The Hit Man

Episode #1
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It was my first full time job, and I was still a teenager.  But – almost by accident – I became a hit man. <shooting> Not really that kind of hit man. What happened was that I discovered that I was really good at firing people. So, I was asked to do it a lot. Now, when I look back, I realize that experience started me on my life’s journey.


I had a crazy variety of jobs as a young man. I mowed lawns and washed cars for practically the whole neighborhood for spending money. Later, I had summer jobs doing maintenance at an RV park and working in a couple of different cherry factories. I printed and sold t-shirts for a while as well. At the University of Michigan, I worked nights as a security guard. They trusted me as a freshman to supervise a crew of guards, and watch over the nuclear reactor in the research labs.

But the most unusual job I had was also my first full-time job. It was during a hiatus from college and it was supposed to about installing car stereos. But it ended up being mostly about firing people. I fired a wide variety of people: my peers, people who outranked me, and people with decades more tenure than me. I fired more than a dozen people in the little more than a year that I had that job. I got pretty good at it. But I could also outfit a VW Rabbit with an AM/FM/Cassette player and two door speakers in under an hour.

That unusual job began a lifelong fascination for me with organizational dynamics and managing people. It taught me about hiring and firing, about how teams are built, and about how organizations work. I carried some of those early lessons through my career in the tech industry and all the way to the top HR job at Microsoft.

Some four decades after that first job as a hit man, I’m still fascinated by the stories, questions, and challenges of managing people and building teams. And that’s what this is all about.


This is Leading Smart, the show about Managing in the Brainpower Age. It’s a field guide to the joys and challenges of leading and working in the modern workplace. I’m Chris Williams, your guide to the stories and ideas that I hope will inspire you to be a better leader in the world of knowledge work.

In this podcast, we’ll take a look at how people meet the challenge of managing smart people in this Brainpower Age. It’s an era where work is increasingly hard to measure and control. An era where output is a lot less about building things and a lot more about the raw output of people’s brains. It’s also a time where the traditional management techniques and tired HR policies are so out of place. Each episode, we’ll explore everyday problems and provide practical tools you can use to be a better and smarter leader.

But before we dive into these, let me tell you about how I got fascinated with these problems. This is Episode One: The Hit Man.


I grew up in Perrysburg, Ohio, a small tree-lined suburb of Toledo, on the Maumee river, near the west end of Lake Erie. Toledo is a quintessential Midwestern industrial town in the heart of the rustbelt.

Toledo likes to call itself The Glass City. For most of the last century the leading companies that made beer bottles, wine glasses, windowpanes, or fiberglass were headquartered there.

But like many cities within the shadow of Detroit, Toledo has always been deeply involved with the auto industry. The motor city is less than an hour away, so many car-related companies made their home or their products in Toledo.

It was, until recently, where the world-famous Jeep was built. Since World War II, the enormous red brick chimney emblazoned with Willys-Overland — the original Jeep company — loomed just outside of downtown. Other than Jeeps, though, Toledoans didn’t build cars as much as they built the things that went into cars. It was the home of Champion spark plugs and Dana axles. There was the nearly mile-long Libbey-Owens-Ford windshield plant and the huge GM transmission plant. Toledo was, in many ways, a car town.

And growing up, I was a car kid. We had a go-cart and I built a mini-bike from a kit and a lawnmower motor. I loved cars long before I could drive them. And like any kid growing up in the 60s, I loved loud music. So, when I took a somewhat forced hiatus from the University of Michigan it wasn’t a long shot for me to apply to a local car stereo chain for a job as an installer. I really didn’t know much about the job. But I did have a bit of experience cobbling together the stereo in my Pinto station wagon. That’s right, this car kid’s first car was a Ford Pinto station wagon. I bought it brand new.

Although suppose I should be, I refuse to be embarrassed by that choice – even today. I worked my tail off as a union construction laborer one summer to earn the money to buy that car. I doted over that thing. I put on wheels and tires that were ridiculously large. I hand-built a center console out of stained wood. And I installed a killer car stereo, centered around a German Blaupunkt AM/FM/Cassette player. All in a Ford Pinto station wagon. But it worked and sounded great, so I thought I knew my stuff.

Unfortunately, the application for the car stereo installer job included a test. To test my electronics expertise. That I didn’t really have. I had just read the instructions on the Blaupunkt box. I was frankly panicked, but fortunately, it was multiple choice, so I tried my best.

A couple of days later Bert, the hiring manager, called and offered me the job. He told me “no one has ever gotten a perfect score before.” In hindsight, that hiring process turned out to be my first clue about the job. The test was a disaster, with most of the correct answers telegraphed in the question. I knew the answers to some, but simply guessed the rest just from the question.

On a side note: testing like this is widely used today to filter applicants for all kinds of jobs. It’s a terrible way to screen people. We’ll talk about that a lot more in a future episode.

The car stereo chain had a 30-day probation period that passed quickly. I began to really enjoy the work. It was a candy store for a car obsessed kid like me. We saw a huge variety of cars, from high-end luxury cars to aging beaters that barely ran. The latter were mostly kids who spent most of their money on pot, not on their car. They insisted they really needed great tunes. Cars of the 70s rarely came with more than a simple radio and a couple of paper speakers, so the upgrades we installed seemed almost magical. I got good with my hands and learned the cars and products quickly.

We worked on lot of Volkswagen Rabbits, a particularly hot selling car at the time. The owner of the chain had struck a deal with a nearby dealer. They ordered them with no radios, and we installed AM/FM/Cassettes and two door speakers in most of the cars they sold. We got really good at those cars and could knock them out in under an hour. We even occasionally did them right there in the dealer’s lot while the customer waited.

Typical of many small businesses, the company had a lot of turnover. Many installers were like me and had little experience. They flamed out during that first 30 days.

One day the owner of the chain was in our store and pulled me aside. Tommy was a curious little man, very smart and ambitious, but also painfully shy. The success of his chain, it was up to a half-dozen stores at the time, seemed miraculous to me for such a leader. But he knew the market and managed the numbers in his business really well.

Tommy asked me what I thought about, David, an peer installer of mine. I told him he was OK, but it seemed like we always had to clean up behind his mistakes. Tommy said, “yeah, he’s just not cutting it, can you tell him he’s fired?”

Stunned, I pointed to Bert, the store manager. He was an enormous loveable big bear of a man with a huge smile, and a passion for beer. Quite commonly we would find an open beer next to the cash register on slow afternoons. Certainly, Bert, the guy who hired us both, should fire David. “You’ve got a way with words” Tommy told me. Bert just nodded in silence. I complained, “I’ve only been here about a month longer than him.” It was to no avail they both just looked at me.

So… I did it. I went over to David and told him that it just wasn’t working out. That he was struggling and making mistakes that everyone else had to fix. That he should just pack up and go. David meekly agreed and quietly packed up his things and left within a few minutes. Tommy and Bert were watching the whole thing at a distance. When it was done, Tommy smiled and patted me on the back for handling it so smoothly. And Bert later pulled me aside to thank me.


So that’s how I began my brief career as a hit man. It started with me firing virtually everyone who didn’t make it through probation. Then it advanced to installers who’d been there much longer. Eventually, I got moved between stores not so much to install car stereos as to clean house. There was even once where had to fire a salesman – some twenty years older than me – who’d been there for years. All of this between crawling under the dash of whatever car was in there that day. I must have fired over a dozen people before I decided to go back to college and finish my computer science degree.

That job taught me a lot about business and people. Tommy and Bert didn’t put in the time and energy to hire well. And they didn’t have the courage to fire their mistakes.

For my victims, the people I fired, the truth was they knew it wasn’t going well. All they really needed was someone to level with them and pull the plug. When treated like real people they respected it. Most were never truly hurt. They just moved on.

I took those lessons with me as I returned to school and began a decades long career in the tech industry. I had a lot of other times in my career where I had to fire people, whether for performance, business, or other reasons. The lessons I learned early on, working in that car stereo business, stayed with me. Whenever delivering bad news of any kind, treating people like individuals, with dignity and a lot of honesty, always pays off. This can be especially true when dealing with creative, brainpower type employees.


For much of my early career I used say that loved working with computers because the problems are so discreet: the program works, or it doesn’t. It’s faster or isn’t. It’s all so clean, and measurable – not at all like working with people. But I eventually learned the real truth. That although the technical stuff was fascinating, I liked the people part much more.

I my decades in the tech industry, I worked on a broad range of technology from factory floor systems in the glass industry to large interactive systems in market research. I wrote code that shipped to tens of millions of people. Some of it, you’ve almost certainly used if you’ve ever installed a program on Windows. I even had the privilege to assist with quality control work on the space shuttle tiles after they caused the Challenger disaster.

But even though I worked on highly technical projects, I’ve always had a fascination for management, teams, and organizations. When I ended up at Microsoft in the 90s I was eager to stretch my wings leading larger and larger groups. I worked in and lead teams of hundreds. I had a role defining and distributing best practices across the company. Following my passion, I found my way to Human Resources. I ended up at the top, becoming VP of HR for the whole company.

That was an enormous job. There was an HR team of over a thousand, and responsibility for the wellbeing of well over 30,000 employees. It was both an honor, and frankly a blur, at the height of the dot com boom, and at a peak of Microsoft’s popularity and hiring frenzy. We were getting in so many resumes we had two shifts of people who did nothing but scan them into the computer so we could review them and pass them around.

I traveled a great deal, going quite literally around the world several times. I met many of my peers at the top of the Fortune 500. I witnessed the best and worst of management in many different companies and in a variety of national cultures. Best of all, it afforded me the chance to work with some of the most brilliant people in the world, both inside the company and out.

Among the important things I learned through my career are that managing people is really hard. That leading a team is a delicate art, an art many people aren’t well suited for. And perhaps most importantly, that every person is unique. Everyone has their own passions and pitfalls. Their own motivations, aspirations, and fears.

In fact, all of these components of managing people have become more important over the last few decades. They have become vital to understand as the world transitions from work focused on what people do with their hands to what people create with their minds.

This change from manual labor to mental labor is a source of great fascination for me. The more I look into it, the more I’m intrigued. We’ll talk about it in detail in the next episode.

This isn’t just a tech industry change, it’s happening in a huge array of disciplines. Whether it’s programmers or architects, teachers or lawyers, managers or creatives, the world of work is more and more defined by the output of smart people passionate about what they do. We’ve entered the Brainpower Age.

At the same time, much of the thinking about managing people and leading teams seems like carryovers from the dawn of the industrial age. The HR policies, hiring practices, and management techniques seem crude and misguided. We see all manner of awkward incentives and inappropriate sanctions. Most of these are leftovers from when the yardstick to measure success was widgets per hour. So much of this simply doesn’t work in this new Brainpower Age.

It also seems that much of the help you see on management these days isn’t really very helpful. There’s a tidal wave of advice from people who seemed to have studied leadership, but not done a lot of it.

Some of them try to get all metaphysical and try to make leadership to be all about your mental state. I guess that’s supposed to magically rub off on your team.

Then there are the academics who make it out to be so straightforward. They draw ridiculous conclusions from a single study. I heard one the other day that claimed a straight line between corporate profitability and the gender of the leader. As if markets and products played no role. Or worse, that men and women can’t be equally poor leaders.

The fact is that leadership is hard. That it’s made up of hundreds of small choices made each and every day. The sum of those choices builds to create an organizational culture that fosters great work from smart people, or it doesn’t. Leaders make those choices, and often times it’s hard to choose.

That’s what this show is all about. Looking at leadership and team building from a modern perspective. With practical and realistic discussion and advice on dealing with problems teams face every day. Each episode we’ll tackle a single issue in a bite-sized package. The target is around 20 minutes, long enough for some detail, not so long as to waste your time. The goal is short, useful episodes that help make you a better leader in the Brainpower Age.


Leading Smart is from me, Chris Williams. You can find out more about the show and find other resources for leaders at my web site, CLWill.com. That’s C-L-W-I-L-L.com. Or find me on social media as theCLWill.

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I also hope you’ll participate. Do you have questions about managing people? Do you work in an industry that faces these kinds of challenges? Are you, or do you know, someone I should be interviewing? Let me know. Each episode has a page on my web site, and comments are welcome. Or just send me an email to pod@clwill.com. I can’t promise I’ll answer or interview everyone, but I read every email I get.

That’s it for this episode. The next episode will be on The Brainpower Age. What do I mean when I say that, and how does that effect leading and building teams? I hope you’ll listen. Until then, please remember that each of the several dozen decisions you make today are part of Leading Smart.