I’m a Check Getter

This book is a collection of short phrases that help keep me on track. I discovered they can also be very useful for employees and others trying to do the best job possible.

Managing employees was the most difficult challenge of the forty years I ran the company. I like to do things myself, not try to get someone else to do it.

I was in sales my entire professional life and was very good at it. I knew how to navigate the complexity and close a high percentage of the deals I worked on. However, it was proving very difficult to pass this knowledge on to my sales team. I tried a wide variety of managerial techniques and provided extensive training, both in group and individual settings. But my salespeople were losing a lot of deals. We had strong competition, and the products were about equal. Often the best salesperson got the deal, not the best product.

I remember one young man who was extremely bright. He did excellent work in our support department for a few years and then he wanted to move on to sales, where he struggled. I tried to help by giving him all sorts of ideas, strategies, techniques, and “tricks of the trade.” We were both frustrated that it had not helped.

One day he went to Florida from our office in Colorado to do a demonstration for a potential client. He spent an entire day with the prospect and called me from the lobby of the hotel. I asked him how the demo went, and he said, “It went great, they loved it, the owner was in the room and thinks we are by far the best.” I asked, “Did you close the deal and get a deposit check?” to which he responded, “No, how do I do that?” I told him to go back to the owner’s office and say, “Can I have a deposit check, please?” So he did and returned to Colorado with the deal completed and the check to prove it.

A few days later I was at lunch with this salesperson and someone asked him, “What do you do for a living?” He responded, “I’m a check getter.” These four words clarified the entire complex sales process for him. He quickly became our best salesperson by far, and eventually the sales manager.

We talked frequently about why he found the phrase he invented so useful. He explained that I had taught him many valuable strategies but had overwhelmed him. He was trying to employ all of them on a deal. Always do this and that in a demo, make sure to use this wording in a proposal, visit customers at their location, bring up all the great references, etc., etc., etc. He went on to say that he realized those things were all just potential tools he could use, but he didn’t have to use any of them. Effectively his thinking had become, “I’m a check getter, and what is stopping this person from giving me a deposit check right now?” Sometimes the answer was, “Nothing, go ask for the check.” Sometimes the person only needed a very short demo on one feature, or to be given one customer reference.

I use this concept frequently. For years I wanted to write this book. I would start and stop, never getting very far. I now think, “I’m an author.” This leads me to, “What can I do right now to get the book finished?” It boils away all the other trivia getting in my way.

Management by Wandering Around

I started a software company in 1982 and sold it in 2022. For the first few years I was a one-man show, busy doing everything myself. As we grew, I added employees and had to manage them. I set out to learn about management and read a variety of books on the subject. Most suggested a pretty formal approach: have scheduled meetings, set goals in the meetings, periodically review progress toward the goals, conduct year-end reviews using a 20-page evaluation form, write a detailed company policy manual, and make sure everyone followed it. I tried to use this approach and hated it. I think most employees did as well. There had to be a better way.

I was fortunate to work at Hewlett-Packard for six years. David Packard and Bill Hewlett had developed an approach that became known as “Management by Wandering Around.” HP was started in 1939, and this style was apparently very effective for them. However, I did not see much of it being practiced. By 1980 HP had grown to more than 57,000 employees and, at least in my part of the company, had evolved toward the formal management style I had read about in so many books.

I couldn’t find any detailed information on how to implement “Management by Wandering Around.” However, I liked the phrase and did it my own way. I eliminated formal meetings in conference rooms with an employee. Instead, I literally wandered around the office, stopping at someone’s desk. “Hey, how are you doing today? What are you working on?” We would chat about it a bit, I might suggest some ways to do it better, and then I would move on. Maybe five minutes max.

I also got people out of the office. The company was based in the ski resort town of Vail, and everybody skied or snowboarded. I would take an employee skiing. We might be on the hill all afternoon, and riding the lifts gave us an opportunity to talk about all sorts of stuff. Often it had nothing to do with work. Sometimes a work item would pop up for a few minutes, but then we went back to skiing.

I created a company softball team and played every game with the group. We always hung around after the game and had a few beers out in the sunshine, bullshitting about this or that. We also had informal get-togethers. Perhaps for no reason, I would call off work early, have some food and drinks delivered, and wander from person to person, chatting about whatever. I took the entire company to Jamaica many times, along with spouses. There was no better way to wander around than between the beach, the pool, and a beverage.

Skiing with employees, playing softball, and holding informal events were fun for everyone involved. I discovered that when an employee was relaxed and having a good time, they were much more open and honest. We might ski for four hours and talk about work for only a few minutes, but in that short time I learned more about what was truly bothering them than I ever would have in a long formal meeting in a conference room.

Employees loved the approach. They might make a suggestion to me and see it implemented the next day. Many were amazed and might tell a friend, “I can’t believe my boss took me skiing all day today, and we’re going to Jamaica next week, and he actually listened to me and did it.”

Management by Wandering Around also eliminated year-end reviews. Employees got feedback from me every day and knew exactly where they stood.

Work Smarter, Not Harder

During the 2026 soccer World Cup, Lionel Messi was on Argentina’s squad. I heard a TV analyst point out that Messi was not running very much; he tended to “stand around and observe.” Other players were hustling all the time, seemingly working much harder than Messi. At first glance, he appeared lazy. Yet Messi was one of the most productive players in the tournament. When he was “just standing around,” he was actually observing the entire field, looking for weaknesses he could exploit later in the game. The seemingly lazy Messi is the GOAT of soccer—greatest of all time—and his ability to work smarter, not just harder, is one reason.

In 1982, I started a software company. After running the business for about five years, I noticed that I was very busy, working hard and running from one problem to the next. We were growing in total revenue, but not in profit. The more customers we added, the busier and more stressed I became. Yet we did not make any more profit. Clearly, what I was doing—staying busy all the time—was not working.

I stopped all the busy stuff, stepped back, and looked at the situation as though I were a third-party consultant. Customers and employees were unhappy because I was not available to handle day-to-day problems. I wrote a document describing the problems, my goals, and possible solutions. Stepping back allowed me to see the forest instead of the trees. Writing that paper was the equivalent of Messi standing around and observing the field.

The major problem was that I was getting too many small customers who required a lot of time and energy but paid very little. I raised the minimum annual support contract from $600 to $2,400—a fourfold increase. Some customers dropped the system, but nowhere near enough to offset the higher price. I ended up with about 25% fewer customers to service and three times the revenue. I was less busy, less stressed, and made a lot more profit. If I had continued with the old pricing, I could have worked hard twenty-four hours a day and we still would have gone bankrupt.

Do I Really Want Employees and Partners?

The first few years after starting my company, I was a one-man show, doing everything except programming, which I contracted out to a third party. I was very busy but enjoyed almost every minute. As we grew, I added employees. I also provided stock to two people, effectively making them partners.

As a one-man show, I was doing everything and enjoyed it. I particularly liked sales, out there competing with the world and trying to get the deal. When I hired salespeople, I tried very hard to pass on my knowledge, but we just didn’t close as many deals. It was frustrating to watch from the sidelines. I quickly discovered that I didn’t like managing employees, yet as my company grew I hired more and more people. It got to the point where I became a full-time manager, not a doer, and I didn’t like it.

Employees also create paperwork—an ungodly amount that increases every year as government bureaucracy grows. There is the expected paperwork, such as filing payroll tax reports. But then I received a 50-page form from the U.S. Department of Labor asking for all sorts of information about the company and its employees. Filling it out properly could take a full week of my time. The first page pretty much warned that if I didn’t fill it out, I could face huge fines and penalties and even possible jail time.

When I worked at Hewlett-Packard, my managers made many decisions I did not agree with, and I had no power to change them. One of the reasons I started my own company was I wanted to be the boss, the person in charge. When I added partners, I had to consult with them, which went against my desire to be “the only boss.”

I was very good friends with the people I made partners at the time I gave them stock. However, people change and there is no guarantee that the friendship will survive and prosper once it is converted into a partner relationship. It is a bit like marriage, which can end in a painful divorce. So can partnerships.

I added employees and partners without understanding any of this. It just seemed like the way companies were supposed to grow at the time. With the benefit of 40 years of hindsight, I would encourage 18-year-old Barry to be an entrepreneur, but to carefully answer the question, “Do I really want employees and partners?”

Today it is possible to start and operate a company where the only employee is you. With the internet, you can contract out virtually all the tasks that in the past would have required employees. There are contract programmers, accountants, marketing specialists, and salespeople.

Some People Interview Well but Are Terrible Employees

Some of my worst hires had a fantastic interview. Some of my best employees were not very impressive during the interview process.

I was very frustrated that I just did not seem to be able to weed out the problem children before I hired them. I tried a wide variety of things—multiple interviews with several people at my company, checking references (which are always good), longer interviews, asking different questions, and many other approaches.

I thought somebody out there must have the solution. I read a few books on the topic and also talked to other business owners to see if they had the answer. I tried some of the suggestions and still ended up with too high a percentage of bad hires. I was stumped.

One of my phrases is, “If you can’t figure it out, check your assumptions.” My assumption was that there was a process out there that would eliminate the bad hires, and I had just not found it yet. That assumption wasn’t working, so I replaced it with a different assumption: Some people are just very good at the interview process but terrible at the job. These people are going to fool you from time to time, no matter what interview process is used.

Once I accepted my new assumption, the solution was easy. If we needed three new support people, I would hire six. After a few months on the job, it would become apparent if any of them had fooled me. I kept everyone who performed well and let the others go. I used the concept of “hire six if you need three” for the next 20 years, with good results.

Don’t Decide from a List of One

I get into a lot of trouble when I make a selection from a list of one choice.

One time, I had a support person quit. One of my employees told me he had a friend looking for a job. I interviewed the friend. He seemed okay, so I hired him. It turned out to be a disaster. I had made the decision from a “list of one.”

“Don’t decide from a list of one” led me to create an entirely new recruitment policy. Rather than hire people one at a time, I decided to hire them in batches. We might have six open slots and interview 100 people. If someone quit, I would not replace them immediately. We would just run short for a while.

The batch approach worked well for me for 30 years. The interview cycle took a lot of time, so rather than do it many times a year, I usually did it only once a year. I was choosing six people from a list of 100, not one person from a list of one. It was also much cheaper to train six people at one time than to train one person six different times.

I have learned to apply “don’t decide from a list of one” to many things. If an employee wanted to talk about salary in May, I would be deciding from a list of one. I couldn’t properly evaluate the request without taking into account all the other employees. I developed a “once and only once” compensation system. Every January, I gave out bonuses for the prior year’s performance and set salaries for the next year. This allowed me to evaluate all the employees at the same time and compare them with their peers. It also saved me a great deal of time because I did it only once a year.

I tend to forget the principle more often than I would like. My ranch manager might come up and say, “Hey, I noticed the west deck needs to be refinished. Do you want me to do it?” I might say, “That sounds like a good idea. Go do it.” That would be choosing from a list of one.

Then I might notice a water pipe leaking badly and potentially damaging property. Fixing the leak would be much more important than refinishing the deck. If my list contained even those two things, I would obviously pick “fix the leak.”

I have become aware that any question that implies a list of one is a potential problem. “Do you want to buy a new tractor?” is entirely different from “How do we want to spend our budget this year?” “Do you want to go to this restaurant tonight?” is not the same as “Which restaurant do you want to go to?”

These types of questions all create the same problem for me. I start thinking only about that one item, forgetting that there may be something far more important to do. Whenever I find myself “choosing from a list of one,” I try to remember that the item probably belongs on a list of choices—and may very well not be the best choice.

Be Careful When Hiring an Exceptional Person

When interviewing potential employees, I would sometimes run into a truly exceptional person—a first-class mind with poise and manners to match. They would be fresh out of college and could have qualified for a much higher-paying job in a big city, but they wanted to live in a ski resort, and our location in Vail fit the bill.

I love being around exceptional people, and I would quickly hire the person. A hire had to last five years for me to break even on the extensive training required for the support job. These exceptional people rarely made it two years. They would enjoy skiing for a year or two and then get a fantastic offer from a company in a big city, perhaps for three times as much money as I could pay them. They wanted to stay with my company. They liked me and their coworkers, but $50,000 with me or $150,000 somewhere else was impossible to turn down. If they remained at my company for five more years, they might get to $80,000. After five years at the other company, they could be making $400,000 and have stock options.

Now, if you own that “other company”—the one that can afford huge salaries and stock options—you obviously should seek out and hire exceptional people.

I didn’t like to tell someone during an interview, “You are overqualified.” It sounded like I didn’t want the best people. It wasn’t about qualifications because it was their first job. They were just too damn smart. They would promise to stay until the five-year mark, but it did not happen.

I was going to title this phrase “Never Hire an Exceptional Person,” but that is too absolute. I think of it as “Be Careful When Hiring an Exceptional Person” because, even though they most likely won’t make it five years, I may still hire them. Hiring an exceptional young person did not make sense from a pure company standpoint. They rarely stayed long enough to make the training expense worthwhile. However, it made a great deal of sense for me personally. Truly exceptional young people are rare, and I love spending time with them. I also think they might enjoy time with me. So I invoked “owner override” and hired them anyway.

You Can’t Hire Yourself

When I hired my first employee 40 years ago, I was frustrated. The person was smart and trying hard, but they were just not solving problems for customers correctly, the “way I would have done it.” I was reminded of the phrase “if you want a job done right, do it yourself.”

There was no way I could do all the work required to be successful. I decided I was going to have to find employees who could do the job as well, or better, than I could. Over the next few years, I was continually disappointed that I could not find those people.

I realized the problem was “I can’t hire myself.” If there was someone who could do the job as well or better than me, would that person work for me for the salary I was offering? No. They would get a job at a much higher salary or start their own company. Would I take the job I was offering at that salary? No, absolutely not.

Since I couldn’t “hire myself,” I had to adjust the way I evaluated employees. It wasn’t fair to say, “This person is doing a bad job because they are not doing it as well as I could.” I started thinking, “What is a reasonable expectation for an employee who is paid X dollars?”

I frequently remind myself that “you can’t hire yourself.” If I hired a painter in the past, I might think, “That guy made a few mistakes, I would have done a much better job, I’ll never hire him again.”

The conclusion “I’ll never hire him again” is the problem. I don’t want to do the painting, so I have to hire somebody. The correct question I now ask is, “How is this guy doing compared to the other people I could hire?” He may be the best of that group and therefore the person I want to hire next time. The fact that I could do a better job is irrelevant.

I struggle with the concept that a task will not get completed “perfectly,” the “way I would have.” It feels like lowering my standards to say, “Well, that wasn’t quite the right answer, but I’ll let it go because I can’t hire myself.”

I wish I could hire myself, but it is just not the way it works.

A Great Employee Is Not Always a Great Manager

I would often promote an employee who was doing a great job to be the manager of their department. My best support person became the support manager. My best salesperson became the sales and marketing manager. This seemed like a no-brainer. I was rewarding someone for a job well done, and it was the way virtually every company did it.

People pursued the manager job because the salary was higher. There was also prestige in being “the boss.” And most just assumed they would like it. Money, prestige, and enjoyment…seemed like a good package.

It rarely worked out well. Doing a great job in technical support or sales requires a totally different skill set than managing. Additionally, for most employees, actively doing the job—being the one who solves the problem or makes the sale—is much more enjoyable than managing. I would promote someone to the manager job, and they would not be particularly good at it and would be miserable. I had effectively lost a great support person and gained a mediocre, unhappy manager.

I created a new position called “senior support.” It paid the same as, or more than, the manager job. There was only one manager job, but I could have multiple senior support employees. The title allowed my best support people to continue to be my best support people. There was also prestige in the title. Internally, we affectionately called the senior job “nerd.” Being a nerd meant you had deep technical knowledge, made more money, and worked on the toughest problems. It implied you were the best of the best. When a new support person was stumped by a problem, they would be told, “Go find a nerd.”

This idea applies to more than just a software business. A fantastic teacher may not be a great principal. A great carpenter may not be the one who should be, or wants to be, a project manager.

I applied this concept to coaching youth hockey. I used to always make the best player the captain. However, being a great player did not mean they would be a great leader. I started selecting a captain based on who would be a great captain, not their scoring stats.

I frequently hear someone say, “I hate my boss.” This may well be because your boss was great at their previous job, got promoted to manager, and does not have the skill set to do a good job. And they probably hate being the manager. If the company had instead hired someone who wanted to be a manager and was very good at it, there is a good chance you would not hate them.

If I had been offered the manager’s job at Hewlett-Packard, I would have taken it, and I would have hated it. As a mid-level manager, I would have had very little ability to make major decisions, as there were many levels of management above me. I also would no longer have been a salesperson, which I loved. Something to think about if you are offered a management job.

The First Time You Want to Fire Someone, Fire Them

After many years running my software company, I came to the conclusion, “The first time you want to fire someone, fire them.” This sounds harsh, but it comes from 40 years of experience.

The phrase does not mean I fire somebody the first time they annoy me. If I think, “I’m not quite sure this person is going to work out,” I wait and see. It only applies the first time I actually think, “I should fire this person right now.” Many times in the past, I thought I should fire someone but did not. I tried to rehabilitate the person—to give them another chance. That would almost always lead to still another chance, another warning, and another talking-to. And eventually I had to fire them anyway. Once I think “I should fire this person right now,” I have learned not to delay the inevitable and to get it over with.

I had one employee who just could not listen. She always had to talk and interrupt. Perhaps a customer would say, “I’m calling because when we print invoices, they—” She would cut them off. “Oh, your printer is jamming. You have bad paper. Maybe you should do this or that.” If she had let the customer finish, the sentence would have been, “The invoices don’t add up correctly. The total is wrong.” They printed just fine; they were just wrong, and here my support person was telling the customer to use different paper!

The support manager, other employees, and I had talked to her about this issue, but it was a habit she could not break. One day, she asked me to help with a customer problem while the customer was on hold. She described the problem, and I started to say, “Now, the customer needs to run utility number—” Before I could finish, she said, “Oh, great idea. Number 456 will do the job. That makes sense.” Number 456 was the wrong utility and would not have fixed anything. She had interrupted me to give the customer the wrong answer, and then told me it made sense. It was the first time I thought, “This person is hopeless. I should fire her.” So I followed my own advice and said, “I’m sorry. You’re fired. Please pack up and leave.”

I don’t like firing people. In fact, I’ve learned that I don’t function well after letting someone go, and the best thing to do is call it a day and go home. So we both left the building.

Find a Person, Not a Company

I frequently make the mistake of hiring a company for a project, not a person.

I remember I wanted to hire someone to remodel my company website. I interviewed several companies, one of which stood out. The person who came to chat with me was the founder, and very sharp. He had a history of producing great results. I was very confident and hired his company, with a $10,000 deposit. When the project started they sent a kid who was not very smart, had been out of college for about three weeks, and had never done a website before. Needless to say, it was a disaster.

I almost repeated this mistake today. I’m getting close to completion of this book, which I will self-publish. The book will need some marketing or nobody will ever know it exists, so I asked ChatGPT to “find me a company that has a track record of successfully marketing self-published books.” ChatGPT, like the good little AI it is, diligently gave me a list of companies. I almost started calling them until I remembered “Find a Person, Not a Company.”

I could hire a company with a great reputation and still get a person assigned to my account who was worthless. I changed my request to ChatGPT to find me a PERSON, not a company. I quickly realized this was a much harder request and decided to put the search off until I’m done writing. However, I am going to make damn sure I find a person, not a company. If it is a company, I want a guarantee of a specific person I have met and have confidence in.

This concept applies to far more than creating websites and marketing books. Mayo Clinic has a wonderful reputation, but that does not mean the particular doctor you get will be any good. They have all sorts of specialties, and the best heart guy might have quit yesterday.

I find it amazing that I can be very familiar with a concept like this, have used it many times in the past, and then totally forget it and make the same old mistake.

Consultants Don’t Usually Choose Better Than You Can

When confronted with a difficult problem that I have worked on and cannot solve, I am tempted to hire a consultant.

I remember a time when I was trying to decide which product my company should create next. This was a very important decision because it takes a lot of time and money to build a software product. Picking the right one could generate great profits, and the wrong choice could bankrupt the company. So I hired a business consultant to help. I spent about $25,000 over two months, and he came back with a stupid idea. He thought we should create software for doctors because that market had “huge potential.” We were in the hotel software business, which has nothing to do with doctors, no synergy. Not to mention that there were several powerful companies already in that space with sophisticated products that would take years to create and over ten million dollars, way more money than we had.

I knew more about my company than anybody else on the planet, and at the time had twenty years of experience. I knew our strengths and weaknesses, and what we could and could not reasonably do. Why did I expect a complete stranger to jump in and in two months figure out a great solution? He had probably been working on a bank problem the week before and would work on a construction company next. The consultant I should have hired was me.

Consultants are often hired to take the blame. Rather than make a decision and take responsibility for it, hire a consultant. If it doesn’t work out, “Well, the consultant had a great reputation, it’s his fault, not mine.” Cover your ass by passing the decision to someone else, even when you are the most qualified to answer.

I’ve seen this principle applied to many things besides business. I had a friend who hired a college consultant to pick the “best school for my son.” The kid loved the outdoors and a small-town environment and the consultant, who had just met the kid, sent him to the University of Southern California (USC) in the heart of a huge city with about 50,000 students. Picking a college can be intimidating, but passing the buck to a consultant does not solve the problem.

I’m not saying consultants are always useless. I may hire a consultant to do some legwork, gather information, and give it to me to help me make an informed decision. That is totally different from hiring one to make the decision.

I am applying this principle to this book. I’m trying to come up with how to organize the phrases. What order should they appear in? Randomly? Or does one phrase logically follow another? If so, which ones?

I was tempted to hire somebody to help and stopped. It’s my material and I’ve been thinking about some of it for thirty years. Is it reasonable to think that somebody who knows nothing about any of the phrases will do a better job? While I may not get the perfect order, I don’t need “perfect.” I just want it to be better than random.