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6 Questions to Prepare for the Biggest Sales Conversation of Your Life

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Written by John Doerr
President, RAIN Group

The following is expanded content from our new book Rainmaking Conversations: Influence, Persuade, and Sell in Any Situation. In this piece, co-authors Mike Schultz and John Doerr stress the importance of continuous self-evaluation in your efforts to reach sales success. Read more about the book here.

Imagine for a minute you’re a master carpenter. You’ve been building houses your whole life, trying your best to hone your craft and deliver the highest quality work every day that you possibly could.

Then one day, you’re presented with the opportunity to teach your craft—a craft you’ve been honing for 30 years—to someone else.

Let’s say for argument’s sake that this person has positively average talent! They have no better raw abilities than anyone else you might run into that barely knows the difference between a router and a miter saw.

But they’ve told themselves that they’re going to be the best carpenter that’s ever walked the face of the planet. They’re going to prove to themself, and in the process everybody else, that they will become a master craftsman, a craftsman with the skills that rival the best carpenters in the land.

Now imagine for a minute that they really mean it. And they have the determination to work hard and learn every day to be the best.

One more person to think about. Imagine that someone with a lot of natural talent comes along at the same time this person with average talent is asking for your help. You ask the talented young person, “Would you like to learn to be a master carpenter?” and their best answer is, “Yeah, sure, but I have a lot to do this week. Can we start next week? And I have a bunch of other things on my mind. What kind of commitment are you looking for?”

Who would you pick to take on as your apprentice? Who’s more likely to succeed? To do you proud?

For us, every time we’d pick the person with average talent but with superior passion over superior talent and a ho-hum attitude. There’s no question who’s more likely to succeed.

The same is true with sales. Regardless of your current skill level, if you have the desire, the commitment and a few other factors in place, your success potential is limitless.

Is this you? To find out, the first thing you have to do, is ask a few powerful questions…of yourself.

To start the conversation with yourself – the conversation where you determine just how successful you are likely to be – ask the following six questions.

  1. How strong is my desire to achieve in sales? The most important factor influencing whether or not you become a rainmaker is your personal desire for success in sales. Note the emphasis on in sales.

    You might think for full-time salespeople this goes without saying. It doesn’t. Some salespeople can’t wait to sell; others are just biding their time until something better comes along.

    The same is true for professional service providers. Many professionals have a tremendous desire to achieve in general, but not so much in sales. Some service providers don’t think they’re cut out for selling. Some are uncomfortable with learning to sell. Some are not money-motivated, and their companies don’t reward them if they sell anyway.

    Some, however, love selling and, like Ralphie waiting to unwrap his Red Rider BB gun, they can’t wait to get to it. Why they desire to sell is mostly immaterial—that they want to sell is essential.

  2. How committed am I to doing what I need to do to succeed? The premise of David Maister’s book Strategy and the Fat Smoker is that people know what they need to do to help their companies and themselves succeed—they just don’t do it.

    Maister compares the practice of management to the challenge of weight loss. How do you lose weight? Eat less and exercise more. Everyone knows it. Doing it is another story.

    Sales people often know what they need to do—make more phone calls, lead more rainmaking conversations, deepen relationships, become experts in their fields, learn new skills, go the extra mile for customers.

    Although you might desire to succeed in sales, without the requisite commitment, you’ll get the same results as you would if you really wanted to lose weight, but then ordered a bucket of wings and hit the couch. For sure, most people who want to lose weight don’t plan to do this, but it happens. It’s 10 PM and you have been good all day. Then you break down and start winging it.

    Commitment is tested when the going gets tough, and the tough eat salad. The going gets tough all the time in sales. It’s not easy to create new conversations every day (Rainmaker Principle 6), live by goals (Rainmaker Principle 2), ask the tough questions, take a risk, hold true to your value without caving on price, go the extra mile for the client…none of these is easy to do when faced with the siren song of doing an alternative.

    Desire to sell is the first step. Committing to action and taking it—that’s the game-changing leap.

  3. How energetically will I pursue success? You’ll hear a lot of advice about how to work smarter. You can always work smarter, but working harder makes a big difference, too.

    Rainmaking conversations require a lot of work—you have to arrange the conversations, prepare rigorously, allot the time to conduct the conversation, and typically make multiple follow-up calls to close the deal.

    Success with rainmaking conversations is a function of how many you have and how well you conduct them. Rainmakers create new conversations every day (Rainmaker Principle 6), lead masterful rainmaking conversations (Rainmaker Principle 7), and always improve their pipeline quality. Living by these principles takes time and energy. You have to be ready to devote both.

  4. How’s my attitude? It’s not our goal here to recount the benefits or rewrite the argument in favor for a positive attitude. We’re here to help you succeed at selling.

    We’ve encountered many salespeople who have the desire and the commitment to do what they should do to succeed, and then proceed to derail themselves with thoughts of doom and gloom about the economy, lack of faith in their company’s products and services, lack of faith in themselves, and worries about their ability to lead successful sales conversations.

    Along with the typical digs on the economy, their companies, and their products, the doom-and-gloomers say things like, "I don’t like making phone calls to people I don’t know well," "CEOs aren’t my peers and I am uncomfortable speaking with them," and "I’m not good at building rapport and developing new relationships quickly."

    They say these words and, like magic, the words come true. Go into a sales conversation with negative thoughts, and even if you think you have built the best dam to keep these thoughts out, they’ll find the holes and flood your mind with doubt. Once your mind is flooded with doubt, the flood can’t help but leak into your sales conversations.

    Sales is a game of opportunity. If you think the opportunity can’t, won’t, or shouldn’t happen to you, it won’t. But if you think it can, will, and should, happen to you, when opportunity knocks you’ll be ready to welcome it in.

  5. Do I accept responsibility for my outcomes, or do I make excuses? There’s always a good reason for why we don’t do something we mean to do, or don’t reach our potential. When this happens, do you blame circumstances or other people, or do you take responsibility?

    Some people succeed despite adversity. They beat a bad economy, they create conversations with difficult-to-reach decision makers, they sell something complex and intangible to someone who never even had an inkling that they wanted to buy it until the salesperson came knocking.

    Yet at the same company, selling the same products and services to the same market, other people tell us, "I can’t hit my goals in this economy," "The decision makers are just too insulated to get to," and "I can’t sell them something they don’t want."

    The excuse makers always have good reason why they didn’t prospect, didn’t prepare well for a meeting, and didn’t make those last few follow-up calls before they left the office for the day.

    One salesperson we were coaching told us that after working to set goals and build a sales action plan, he didn’t implement the plan because he didn’t have a system that met with his satisfaction for updating his progress. (Sure, technology can always help, but in his situation a notebook and a pen would have worked just fine.)

    We all have the same amount of time each day, the same number of days each week, and the same power to make decisions concerning what we choose to do and not to do.

    There’s no one keeping you from getting it done yourself.

  6. Am I willing to face my sales demons? On September 9, 1965, James Stockdale, a pilot in the United States Navy, ejected from his A-4E Skyhawk, descended into a small village in North Vietnam, and was taken prisoner. He spent much of the next eight years, from then until his release on February 12, 1973, in a 3-by-9-foot cell with the light on 24 hours a day.

    Despite great hardship, Stockdale persevered. He went on to a storied career in the navy (president of the Naval War College) and in education (president of the Citadel, fellow at the Hoover Institution of Stanford University). As told in Jim Collins’ book Good to Great, he recounted how he always kept the faith, but was willing to confront the hard, brutal truth of his situation, never willing to sugarcoat or lie to himself that things were better than they were.

    If you’ve been honest with yourself after asking the first five questions you might be thinking, ‘‘I know some areas where I can improve.’’ It may be tempting to stop here, but rainmakers keep going, seek out, and fix any weaknesses that may be holding them back. If you want to be a top performer in sales, you should, too, even if the cold hard brutal truth isn’t pretty.

The outcome of your conversation with yourself will give you keen insight into whether or not you’re ready to be a top performer in sales.

Interestingly enough, the answers to each question typically fall along one of two lines, labeled below as "option 1" and "option 2."


Topic Option 1 Option 2
Desire Want more success Happy with how things are
Commitment Will do whatever it takes Will do it if it's not that difficult
Energy Ready to put the time and effort in Other things take precedence
Attitude The world is my oyster Obstacles are too great to overcome
Responsibility I'm responsible for my success and my team's success My success is not in my control
Hidden weaknesses I want to know what they are for me because I want them gone Better to leave well enough alone


Each option is a choice, and choice is a wonderful, powerful thing. When it comes to success in sales – as in life – it’s up to you to make the choices that are right for you.

For each question, both answer options are available to everyone, including you.

Be honest with yourself. Which options will you choose?

Topics: Sales Conversations