Carry That Quota: Sales Tactics and Stories By the Rep For the Rep -Jesse Rothstein (LinkedIn Sales Solution- Key Account Manager)

I thought that Jesse did a great job of explaining the jobs of cons of someone who is pursuing a career in sales. Many of us see from the outside the glamour, the travel, and the lifestyle of a Professional Career Sales Rep but do not realize that there are pros to cons with any career decision. I would recommend this book to anyone who is interested in pursuing a career and committing to the craft. I enjoyed how he spoke about both sides of the coin- too often sales reps only speak about their President’s clubs and trips but we not take about the stress of being in sales as often.

These are the passages that stood out to me 

“Jesse makes everyone around him better. He is a leader by action, and those around him take notice and emulate his behaviors and attitude. He comes into work every day with purpose, conviction, and focus to help solve the  problems of both his customers and his teammates.” 

“Jesse is a student of the game. This shows up in his distinct style of salesmanship—the perfect combination of old-school and new-school sales tactics. He’s taken more traditional approaches like handwritten notes,  personalization, and deep relationship building and made them core to his approach to modern selling. I’ve personally received roughly ten handwritten notes and gifts from Jesse in our time as friends—a relevant book, a  letter of encouragement, a note of gratitude—that have always inspired me. It’s in these moments that I’ve been truly in awe of his ability to connect with people in meaningful ways.” 

“However, not until I met Jesse had I experienced a sales professional who cared so deeply about helping others succeed. He marvels in the art and science—as well as the history and future—of the sales profession. In many ways, Jesse has been a mentor to me these past few years and is the perfect person to showcase the opportunities that come from a career in the sales profession.” 

“Whether we realize it or not, we are all salespeople. Most people don’t realize this. Sure, not everyone sells professionally for a living. But we all represent a brand and attempt to get people to invest their time in us and our ideas. Instead of appreciating that fact, however, salespeople are often viewed with disdain.” 

“From my point of view, sales is a craft—not dissimilar from a doctor performing surgery or a lawyer prosecuting a case—that is both applicable to a wide variety of people and integral to helping people solve problems. When framed that way, sales takes on a whole different meaning.”

“I’ve sold my entire professional career, and I love the profession. As a result of fifteen years in the field, I’ve attended hundreds of meetings and taken thousands of pages of notes. I’ve also read the many wonderful sales books on the market and highly recommend that you read them, too. Nonetheless, Carry That Quota is designed to fill a particular niche. No one has written a book that is “for the rep” and “by the rep” and a relatively young sales rep at that. My hope is that by providing insights while I’m in the trenches, I can offer a unique perspective on the sales profession.” 

“It was the first time that the idea of writing a book entered my mind. But here we are, and I tell the story because, as you’ll come to see from this book, I see sales—and work in general—in the broader context of our purpose in life and what we leave behind. Thus, the title of this book, Carry That Quota, is not just about exceeding a sales target but also about the quota we carry in life. What I mean by this is that there should be a  sense that we all stand for something. To me, that means embracing the concept of leaving a place better than we found it, in our lives and at work.” 

“He was building rapport, trust, and an emotional connection—qualities that are integral to a successful sale, and on that evening, the approach paid dividends in an enormous way. At the end of the night, I watched as the customer handed over his American Express card,  and Larry rang him up for over $25,000 in purchases. If Jacob and me breaking that glass mirror was the epitome of carelessness, Larry’s work with that customer that night was the embodiment of professionalism. His execution and tactfulness enabled that relationship to blossom not only on that night but also in the future. 

“Films such as these reinforce the misguided stereotype that salespeople are not only pushy but also unskilled  (indeed, Keaton’s character comes across as vaguely animalistic). I couldn’t disagree with this more strongly—I  view sales as a serious discipline, embodied by people like Larry Moore, who have high standards and a precise approach.” 

“I therefore believe that success in sales depends on having a multifaceted skillset that includes a strong sense of self, the ability to manage a complex set of delicate relationships, tactical awareness, and an understanding of how the field is evolving and how that does or does not align with your personal and professional aspirations.” 

“If you asked ten people on the street to describe salespeople, would you imagine they would say “extremely  skilled, caring, and thoughtful?” Read on, and I’ll help to show you that successful salespeople are just that, and more. Then, I’ll help you transform into that successful salesperson.

Since arriving at P&G earlier that summer, I had felt pressure to perform. This was in part a by-product of being insecure. I feared going back to Cornell University for my senior year without a full-time job offer; I thought I  would be viewed as a failure. The feeling of being evaluated was also baked into the environment. There were sales leader boards on the walls of the office, and the P&G staff were weighing whether to offer the interns full time jobs. My trip with Hilary was part of an extended interview during the eight-week summer internship, and I  wanted to go back to Cornell for my senior year and tell my friends that I had a full-time job offer from P&G. I  didn’t want to make a bad first impression on Hilary.” 

“Looking back, I was wrestling with two questions that anyone considering becoming a salesperson should ask— was a career in sales right for me, and was I right for a career in sales?” 

“This points to an important lesson: in business and in life, pay attention to your gut feelings. Most of the time,  your instincts are correct.” 

“That feeling intensified during my time with Hilary. With a pressed shirt and pants and freshly shined shoes, she made an outstanding first impression. I was also struck by her manner. Whether she was meeting with a  customer or ordering from a waiter, she exhibited something that New Zealanders call Mana, a presence that reflects confidence but not arrogance and immense respect for others.” 

“A Salesperson Is a Consultant Salespeople do not often get mentioned in the same conversation as consultants,  but they should because great salespeople help companies solve problems. In Altoona, Hilary was always asking customers about their experiences and what their pain points were. Similarly, when I was back at Cornell for my senior year, I became an independent sales representative for a local wholesaler of Under Armour® as part of an entrepreneurship class at the business school. I was helping local sports clubs and college teams discern how to reach their fans. These were not isolated instances: a customer once told me that, when they identified that they were dealing with an intelligent, competent salesperson, they would go out of their way to give him/her more business.” 

“The Constant Ability to Learn Sales provides tremendous learning opportunities. One is the opportunity to gain exposure to many different types of companies and people in a variety of industries. This forces the salesperson to gain experience and knowledge quickly about the type of company to which they are selling. I often feel that selling to a new company is like taking a new class at school. Researching the industry, the trends, the competitors, and everything that goes into gathering that knowledge is an ongoing learning experience. In fact, I think that, thanks to my work in sales, I could hold a conversation with anyone in any macro-level industry.” 

“This points to another learning opportunity in sales: you get the chance to learn about how to relate to a diverse group of people in a wide range of contexts. This is in part because of the volume of interactions you have with people; it is also a by-product of interacting with people in such a wide range of roles and settings. Sales invariably cultivates interpersonal skills because you are constantly being challenged to interact with people. 

“There is also a large body of research suggesting that the ability and opportunity to learn is a critical predictor of job satisfaction. This is one of the greatest benefits of a career in sales.” 

“Solving Problems for Customers Is Rewarding Sales is really problem-solving. Clients often deal with challenges, and good salespeople are constantly on the lookout to diagnose these problems. Sometimes clients can self-diagnose their problems, but more often than not, it is the salesperson who helps the client diagnose the problem. Co-designing solutions to solve these problems can take time, resource allocation, and in many cases large amounts of money. But solving complex problems for clients is like being a mechanic and working on a  car or, as Jeff Thull points out in his book Exceptional Selling, being a physician who creates a “diagnostic map”  to treat a patient. Getting the problem solved or the car running or the patient healthy is the end game.” 

“Finally, there’s a sense of satisfaction that accompanies selling someone a concrete product or service. In fact,  one of the reasons I prefer sales to other professions (e.g., consulting) is that it produces a concrete output that someone can use. Whether it is offering a new software product to an IT company or introducing a wholesale food supplier to a new product, equipping people with tangible solutions that will help improve their bottom line  (and in many cases, better serve their customers as well) produces a positive downstream effect.” 

“Sales is not equivalent to teaching or working in government, but contrary to the very negative stereotypes of the profession, salespeople can go a long way to helping people and the people they serve. This is one of the  most rewarding parts of sales.” 

“Sales, especially outside sales jobs, offer tremendous variety. (An outside sales job involves meeting with clients  outside the office, whereas internal sales jobs typically involve someone making phone calls from an office.)  Traveling to client meetings, learning about different industries at conferences, and just mixing up the daily routine enables variety to happen. I love the variety of sales and the constant ability to mix up my routine. I often think differently when traveling, I get to see different places, and most of all, I’m not going to the same place and doing the same thing every single day. This makes the job fun and not boring. And, once again, there’s a  substantial body of research to support this: variety dramatically increases job satisfaction.” 

“From my perspective, the balance of competition and cooperation in sales is a huge plus. On one hand, the chance to challenge yourself to grow and improve is stimulating and ensures that you will not remain stagnant.  On the other hand, the opportunities to work with others mean that you will never have to be exclusively self reliant and can instead look forward to working with others inside and outside the organization to do more than  you could on your own.”

“Running a sales territory is like running your own business. You can control your destiny based on how you allocate your time and resources to develop this business. The relationships you build, the clients you engage with, the way you market myself—you are acting and working like a true entrepreneur, but you do not have to incur the monetary risk to do this. While you have incentives with your commission structure, you also have your company’s resources behind you, so you are not burdened with debt and other things that would cause you stress.” 

“My father always reminds me that having flexibility with my time is an enormous asset, and there is an ample body of research that supports this: I am able to focus on what is most important to me at work and also in life,  and I feel more empowered because of my autonomy.”

“A final major factor outside of your control is that performance measurements are based on arbitrary timelines.  Salespeople who deliver their quotas within the pre-determined timeline (a company’s fiscal year) are celebrated. The ones who miss their quota within the pre-determined timeline are made aware that they did not deliver their quota. Even if they deliver more revenue over a longer period of time, it almost does not count unless it falls within the measurement period of the fiscal year. This arbitrary system of measurement does not provide the true detail on how the salesperson is actually doing his/her job. Not being in control can be frustrating in any profession, but I think it affects salespeople more because most salespeople want to be able to control their destinies.” 

“Over time, I have become better at getting outside of myself and accepting that there are a large number of things outside of my control. I attribute this in part to my time in Australia where I learned to develop a more balanced lifestyle.”

“It is also a byproduct of different hobbies I have developed, especially yoga, which emphasizes mindfulness.  This helps me to avoid getting too high or too low, whereas earlier in my career, I was often impatient and failed  to see the bigger picture. It’s having the professionalism to say that if a client is not going to buy a product, it’s okay, and I need to stay calm.” 

“Framing Client Expectations Is Difficult One of the most challenging aspects of being a salesperson is managing client expectations.” 

“Thus, one of the hardest parts of being in sales is finding a way to communicate to clients what you think is realistic and in both of your best interests.” 

“Based on what you’re trying to do, I’m not sure if this is the right fit. What are your thoughts?”)16 This is a  way to gauge people’s interest, and if they are not engaged, then you know that it makes sense to move on to a  different project. 

The best way to mitigate this is to control the things you can control. This includes certain aspects of time management, including saying no to the things that you do not have to do and that are not connected to your highest priorities. Nonetheless, the point remains: while travel is fun and stimulating, it can also be extremely stressful, especially if you spend too much time on the road.” 

“In trying to summarize the cons of a career in sales, I often think of the parallels between a salesperson and a  professional baseball player. In both professions, you are seen as very successful even if you fail a lot (as a  Sports Illustrated article on baseball and mental health points out, a great hitter might have a .300 batting average, which means he gets out seven out of ten times, and a salesperson similarly misses on a large number of sales attempts).” 

“There is also a significant amount of time on the road, which means being away from typical routines, home,  and familial support structures. And, once again, there’s so much outside of both a salesperson’s control (the  client’s openness to buying, the economic climate, and the health of the company) and a player’s control (pitch quality, weather, and the stadium’s condition) that the experience can be extremely stressful.”

“In one particular instance, I had a meeting with a client over coffee for forty-five minutes at an outdoor café in  Sydney. There was no discussion of business during this first meeting. It was simply a “get to know you” type of conversation where the client sized me up. I should note that I was over-prepared to sell and get into business after the initial small talk, but I had this moment where I took a step back and realized that I was invited to this coffee meeting and that it was the client who chose to set the agenda and tone of the conversation. The café was packed with other businesspeople having conversations over coffee, but the vibe was relaxed. Part of me was frustrated when the meeting ended because I felt that I did not accomplish what I had planned. I did not get a  chance to show the PowerPoint deck that I had prepared. I did not get to pitch anything. I did not get an opportunity to sell. Looking back, I realized that I was able to take a step back and make the meeting about the client. It was the client’s coffee meeting, their informal agenda, and their terms. Not my terms—their terms. I gained credibility by not selling.” 

“This was the first time in my career when I had this moment of understanding, and while I am confident that this moment would have occurred at some point in my sales career, it had a more profound impact because it  happened abroad and at a relatively early stage in my sales career. It taught me that one of the most important qualities in succeeding as a salesperson is to be able to make the conversation and the entire sales pursuit about the client and not about you. This takes maturity, patience, discipline, and empathy. It also points to some of the most important characteristics for succeeding in sales.” 

“You also need to believe in your ability to bounce back from setbacks.” 

“This is not something that happens overnight. When I was in my early twenties, I did not have the confidence I  have today. However, over time, you gain more experience and become more mature and develop a sense of what is important, including recognizing that sometimes it is not just okay but also important to say no to things that are not important. I have also made a point of asking the question, “Why?” If someone wants to meet with me, I make a point of asking for details about what they want to discuss and why. I am then in a better position to gauge how important the meeting is and when to schedule it, if at all. However, it took me time to develop the confidence to recognize that my time is valuable and that I should approach my schedule with belief in my value.” 

“The broader point is that you need to have confidence in your value and be able to have a thick skin if others push back or fail to recognize that. Thick skin and confidence are integral to having a successful career in sales.”

“Discipline—especially as it relates to time management—is imperative to succeed in sales. As much as sales is a people business, it is also an industry in which success depends on making incremental progress every day, and that requires staying focused on both your big-picture objective (your quota) and the next step to achieve that objective. Sustaining that focus requires an enormous amount of discipline, most notably the ability to tune out noise or what I often view as the cacophony of distractions a salesperson (or any professional, for that matter) routinely faces (e.g., emails, trainings, and customer requests that are not value added) that do not significantly advance the objective of moving sales forward.” 

“According to New Zealand National Geographic, Mana “is a source of both personal and collective strength,  pride and identity.” For additional details, see “The Meaning of Mana,” New Zealand National Geographic,  available at https://www.nzgeo.com/stories/the-meaning-of-mana/ (accessed on September 9, 2019). 

A BCG survey found that “learning and career development” is the sixth-most important predictor of job satisfaction. Jacob Morgan, “The Top 10 Factors for On-The-Job Employee Happiness,” Forbes, December 15, 

chemicals that the companies used on a monthly basis. These chemicals were like annuities, and these distributors realized that selling an innovative device that eliminated the need for these chemicals had the potential to torpedo these ongoing monthly sales and, with it, their business. As a result, they often stalled on  getting me in the door with potential clients, especially in Rochester. I finally took matters in my own hands and  got in the door myself. That was how I had gotten these pivotal meetings scheduled in Rochester, and I feared if  I rescheduled, I would damage my brand and jeopardize the sale. 

While an unfortunate combination of circumstances (funder-driven pressure, uncooperative distributors, and likely an undercooked chicken sandwich) led to me getting sick that week in Rochester, that experience underscores a critical lesson for salespeople—the importance of self-care. This is vital in any profession, but salespeople face unique challenges. At the most basic level, self-care is challenging for salespeople because the work is stressful. 

Fortunately, companies are taking steps to alleviate employee stress (e.g., creating wellness activities, such as offering yoga at lunch or massages), but it is ultimately up to individual salespeople to find self-care strategies.

In sales, it is tempting to look at the leaderboard to see if you are making progress toward your quota. While understandable, this tendency can have a paralyzing effect. I recommend prioritizing the process. To me, this  entails doing as great a job as possible with each incremental step of your job (e.g., every sales call, meeting,  

follow-up note, etc.). In my experience, if you are able to live in the moment and know that you have done everything you can, the results are more likely to follow. Prioritizing the process leads to outcomes and the  comfort knowing you have done the best you can. 

“As the bus pulled up to the Maroubra Beach stop, I got off and began trekking up the hill to my apartment. With my head still buried in work, I noticed a group of men in business suits getting off the bus with me. They walked over to their parked cars, but as they approached the vehicles, they did something unexpected. They started taking off their suit jackets and ties and took out surfboards and wetsuits. As I kept walking up the hill, I turned around a few times and marveled as they sprinted into the ocean with their surfboards. Here I was headed home to continue working, and these guys were headed into the Pacific Ocean to wash the day away. I was clearly missing something.” 

Running marathons is a powerful analogy for a career in sales and life in general. It is inevitably stressful, and there are significant ups and downs, but if you can have a healthy mindset and routines, it becomes more manageable. It serves as a vital reminder that your health is paramount, and no job or race is more important than that. 

Whereas Peter had built his business by putting in the hard yards for years and grinding every day, sales representatives from large companies, in his experience, had the cushy jobs. Peter referred to several people he dealt with from P&G who did not work hard and often did not follow through. This contributed to his sense that  salespeople from P&G were complacent and not driven, traits that bothered him because they stood in such stark contrast to his experiences and approach. He was hungry, and he expected his vendors to be equally hungry, if not hungrier. 

Peter’s emotional inclination to avoid working with large companies represents an especially intense manifestation of a major challenge for salespeople: customers can be unpredictable because purchasing decisions are often emotionally driven. 

All of this points to a more foundational observation from the late writer and lecturer Dale Carnegie: “When  dealing with people, remember you are not dealing with creatures of logic, but with creatures of emotion.”

All customers are individuals with unique and complicated personalities, and as a salesperson, you only get a  limited amount of time to interact with each of them. What’s more, customers’ moods are often volatile because people are often frustrated at work, and there is a temptation to take those emotions out on external vendors, like salespeople. In short, salespeople face the challenge of quickly building trust with and a connection to busy and often volatile customers. 

I realized very quickly that building trust with Peter was going to be my top priority. I also realized that trust would be a byproduct of working consistently with Peter over time. This was not going to happen overnight; I  realized that I needed to exercise patience and create a consistent schedule of meetings, events, and reasons to show Peter that I was not going away and I was for real. 

Remember to prioritize “quality interactions” (i.e., doing things that emotionally connect with the customer). For example, a quality interaction with a customer may be an off-site meeting where you and your customer have a  conversation and get to the heart of an issue that has been in play for some time. Good salespeople recognize that having several interactions like this is more valuable than having a large number of less significant interactions (e.g., phone calls, emails, etc.). Simply put, always endeavor to ensure that you are making the most of your and your customer’s time. 

The end of the quarter, the end of the year, these are the times when most salespeople often try to speed up sales cycles. Remember, relationships do not always evolve on pace with the end of the quarter or the fiscal year.  Good salespeople have the discipline and emotional intelligence to take the long view and not push. 

In those scenarios, communicating transparently builds trust, and sometimes having a timely, nonconfrontational conversation will push a relationship forward. Nonetheless, keep in mind that humans do not like pressure when  having to make decisions, so, when possible, do not force the issue based on timing. 

A final point: what a lot of these interpersonal interactions come down to is building trust, and the last thing you want to do is do something that damages trust. This requires being direct and to the point (something that is appreciated in business and in life) and communicating authentically. Too often, salespeople (and people in general) revert to jargon instead of genuine observations. For example, I remember speaking with a client while  working in Sydney and telling him that I thought he and his team could be more “strategic” and that I would like to have a conversation with him about that. He cut me off and said, “Let’s have the conversation and hear what you and your company are all about. Then I’ll decide if this is strategic or just another meeting with a  salesperson trying to sell me something.” The takeaway from that is not to hide your agenda; busy clients appreciate when you are direct and honest. 

It is also a major reason that, in 2015, only 57.1 percent of sales representatives met their quotas.

The best way to compensate for market pressure is to do things to stand out. You can accomplish this in part by doing the following: Following through and doing what you say you are going to do (e.g., sending follow-up information when you said you are going to send it). This is something that is rare in business and still rarer in life. Thoughtfulness can also pay enormous dividends. For example, congratulating a client on a major life event  (e.g., a wedding) shows concern for someone beyond your business relationship. So, at one level, standing out involves being conscientious and showing a genuine interest in the client’s broader well being.” 

“Over time, I was discovering the internal language, culture, and priorities of Restaurant Depot. Store managers were educating me on how they were measured and what mattered most to them. This led to valuable insights.  For example, I discovered that there was an internal code that was spoken at Restaurant Depot. How they reported their results, the key measurements across a store, the items they sold that were most profitable—all of these things had their own internal name that no one would know unless they worked directly for Restaurant  Depot. As I had more conversations, I would learn more about this internal language, and it enabled me to become immersed in their business. This also showed how well I got to know their account and how they operated. I was literally speaking their language.” 

“No other vendors were asking these questions, and the store managers were more than willing to share this information with me. I was seeing, for the first time in my career, that people respond to curiosity. I am not sure why this was the case. Maybe I was boosting their ego? Maybe my curiosity impressed them? Maybe I just provided a different perspective and mixed up their normal daily routine? Regardless of their motivation, I was able to obtain an enormous amount of information about Restaurant Depot by visiting these stores every single week.” 

“The names I dropped and the information I was sharing began to leave an impression. Moreover, Peter realized that other vendors were not speaking in “Restaurant Depot” language. I was separating myself from other vendors and building trust with Peter by proposing ideas through the internal code of Restaurant Depot.”

“Take unexpected and even contrarian views as a way to stand out. I am a big fan of this method. One of these techniques is “going for the no” (i.e., asking the client if it makes sense to conclude a sales discussion), an idea that Jeff Thull discusses in his book Exceptional Selling.26 From my perspective, this entails figuring out if it makes sense to spend more time with the client, and by “going for the no,” I am able to gauge how interested or uninterested the client is in working with me. I see this as a “two-way tango”; like dating, there needs to be a  mutual feeling that we should work together. I should also add that I am willing to walk away because most salespeople don’t; they persist even when they should walk away, which makes poor use of their and the client’s time.” 

“My favorite tactic to get in the door is getting a referral from a colleague, another client, or someone else in your network. Data from the Corporate Executive Board suggest that you are seven times more likely to get in the door with a referral versus a cold phone call or email.”

“Salespeople Must Conclude That Their Network Is Their Net Worth Buyers shop online to research salespeople and their companies and quickly obtain a large amount of information through a simple Google search. Success in this area requires having a strong online brand, including passing the “Google yourself” test. Salespeople should Google themselves and see what comes up, which is often what buyers will do. Having a strong online brand is nonnegotiable for salespeople and almost anyone in business today. The specifics of this may vary by industry. So, while every sales professional should have a LinkedIn profile, having a strong online brand may also include writing for online industry publications, sharing thoughtful content, and being part of the overall digital conversation for that field.” 

“So, when you meet your version of Peter Carter, do not be intimidated. Instead, believe in your ability to understand and leverage your interpersonal skills, identify ways to stand out, and employ strong tactics to perform and meet his/her needs.” 

“Robert,” I asked, “how do you deal with colleagues who fail to follow through on commitments?” “Look,  Jess,” he began, “there are two types of people in this world. The ones that get it done and the ones that don’t.  Plain and simple.” “Yeah, I hear you,” I said, before sharing what had happened with Stanley earlier that day.  “This example has me baffled,” I continued. “Stanley, on our team, works with us every day. He should have the motivation to want to help our team succeed. Am I wrong here?” “You might be wrong,” Robert candidly replied. “You cannot assume that Stanley gives a shit about his job or the proposal. Have you asked him what he cares about?”

“You have got to make more of an effort to make the situation a ‘people business,’ and not a work transaction,”  Robert continued. “You have got to figure out what is most important to Stanley at work and in life. Learn what makes him tick. This will enable you to figure out what motivates him.” 

“Over time and with the proliferation of the internet, the medium of communication has changed. Customers and prospects are no longer reliant on salespeople to deliver information to them about their products and services because a simple search on the internet will enable anyone to find information about the product or service in which they are interested. Websites, such as TripAdvisor and Yelp, have been developed to enable all of us to become more informed consumers for our personal and professional lives.” 

“The main point is that information is everywhere, and the internet has changed the medium of communication for how we take in information. As a result, the lone-wolf mindset of being able to influence and sell every single customer is long gone.” 

“Setting clear expectations with your manager is the most critical component of the relationship. By setting clear expectations, you will establish criteria for what you need from one another, what your working hours will be,  and how frequently you will formally check in with one another. I would not expect every manager to take the time to set these expectations up with each of their direct reports, but I do recommend that you make sure that you take the proactive approach to set them up with your manager.” 

“Ultimately, great managers have a “so goes you, so goes your team” mindset. They realize that they need to set an example and lead from the front. I find that sales managers who have been sales representatives themselves make the best managers because they have done the role before. In other words, they have walked in the shoes of the sales teams they manage, and they know what goes on each day. In fact, I would venture to say that this holds true for any profession. Any manager who has not done the job his/her people are currently doing is going to struggle to fully understand the ins and outs of the job.” 

“This reminds me of a quote from Steve Jobs, who said in a commencement address at Stanford in 2005, “You can’t connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something—your gut, destiny, life, karma,  whatever.”28 I would add to that: you have to trust your manager and believe that you will be able to look back  and say, “He/She helped me to connect the dots.”

“Build Trust by Following Through Simply put, your relationship and brand with coworkers will improve quickly when you do what you say you are going to do.” 

“Understand Your Coworkers’ Personal Goals and Why They Are Doing What They Are Doing This requires recognizing that people measure success in different ways. I have found that everyone has a different internal reason as to why they come to work every day. Many people are focused on making as much money as possible.  Some simply want to come to work every day, earn a decent wage, and provide for their family.” 

“Still others have different desires. My point is that if you can figure out what drives your coworkers, you can then figure out ways to help them get closer to their personal goals.” 

“Say “Thank You” It is a small act, but saying thank you or expressing it in an email or handwritten note is something your coworkers will appreciate.” 

“This connects back to Robert’s central point during our conversation at Yankee Stadium: business, at its core,  revolves around people, and if you invest in those relationships, you are more likely to succeed. It does not mean that every relationship will develop seamlessly (Stanley never really improved with meeting deadlines), but it maximizes the likelihood of success and fulfillment.” 

“After his death, I began to question what I was doing each day as a salesperson at P&G and whether this was the right career path for me. I realized that I was wrestling with these questions because of the impact that George had on my life. He was one of those people who literally could have done anything he wanted: in addition to being the captain of the lacrosse team, he was the president of our fraternity and led reading initiatives in the local Ithaca public schools. He was a renaissance man in every sense of the word, and he could have gotten any job in any field he wanted, whether it was on Wall Street or Capitol Hill. But when that lacrosse ball hit him in the chest, he had already committed to spending the next two years of his life with Teach for America working in a school on a Native American reservation in South Dakota.” 

“What,” he said, “do you want your retirement party to look like in twenty or thirty years? What do you want to have accomplished? What do you want people to say about you?” “I have no idea,” I responded. It was an honest answer, but Steve took a more serious tone and pushed me to probe more deeply. He encouraged me to reflect seriously on what I wanted to accomplish and said it was important to put myself in the position of the future to think about that. Looking back, it had a profound effect on me. The crux of Steve’s advice was that, if you don’t know where you’re going, you’re going to have a hard time getting there.” 

I find that most companies have sales enablement teams to help train and develop the sales teams, but I have yet to find a sales enablement team that provides value. Rather, having worked for companies both large and small, I  have found that the best way to make yourself better is to be proactive and own the learning and development process itself. 

These accounts will be low-risk opportunities for me to try new ideas and concepts with the intention of creating value for both the client and me. 

“To some extent, this required reorienting my mindset and increasing my attention to detail. Just as Saban highlights the importance of every play rather than winning games, I needed to learn to focus on and fully invest myself in every stage and phase of the sales process—from expense reports to individual mailings—instead of constantly measuring myself against my quota. I came to understand that focus and an even-keeled mentality is valuable because it can help you do a lot of small things well; and excelling at a lot of small tasks will eventually enable you to put them all together into bigger, more complex things, whether it is winning football games,  writing a book, or carrying your quota.” 

“distracted and not 100 percent focused on the conversation. In fact, research suggests that after a week, people retain only about 10 percent of the information they received in a presentation.”

“Begin with the outcome in mind. You should always know exactly what you want to accomplish in a meeting and work toward this goal. This entails having the agenda clearly defined and agreed upon (this can be accomplished verbally or via email) and communicating with any colleagues who are attending about who on your team will be driving the meeting.” 

“Be flexible. The truth is that most meetings do not go according to plan, so it is important not to get frazzled if something happens and instead adapt to the flow of the conversation. (I’m also often prepared to deliver less  content, in case the conversation unexpectedly goes off on a tangent.) When you close the meeting, clearly define next steps. This should happen with about ten minutes remaining (which is also a good opportunity to confirm whether the client has a hard stop). This is critical to make sure that you know who is doing what so that you can document this in your follow-up note or email. This helps build credibility and accountability.” 

“Do you know where ‘so and so’ sits?” This usually results in getting new information, including figuring out other people who may be worth knowing. I will make mental notes of the people with whom I speak, and I will look at names on offices and phones and anything that is in public view. Doing this hall walking for thirty minutes will often yield information that I could not have found on my computer.” 

“In fact, this is something that Michael Bloomberg did to get his company’s first customer: he was targeting  Merrill Lynch, and every morning for about a year, he would stop at a deli near the firm, buy two cups of coffee and tea, and roam the halls until he met someone with whom he could speak. As a Yahoo! Finance article about  this explained, he eventually got to a meeting where he expected to be turned down, but then the chairman of the  board—with whom he had enjoyed a cup of coffee—walked in and said, “Hey, Mike, how are you?” Bloomberg then explained that he was there to sell his product, which the company could cancel if they ended up preferring an internal version. The board chairman responded, “That’s a great deal. We’ll do that.” 

“planning fallacy,” which means that they are overly optimistic about what they can accomplish and when. First proposed by Daniel Kahneman and Amos Tversky in 1979, the “planning fallacy” has borne out extensively in subsequent research and real life. To cite one example, Boston’s “Big Dig”—an effort to redo the Central  Artery and Tunnel—ended up “being the most expensive highway in US history” (the preliminary cost estimate of $2.6 billion ended up totaling $15 billion) and was delayed by eight years.46 Simply put, it is very easy to overestimate what you can accomplish and when. 

“While I know during the end of quarter or the end of year, there may be time-sensitive communications and tasks that need to get done, I find that nothing is super mission critical during “off-work” hours on most nights and weekends. But I still see most salespeople “remaining connected” during these “off-work” hours. Checking emails on their mobile device may only take three to five minutes, but it enables their mind to remain “on” and thinking about work. I would argue that this interferes with their productivity during work time. As a result, over time, these salespeople will actually run into more time challenges because they are working longer hours with less productivity per hour.”

“It may seem counterintuitive at first, but most salespeople do not think about their productivity per hour in this context. I personally would rather work at maximum productivity for six hours rather than work at average productivity for nine hours.” 

“Maintain One Master Calendar for Your Entire Life I have seen people attempt to keep multiple calendars for business and personal, and I find it does not work. Pick a calendar system in digital or physical form (e.g., a  notebook planner), and stick to it. Most digital calendars sync seamlessly with your mobile device to help you track appointments and tasks. (I will share my system later in the book.) That way, you can consistently monitor how you are balancing your free time and work time and make sure you are giving yourself the time you need to recharge.” 

“Allocate “Buffer Time” on the Calendar to Complete Important Tasks Let me share an example to illustrate this.  After a day of meetings with a client, I will allocate ninety minutes of time to handle the various follow-up items from these meetings (e.g., writing follow-up emails and thank-you notes and scheduling follow-up meetings and calls). I know that these tasks will only take approximately forty-five to fifty minutes, but I schedule the “buffer time” to allow for additional research, thinking, and the opportunity not to be stressed when completing this follow-up work for the client. I find that the added time enables me to be more creative with my thinking and approach.” 

“to give an answer that they were not yet ready to provide. There’s often a healthy tension in the relationship between salespeople and their managers, and it was my job to be candid with my boss that we had to be patient.” 

“Zealand to do business and think that they understand the industries, culture, and country. In practice, however,  they are neither deeply devoted to the region nor consistently committed to the business. The bank wanted to know—no, they wanted me to prove—that I was not one of those interlopers, and the consistency of my overall follow-through would be the key to accomplishing this.” 

“Hence, the message I was trying to convey to my sales manager—we had to be patient, because by doing so, we would be communicating to the client our commitment to meeting their needs.”

“After those initial face-to-face meetings, I had to continue building credibility by following up effectively. This meant that I had to get information to that person and do it in an effective and memorable way (i.e., in a manner that was timely and personalized, which could often come through communicating in a physical form). It was also valuable to deliver useful information (e.g., reports) to demonstrate credibility.” 

Being part of the digital conversation was a critical part of building a rapport with this client; by joining the conversations that were important to them, I was demonstrating my commitment to listening and understanding what was on their minds. 

“The bigger takeaway from all of this is that by communicating effectively, I was telling my story to a potentially skeptical client. It was a story about commitment and dedication, and it ended up paying dividends. After my conversation with my boss, I waited several days and then followed up. This time, the client informed me that they wanted to sign the contract in the next few weeks and that they appreciated my commitment. My boss then lauded me for my ability to navigate a complicated situation, and to this day, my main point of contact from that project, Jamie Stone, is a friend and mentor. (As you may recall, he helped to inspire me to write this book.)  Telling a story—and letting a deal unfold patiently—is a critical part of communicating effectively with clients.” 

“A few years ago, I was meeting with a client, and it was obvious to me he was distracted. He was jumpy during the meeting: tapping his knuckles on the table, checking his phone, and doing all of the physical things that let me know that he had something on his mind unrelated to our meeting. I mentioned to the client that he seemed visibly frazzled. The client was very open and mentioned that he needed to make a personal call. His child was sick at home, and he needed to check in to make sure that everything was okay. I told him to go make the call and that we could reschedule for another time later in the day or another day. The client immediately said thank you and made the call. As it turned out, the call took only two minutes, and then the client came back in a totally different mental state. We continued the meeting, and it went extremely well. I had gained credibility, and it started with me observing body language. Visual listening is extremely important, and it helps to illustrate the importance of adapting your communication in different settings.” 

Finally, there are a few specific communication techniques that can be extremely helpful. Early in my sales career, I was taught the value of “the pause” in selling situations. Most salespeople love to talk and they will often speak excessively, but pausing can be extremely valuable during client conversations. People do not like silence, and pausing at the right time can create a healthy awkward situation that will result in the client talking  simply to fill the silence that has been created.

“The bottom line is: you are not just selling a product. You are selling yourself and your personal brand. Thus, if you can tell a story, adapt to different settings, and employ specific techniques, you have an opportunity to differentiate yourself and enhance your brand in the process.” 

“Reduce decisions. Each day, we are all asked to make decisions as part of our lives. Reducing the number of decisions you need to make each day will enable you to direct your brainpower to other, more important things.  Basic decisions like what you’ll wear to work, what you need to pack for a business trip, or what you’ll be eating for lunch can slow you down and hamper your productivity.” 

“Be on the lookout to find small productivity hacks to enhance workflows and add small pockets of time back on your calendar. These may be little things such as figuring out keyboard shortcuts on the computer to avoid having to pick up my hand and work with the mouse on my computer. Or, I may build out standard email response templates to avoid having to write the same email four or five times a day for common client questions.  The key takeaway here is to challenge yourself and constantly be on the lookout for ways to be more productive within your current system of workflows. Salespeople are constantly being given more tools to help them gain productivity, but I find that most salespeople do not use any of them to their full potential.” 

“Find comfortable but work-appropriate footwear. I wear Cole Haan shoes for work. The base of these shoes feels like a sneaker. They are comfortable. If I had to run or jog in them, I could, which is helpful when walking fast or moving quickly through an airport to catch a flight. Keep meals simple and stay hydrated. I eat very simply when traveling. I avoid being adventurous because I want to avoid getting sick when on the road. I’m simple and boring, but it works for me. I will also go out of my way to drink large amounts of water during the workday.  Research shows that people think better when fully hydrated.” 

“Having said that, technology and automation will continue to make it easier for companies to obtain information about products or services they may need.” 

“Nonetheless, in complex situations that require in-depth analysis, skill, and understanding, salespeople will be in high demand. This is the exact kind of situation that my colleague encountered with this company, and his ability to understand the business challenge his client was facing enabled him to make an extraordinary sale.  This is the kind of expertise that clients will reward over time.”

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