Sales and Sales Management Blog

February 29, 2012

Guest Article: Strategic Questions Will Uncover Strategic Opportunities, by Andy Rudin

Filed under: Uncategorized — Paul McCord @ 11:53 am
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Strategic Questions Will Uncover Strategic Opportunities
By Andrew Rudin

The late Peter Drucker said “true marketing starts out with the customer, his demographics, his realities, his needs, his values. It does not ask ‘what do we want to sell?’ It asks ‘what does the customer want to buy?’ So, why have so few people figured out how to routinely and systematically uncover this fundamental insight? And why do few senior managers pay more than lip service to encouraging or requiring their sales forces to discover the answer?

One reason is that in the quest to create a “sales-driven culture,” companies push muscular sales tactics that often subordinate the importance of questions. “ABC—Always Be Closing,” or “Show the ROI!” or “Go for a trial close after showing our key features,” are part of sales-process DNA. Does anyone remember this recommendation–“When you get the customer to answer ‘yes’ to three consecutive questions, ask for the order.” ? One sales training tape I heard ignored asking questions altogether, offering this nugget: “If the customer voices an objection, give them a ‘yes . . .but.. . .” (I am not making this up—and I’m sure the phonic similarity to “headbutt” is not just a coincidence!) These superficial tactics fall short by not embedding strategic discovery into the sales process.

What is strategic discovery? It’s the process of learning how an organization plans to create, monetize, and deliver its value. Why is strategic discovery a vital competency for sales forces? Because compared to operational problem solving, strategic collaboration tightly connects enterprises in a value chain. Those tight connections increase a vendor’s value and reduce selling risks. Why?  Because strategic initiatives are mission-critical and are often less ephemeral than operational initiatives. When a salesperson says “my solution enables your strategy,” she has a competitive advantage over the salesperson who says “my solution provides the highest ROI (and/or lowest Total Cost of Ownership).” I know from numerous sales engagements I’ve managed that “high ROI” alone provides a wobbly sales-value foundation. (See my recent blog, A Sales Team Needs More Than “High ROI” and “Low TCO” To Compete and related article The Right Sales Questions Will Get the Right Answers.)

Strategic discovery doesn’t have to be difficult, but the process makes many salespeople uncomfortable. Strategy questions must uncover business and financial challenges. They examine forces that are outside of anyone’s direct control. Part of the discussion includes blurry concepts like risks and trade-offs. Few strategic questions can be answered with a simple ‘yes’ or ‘no.” And strategic plans aren’t guided by ordained roadmaps or prescriptive methodologies.

So, what are the steps that a Sales-Discovery Black Belt should follow?

1. Begin with a foundation of mutual trust. As Jim Collins said in the bestseller Good to Great, “create an environment where the truth is heard.” Prospective customers don’t spontaneously open up and provide meaningful and honest answers to questions. And if you wait until the second meeting to start thinking about how to cultivate trust, it’s probably too late. Mutual transparency of goals and objectives must characterize the business relationship from the beginning. The best book I have read on this topic, Mahan Khalsa’s Let’s Get Real or Let’s Not Play, provides an approach that is as eloquent as it is sensible: “The decision to trust doesn’t start inside (your prospect)—it starts inside of you. Intent is a choice, and your choice will have consequences. You will communicate your intent whether you want to or not . . . Based on your intent, people will decide to trust you or not.”

2. Ask the right questions. Here are some of my favorite strategy questions, culled from a list of hundreds I’ve compiled over many years:

  • ·         What are the key capabilities and resources required to execute strategy and achieve your goals?
  • ·         In order to execute your business strategy, what are the key things you must do well?
  • ·         What proprietary advantages must your company create for your strategy to be successful?
  • ·         What are the most valuable outcomes your organization enables for your customers?
  • ·         What are the major forces driving changes in your business?
  • ·         What conditions have the most disruptive impact on your business now, and will have in the future?
  • ·         What are the greatest opportunities for your company to change the basis of competition in your industry? How might these impact barriers to entry? Switching costs? Relationships in your value chain? Product differentiation?
  • ·         How sustainable is your market position and the business model needed to achieve and support that position?
  • ·         What are your options for growing your business in the future?

3. Identify capability gaps. Specific operational questions will uncover gaps between strategic imperatives and current capabilities. For example, the question “What are the major forces driving changes in your business?” might yield that global competition is a condition of growing importance. If the prospect company lacks operational capabilities to manage a worldwide supply chain, a strategically-significant impediment has been identified. From this finding, the essential work of sales takes place—enabling a client first to believe the facts about an issue—then to care, then to act. Operational questions are instrumental for crossing the belief threshold, so caring and acting are more likely because of the strategic ramifications of the capability gap.

4. Align the gaps with a recommended solution. This final step ensures that the recommended solution matches the client’s strategic imperative. A scenario from my sales past illustrates the importance of this step. Several years ago, one prospective client told me “Our goal is to get our organization 100% on bar coding by the end of next year.” Although I was pleased he believed in my product, I cringed at his remark, wondering how he would handle the Q&A from his management peers at his next planning meeting. The strategic goal was to improve cash flow by cutting order cycle time. Bar coding was one enabler. By establishing a foundation of trust described in Step 1, my commitment was to help my client achieve that outcome.

Achieving the right sales outcome–my client’s success–required both my client and me to keep the strategic objective in focus.

Andrew (Andy) Rudin is Managing Principal of Outside Technologies, Inc., a Virginia-based sales strategy consulting firm.  Andy specializes in sales risk management, which in a nutshell means that he helps his clients improve their odds of achieving successful sales outcomes.  Most of his client work involves information technology products and services.



  1. Excellent post Andy. Thanks

    Comment by David — March 1, 2012 @ 1:52 am | Reply

  2. Andy, great list of questions! As you imply, strategic questions can increase trust *because you really want to know*. My firm qualifies prospects rigorously, but we tell them openly that we don’t know whether we should work together, that our pre-engagement process is designed to figure that out. So questions are key. We try to eliminate prospects as quickly as possible.

    A similar use for your questions, but in a different context, is when a firm is creating a social business strategy (our focus). Most firms want to increase business, but the way to earn trust and engagement goes through relevance and consideration. Easy concept, but what does it look like, given the firm’s stakeholders (often prospects)?

    Thanks for a great list!

    Comment by Christopher S. Rollyson — March 1, 2012 @ 2:16 am | Reply

  3. Thanks, Christopher. Formulating the question list is fairly easy, when compared with the rest of the sales challenge. The harder parts are incorporating questions in a meaningful conversation, and then using the insights to develop a strategy for the opportunity, which could involve not recommending one’s own product or service, as you point out.

    Comment by Andy Rudin — March 1, 2012 @ 10:03 am | Reply

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