relationships, or at least having some guidance. It’s not a silver bullet, but what made you decide to get in and share your time and be a mentor?

Jess Kessler:

Well, Audible as a company has a couple of people principles and it’s really the core values. And one of those core values is Activate Caring. And I subscribe to that quite a bit, both in my professional life and in my personal life. And it’s really about serving the needs of others. And that was one of the main reasons that I decided to join as a mentor, particularly because I wanted to create a safe environment for somebody to ask the questions that maybe they felt they couldn’t ask in their current position, or of their current colleagues.

But also then for me, I was really looking forward to understanding just through a different lens, how people are approaching their jobs right now, in the pandemic, especially, and really wanted to hear from Ashley what her core values looked like, and what she’s looking for in the next role that she’s after. Then I can take that back and work with my team and maybe find some similarities in folks on my team. And I can use that knowledge to create a better, more holistic environment.

Adam Morgan:

That is awesome. And before we get too far along, I also want to introduce your other program that you were going through simultaneously, Jess, which is, tell us about the Adweek program.

Jess Kessler:

Right. So at the same time, I was very interested in furthering my professional development, and so I signed up for the Adweek Executive Mentor Program. And that’s where they take emerging leaders and pair them up with CMOs, CEOs, those people who are very well established in their career and who have a lot of advice to give. So I joined up with the Adweek Executive Mentor Program, and I got paired with a really outstanding mentor.

And that was for me a place where I could actually ask some questions about, “How have you handled a situation when you were faced with X, Y, Z?” And that actually, I was able to take that information back and put it into practice, and become a better leader, and become a better listener. And actually then get some real time knowledge on how successful CMOs and CEOs are handling very complex situations.

Adam Morgan:

I think that’s pretty cool that at the same time you’re both on both sides of things. You’re both a mentor and a mentee in… Or at least Ashley, with you, had two different types of experiences. Both one with your professor and one with Jess.

Well, let’s just dig in a little bit more. Let’s start with Ashley, and then we’ll come back to Jess, but what were some of the unexpected benefits you got out of both of these situations?

Ashley Walsh Lopze:

So I think for me, it was hard skills and soft skills. So really, having Jess helped me with my networking abilities in the digital age, and in the COVID era, where I’m not necessarily in a city and I’m networking with people face-to-face. It’s more of going on LinkedIn and how do I get a benefit out of that? So that was so great to be able to really learn how to properly utilize that platform, from someone who has had so much success with it, and definitely brought success in my life as well. I guess that’s an example of a soft skill turning into hard skill. But also, just how to like Jess talks about a lot as well, reach out, go on Google and see who to follow, see who these thought leaders are in my industry. And like, what are their job titles? What can I be reaching for? (silence)

Adam Morgan

Ashley, that’s awesome. And now tell us more. You talked on an earlier call a lot about a little more detail of updating your LinkedIn profile that I thought was pretty interesting. Tell us a little bit more about that.

Ashley Walsh Lopez:

So LinkedIn was sort of something I had and forgot about. It was something I set up out of college, and just didn’t really think much about. I was like, oh, Instagram’s more fun, kind of a thing. And Jess really walked me through, “Okay, here’s how you can utilize this as a tool. And this is really the point of what this particular social network does.” So, I did. I got a new headshot. I updated my resume on LinkedIn, just basic stuff.

And then on the networking side, the thing that I never even really thought to do was use it as a social network, right? So I gave myself a calendar of how often do I need to just comment on stuff people are posting? How often should I be posting? Just to remind myself to do it, and get that visualization out there. And one that I started doing that simple stuff, I started getting contacted by so many recruiters. It was incredible. And I had so many opportunities opened up to me.

Adam Morgan:

That’s awesome. That’s just like a huge instant benefit of, “Go do this, things will change. things will happen.” And it totally turned out for you. That’s awesome. Right. Jess, back to you, what are some of the intangible benefits you got out of both, first, the CMI one, and then the Adweek program that you weren’t expecting, and then maybe some of the ones that you were expecting.

Jess Kessler:

Sure. So for Content Marketing Institute, I think I was purely expecting to form a relationship with Ashley, and then to hone that over time, and open up my network to her. That was really my main goal going into it, was to share advice and open my network, and then hopefully allow Ashley to find greater opportunity in the years to come.

But I think the tangential wins that we both received were we were invited to Content Marketing World, and we were invited to speak on a panel about the mentorship program, which obviously wouldn’t have come to fruition had we not participated originally.

We got to meet you, Adam, so this podcast is a benefit that we weren’t expecting. And I think broadly, the idea that then we got to walk the Content Marketing World floor, and we got to listen to keynotes, and we got to meet some pretty phenomenal people within the Content Marketing space. And we got to go to a happy hour at the Rock & Roll Hall of Fame. So all of that was really great stuff, and not anything that I would’ve predicted when I hit that sign up button.

Adam Morgan:

What about on the Adweek one? What were some of the benefits you got out of that program?

Jess Kessler:

I found myself speaking with my mentor on a regular basis, through text through email, and then of course on our scheduled calls. And the relationship was much more broad than I had anticipated. I really thought that I was going to be asking very tactical questions about situational leadership, and how I could address certain things that were developing within my own team, and how I might tackle that with a bigger perspective.

But instead, not only did I receive that, but then I also received some greater insight into industries that he was tapping into that I didn’t know anything about. Things about climate change, things about cannabis growth. All of these different industries that were really brand new to me, and I was hearing his investment strategy. I was hearing where he thought the next trends would be. And to hear that from somebody who’s a former CMO of two very major companies, I felt like I was on the inside track, and receiving insider information that I could then sort of take back with me and make my next steps.

Adam Morgan:

Oh, that’s fantastic. I think I was digging into a lot of what the unexpected benefits are. It’s just because when I hear both of you talk about the things that you got out of these programs, they both are surrounded around these ideas of, it was insights or guidance or relationships, connections, things that you would’ve never been connected to before if you hadn’t reached out and tried something. So I think those are all fantastic things that we can get out of a mentor program.

I didn’t hear things like, “Totally fixed my career, solved all my problems. Changed the trajectory completely of where I was trying to go with my career.” And I think that I just wanted to point that out, because I think that’s really important so that as people go into these different formal or informal relationships, or mentor programs, they have a clear idea of what they can get out of it. And it’s clearly going to be those relationships and some guidance.

The next thing I want to dig into a little bit is like, tell me about when you met and talked about things. I know the LinkedIn story is a good example of giving some homework assignments from Jess to Ashley. So what are some of the things besides just talking about — I’m sure it was like also personal life and all those great things — but what were some of the actions that came out of that?

Jess Kessler

So when Ashley and I first started, it was really a get-to-know-you session. And I think we both sort of structured that on purpose. We really wanted to get to know who each other was on a personal level. So I learned all about where she lives, what her husband does for work, her sort of family setup. And then I also learned what her long-term goals were. And that really helped me to put an Ashley picture together in my head and to understand not just what she was doing for work — because that doesn’t actually describe who we are, right, at the heart. So we talked a lot about that. And then I would say we also did a lot of speaking about changing jobs. I think, Ashley, you were in the midst of a job change when we started talking.

Ashley Walsh Lopez:

Yeah, absolutely. So it’s kind of interesting. I had just gotten a new job. I’d started the mentorship, and actually, kind of going into that when I realized, “Oh, I’ve been accepted into this mentorship program,” I was thinking, “Well, what am I going to do now? I have a great job that I just got. What can this bring for me?” But, of course, it brought so much more that I had anticipated.

I think just the opening conversations that Jess and I had of small talk and getting to know you, it made me comfortable to tell her about what my objectives are and also made me comfortable to be vulnerable about. I’ve come from this marketing generalist background and I don’t know how to pull out the specific skills that I’m really good at to sort of specialize and continue my career, which is with somewhere I was kind of stuck. And I think that without those more fun conversations, or just lighter conversations about what was happening in our lives, I may not have asked those questions. I may not have gotten out of the mentorship, what I ended up getting.

Adam Morgan:

That’s pretty awesome. We talked about jobs. It’s funny. It’s like you had a job and you got other job offers and you got a new one. And I think, Jess, talk to me a little bit about informal mentoring, because there is a difference of… Like normally on a formal one here, you’re not like offering a job to someone who you’re mentoring, but in informal ones where you’ve had them at work or with others, there’s a little bit more of that opportunity to know the space within the actual company and how you can make some impact there as well.

Jess Kessler:

Yes, absolutely. I think with Ashley specifically, I know very well now her strengths and her passions. And so when I am seeing people in my network who may have those openings and that sort of thing, I’m immediately thinking of Ashley. But the same thing happens when you’re in an informal mentorship program. And that’s something that, it’s not a structured thing. It doesn’t even need to be discussed. You can form the bond of mentorship without actually documenting it or verbalizing it. And it’s really about creating a safe space and a place of trust where someone can come to you and confide or ask a question that may have some negative connotation to it if it were asked in a broader group. And so I think that’s really valuable as people try to navigate their way through their careers.

And I think one thing that I’ve learned over time, both through being guided in informal and formal mentor programs, is that there’s no wrong question to ask, and everybody should feel like they have a safe space in order to do that. And when I form those bonds, it then allows me to see deeper into what that person is thinking of, where they want to go, what they’re challenged with in front of them versus what their vision is. And then I can start to think about, “Oh, well, maybe this opportunity would be great for you. Or maybe you want to talk to someone over here who can give you more insight.” And it really just creates a circle of information and guidance that may not be an immediate solve, but may then set the stones for you to take the next step, to get to the solution that you’re looking for.

Adam Morgan:

Wow. That sounds so exciting. It makes me want to just join in too. Like how do I… And I think that leads to the question a lot of people have is like, “This sounds fantastic. Awesome. I want this as well. How do I get it? How do I join something like this?” And maybe you could both just give advice of like, how did you even find the programs that you were looking for or gotten involved with being a mentor or mentee.

Ashley Walsh Lopez:

How I did find out about this program was actually through a coding bootcamp. So there are formal institutionalized settings for these mentorships, right? There’s your school, or even the company you’re at there may be mentorship opportunities. And then also on the software skill side, just talking to your friends that are in the industry, what has worked for them. Maybe they know about a mentorship program that wasn’t on your radar.

Jess Kessler:

For me, when I signed up for AdWeek and when I signed up for Content Marketing Institute, I actually just found those through online searches and through membership in certain professional groups on LinkedIn or Facebook or other social platforms. So it’s really just, for me, it was about setting aside about 30 to 60 minutes of research and Googling the right phrases. So “mentorship and entertainment,” “CMO mentor,” “How do you create a mentorship” those types of things.

And all of those results led me into a pretty deep hole where I learned a ton of information. And then I was able to identify the programs that I found most applicable to my world.

But I will say that those more informal bonds that you can create with people, they can happen organically. And it’s really just about you taking ownership of yourself and reading the room, and identifying that right time to ask those questions. So if you find yourself forming a bond with someone who may be senior to you at work, or does a different role, but with immense expertise, and you want to learn from them, it’s really just about starting to feel comfortable in seeding those questions. And then the more you ask, the more you’ll learn. And then you really can get to a space where you can push the boundaries and ask some things that you normally wouldn’t.

Adam Morgan:

I love it. That was a perfect answer. Perfect answers. Thank you so much. For those listening, what great advice. Because so often people think, “Oh, I’ve just got to blind call someone in the industry or figure it out.” But I think it couldn’t get any easier than just searching on Google for some formal programs, right? And I love the different types of phrases that you were looking for.

I wouldn’t have thought of like, “CEO mentorship.” I would’ve just thought… for a company and think of what they have. And many companies don’t have a formal mentor program, which is fine. And so there are other avenues. So I loved that, or going to your professors, higher education, it’s all about relationships and connections. Also, going to your professional organizations, whether they’re on LinkedIn or somewhere else, or there’s like a local chapter in your city.

I think those are also all great places to go, because that’s what it is about. Right? It’s like getting to know someone or getting involved. I even think like on podcasts, follow podcasts, share, get involved, ask questions. Those are ways that people get to know who you are and you’re seen. And then it’s a lot easier to start a mentor program, even if it’s an informal one, rather than just kind of… I get a lot, I don’t know about you, but I get a lot of different people just hitting me up on LinkedIn. “Hey, can I set up a call? I’d like to talk about X, Y, Z, and have you do this or that for me.” And so it’s so much easier if I have at least an inkling of who they are before I agree to do something like that.

The last question I would love to hear from both of you. What advice would you have for someone else, either going to become a mentor or a mentee as they start this journey, or even if they’ve got one that’s supposed to start in a month or in a week, what advice would you give them to have a successful experience?

Jess Kessler:

So my advice on how to be a solid mentor or mentee — it goes both ways, right? It doesn’t matter which side of the coin you’re on — is to commit to it, because it really is what you make it. And it was very easy for both Ashley and I… We have very busy lives outside of this. And there were times where we had to reschedule our check-ins, and it could have very easily, we could have just let them fall off the calendar, but we didn’t. We committed to it. We 100% were committed to each other and to the journey and to the process. And I think ultimately that led to where we are today, which is now a trip to Content Marketing World and a feature on your podcast and hopefully more to come after this. You know, hopefully the fun doesn’t stop here.

Ashley Walsh Lopez:

I think my answer is also going to be on two sides of the coin here for both mentors and mentees. And I would say to have confidence going in, because for a mentee you may not be so sure of yourself in the industry you’re getting into, but I would say take stock of your skills and realize how far you’ve come and that you may not even be entering this program without those skills. So to appreciate that and make sure that’s highlighted when you’re discussing career questions and also being open to listening about from your mentor’s experience.

And then for any mentor or someone who might be thinking about mentorship, same. Have confidence in what you bring to the table and that’ll go such a long way, for sure.

Adam Morgan

Great advice. I appreciate both of you coming and sharing your lived experience on this topic. It’s super valuable. I hope that anyone listening at least has a few nuggets where they can go follow up and try something new, or at least get involved with something where they can get some career guidance.

So last question, where can people follow you? Where can they find you? If they wanted to follow up with a question or at least just follow your work.

Jess Kessler:

You can find me on LinkedIn. I’m under Jess Kessler. You can also search Jess McNeil, my maiden name.

Ashley Walsh Lopez:

And I am also on LinkedIn, under Ashley Walsh Lopez, but you can also find me under my maiden name. That’s also still my URL, which is /AshleyTWalsh.

Adam Morgan:

Thank you so much. Thank you. And for us in the show, you can always find us at realcreativeleadership.com. We have a full catalog of past shows. You can also listen to the other session on mentorship that’s coming out. You can also email us or ask questions or suggest future topics. We would love to have any involvement and again it shows interest or if you’re involved, greater chance for us to connect together on a more personal relationship. You can also follow Real Creative Leadership on all the major social channels. We have a YouTube channel or you can follow it on your favorite podcast, whatever it is.

And you can find me, Adam Morgan, at adamwmorgan.com. You can learn more about The Stoke Group, the digital marketing agency that is helping produce this show, at thestokegroup.com.

Again, we’d love to hear from you, leave a comment about one of the shows, share a quote, whatever it may be, and we appreciate you. So thanks for listening. We’ll see you at the next episode. Thanks Jess and Ashley for joining us, and we’ll wish you luck in your future career.

Jess Kessler:

Thank you.

Ashley Walsh Lopez:

Thank you so much.

Adam Morgan:

All right, we’ll see you in the next episode.