How This Product Manager Prototypes Her Own Career: Insight from Teachers Pay Teachers’ Brooke Henderer
Prototypes are to product managers what decks are to consultants.
They're a way to showcase one vision of the future—to give people an opportunity to experience it and to decide whether to pursue it.
As a senior product manager at education marketplace Teachers Pay Teachers, Brooke Henderer is quite familiar with the practice. She's made dozens of prototypes for different work projects over the years.
Recently, she's started to think about her own life as a series of prototypes, of different future options that she's explored and that have taught her what it is she really wants to pursue.
We sat down with Brooke to hear about how she got into product management, how she's applied her PM skillset to understanding what it is she wants to do with her life, and what advice she has for people who are looking to do some self-discovery and self-prototyping of their own.
A three-part framework
Brooke tried a lot of things in college. "I was definitely one of those people who did not know what they wanted to do," she says. "I had such broad interests that it was really hard for me to narrow them down."
She took classes that interested her, from chemistry to economics, and applied the same approach to her extracurricular activities, exploring everything from jobs in retail and customer service to internships in sales. "I really enjoyed getting to work with customers and helping people in some capacity," she says. She was particularly interested in tech—"It felt very future-proof," she notes—but realized that tech sales wasn't for her. "I didn't love the repetitive nature of being on the phone all day," she says. Becoming super-specialized wasn't appealing, either.
"I didn't want to be a craft developer because I don't know how to code. I'm not going to be a designer because I don't know how to design," she says. "I got really lucky stumbling upon product management, because it has the aspects of the customer-facing side of things I enjoy, and sales, but is also a mix of more creative and strategic work on different levels, and gets me exposure to a lot of different kinds of work throughout the day."
After getting her first PM job with Intuit from a career fair, Brooke stayed with that company for a while before looking for something new. When she set out to look for her next challenge, she had a clear framework in mind. Brooke was looking for:
- A mission she could connect to. "During my time at Intuit, I discovered that what ultimately motivates me and drives me is creating something for someone else and ideally creating a positive change for them. It was really important for me to know that whatever I was building or doing, it was something good for someone else," says Brooke.
- A smaller company. Brooke knew she wanted to work somewhere that wasn't so big that she wouldn't be able to be in the mix with different tasks each day. "There's something about doing something different every day and not having a lot of repetition that I really enjoy," she says. "And I'm comfortable with the rapid change and quick adaptation of smaller companies, because we're always building new products and we stay flexible to changes."
- A product roadmap that interested her. "I just knew that if it wasn't exciting on the surface, it probably wasn't gonna keep me there for long," says Brooke.
Teachers Pay Teachers met all of her criteria, and Brooke realized it was the place for her from her very first interview. "It really stuck out to me how clear the mission and strategy was, and how much love every single employee and leader had for educators," she says. "It was genuine."
She felt particularly drawn to TPT's mission. "Our strategy has to do with unlocking funds for educators so they don't have to reach into their own pockets to get the resources and tools they need. It's a really unique opportunity to work somewhere where the business goals align with doing something really good for customers," says Brooke.
Stepping back from a job to consider a life
After Brooke got her first product management role, she expected her questions about her career to abate. They didn't.
"Getting that first job was this big thing. Then you realize, 'Oh, this can grow, this can change, this doesn't have to be the single thing I do for the rest of my life.' So how do I make sure I'm still in a career I like, and that I'm figuring out how to hone in on my interests over time?" she reflects.
She started applying her product manager skill set to her own life.
A book called Designing Your Life helped, she says, by teaching her how to ask herself what she wanted out of life beyond her job. It led to her realizing that she really enjoyed building tangible things, so she decided to explore content creation.
After taking a film class and producing a short documentary, Brooke realized she wanted to stay in product, and credits her exploration with her renewed sense of commitment to and peace with her career decision.
"Going through that process, taking the film class, doing those things really proved to myself, 'Oh, there's actually not a whole lot of other things that really fit what I want,'" says Brooke.
"Because I was able to prototype those things and try them out, it helped me feel better about doubling down on staying in product. It made me feel more secure in the path I was choosing," says Brooke. "I learned other things I might like, but that might be better as hobbies for me."
6 tips for self-discovery at work and beyond
If you've wondered if you should blow up your life and start all over—and if you should, how exactly you're to begin that process—Brooke has some perspective for you. Spoiler alert: it's a gradual approach.
- First, recognize that there's no single right path for you. "There are many possible futures you can have, and they're all great," says Brooke. "The best thing you can do is just not to be afraid. Don't feel like you're stuck and can't try anything new."
- Try a "good time" journal. Keep an activity log of all of the things you do in a given day and note how much energy you get from them. "You could do it for a week or for a day," says Brooke. "I think you'll be surprised at what you learn about what fills you up. What type of things were you doing? What types of people were there? What role were you in? What sorts of things were there—computers, sticky notes, whiteboards?"
- Be more conscious of your schedule. Once you know what kinds of things drain you, Brooke suggests adjusting your schedule to better absorb them. For example, if she has a long day of draining meetings, she'll schedule some time to talk to a customer right afterwards, since those chats always give her energy. "Not everything in work is going to be perfect," says Brooke. "But as much as you can fill your bucket up with those things that give you energy, you can use that as a guide to help you figure out where you want to go."
- Carve out enough time for deep work. Even if meetings do bring you energy, too many of them will make you feel like you're unable to make progress on any longer-term goals or even to think about what your personal goals are. Make sure you're getting at least a few hours a week for heads-down work, notes Brooke.
- Set boundaries, including around breaks. To avoid the constant interruptions of Slack messages and emails, Brooke responds to them at certain times of day. She also has scheduled small breaks that she sticks to. "It's about actually standing up and stepping away from your computer," she says.
- Ask if you can shift enough within where you are to meet your needs, or if a bigger shift is needed. Sometimes it's enough to adjust smaller parts of your life, whether that's what your schedule looks like or even the company you work for, in order to feel more aligned with the things and activities that bring you energy. But sometimes it's not. "Long term, you need to think about changes you want to make," says Brooke. In that case, the same advice applies, just starting with a bigger scale. "Everything might not be clear just yet, but you'll figure it out as you go."
When Kim Beauchemin is leading new backpackers on a hike, there are certain rules she always follows.
"We go in groups, and every group I lead is a team. We hike together, we stay together, and if the weather's bad, we all don't go to the summit, we turn around and go back down because we're a team," says Kim, who lives in Massachusetts and is a leader with the Appalachian Mountain Club.
Those are the same principles, more or less, that Kim, the Director of Engineering and Agile Practice at application security company Veracode, has used to manage herself and her team at work through several company transformations.
We sat down with the engineering leader to talk about how she approaches leading through change, how she invites change into her own career and development, and what tips she has for others who are finding themselves facing change at work.
Staying Agile through pivots
Kim was at CA Technologies for 12 years before they were bought by Veracode. She'd been through rounds of internal change and growth, but integrating into a completely new company was hard.
"Change brings challenge, but some people are motivated by change," says Kim. "I'm one of those people."
Kim started off as a technical writer and learned about agile practices when she was managing a team of other technical writers. She took on a program manager role where she leaned on Agile methodologies, including scrum and kanban, to drive her team towards results.
"I had to step away from being the domain expert or the person that's the expert in the content, but rather try to invite people into their own leadership and ask good questions so people could work better and collaborate better," she says.
That same skill set served her when Broadcom bought Veracode several years after the CA Technologies changeover—and then again when Broadcom later sold Veracode.
"[Veracode] went from being its own entity to being acquired by CA to being acquired by Broadcom and then sold again as its own entity under private equity," summarizes Kim. "My awareness of how change impacts people, both positively and negatively, helped," she says. "So did being able to work with and collaborate with different personalities to understand what individuals and teams need to be successful, and, especially during times of change, how to support them."
The top skill she relied on? Communication. "I'm a true believer in transparency—maybe too much sometimes," says Kim. "You do what you can to assure your team and make the transition as un-scary as it can be."
Learning to think strategically, with institutional support
Through those transitions, Veracode went from a startup to part of a 10,000-person company and then back to its own entity again. Along the way, leaders like Kim had to step up and think strategically at a different scale. She welcomed the chance to change the way she led her team.
"A new SVP wanted to create an Agile PMO for the whole organization," she says. "I had to be more strategic in order to define an organization, then build it and hire for it and lead it."
Becoming the director of that organization stretched Kim beyond what she'd done before. "I was so tactical before that, great at getting my tasks done," she says. "The ability to understand the bigger picture, develop a long-term vision and figure out what the strategic roadmap is to get there was a completely foreign thing to me."
She reached out to Veracode's VP of Corporate Development, Pete Ellis, for coaching. "He immediately responded with, 'Absolutely, let's set up a six-month thing,'" says Kim. "And he led me through six months of some great exploratory thinking around strategy and how to think about things in a different way and at a strategic level."
A particularly memorable lesson was around the idea of zooming out. You could look at a car accident and see a person who wasn't paying attention, or you step back and see the road conditions, the disruptions to a morning routine, and the other factors that could have contributed to what happened, Kim explained. "Having more than one lens to examine challenging situations through provides more perspective that can inform better decision-making and strategy," says Kim.
Her mentorship relationship with an executive isn't unique to her, says Kim. "Veracode is big on supporting its employees, especially if an employee shows initiative. Veracode often does anything they can to support them growing professionally."
3 ways to adapt to changes that are outside of your control
Kim's tips for adjusting to organizational change include:
- Don't panic. Take a breath. "People can get so worked up even before anything actually happens. I encourage people to take a step back, take a breath, and know that we'll get through it."
- Know that it will be uncomfortable. "You will be pushed out of your comfort zone, and while change and transformation are difficult, that's how we learn and grow as individuals, as an organization, as a company. There's a lot of potential and possibility that comes out of uncomfortableness."
- Realize that it won't be right the first time. "If you're going to transform, if you're going to try new things, some of them are going to work great. Some of them are not. You'll have to adapt, and that's okay. As long as we're learning, as long as we're improving, or trying to improve, we have to forgive ourselves in advance for making mistakes."
And remember the Appalachian Mountain Club's top recommendation—never hike alone—and stick together, says Kim. "The more you have, the better."
Below is an article originally written by Kate Kalil, Account Executive II, EMEA, at PowerToFly Partner CarGurus, and published on April 4, 2019. Go to CarGurus' page on PowerToFly to see their open positions and learn more.
Can I let you in on a little secret? I've never traveled abroad. And, man, I hate Guinness.
I met Wendy Harris, our Vice President of European Sales, at the August Women in Sales Event hosted at CarGurus. Wendy gave an inspiring presentation in which she shared insights into her career path, what she looks for when hiring sales people and challenges that she faced personally and professionally. One of the topics she spoke about was an opportunity she had to step out of her comfort zone and join a growing team and learn something new. She described this opportunity as the path less traveled. In the midst of her presentation, I started to think about my own experiences.
My heart beat strong in my chest as I started to ask myself: When was the last time I stepped out of my comfort zone? Was I too comfortable? Was I truly challenged? Was I flexing any new sales muscles? Or just doing the same old song and dance that's worked for me?
The last time I felt out of my comfort zone was the day I walked into this office to start my new job, over 2 years ago. A sales job unlike my previous, in a traditionally male-dominated industry, I was wildly intimidated. I spent my first few months on the phone with a weak pitch and a shaky voice. I felt out of place and my quota attainment was nothing to be proud of.
In order to conquer the intimidation that I experienced, I came in early and stayed late in order to perfect my pitch. I shadowed our best reps, took notes on industry jargon and scoured the prospecting queues. Within a few months, I had found my groove and was performing like the salesperson that I knew I was. If I had never been out of my comfort zone, I'm not sure that I would have ever evolved in the ways that I did – I don't know if I would have achieved the same success without the setback.
When Wendy presented the opportunity to do an expat assignment in our Dublin office – everything inside of me told that I would never be able to do that. I had never been to Europe, had never lived more than 45 minutes away from my family and I was happy and content doing what I was doing here.
That's when it hit me. Again, I found myself content with being comfortable, even more so than when I first started at CarGurus. This opportunity in Dublin would push me so far out of my comfort zone, personally and professionally. I would come away from it with new knowledge, different sales tactics, a fresh perspective on a new addressable market, new friends, increased confidence in my skills and finally a passport stamp.
So, I applied. I poured over information on our UK market, compiled countless questions for my interviewers, spent time with former and existing expats and spent hours preparing for the interviews. Once I realized that I wanted this, I approached it with the same tenacity and perseverance that I approached my sales.
When the role was offered to me, it became extremely surreal. I have no idea what to expect; I'm both excited and scared at the same time. But what I do know is this – without being out of my comfort zone two years ago when I joined this company, I would have never been pushed to achieve the goals that I have achieved today – I would never have learned what I have, and I certainly would not appreciate the immense growth that has happened.
CarGurus has given me much more than a paycheck. They've taught me about myself – my abilities to learn, grow and evolve. They have given me an incredible opportunity to experience a new challenge in a new country, selling to a foreign market.
I will be greatly out of my comfort zone – but the most important thing I've learned thus far, from Wendy and from my own experience, is that with great risk comes great rewards.