Leading with Compassion, Trust, and Soul

At age 21, I learned some lasting lessons about leadership from my first real boss, Andy Walton.

I met Andy Walton in a West Hartford coffee shop. I wasn’t thrilled to be there. I had become extremely politically active during college, and during my senior spring had scored what seemed like a dream job working on a 2004 Senate campaign. But the night before graduation, I got a frantic call from the campaign manager: the campaign treasurer had absconded to Mexico with the campaign funds, and our candidate was dropping out within the hour. I was out of a job, and instead of a New Hampshire Senate race, I got a last-minute lead to work on Senator John Kerry campaign’s fundraising arm. The downside: I was being assigned to Hartford, Connecticut. 

Andy’s path to get there had been far stranger than mine. Born in Detroit, Andy took off for LA as a teenager to make it in music, and he was playing in a local band when his best friend’s brother’s band, Guns & Roses, got their break opening for the Rolling Stones. Andy was a roadie on the Appetite for Destruction tour, working merch and other odds jobs with the band for years, until the infamous “November Rain” music video. From there he drew comics as a graphic designer, rode the boom and bust cycle of a Dot-com start-up, and worked the casino circuit as a professional poker player. Along the way, he nearly died over a freak medical issue, and healthcare became both his political rallying cry and his need for a stable job. When he interviewed with the Kerry campaign, they looked at his resume with understandable skepticism, but he challenged them, “If you want a political junkie, you’ve got your choice of 25-year old public policy grads in the other room, but if you want someone who has been through real stress and knows how to handle tough situations, I’m someone who won’t fold under pressure.” The Democratic party hired Andy that day. And sent him to Hartford. 

Meeting this diminutive dude with glasses, a baseball cap, and a sarcastic vibe for the first time, I didn’t realize I was embarking on a 20-year friendship that would take us on adventures across the country. He was 35, which seemed ancient to me at the time. But we quickly bonded over politics, music, and sports, and one night I finally got him to cut loose enough to unseal those wild “Guns” stories from the vault. 

Andy was my first real boss, and in the short time we worked together he showed me a model of leadership that I’ve cherished ever since. He showed me that you could lead through warmth, build a team through trust, and get the best out of people by letting them be themselves. Here’s how:

1. Create an atmosphere where people want to show up. This wasn’t the West Wing - we were doing grassroots fundraising out of a Hartford office park. Our staff was skewed heavily towards young people who needed to make a few bucks for the summer going door to door and asking for donations. It easily could have been a dreary operation. But it wasn’t. 

   The office was welcoming. Music played as people cut turf. Canvassers showed up early just to hang out. We found a way to celebrate high performers without creating unhealthy competition. There was a lot of post-work partying (perhaps too much by 2023 standards), but it happened off-site and wasn’t forced on anyone. No one even minded working late - that’s when shenanigans happened. One night we huddled around the speakerphone, posing as the national HQ and pranking California field offices by announcing mandatory drug tests. The Berkeley office was particularly freaked out, and HQ was less than pleased when they caught up to us. 

   Because so many of our canvassers were seasonal, we had to say a lot of goodbyes, and Andy borrowed the sports arena tradition of “retiring jerseys”, hanging peoples’ names around the office along with sentimental notes from their coworkers on their last days. I was so moved by this process that a few years later, when I was doing Katrina relief in Mississippi with a similarly transient workforce, we hung signed t-shirts from the rafters on folks’ final night at dinner. Harder to do in the zoom era!

2. Don’t lose your cool. Something I’ve also come to appreciate about the leaders that have inspired me is how rarely they lose their cool, even privately. In contrast, I can’t stand all the leaders who get fawned over, particularly in our political system, who have sunny public personas but treat their staff miserably behind the scenes. There’s just no need for a yeller.

   Andy didn’t need to yell because he was just so damn calm. He’d seen enough in his life to know that petty office stuff just wasn’t worth the drama, and that getting rattled was only going to make a situation worse. It was a revelation that so much of the negative energies that affect work life - stress, tension, jealousy, poor treatment - flows downhill from the top. As a leader you can set a different tone. 

   Andy still held people accountable, but knew berating doesn’t add much. I did a poor job giving a “last warning” to an underperforming canvasser, which led to an awkward scene when we had to let her go. Andy could tell that I felt terribly about messing up, and little needed to be said after.

   That doesn’t mean he never got angry, particularly when he was fighting for his staff. He could be cutting and get frustrated, and I’m certainly not trying to canonize him. But he rarely raised his voice, never punched down, and never injected more stress into our lives, no matter what was going on behind the scenes at the national HQ. As someone who is generally positive and forgiving, it meant a lot to see that a leader could still project strength without resorting to the bad behavior our society so often waves away. 

3. Believe in your people. When properly motivated, most people are capable of more than their job gives them credit for. That’s why I believe in stretching people - giving them more challenging work until you bump against their limits. 

   Young Me was a handful - rebellious, distrustful of authority, and pretty sloppy. In college I’d worked on campaigns and paid the bills with cafe gigs and catering, but most of my Hartford job (training, HR, canvass mapping, fundraising) was stuff I’d never done before. Andy’s assumption was that I could do something well until I proved otherwise. That’s how I wound up leading our training sessions and daily warm-ups before canvasses - it played into my uber-extroverted personality, and helped move me in the direction of becoming an organizer.  

   He also indulged my wackiness. We could only fundraise on designated turf, and when I realized that Andy had conceded lucrative Connecticut coastal towns to the New Haven office and Massachusetts border towns to the Northampton office, I called those offices, demanding they cede their territory, or at the least, defend it on the basketball court. New Haven countered with a chili cook-off, and we ultimately settled on a fair compromise. Northampton accepted our challenge, and then absolutely demolished us on the court. The escapades brought the office closer together.

When I think about Andy and the two other formative bosses I had at later stages in my career, Danya (Moreland Commission) and Glenn (#CLOSErikers), the common through-line was that all of them gave me permission to cook and deliver work better than anything I’d thought myself capable of before - whether going after corruption or building a dynamic jail closure campaign. Their trust in me engendered trust in them, because don’t we all want to work for someone who believes in us? To this day, when I’ve got someone new on my team, I size them up to see if they are ready to excel without me looking over their shoulder. Once they are, I let them fly. This is how most stellar people excel. 

Building trust and seeing people for their strengths - that’s how you build a great team. In 2004, Andy built one on the fly in weeks with a bunch of recent college grads as his deputies. Yet, as much as I dug working for Andy and the aforementioned office vibes, I couldn’t stand fundraising, and the big bosses in Boston knew I wasn’t great at it. So I bid my farewells and headed to Aberdeen, South Dakota to run canvassing for a U.S. House race. That *really* wasn’t a great fit (the one pager on the values our candidate shared with George Bush put me over the edge), and after a short stint I headed to Vegas, where I’d spend the remainder of the election doing presidential GOTV in the cycle’s marquee western swing state. I called Andy to thank him for being a reference, even though I’d just bailed on him. “Of course,” he said. “We had to get you the hell out of South Dakota.” 

We stayed tight for the next two decades, having adventures from DC to Vegas, jawing on politics, and trading life advice. Last July, he flew in from Utah for my 40th birthday, even though he was coming off a rough year health-wise, including a bout with cancer. When the bassist for my band was late to rehearsal for a show we were doing that night, Andy quietly learned the bass lines and performed them a few hours later. The ultimate team player. 

Everyone in my life who met him through the years liked him, the quintessential “good guy.” But what made him a remarkable leader is that all the qualities you appreciated in him as a friend were still there in the campaign trenches when the going got hot. Anyone who’s been through stress, handled tough situations, and been in leadership knows that it’s easier said than done to remain “the good guy” in those environs.  

Andy passed away recently after a brutal, drawn-out fight with cancer that flared back up soon after my birthday. He handled the last months of his cancer with all the grace you’d expect from someone I’ve just been describing - keeping upbeat and low on stress, but also real and honest. The last time I saw him in person, he was in considerable pain, and the former poker champ sighed, “Eventually everyone has their last hand at the table.”

We all get a certain amount of time here, and then our time at the table is up too. We all leave different things behind - family, professional and creative works, small and large impacts we make on the world around us. If we are going to take on the immense challenge of bringing justice to this world, we need to do it with kindness and compassion. We should ask that much of the people we call leaders. Andy showed me that was not only possible, it was the best way to lead. I’m going to miss him tremendously, and hope his influence continues to ripple out for years to come.