Tough Calls from the Corner Office: Top Business Leaders Reveal Their Career-Defining Moments

Introduction

What if you could have private conversations with some of the top executives and business builders in the country?

What if you could sit down with them and discuss the most important decisions of their careers, the moments that made them what they are, the catalysts that pushed their companies to the pinnacle of success and created their legacies for all time? Imagine what you would learn: the lessons, principles, strategies, ideas, and solutions to all the business issues you might encounter in a lifetime.

I decided to do just that. I reached out to some of the most successful and respected businesspeople in corporate America—leaders from companies such as Verizon, Chrysler, McDonnell Douglas (now part of Boeing), ESPN, Ogilvy & Mather, A. G. Edwards (now part of Wells Fargo), Fleishman-Hillard, Enterprise Rent-A-Car, WellPoint, and Panera Bread Company. The results are in your hands: a treasure trove of rich business wisdom, stories of tough decisions and hard-won victories, and lessons from lifetimes of achievement.

My name is Harlan Steinbaum, and I am a former CEO.

In looking back over my own career in business, I realized that among the many choices and decisions I had made, there was one that stood out above all the rest in terms of its impact on my company, my career, my family, and my subsequent success.

It was the moment when my brothers-in-law and I decided to buy back the family business from the conglomerate that had purchased it from us several years earlier—and to run it ourselves once again. That decision, and the actions that flowed from it, came to define me and my life in business. My life would never be the same because of that decision. It was the gateway to my future. It was my defining moment.

Over the years I’ve become fascinated with these career-defining points in time, not only because they are so often interesting and dramatic as stories in and of themselves, but also because they have so much to teach us.

A defining moment, I have found, isn’t always the decision that makes the most money for the company or the person. Years after buying back the family business, we founded a very successful joint venture called Express Scripts. Yet, in looking back, I don’t find that that decision or the resulting enterprise, as successful as it was, really defined me professionally.

In my view, a defining moment is the decision or action a person takes that has the greatest impact on his or her career. It’s a moment that shapes us as individuals and as businesspeople and sets the trajectory for the events that follow. It doesn’t necessarily have a positive short-term outcome. Sometimes our most significant learning experiences come from our failures, not our successes.

Many of us won’t know our defining moment until we reflect on our careers after the passage of time to see how certain events, decisions, and judgments played out—when we can measure their effect on us and our work. That’s how it was for me. Even after many years, I can still clearly see my own defining moment. It began with my restlessness and dissatisfaction with the status quo and my desire to take greater control of my future.

My defining moment starts with a company called Medicare-Glaser Corporation, a retail chain of drugstores and pharmacies. The company was founded by my father-in-law, Morris Glaser, in 1923. (By the way, we had nothing to do with the U.S. government’s Medicare program, and in fact we had the name before that program was created.) At one point we owned stores in Missouri, Illinois, Connecticut, Tennessee, and New York. In all, we owned and operated over one hundred stores. As the company grew, we became the first drug chain to open its own chain of stand-alone retail pharmacies, with a focus on dispensing discounted prescriptions. Its purpose was to help the many people who could not afford the cost of their medications.

In 1970 I became president of the Glaser Drug Stores and Medicare Pharmacies. Soon after, we began to consider an initial public offering to provide additional capital to grow the business. In 1972, while these discussions were taking place, we were contacted by Pet, Inc., a diversified conglomerate listed on the New York Stock Exchange. Pet was interested in acquiring us. After months of discussions, we decided to make a deal and become a division of Pet.

When Pet first became interested in purchasing our drugstore chain, we were enthralled by the prospects. Pet’s plan was to grow the chain into a nationwide competitor. With its resources, we could expand both organically and through acquisition on a scale we had never dreamed of before, and we could then really compete with the big boys in our industry.

I was tired of seeing a Walgreen’s open up across the street from virtually every store we opened. Walgreen’s, with its size and sheer buying power, would lower prices on key products to get people in its doors. It could sustain lower prices much longer than we could. As a result, we had to be more innovative than Walgreen’s to keep our customers from going across the street. Now, as part of Pet, we would finally play ball with Walgreen’s on a more level playing field.

Once our company became integrated into Pet, I became a group president with profit-and-loss responsibility for six out of its seventeen operating divisions. From that vantage point, I gained a better view of company management and philosophy and came to realize that Pet was weighted down by some classic big company structures and thinking. The company moved slowly, people deliberated about deliberating, and good old-fashioned entrepreneurial-style risk-taking was avoided, not courted. When challenges arose, the pattern and practice was to take the path of least resistance. On one occasion, Pet’s supermarket customers, who represented an important part of its distribution base, were complaining because our drugstores and liquor stores, which I also managed, were taking high-margin business from them. They threatened to stop buying some grocery products from Pet in retaliation. In response, Pet slowed the growth of the drugstores and liquor stores.

In general, a premium seemed to be placed on managing problems rather than solving them. I didn’t have confidence that in the long run this was good practice, and I simply didn’t want this type of culture to dictate my future or that of my family or my company. My original partners and I became convinced that we could grow the company smartly by being nimble and taking the right risks, even though we wouldn’t have the same resources to draw upon. As with most business decisions, there were pros and cons on both sides, but in the end we felt strongly about retaking control of our destiny.

We decided to approach Pet management and try to reacquire our company. After a lot of surprised reactions, followed by some tough negotiations, we arranged a leveraged buyout. We had won our company back, but not without taking on a lot of debt.

Although I felt that this was the right decision for me and my company, I don’t want to leave the impression that Pet itself seemed like a lost cause to me—far from it. Like any successful company, it did a lot of things right and was rewarded for it. We learned a lot from our Pet years that we were able to put to good use. It was a professionally managed company with a lot of good people, and its management sophistication rubbed off on us, giving us an advantage that few other companies our size had. As a result, our newly reacquired company was blessed with both an entrepreneurial spirit and professional management. This is a rare combination.

With our destiny back in our own hands, we built a unique and dynamic company. We continued to grow, opening a chain of low-cost prescription vision center stores as well as developing other retail concepts. In time, we had an initial public offering that provided us with growth capital.

We transformed ourselves and our firm into leaders in the retail drug industry. Some of our moves transformed the industry itself. For example, we developed the first chemically based drug interaction database used by pharmacists to alert them to potential drug-to-drug or drug-to-food reactions. Then, in the late 1980s, we became the first in our industry to open a health care center in one of our pharmacies. We began to fill mail-order prescriptions, and the business continued to grow.

We also started a joint venture with one of our business partners. The new company, called Express Scripts, was a pharmacy benefit management business that included prescription fulfillment through the mail. I was its first chairman. I’m proud to say that the company now serves the prescription drug needs of over 50 million Americans. Express Scripts has grown into a Fortune 500 company.

All of these events are a direct or indirect result of my defining moment, which put me on a path that I can look back on with satisfaction. It also taught me some important lessons.

I learned to have the intellectual honesty to face problems head-on—not rationalize them away or try merely to manage them, but to get to the sources or causes and then figure out a way to eliminate them.

I learned that hiring the best people pays off.

With cash flow tight, I learned to be careful and tough-minded when it came to management and planning. Only with great discipline and tight control could we have grown and prospered through the early, fragile years of the repurchased company.

I also learned that in business you never do anything alone. I had a long and interesting career, and at every step of the way I worked shoulder to shoulder with three wonderful people: my two brothers-in-law, Lou Glaser and Ralph Silversmith, and another executive, our CFO, Stuart Bascomb. Everything I did, I did with them. They were great partners, colleagues, advisers, and friends.

The personal impact that this one business decision—my defining moment—had on my life made me curious about other business leaders. I wondered whether others had experienced similar kinds of moments in their careers. To find out, I decided to contact top executives around the country and ask them.

The results were fascinating. In the course of their careers, these business leaders had made thousands of decisions, but most of them felt that there was indeed one decision that stood out above the rest. That decision had served as their crucible and made a profound impact on them both personally and professionally.

I’ve elected to have these executives tell the stories of their defining moments in their own words. In no other way could I capture the authenticity of their experiences, the depth of their knowledge, the knowing quality of their voices.

I’ve organized the book around the classic arc of a successful businessperson’s career: early key career choices, risks and opportunities, working with partners, business transformations, and the final leave-taking from the world of work. I end the book with a special chapter on defining moments that transcend the typical concerns of business.

I’ve also assembled a great collection of business advice from these executives in an appendix called Executive Advice and Wisdom. I asked them to provide an unconstrained list of advice, suggestions, and pointers—whatever they wanted to pass on to readers. The result is a document that, in my opinion, may be one of the more interesting lists in all of business.

I invite you now to sit down with these men and women, listen to their stories, absorb their wisdom, and learn.

Chapter 1

The Road Taken: Making Key Career Choices

Defining moments often come during periods of transition, when the atmosphere is charged and the business environment is changing. It’s at these times that leaders step forward and make their mark.

Another kind of transition, however, has little to do with company or business issues, but instead involves personal career issues. It’s a defining moment that occurs when we look inward and begin to ask questions like: What do I really want out of my professional life? What are my goals? What’s going to make me happy? This chapter and the next feature executives whose defining moments came out of such questions.

Few of us really know what our professional goals are from the start. None of the executives in this chapter—and just a handful in the rest of the book—had it figured out from the beginning. Stories of major changes in midstream or several changes over the course of a lifetime are the norm, not the exception.

As diverse as these stories are, an important common thread runs through them: at some point these people figured out what really made them tick, and they let that insight guide their decisions.

Some people find it easy to figure out what excites them professionally. In chapter 4, we’ll see that Monty Hall, the famous game show host and producer, knew from the beginning that he wanted to be in the entertainment business. But for many of us the difficulty of getting to a useful and revealing analysis of our professional goals is separating what everyone—family, friends, society—tells us is important from what’s actually important to us personally. There are a lot of red herrings out there, and sometimes it can take a while to figure out where our own true north lies.

Danny Meyer, the famous New York restaurateur, was about to pick his second (and possibly wrong) career because he never let himself entertain the idea of becoming a restaurateur. It was simply not the type of career to which an expensive liberal arts education usually led. A doctor or lawyer, yes. But not a restaurant owner. He had to admit to himself that he really wanted to be in the restaurant business, and then he had to have the strength to take an unconventional path that some in his family did not fully endorse.

The starting point for any career decision must be what a person knows about himself or herself. If prestige makes you tick, great. If you have to be in a creative pursuit, fine. If you know that you need a career where you can make discoveries or educate children or build something or work with animals or deal in rare books—fantastic. The key is to figure this out and make it part of your decision-making criteria.

For most of my career I was in the drugstore business; once my partners and I had established ourselves in the marketplace, we expanded into vision stores, hearing aid stores, and mail-order prescriptions. When I was at Pet, Inc., I had a diverse group of companies reporting to me: a liquor store chain, a label manufacturer, an upscale party center chain, a specialty and gourmet foods manufacturer, and a fireplace retailer. I’m sure there was something that tied these companies together, but I never found it.

The fact is that it never mattered to me what industry I was in because I love the process and challenge of business in general. To me, it’s a multifaceted game. There’s the financial game, the marketing game, the strategic game, the operations game, and the interpersonal game. I think I could have been happy in virtually any industry because I found each of these fundamental aspects of business exciting.

Of course, not everyone is fortunate enough to pick a career they love, but I believe that those who do will have a better chance at succeeding. Back to Danny Meyer—he was on track to become a lawyer, but decided not to. Good choice. It wasn’t his passion. I know a lot of unhappy lawyers who are quietly looking around for something better suited to them. I also know a lot of happy lawyers who really love everything about their work—the thought process, the cases, the deals, the complexities. These lawyers love helping clients and love winning for them. You know who I want to be my lawyer when I need one? One of these people. Not one who would rather be a sports agent or a politician or a screenwriter. It’s not that lawyers who are searching for their true passion are bad legal practitioners, but I want someone who is passionate about the law working on my case or my deal. That person—the lawyer who goes the extra mile—ultimately is the best counsel for his or her clients. When you love what you do, you can be passionate about it without faking it. As Joseph Plumeri, the CEO of Willis Group, told me, everyone wants to be around people with real passion.

There is one more common thread that runs through the stories in this book, especially those in chapter 1. None of these executives looked for an easy way out. All of them knew they were in for a lot of grueling work and long hours while they paid their dues.

When I started at Glaser Drug Company, I had come from real estate. I knew little about the drugstore business and less about retail operations. I had no background in marketing, inventory management, pharmacy operations, product selection, and so on. I had to learn it all on the job. The first thing I did was get into the field so I could be exposed to all aspects of the business. I spent time at the cash register, in the warehouse, and behind the pharmacy counter. After I had been on the job for probably a month, I was working behind the pharmacy counter when a woman came up and asked for her prescription. I got the package and gave it to her. She took the package but gave me a suspicious glare. She kept looking at me and didn’t walk away. Finally she blurted out, with no small sense of shock and a bit of horror, Hey, I know you. Last month you sold me my house—and today you’re filling my prescription? I did know enough about retail customer relations to assure her that I hadn’t actually filled the prescription but was simply handing her the package.

These kinds of stepping-stones in a career might not be the sexiest and most satisfying, but if they lead in the right direction, they provide valuable and necessary learning experiences. And since there are no shortcuts around them anyway, go ahead and embrace them.

I’m not suggesting that you can develop a career plan for yourself in the same way you would develop a business plan for your business, but there are some processes that can be taken from business planning that provide a model for moving forward and reacting to career situations.

It’s as simple as setting goals, knowing your decision-making factors, and establishing priorities. This provides a starting point for assessing opportunities. For some people, the goal is money, regardless of how it’s made. For others, the goal is attaining a lofty position or having a high level of responsibility in a specific field. Some people insist on doing interesting work, or working in a specific location, or achieving a healthy work-life balance. No one can tell you what your goals and priorities are (or how much sacrifice or risk you’ll tolerate to achieve them), but they should be articulated and factored into every decision you make.

In this chapter, we see some far-reaching decisions that were made in the early part of a person’s career, while others involved midcareer job offers that forced the issue. These weren’t decisions based simply on where the most money or the most prestige could be earned. Each person looked at the totality of the opportunity and filtered that view with his or her personal decision-making factors. All of these executives seized an opportunity and gave it everything they had to make it a success. This kind of relentless effort—the final common element here—certainly has a way of covering for any deficiencies in the career script.

DANNY MEYER

CEO, Union Square Hospitality Group

Without Danny Meyer, New York would be a far less tasteful place. Meyer is the owner-operator of some of the city’s most legendary eateries, including the beloved Union Square Café, the top-rated Gramercy Tavern, Tabla, Eleven Madison Park, Blue Smoke, and Shake Shack. As head of the Union Square Hospitality Group, he runs a group of highly regarded Manhattan restaurants that are visited by tens of thousands of discerning diners each year. Now that he has brought his cuisine and renowned hospitality to the New York Mets’ new baseball park in Queens, his reach has extended into the outer boroughs of the city as well.

Meyer’s career in the restaurant business almost didn’t happen. It was almost a road not taken. As a young man out of college, he started in sales at a company that developed electronic article surveillance security systems. An offer from his employer to take on a bigger, more important role in the company forced him to make a tough decision: should he stay with this career and start moving up or should he move on? The situation was a turning point for Meyer, but he almost turned in the wrong direction!

Meyer struggled to make the right choice. He weighed his passion against more practical and typical career considerations. His emergence as one of the most successful restaurateurs in the world certainly validates his early decision and suggests to all of us that following one’s heart is the surest way to a satisfying career.

The job I had before opening my own restaurant was account manager for a company called Checkpoint Systems, which sold electronic tags to stop shoplifters. This was in the early 1980s. The company was based in a wonderful town called Thorofare, New Jersey, and I had the New York territory. I was their leading salesman for three consecutive years and was becoming a star, getting awards, trophies, free trips. Everything was working out nicely.

The company approached me about moving to London to help launch their product overseas. I was fascinated with the idea of living in London and being able to explore Europe. But instead of jumping at the opportunity, I had to admit to myself that this work was not my passion. Actually, I wasn’t sure what my passion was. I had a degree in political science from Trinity College, and I had some thoughts about running for public office—becoming a politician.

I spent my entire youth fascinated with politics and had worked in it both professionally and as a volunteer. I worked for U.S. Senator Symington in Washington, D.C., one summer; I worked as the Cook County, Illinois, field coordinator for John Anderson’s presidential campaign in 1980; and in 1977 I worked in the Connecticut State Legislature. Maybe it was time for me to go do it.

The London job offer forced my hand: I was either going to go forward with Checkpoint and the opportunity they were giving me, or I was going to stop doing the job altogether and move on.

I thought, All right, here’s your opportunity to see if politics is the way to go, and the way to figure it out is to become a lawyer first. The traditional path to public office had always been to study law before running for a government office.

So I signed up to take the LSATs, the exam law schools look at to decide if they’re going to accept you. Literally on the eve of taking my LSATs, I knew something was wrong with my decision.

Just before the day of the exams, I had dinner with my grandmother, who was in town from Chicago, as well as my aunt and uncle who live here in New York. I guess I was showing my confusion, because my uncle said, What’s wrong? I blurted out, I don’t really want to be a lawyer.

He came back with, Well, why don’t you do what you’ve been talking about your whole life?

What’s that?

All I’ve ever heard you talk about is restaurants. Why don’t you become a restaurateur?

It was true. I was always talking about restaurants, but back in 1984 it was just about unthinkable to parlay a liberal arts degree into a job in the restaurant business. It just wasn’t a valid career choice. It certainly wasn’t the kind of career you wanted to tell your parents that all of your education has led to.

Without any question, the defining moment in my career was realizing I had the courage to pursue