Interviews with leading tech women about their careers and lessons learned

EP 03

Betsy Bland



When Betsy Bland (Director of User Experience at The Motley Fool) identified an opportunity for improvement within the business, she approached the CTO and was inevitably asked to lead up the team of designers – her peers – to implement the change. In Episode 3 of The DevelopHer Show, Lauren and Betsy unfold the challenges behind transitioning from peer to leader, and what strategies tech women can utilize to own the strides they make when moving up in the industry.

If you identify a business need, speak up.

Growth and redevelopment can only take place if the person who recognizes the need brings it to the attention of the appropriate superior. Doing so may open doors for career advancement, if you wait to be asked. Doing so will open doors, if you have the confidence to say what you want.

If you want your peers to be invested in their work, get stakeholder buy-in.

Take the time to understand the challenges and desires of your teammates in order to help them determine how they may contribute to the company’s overarching goals. Grant the opportunity for people to feel heard and they will put their full heart into their work.

Realize that sometimes you may have to let success speak for itself.

Rather than trying to move a boulder, go around it. As a leader, it can be challenging to get your team 100% on board. Present your ideas and goals, shoot for the small wins and let those that are uncertain observe the insights on their own.

You don’t have to have a huge collection of reports to be a leader.

A leader is someone who has influence and who gets things done. “Leader” isn’t necessarily a title, a position or a number of reports; it’s someone who as the ability to make impactful movements across a team and a company as a whole.

Everyone makes mistakes.

It’s what you make out of those mistakes that shape you. Don’t wait around for things to go wrong or for opportunities to pass you by; take your mistakes at face value, learn your lesson and use them as tools to improve upon future actions.

Episode 3 – The DevelopHer Show


[Background music]

Hi, I’m Lauren Hasson, and this is The The DevelopHer Show, a career development podcast for tech women, by tech women.

My guest today is Betsy Bland, who is the Director of User Experience at The Motley Fool. In this episode, Betsy and I are going to talk about her own career journey and how she identified a need for and jumped into a new leadership role at The Motley Fool, and the valuable leadership lessons she learned along the way.

Start of the Interview

Lauren: Welcome to The DevelopHer Show! We have Betsy Bland here with us today. Betsy is the Director of User Experience at The Motley Fool, which is one of the world’s leading multimedia financial services companies. She’s held multiple leadership in senior level roles throughout her career, and she’s unique in that her experience and background blends both technical and the creative. Betsy and I first met as classmates at Duke, where we learned computer science together, and were sorority sisters. In addition to computer science, Betsy also has a degree in Visual Art, which means she’s a whole brain thinker. Betsy, welcome!

Betsy: It’s great to be here. Thanks for having me.

Lauren: It is honestly fantastic to have you here. I’m so proud to be interviewing one of my fellow classmates. As you and our listeners know, the DevelopHer Show is about leading tech women, having open and candid conversations about their careers, lessons learned, and how they got to where they are today. So, help us read between the lines in your career and give us your own take on how you got to where you are today.

Betsy: I think the first place it really started was actually at school. I know a lot of people end up with degrees that are pretty unrelated to the work they’re doing now. But, I actually created my degree. It was an inner-departmental major. I wasn’t necessarily interested in committing to just Computer Science or just Visual Arts so, I picked every course in there and shaped it into what I wanted. And, that has been my approach since then for my career. I was first hired at a consulting firm to be a Developer but was immediately pulled into the requirements phase and interested in understanding the entire thing that we were trying to solve. This eventually led me into getting into Design, which is a lot more than just trying to make a pretty picture. It’s about understanding what people are really trying to accomplish and what you can create to make that happen easier, faster, better for them.

Lauren: Today at The Motley Fool, you are leading a team of multiple designers and you’re blending both the technical and the creative. Was this something that was a natural transition for you? Were you hired in this role? How did you get into the management side of this?

Betsy: I was first hired at The Motley Fool as an Individual Contributor, a UX designer, and worked on a couple of projects and had a couple of kids during that time. When I came back about two and a half years ago from maternity leave, our CTO changed and at that time, User Experience Design was under the Tech Department. When the CTO took over we were talking about what I thought were some of the places that we could improve our approach to design. At that time, all designers were on separate teams and even though we reported to the same person, we never worked together, and I thought that was a big weakness. Design is best done with feedback from others and learning from others. And we also were missing the opportunity to build on each other’s skill sets. Not everyone did or loved the same things, but we weren’t able to play off of each other. After that he asked me to lead up the team. That was an interesting shift because I was now leading people who had been my peers. So, I really wanted to make sure that they understood it was their choice. Each person met with me and we talked about where I saw the team going and they ended up deciding to join the team rather than to continue to operate more in their separate system.

So, we started building out our skill sets. I sent a survey to each person asking real detailed questions about what they loved to do, where they thought their greatest strengths were, where they thought they could improve and the places that they hated. Because design is a very broad skill set. I have a deep understanding and appreciation for that, having been both a developer and a designer. It came out that one of the biggest holes was user research, and instead of trying to force people who weren’t interested in doing that work to do that work, we hired a new designer that would do more of the user research and translating those insights into early concepts and strategy for products.

Lauren: So, there’s a lot to unpack there. I love that it started with it not being a clear opportunity, but something you identified yourself. You spoke up, which is key. How was how was that for you? Was it something that came naturally to you, or was this something that you had any trepidation over doing, saying, “Look, I see this opportunity, and I think I have an opportunity to make a change.” Can you walk us through what was going through your mind?

Betsy: You know, it’s funny. It was very easy for me to observe the hole and the opportunity. But, at that point it was really hard for me to put myself out there for the role. I really lucked out that the CTO recognized that I could be an appropriate person to fill it, and offered the role to me. I greatly appreciate that, and looking back I regret not having the confidence to say, “I want to do this.”

Lauren: You looked at the organization first. You didn’t look at this as, “This is Betsy. This is Betsy Bland,” first. You said, “Here’s the context of the organization. There’s a true business need,” and you approached it from the business-need standpoint saying there’s a business need in the company, and I have a solution for it. And you spoke out based on the business versus speaking up on yourself, and it sounds like now you’ve put the two together and said, “These can live together, and I can advance the company while advancing myself.” It sounds like if another opportunity like this came along or you were advising someone else, you would say, “Absolutely. Look at the company and how this helps me at the same time.”

Betsy: Right. Totally.

Lauren: The other thing that I love about this is that you took your discipline of Design and Design Research and you applied it to leadership. So, when you were appointed the new Head of User Experience and you suddenly went from being a peer to being a leader for your peers, you sat down and said, “I’m going to get user feedback from my peers.” And you applied that principle. And then in talking with you about your leadership style, I think that’s something that you do really well, in fact, I really admire it in you. You think about it in terms of your team, and that translates into how you’re able to talk about what your team does and ultimately what you do. So, can you walk us through your own leadership style because I think our listeners will really benefit from hearing about how something that can seemingly be difficult when you’re being thrust into a difficult or new leadership role, how you can make it normal and then get your team acclimated to you being the new leader.

Betsy: One of the things I think is super important is having stakeholder buy-in. I treated my teammates as stakeholders, and understood their challenges and the desires that they had for the work they’re doing. We sat down and defined what our long-term vision for the team was, and looking out five to 10 years, what we wanted design to be at the Motley Fool. We concluded that we wanted our organization to be recognized as design-driven, not only internally but externally.

Then we broke down what we needed to do in the next six months to start making progress toward that, and laid out about five to six goals. Then I met with each individual and we talked about what they needed to do to grow both within their own careers and to contribute to those overarching goals. At about three to four months in, we revisited them. So, much like with agile work, you see if what you thought was the right idea or the right direction, was really the way to go. We had already accomplished most of our goals, so it was great to see that people wanted to work and strive toward them. And there were a few that we realized probably aren’t going to happen anytime soon, so we shifted our focus on a couple of others. Everyone was much more bought-in I think, because we worked together to define it and to understand it. It gave people an opportunity to feel heard. Much like with any product that you’re working on, if people feel like you’re just telling them what to do and you just get it done, they’re never going to put their full heart into it.

Lauren: One of the things I love about that is that you are embodying the true spirit of a leader. So many people think that being a manager is telling people what to do, when to do it, and taking care of things when things go down the hole. But what you’re truly doing is leading a team from a place of power and abundance, and power in the most positive terms. You took in peers and you figured out how you could align each other towards a common goal.

Was it always the case that everyone came on-board and said, “Yes, I’m here with you. I appreciate your process and I’m ready to get behind you.” Or did you face any pushback in that process?

Betsy: I definitely faced some indirect pushback. A couple of people weren’t that interested in even defining their own individual goals. At first that was very stressful for me and I tried to figure out different ways to convince them to get on board. But in the end, they ended up changing a little bit anyway. I stopped stressing about it and remembered what a friend told me: “Rather than trying to move a boulder, go around it.” It was the best advice I could have gotten because it just eased the stress of trying to let them see success coming. And then if they can come around and get on board, great. If they can’t, we’ll figure it out from there. It was great to see that the success spoke for itself.

Lauren: I love that, that’s quotable. I feel like I should write that on my bulletin board and paste it all over social media. What did that look like in terms of actions at work and things that you did?

Betsy: One of the biggest challenges, in addition to the team not necessarily working as a team, is our general approach to creating and iterating on products as the Motley Fool left out the user, left out our customer. We were doing a lot of things based on what either we were seeing in site usage data, or maybe some survey data. I wanted to build out connecting and speaking with users. So, that was probably the biggest challenge. People were not bought into that. For a couple of projects, I partnered with whatever designer was working on that project and I either facilitated sessions, usability sessions, went for those small wins and had people observe the insights that they would gain, rather than trying to force them to do it. And even just sitting in a room and having them see what people were challenged by or what people were saying about what they were trying to accomplish, that ended up doing a lot of the work for me.

Lauren: I love that you took an iterative approach to that, it comes back to the agile lean methodology. So many women think that you go from point A to point B in one quantum leap, and as you and I know, and some of our peers know, change doesn’t happen in quantum leaps, but in small, small steps. It happens gradually and iteratively over time, and you don’t immediately see the payoff. You have to be persistent in that. It sounds like that’s exactly what you did, and that you got results from that.

Betsy: It was something that I had to learn for myself. At the very beginning, I was very frustrated, letting myself become discouraged because teams weren’t bought into any form of user research. I could not understand why they didn’t want to build their entire strategy off of it. But I hadn’t shown them why it even mattered or why it was helpful. So, through the help of others, helping to see that and also just through experience, I have a much greater appreciation for the fact that sometimes you just gotta start somewhere.

Lauren: Yes. You know that’s what we need to be honest with ourselves about and honest with other women about: we don’t all have it figured out from the get-go, and a lot of us have had to learn this on the way. And in my case, I’ve learned a lot through good experience, but I’ve also learned even more through bad experience. And for you to be open, honest and candid about how you didn’t have it figured out but started and tried something, pushing and adjusting… I think that’s so, so powerful for other women to hear. “Yes, I’m just like Betsy. I get it. And I can also achieve great results.”

Betsy: Another super important lesson I had to learn around that, when I first took the team on, I didn’t work with them to define team goals. I defined them and came down from on high, and nobody cared about them. They kind of cared and they kind of did a little bit toward it, but it wasn’t until we completely scrapped them and redefined everything together, that people cared a lot more. And I’m very thankful that I had that lesson, because I’ll be honest, I don’t really like to be told what to do either.

Lauren: I’m the same way, I get it. And yet at the same time you somehow forget that when you are a new leader, what it’s like to be someone who is following that new leader. And that’s a valuable lesson to learn.

Betsy: Absolutely.

Lauren: I want to shift gears a little bit because we’ve talked about how you learned to get those results. Ultimately you did. You got fantastic results. And I know you were nominated for a number of women in tech awards. You actually reached out to me with your story, and said “Look Lauren, I’ve accomplished these things, and I’ve been nominated and honored, but I have to write about myself and it feels incredibly awkward.” You’re accomplished. Looking at your accomplishments on paper and listening to you speak… it’s clear that you know what you’re doing. You’ve accomplished awesome things, yet talking about your accomplishments, and then owning that you’re an ambitious woman and not feeling bad about that: that was a struggle for you. Can you talk to us about how you moved through that process?

Betsy: It’s definitely day to day, too. But, at the time of writing for that award, my role had gone from being a full-time leader of the project of the team to a more hybrid role because of a business unit shift at our company. Even though it wasn’t at all my fault that the team shrank, I needed to take responsibility for it. And at the time that I needed to write that, it was very hard for me to talk about the accomplishments as a leader, when I was redefining myself yet again. Now that I have embraced the fact that a leader doesn’t have to have direct reports to still be a leader or a huge collection of direct reports, you are still a leader, you’re still impactful. It’s made it easier for me to talk about the impact that I have on my direct report but also at the company as a whole. I try to find the best way to make the best of a situation.

Lauren: I think that’s absolutely key, that it comes with your mindset and mentality of, “This is where I am. Let me accept it and figure out how to make the best of it.” And that’s where true results come. Society wants to tell us a leader is someone who manages a department of 50 or a department of five. And what you and I have both learned through our own personal experiences is that a leader is someone who has influence, and influence doesn’t mean you have a team of five reports, it means you get things done. There’s another word I’d like to use but it’s a four letter one. You get things done across the organization and leader isn’t necessarily a title, leader isn’t necessarily a number of reports or a position, leader is the ability to move things ahead across an organization and ship product. And that’s what you’ve done, and you’ve owned it now.

Betsy: I have also taken the opportunity to mentor a woman that recently made a very similar shift. She was an individual contributor on a design team and is now running the team. I have great empathy for much of what she is experiencing and it’s both helpful to see that you’re not alone, but also take the opportunities to apply what I’ve learned to someone else’s experience as well.

Lauren: I’m going to flip that just a little bit and close with this. If you had to give your younger self one piece of advice that you wish you would have known then that you know now, what would that be?

Betsy: Everyone makes mistakes and it’s what you make from those mistakes that shape you and make you awesome.

Lauren: I love that you put the word awesome in there, because you truly are! For our listeners out there, Betsy, I admired her so much in college and I’ve just loved tracking her career, and I particularly love that you didn’t just try to fit yourself into a cut out or a mold, and that you created your own. You created your own interdisciplinary degree at Duke. You have shaped your career into what fit you and your passions, and you’ve shaped your team and your role within the company into something that really brings out the best in you. I admire that. I admire you, and I know that our listeners have learned so much from you today. I also know that you are working on something new with The Motley Fool. Would you like to tell our listeners about that, who are in the D.C. area?

Betsy: Sure. We are now organizing a jobs-to-be-done meet-up. It’s a new framework. Well, not that new, but spreading framework of understanding what jobs people have in their lives that they’re trying to get done. You can search for “jobs to be done in Washington D.C”. on Meetup.com to find out more.

Lauren: Fantastic. Betsy, thank you for joining us today.

Betsy: Thank you so much. This was great.


Thank you, everyone, for joining us today. Make sure to subscribe to our mailing list to receive updates on new episodes and other fun goodies, and until the next episode make today better than good.

Everyone makes mistakes and it’s what you make from those mistakes Betsy Bland

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