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Who Was Your Sales Mentor, and What Was Their Greatest Lesson?

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Whether it’s a killer closing tip or just some well-timed encouragement, guidance from a sales mentor can change the course of a young salesperson’s career. Even the simplest principles can be powerful when you learn how to apply them.

We asked 11 sales professionals, entrepreneurs, and business executives about their mentors and the greatest lessons they learned from them. Got a story of your own? Tweet us @nutshell and share the best piece of advice that a sales mentor ever gave you.

Erica Fultz, Senior VP & Matchmaker at LUMA Luxury Matchmaking:

My first mentor was my father. He was a door-to-door salesman all his life. From a very early age, he told me that whenever I enter a room to know everyone’s name and make sure they know yours. That is the single most important lesson I’ve ever learned and take with me in my sales life today.

My sales idol is Zig Ziglar, who taught me that, “You can have everything in life you want if you just help enough other people get what they want.”

Related: Six closing lessons from a traveling salesman

Ally Compeau, Founder of Woof Signs:

My sales mentor was my first coach at a tech sales job. He had a serious passion for sales as well as for our product and it was infectious.

I remember his first “pitch” to me wasn’t about the product, it was before I was even hired—he was pitching me about the company, the role, and the team. After that pitch, I couldn’t even think about working anywhere else.

From there, I started at the company and he put me through a very intense sales/product bootcamp. For me, he made sales so much less sleazy and so much more about helping our clients as well as working on ourselves and honing our skills. He pushed us to our full potential and didn’t hold back on honest feedback, but was also there to support us through the ups and downs of being in a sales role (which there always are).Here’s what I learned from him:

Practice. There is nothing that will help you to refine your skills and style more than good old practice. We had multiple sessions each week. During these sessions, we would pitch to each other, throw out objections and discuss the best strategies to handle those objections. I was put on the spot many times. That’s what got me ready to sit in front of senior executives and have real, meaningful conversations about their business.

Perseverance. In sales, your prospects will always say “no” or “sorry, it’s not the right time.” Still, you have to persevere if you truly believe in the product or service that you’re selling. You’re doing your clients a disservice in taking no for an answer and not finding a way to help them (tactfully, of course!).

Accountability. The best way to build relationships with your clients is to be accountable for what you’ve committed to. You also have to keep your clients accountable for what they’re looking to achieve. The second part is key; people don’t often think of keeping a client accountable, but I’ve found that they really appreciate it. It helps to build clout and trust.

The biggest lesson I use to this day is the discipline my mentor instilled in me. Practicing my pitch, objections, etc., and staying refined. I am also disciplined in doing what I say I’m going to do and keeping others accountable as well in order to keep things moving forward.

Steven Benson, Founder and CEO of Badger Maps:

My first Sales Manager at Google, Mark Flessel, was a mentor to me. He told me to focus on understanding my prospects’ and customers’ business—to understand what their KPIs were and what their goals were. Then I couldmap my solution to what makes them successful.

Time and time again in sales, I have found that taking the time to ask the right questions and understanding my customer’s business drivers allows me to differentiate my solution over my competitors.

Sacha Nitsetska, Founder & CEO of

My first sales mentor was Jon Clark from Adjacency. He inspired me by telling me his stories of successful sales at HP, explained the importance of relaxing and being positive, and gave me a “prep cheat-sheet” that has never failed me and only takes about an hour to complete.

He calls it the “end in mind” process because that’s what you start with.

  1. Decide and write down what you want the prospect to think, say, do, and decide at the end of the meeting.
  2. Prep the logistics (who/what/where, including background research on who you’re speaking to).
  3. Write down your proposition in the following format: If they wrote a press release tomorrow about your partnership, what would it say? How much time/money does your product save them? What’s exciting/new about this? Why should investors be pleased about this deal? Who benefits? How? How long does it take to reap the benefits? What’s the ROI?
  4. What beliefs must they have to reach the end you have in mind (this is one of the most helpful aspects of this method):
  • Write a list of 3-5 core beliefs and the corresponding evidence you need to present in order to engender these beliefs.
  • Split the evidence into: info about you and your experience, info about your company, data/external research, and info about their business.
  • Deliver the evidence in a way that doesn’t sound like a pitch, e.g., ideally as side-stories peppered throughout the conversation.
  1. Challenges: Prepare for 5-6 questions that you do not want to be asked, which should include typical worries and concerns you encounter. Ideally address these questions in a plausible and confident manner that passes the integrity test but in such a way that you cannot be held accountable. This is best done before they ask the questions, in as conversational a manner as possible.

Then, when it’s time to meet with the prospect…

  1. Start with an overview of their roles and responsibilities, some small talk on the news in their industry, company priorities, who else they have spoken to, and what their biggest concerns are about competitor propositions (this one alone is gold).
  2. End by asking for referrals and next steps. The most helpful and counterintuitive advice I got from Jon is to do all this without any slides. Because clients expect slides, they come out feeling like you’re their friend (because you gave them a conversational meeting rather than boring salesy pitch) and will often come back and ask you for materials anyway—except at this point you know exactly who they are, what they want and what they like about your proposition.

I used to spend days creating custom materials for each meeting. I now spend an hour or two working through the prep cheat-sheet and the results have been astonishing.


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Jeffrey Orens, retired chemical industry executive:

All my success in business was based on what I learned in selling, most of it from two mentors. My first mentor was my father, who indirectly infused me with a desire to sell. He was energized by selling and managing his sales force. His enthusiasm for his profession was unmistakable, as was his love of using his offerings to solve the needs of a worldwide customer base.

From him, I learned that selling can be an activity that connects people, and is universal in the way our world works. It can be tremendously gratifying in not only making a living but in developing friendships in the process. These feelings were the underpinnings for my foray into sales.

An early sales manager in the chemical industry was my second mentor. He taught me the basics and instilling a drive to succeed at selling while grounding me in the realities of the profession. In my young sales career, I was fortunate to have a sales manager who took some time to guide his sales force with a steady hand and sage advice, all wrapped in good humor and a slightly southern drawl. Three of his principles stand out…

Keep lots of irons in the fire. This relates to the numbers game of sales; more live prospects increases the probability of success.

Don’t just get the order, get the business. Laying the groundwork for cooperation between customer and salesman encourages a supply relationship beyond the initial order. This means that the salesman should look beyond securing the order to securing the relationship. That leads to successive orders as well.

There will always be another bus. The is a simple axiom that is often overlooked by some salespeople. There is a large world of potential customers out there. Don’t be discouraged if you miss this bus; another will be along shortly if you have followed rule number one.

Nancy Cramer, Founder of Correct Course Consulting, LLC:

My first Sales mentor was Joe Charbonneau, a famed professional speaker. The National Speaker’s Association named their training academy after Joe. He was an exquisite salesperson.

Selling is hard. It requires pitching, asking good questions, close listening, facing rejection, and persistence in the face of ambiguous or even hostile situations.

Joe taught me that successful salespeople listen intently. They pick up on subtle cues, adjusting their conversation to fit the prospect. They also manage their emotional state with precision, maintaining balance in the heat of business battles.

Finally, sales is a game of averages. Those who follow a set procedure religiously will, by the law of averages, close more business. To a true professional salesperson, the answer “no” is just one step closer to a “yes.”

Nate Masterson, Marketing Manager of Maple Holistics:

Meg Whitman was my sales mentor thanks to her tremendous influence on the online marketplace. As the CEO of eBay, Whitman took the iconic E-commerce brand from a $4 million a year company to an $8 billion a year juggernaut in just 10 years. After leaving eBay, Whitman went on to become the CEO of Hewlett-Packard, and is currently the CEO of NewTV, Jeffrey Katzenberg’s mobile media startup.

The way she manages to accomplish her high levels of success wherever she goes is by taking the positivity approach.

According to Whitman, there is an impulse to immediately fix what’s going wrong upon entering a new organization. Instead, she recommends focusing on the business’ strengths. This way, company members will be more receptive to the changes you have in mind.

This has become a motto to live by for me. I’ve learned the importance of viewing myself in the eyes of others. Whitman conveyed this message so clearly by restraining the urge to burst onto the scene and make significant changes. It’s natural to want to justify your presence and assert your status, but it’s crucial to know your place in new environments.

Blake Plumley, CEO of Capital Pursuits:

My mentor was a VP of sales that I had when I was just out of college, Scott Alkire, who taught me that to succeed I had to know myself and trust myself to close deals. He taught me that I had to recognize that people act in their own best interests, and understanding that would help me to help them and therefore help myself.

The key to sales is to let your sellers be who they are. Understand that everyone sells differently and you have to trust your staff to sell their own way but within the bounds of your organization.

Elizabeth Ortiz, Business Development Operations Manager at Geek Powered Studios:

I have had several sales mentors throughout my career (Christine Escobar, Robert Getz, Adrian Salazar, and Mary Reding to name a few) but they all taught me the same three fundamental things.

1. Immerse yourself in your client’s vertical

Business owners are inundated with product offerings from providers every day. This can range from the tile on the showroom floor to the commercials you see on television. They are tired of hearing why you are special and why you are number one.

As sales professionals, we often make the mistake of gearing the conversation towards why WE are special versus getting to the know the business needs. Those who take the time to do research on the client, their business, and their vertical can speak more intelligently to the business’s needs and can find ways to tie their products to those needs.

2. Present clients with concrete information on your product value. How will it drive ROI?

Research is key. Will your product make something faster, more cost efficient? Will it allow the buyer to capture a missed revenue stream? If so, what impact would it have on their business? Give them concrete projection figures, case studies, and references. Why should they invest in your product?

3. The follow-up is key

A fatal mistake that sales professionals make is moving onto the next sale and not following up with previous sales. Wee are all busy and it’s easy to get caught up in the next big deal in the pipeline. Those who nurture their book of business will find that it’s worth it in the long run. Through follow-up, you can ensure that what you have sold is working and it helps solidify a working relationship.

Kasey Bayne, CMO of Redstamp:

Andrew Peek was my mentor. He was the leader of the newly founded sales team that I joined at FreshBooks. As the first sales team at this growing company, it was very much the startup adventure of learning as you go (and going fast!).Andrew’s best advice to me was to do sales my own way—to use my strengths and skills to be the best kind of salesperson I could be, rather than trying to fit into the same mold as everyone else. I was able to use my consultative selling approach, helping customers solve problems, grow their business, and being up front when we weren’t the right fit. I crushed my sales goals and built long-lasting relationships with customers that still exist today.

Jason Parks, President of The Media Captain:

My mom was my sales mentor.

She is extremely ambitious and has always worked in a role in my dad’s medical practice. She was focusing on new business development and expanding the business in different ways.

I’m the owner of a digital marketing agency and I’m the one responsible for driving new business into our agency. My mom taught me from the get-go how important it is to fill up the pipeline with leads. Regardless of how good of a job you do on the service side, without new prospective clients, you can run into trouble. It was this mindset from the get-go that helped us grow tremendously over the years.

My mom inspired made me realize how important sales are. Some people look down upon sales but they don’t realize that it is the lifeblood of any business.

Persistence is a life lesson I learned from my mom that carries over to sales. You are going to get rejected but you can’t get discouraged. You have to keep moving forward.


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