Bossing It: Meredith Weiss on Why Failure Is a Part of Learning

Meredith Weiss is the managing director of Boomshot and 77 Ventures. After graduating from college, Meredith worked for FCB and Ammirati Puris Lintas before moving to the client side in television, working for the Discovery Channel, HBO, and ESPN. While at ESPN, Meredith managed marketing for their college sports portfolio. She brings her strategic yet people-centred leadership style to her role at 77 Ventures and Boomshot, where she has collaborated with some of the most renowned sports and lifestyle brands, including NASCAR, ESPN, FoxSports, MSNBC and Tabasco.

LBB> What was your first experience of leadership?

Meredith> My first big leadership opportunity was managing marketing for the college sports portfolio at ESPN. It was exciting; it was my dream job. I was a college athlete, so it was amazing to have an opportunity to work at ESPN and then, on top of that, to be running the college sports portfolio. I had the chance to work with a group of people on the marketing team that were really incredible people. Initially, it was overwhelming, but the opportunity fit because I knew the environment. From there, it was learning the inner workings of ESPN and then learning to manage a team. 

LBB> How did you figure out what kind of leader you wanted to be – or what kind of leader you didn’t want to be?

Meredith> I have drawn from the experiences of the leaders I have observed or worked for in my personal and professional life – some of those leaders were excellent examples, and some weren’t people I aspired to be. I like to think I still draw from those experiences today.

I had the positive experience of working for someone who was really smart, a strong leader and who was also grounded in values and placed an importance on people and relationships. Stepping back and creating a foundation for a team based on values and people first mentality can be more challenging than it sounds, but I think there’s something fundamental to be said about coming from that place. 

I have also had the unfortunate experience of working for someone who really didn’t care about the people on their team. And, while their decision-making may have been strategic, none of it was about relationships or people. To me, that’s a huge, inescapable part of leadership. You have to always think about how you want to be treated professionally, and replicate that in leadership.

LBB> What experience or moment gave you your biggest lesson in leadership?

Meredith> I was very fortunate to work at ESPN when it was a small and hungry environment. The culture was all about having each other’s backs, working hard, working late and having fun. It was a great group of people, who no matter what, would always figure things out. Those relationships are relationships I still lean on today.

 
LBB> Did you know you always wanted to take on a leadership role? If so how did you work towards it and if not, when did you start realising that you had it in you? 

Meredith> No, it was a natural evolution in the progression of my career. It was nothing I set out to do, but I love working with people, and I really enjoy the leadership aspect of my job. I don’t know that I ever had a moment when I knew being a leader was inside of me, but I had the moment when I realised that I had to take on that responsibility. 

As you do your best to lead every day, I think you can gauge how well you’re doing by looking around and noticing that you’re running a successful business or realising that the team you lead is being successful.

LBB> When it comes to ‘leadership’ as a skill, how much do you think is a natural part of personality, how much can be taught and learned?

Meredith> I really believe it’s 50/50. I think it’s a true balance of personality and who you are as a person, and then there’s a piece that can be taught or learned.

LBB> What are the aspects of leadership that you find most personally challenging? And how do you work through them?

Meredith> When you have to make tough decisions around situations that you can’t control. When faced with COVID, for example, it was incredibly tough to find ways to keep small businesses afloat. I had to make difficult decisions to ensure we stayed afloat, but we came out on the other end of it as a success. 

LBB> Have you ever felt like you’ve failed whilst in charge? How did you address the issue and what did you learn from it?

Meredith> Failure is a part of learning. You could look at each week and find things that you would change or do differently, or there are things that you would look at and say you failed. I think that’s the way that you learn. You don’t learn from your successes. Success is really nice, but you learn a lot from failure. And I think it’s important to acknowledge it, to pull it apart, and to learn from it.

LBB> In terms of leadership and openness, what’s your approach there? Do you think it’s important to be transparent as possible in the service of being authentic? Or is there a value in being careful and considered?

Meredith> I can be both. In the world we live in today, I feel like there’s a feeling or a trend that implies if you’re not putting everything out there on social media, then you’re not being authentic. And I don’t think that’s necessarily true. To lead and consider the people on your team, you must be a critical thinker and careful. And that doesn’t mean you’re not authentic or transparent.

It comes back to what I said earlier. It’s about building relationships, understanding the culture you’re working in, and considering the people you do business with every day.

LBB> As you developed your leadership skills did you have a mentor, if so who were/are they and what have you learned? And on the flip side, do you mentor any aspiring leaders and how do you approach that relationship?

Meredith> I would say that I have two mentors – one a female and one male – who taught me the importance of thinking about people in your decisions while also being a critical thinker. The people you work with have feelings and bring their hearts to work every day. You owe it to them, yourself, and the business to be a strategic, careful, and critical thinker.

As for mentoring aspiring leaders, share your experiences and conversations about what you’ve done, accomplished, or failed to do. If they can pull something positive from your success or your failures, that’s mentorship. 

LBB> It’s been a really challenging year - and that’s an understatement. How do you cope with the responsibility of leading a team through such difficult waters?

Meredith> Again, it begins with thoughtfulness and critical thinking. We’re a small group of 22, so we have to take a step back and think about the people we work with, how they’re affected by the decisions we make, and how those decisions affect our clients. Our businesses were built on solid relationships. Recognising the strength of those relationships – both our clients and our small team of people – we owe it to them to be thoughtful. And, while I feel like I’m saying the same things repeatedly, they’re the things I value.

LBB> This year has seen the industry confronted with its lack of action/progress on diversity and inclusion. As a leader how have you dealt with this?

Meredith> Diversity and inclusion are priorities that we think about in all aspects of building a team. We have a lot of women in leadership roles in our businesses, which I’m super proud of. We’re always working to be more inclusive and represent true diversity of thought and experience.

LBB> How important is your company culture to the success of your business? 

Meredith> It’s hugely important. We were founded on layers of relationships, so our people are the most essential aspect of our culture, which is reflected in our core values. 

LBB> What are the most useful resources you’ve found to help you along your leadership journey?

Meredith> Fostering strong communication is incredibly important. In the digital age of texting or sending a quick email, we’ve lost that connection of picking the phone up and being together in an office every day. And while remote work is great, I think it’s super important to have genuine interactions that are based on real, human connections – even if it’s over Zoom. That’s a vital part of building teams; especially in a creative environment, people work better together.

LBB> Your role is unique. As managing director of 77 Ventures and Boomshot, you take the lead on both the creative and the production sides. How does the hybrid nature of your role serve the business?

Meredith> My hybrid role serves the business well by making it much more streamlined. As a client, you make one phone call and you can sort out whether you need concepting at a high level, positioning, or strategy work on the agency side, or, if you know what you want and have a script, then you can work with our production side. And I stay involved throughout the entire process.