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I was overly aggressive when I interviewed with WeWork's Adam Newmann for the Meetup CEO role — and it paid off. Here's why I recommend all leaders negotiate every detail.

David Siegel   

I was overly aggressive when I interviewed with WeWork's Adam Newmann for the Meetup CEO role — and it paid off. Here's why I recommend all leaders negotiate every detail.
  • In his new book, Meetup CEO David Siegel shares his best decision-making advice for leaders.
  • Siegel describes how he got Adam Neumann and WeWork to agree to his '3 conditions' before accepting the job offer.

Meetup was acquired by WeWork in November 2017. David Siegel joined as CEO in October 2018, succeeding Meetup's founder Scott Heiferman.

The following is a book excerpt.

I have been asked often what it's like to interview with a maverick like Adam Neumann. And my answer is always the same: "It's exactly as you would have thought. Insane."

Adam didn't ask about my past work experiences. Most of my interview was about family and spirituality. I was given a tour of his private ice bath and sauna (which he apparently would use at 5 or 6 a.m.) and was offered a full- course Israeli vegan spread. While we had a meaningful conversation about life, Adam wasn't convinced that I was the right person to lead Meetup.

So, I decided that if given the opportunity for a second interview, I would up my game and channel my inner Adam Neumann. Leaders like to hire leaders like themselves, and if I were to get the job, it would be because Adam would find me similar to himself. Having Adam as an employer, you had to be prepared for anything. Be surprised only about being surprised.

A few weeks later, as I walked into WeWork for my second interview with Adam, I spotted a young employee wearing a T-shirt that said "Meetup + WeWork." I was wearing a white dress shirt. Adam surely wouldn't be, so I decided I needed that shirt. I approached the employee and explained that I was interviewing for the Meetup CEO job and that I'd like his shirt.

We went into a closet and I traded my Brooks Brothers button-down for a ragged tee

When Adam saw me, he said, "Man, if you can convince someone to give you the shirt off their back, then you can sell anything." As I had learned earlier: Be bold.

WeWork made the decision to hire me, but Adam communicated that he wanted Scott and Meetup's executive team to feel that I was their choice and not WeWork's choice. So, after fifteen interviews with WeWork leaders, I needed to start the process over and have another twelve conversations with Meetup executives.

Three of those would be with Scott. The first went OK. The second, better. Still unconvinced, he wanted to meet a third time, this time for sixteen years at the helm, it seemed like he wasn't about to turn it over to someone he barely knew. So he took me to Meetup events around New York City to show me the mission of Meetup in action.

We first visited an early-morning soccer game in Brooklyn, where I spoke with a new member of the group who had just moved from Germany. He missed the group of friends he'd played soccer with every week. Thanks to Meetup, he now had twenty new friends to play with and afterward join at the pub.

Our next stop was a daily event hosted in a WeWork conference room, a chance to see their synergies in action. I listened in as nearly a dozen women who were all working on their PhDs strengthened and supported each other during what is often an incredibly painful and lonely task.

We then headed to Central Park where I met the founder of City Dads, one of the most successful Meetup groups. Many stay-at-home dads had felt marginalized going to mommy-and-me classes and looked to meet other guys in a similar situation to their own. The bonding was awesome and inspirational. Even more amazing was that the group had expanded to more than thirty chapters across the United States and abroad, because when the dads moved they started City Dad Meetup groups in their new cities.

I saw firsthand the growth potential of this very special company

I also realized what a powerful force Scott could be going forward by taking new hires out on similar field trips. It was a wonderful experience.

Then reality struck. Scott, apparently still unconvinced I was the one, asked me to have dinner with the entire Meetup leadership team, each of which I'd already met with, and I had to decide whether it was time to put my foot down and say, No. Put up or shut up.

I had already spent more than three hundred hours preparing for, traveling to, participating in, and following up after each of my interviews. I felt I was being taken advantage of and at the whim of a founder who was unable (or unwilling) to step aside. On top of that, while they'd been struggling to decide whether I was a good fit for them, I'd been struggling to decide if they were a good fit for me.

At the risk of blowing everything up, I told WeWork that I wouldn't go on another meeting with anyone. I was done. If they wanted to hire me, they should make me an offer or let me know they were going in another direction.

And they offered me the job, which I would accept — with three conditions.

One of my core beliefs is that if there is an opportunity to negotiate, take it. Don't worry about looking too financially driven. It is that worry that has kept millions of leaders from negotiating aggressively.

I've always believed that not only is it not a negative reflection to negotiate compensation, it's actually a negative reflection to not ask for it. Never be shy about negotiating your compensation. Be confident.

When I accepted a general manager role at Everyday Health about ten years prior, I learned a great lesson from my boss and founder of the company, Ben Wolin. Ben would often do the direct salary negotiations with executives whom he hired. I was particularly aggressive in a number of my requests.

After the contract negotiation, I asked Ben if he was put off by my aggressive negotiating

Ben responded, "When I hire executives, I like to see how strong they are in advocating for themselves, how willing they are to debate and compromise, and their confidence in themselves. If an executive isn't going to push for a higher salary and benefits for themselves" — or push to stop an endless interview process, I should add — "then they won't push for a key company priority, which likely has less of an impact on them."

My first ask of Artie Minson, WeWork's president and chief financial officer, was that I wanted to confirm that I wouldn't be reporting to Adam Neumann. Adam had told me during the interview process that he'd plan to spend one day a month with me at Meetup.

That was too much. Even one visit seemed too much. I had nothing against Adam, I was truly awed by him in fact, but it became clear that he had very strong opinions about how Meetup should be run, and I needed a buffer between Adam and me to provide support toward where I wanted to take the company. Artie agreed. What actually happened: Adam never visited even once while I was CEO. I was beckoned often to his office, and that suited me just fine.

My second ask was that I didn't want to run a company whose entire purpose was to serve the needs of WeWork. I had concerns about the hyper growth of WeWork and didn't want Meetup's future to be completely based on supporting WeWork's growth. I needed to choose what was right for Meetup instead of what WeWork preferred. Do what is right for the business.

In hindsight, this was definitely a smart decision! The company needed to be viable as a stand-alone business. I was uninterested in a mission focused primarily in selling more WeWork seats by creat- ing Meetup events in WeWork offices. Artie quickly agreed to both of these asks.

My third ask, the walk-away ask, was related to Meetup's founder. I really liked Scott but fundamentally believed that it wasn't possible to succeed with Scott reporting to me. I loved the idea of Scott being the chairman who would assist on key strategic projects, but Adam insisted to me that he take on an operating role. I made it clear that this wasn't going to work, and we found a compromise that Scott would take a three-month sabbatical (which he deserved more than anyone), then we would reevaluate his role, and I'd be able to make the final call on what it would be. Adam called my decision "Solomonic," and I learned that any time you received a biblical reference from Adam, it was usually good.

While these requests might sound aggressive, the best time to negotiate for anything is actually before you accept a job. If a leader does not set up the decision-making processes, reporting relationships, incentive structures, investment needs, and other key priorities prior to starting, then the leader will possibly fail before they even start. Many do.

Let me underline that: Many leaders fail before they walk in their door. They are so fearful of asking for specific needs to set themselves up to succeed, perhaps because they fear the job offer will be rescinded if they seem too aggressive, that they often naively believe "it will all work out." It won't. Or they think that their compensation is the most important thing to negotiate. It's not. You need to establish what is important before day one, and how the job will be right for you. Be pragmatic.

Now it was time to negotiate my final compensation package. I knew I would take the job at what was offered, so instead of pretending that I wouldn't take it, I said: "Artie, I'm going to accept the job. But I can feel great about accepting the job or I can feel good about it. I don't want to pretend that I won't be accepting it. I want to feel great and I know you want me to feel great. This job is going to be hell for the next three months [Note: I was wrong. It was much longer.] and while I am going through that hell, I want to look back on it and remember that you went to bat for me with Adam Neumann and have no regrets."

Even in negotiations, always be honest

Artie walked out of the room. He called Adam. And Adam gave me what I asked for.

I signed the contract immediately and felt elated. I was excited to be reporting to Artie Minson whom I deeply trusted. I had drunk the Kool-Aid and believed WeWork was going to be the next Tesla and couldn't wait to get started. While I had obvious concerns, the moment I signed, they vanished. I was now focused on putting a plan in place. All I needed was a strategic plan and all would work out just as it had always worked out before. I was, of course, dead wrong.

A few takeaways from making my Decision 0: Put in the work to make the right choice:

  • Interviewing is dating. Don't marry your first date, and if there are red flags during the dating process, those red flags will only become stronger during marriage.
  • Be retrospective after leaving a job. If you left for specific reasons, make sure you don't go back to the same problematic situation.
  • The expectations you set during the interview process will come back to haunt you. Be privately aggressive in setting goals, but better to underpromise and overdeliver.
  • As a candidate, you have more agency than you may realize. If you feel like you are being taken advantage of, then point it out and say something.
  • Don't miss out on pursuing a company whose mission you are aligned with. Try; if you can't succeed, fine, but always try.
  • You are always negotiating and everything is negotiable.


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