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Five Questions

by David Brock on October 17th, 2010

When I started my career in sales, I had the privilege of getting some of the best training available in selling–IBM’s Sales Training program was a combination of classroom and field based experiences, that few other organizations could match in terms of quality and experience.  However, when I think about the most valuable training I got in my first years at IBM, it was from the weekly sessions and reviews with my sales manager.

I’d sit down with her once a week, she’d start reviewing the deals I was working on.  She would take one opportunity and ask me 5 questions about the deal and the progress I was making.  I remember being really embarassed in our first review, I couldn’t answer the 5 questions.  We talked about it, and why having that information was important.  I walked out of her office ashamed, wondering if I could make it as a sales person.

In our next meeting, we started reviewing what had happened, she picked another opportunity I was working on, she asked the same 5 questions she had asked the previous week.  I felt like a dolt, I could only answer 1 or 2, I couldn’t answer the 5 questions.  Again, we talked about why she was asking the 5 questions and why it was important for me to know the information to build and execute a winning sales strategy.

This went on for several weeks, she kept choosing a different opportunity, but kept asking the same 5 questions.  Finally, I got the message.  One week, I was really prepared, I had the answers to those 5 questions–for every opportunity we were reviewing.  I didn’t know what she was going to ask, so I was ready to answer the 5 questions for every deal in my pipeline.  In doing this, I noticed something, I started thinking about my strategy, the next steps and what I should do to win the deal.  Preparing to answer those 5 questions, doing it for every deal, really had me focus on critical things I needed to execute.

I was proud (and I think she was) in our review where for every deal, I could give thoughtful answers to those 5 questions.  For several of the opportunities, we discussed, the answers and what they meant, and came up with great ideas to improve my strategy–in some cases to improve my likelihood of winning, in others, to shorten the sales cycle, in others to maintain the pricing strategy we were pursuing.  That morning we reviewed a lot of stuff, I answered the 5 questions every time.  We were about to wind up the review, I was tired, but pleased.  She asked to talk about one final opportunity.  I knew I was ready.  I had the answers to the 5 questions, I could handle things well.

We started the review.  She asked 5 questions—only they were different questions.  It was kind of like peeling an onion, we got deeper into the opportunity, deeper into the strategy and thinking about how to win.  You might guess what happened.  She asked the 5 new questions, I couldn’t answer a single one.  I was ashamed.  She was patient, we talked about those 5 questions and why they were important in thinking about and executing my sales strategy.  I left her office having snatched defeat from the jaws of victory.

The next week, we started the review, she asked 5 questions–they were the 5 new questions she had asked the previous week.  Now contrary to what some would claim, I’m not as dumb as I look.  I understood what she was trying to do in developing me as a sales professional.  This week, I was prepared.  I didn’t have the answers to the 5 new questions for all the deals in my pipeline, but I had a lot of the answers.  Again we talked about it—in those deals where I had the answers, I noticed the strategy was richer and much sounder.  I noticed my sales cycle was accelerating in those deals.   I knew I had to get the answers to those 5 new questions for all my deals.

Another week passed, another review session.  I walked in prepared to answer the 5 original questions, the 5 new questions, and how I was going to win every deal in my pipeline.  Perhaps my swagger walking into her office betrayed me.  I sat down, she said she wanted to review a specific opportunity, I knew I had all the answers.  She asked me 5 questions—-you guessed it, they were 5 newer questions.  We didn’t even bother with the first 10.  She knew I had the answers.  She knew that I had tuned my strategies and better focused them.  She wanted to go another layer deeper.  She wanted me to tune the strategy even more, she wanted me to think more deeply about what I was doing and how I could win.

As I reflect on it, I think that was some of the best training and coaching I have ever gotten.  5 simple questions, asked over and over until I could respond for every deal.  Then 5 new ones, asked over and over, Then 5 new ones…….

If you are a manager, what 5 questions are you asking your people?  Are you asking them over and over?  Do your people know why the answers are important to their sales strategies?  Do they have the answers—for every deal?  Do you know what the next 5 questions will be?

If you are a sales person, do you know the 5 questions your manager will ask?  Do you know why they are important?  Do you have the answers?

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  1. Hey Dave,

    Great article.
    First of all, I would like to know the 15 questions asked 😉

    Making your sales review their sales technique, think about each deal and learn is a great way to develop them. That training is probably a big reason you are where you are today.


  2. What a great idea!

    Like Daniel, I’d kill for the list of questions. You would be doing sales manager’s everywhere a favor by providing the list. The questions may not be applicable to our sales people but it would allow us to develop our own questions without having to reinvent the wheel.

    • Brian, Daniel: You don’t have to kill for the questions. I’ve gotten a lot of responses asking for the same. Stay tuned! Tomorrow’s post addresses this. Regards, Dave

  3. Robert Koehler permalink


    You powerfully reiterate the power of front line sales coaching, something that I have too often overlooked in implementing sales performance improvement programs. If I could only have one choice of a strategic account planning program and a consistent, challenging sales coaching “program” like the one you had at IBM, I would choose the sales coaching: less expensive, more impactful, more meaningful and memorable.


    • Robert, thanks for the great comment. The ongoing sales coaching role of managers is the most critical element of sustaining the results of any training program, and driving performance improvement. We take a pretty strong stand on this, saying training should not be implemented, without concurrent coaching program and management’s commitment to implement it.

      As you suggest, it’s far cheaper, more meaningful and creates results. Everything else is an event. Thanks for the great comment.

  4. Dave

    It seems it’s those moments when we reach inside to find the answers when we learn the most. Your post reminds me of the ancient notion of the sensei.

    In Japanese martial arts, the sensei’s role is not to tell the student the right answers, but to challenge the student in such a way that they acquire the capabilities they need by their own experience. Sensei don’t lecture, instead they create an environment that forces the student to make choices and grow from them to reach the next level of competency.

    There’s great power in this concept – because lessons learned this way are not quickly forgotten, and they typically have much greater ownership among students.

    Don F Perkins

    • Great comment Don, there are a lot of parallels to the martial arts. Additionally, some might recognize this as a form of Socratic conversation. Thanks for the great comment.

  5. Love the blog! This is a great one…..the art of questioning is very under estimated, not just in sales but in general business as well. Goes to the axiom that we have “2 ears and 1 mouth” for a reason, and questions unlock that power.

    • Thanks Mark! Look at the post, “What Questions Are You Asking Your People?” It continues the theme.

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