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Leaders Letter 138 – David Siegel 5 Questions

Dear Leaders, this week I ask five questions to David Siegel. David is the CEO of meetup.com & led Meetup through the pandemic, for a company that is built around connection and real-life community you can imagine the hugely negative impact and the fight for survival David and his team went through and how they bounced back, through brilliant and deliberate leadership.

David’s book is an essential read, it is my essential company culture books to reads, I also buy it for my exec coaching clients and when I run workshops I enforce the exec team to read Decide & Conquer: 44 Decisions That Make or Break All Leaders.

Onto the Q&A, this is fascinating and brilliant.

Q1. You led Meetup throughout the pandemic in near-impossible circumstances, what is the biggest lesson you took away as a business (and people) leader? 

When the pandemic hit, Meetup faced an existential crisis that could have destroyed our 18-year-old company. Until then, the focus of our business had always been about bringing people together IRL (in real life) to make connections.  When COVID-19 hit, we had to ask ourselves whether our mission was more about meeting IRL or about fostering connections. Our answer was clear: we are a connections company. For the first time in our history, we allowed groups to meet online. And it was so fortunate that we did. Online Meetup events and groups helped millions of our members get through the most isolating periods of pandemic. 

I won’t downplay how rocky that period was. Running a company called “Meetup” in a time when no one was meeting was a tremendous challenge.  We saw decreases in many key metrics including the number of events on our platform and event RSVPs, which negatively impacted our revenue. As a leader, my focus was on transparency. If the company had challenges, my job was to address those challenges head-on so we could find solutions. Building trust during a crisis by sharing the good, bad, and ugly was critical. The crisis is behind us, but our culture of trust and transparency will continue to strengthen the company.

Q2. You wrote brilliantly about your 44 decisions to make and break all leaders, which one do you feel are the most important to start with? 

First, thank you. Of all my decisions for new and seasoned leaders, I think I need to start with what I call “Decision 0,” which is deciding whether you should take the job in the first place. 

One of the most hazardous biases in decision making is the sunk cost fallacy. This is the tendency for people to be biased toward actions because they overvalue the time, money, or other investment they’ve “sunk” into an action. Most of us don’t appreciate that this time spent preparing for anything is gone. Our job is to make the best decision we can. People are often reluctant to reject a job offer after they invested so much time in interviewing. The fact is, the time spent interviewing is gone and it has no bearing on whether the job is a good fit.  

Before I became the CEO of Meetup, I went through no less than 27 interviews with WeWork (our corporate owner), followed by meetings with every Meetup vice president. After three months and hundreds of hours of interviews, it would have been easy to accept the position based on my time commitment alone, but I knew that time was gone. I needed to make a decision based on the facts about the role and the company I’d be working with, and I strongly considered not accepting the role in the first place. 

I caution all leaders (and even non-leaders) to make the right decision for you and not be influenced by how much time was spent leading up to a decision.

Q3. The power of community is a key message throughout your book, what do you think CEOs (and their leadership teams) should truly understand about community and then embracing community into their business? 

Hundreds of studies have found that community is one of the most important elements to both a happy work life and personal life. Yet, having a strong sense of community is also on the decline in nearly every country and age demographic. Early humans relied on community to survive and the need for community is hard-coded in us.

Meetup is the ultimate source for building community, whether it’s personal or professional. Many companies—IBM, Microsoft, Google, etc.—use Meetup to enhance their communities and build user networks. Community drives employee retention, motivation, collaboration and ultimately results in greater success. As more companies move to remote work, the importance of community is becoming more evident. It is incumbent on every leader to incorporate community building into their business.

Q4. What are your three leadership non-negotiables for your exec leadership team? 

First, no assholes. The members of my executive team are all kind people. We spend more time working with colleagues than we do our spouses in some cases. I only want to work with high integrity, empathetic individuals. Life is too short to do otherwise.

Second, they must have a data-driven approach. Leaders shouldn’t ignore their instincts when making a decision, but we always need to look at what the data tells us. We need data to size gauge the impact, priority, and opportunity of any choice.

Last, I look for the ability to embrace change. Leadership requires adaptability. And if a leader is not flexible then they won’t be able to steer the ship for their team during times of crisis. The ability to listen and change one’s approach based on data and experience is one of my top priorities when looking for a leader.

Q5. How has your professorship at Columbia university helped you to develop your leadership? 

I’ve always believed that when you teach you have the greatest opportunity to learn. For nearly ten years, I have been teaching undergraduates at Pace University and then graduate students at Columbia in the entrepreneurship and strategic planning program. My former students have gone on to found startups that have helped millions of people around the globe. Having even a small impact on their path to success is incredibly enriching. One of the reasons I wrote Decide & Conquer was due to my interest in helping people beyond the 70 students in my class. The book has now been read by more than 15,000 people and is being translated into Chinese and other languages. I consider the book to be an extension of the concepts we learn in class. I’m incredibly fortunate to have the opportunities to teach and learn that I do.

Links 

Go and have a great week and I’d love to hear from you about how you are going to take inspiration from David moving forward.

Thanks,

Danny Denhard

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