The Right Sales Questions Will Uncover Enterprise Risks and Golden Opportunities


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Sales is a set of interconnected business processes.

Gaaaaaaaahhhhhhhh! Got that out of the way!

I hope the buzzword-encrusted introduction didn’t turn you off. And you’re right to ask what it has to do with the title.

Everything. All business processes carry risk. Stuff happens. Things go wrong. And because risks don’t walk up and say “Hi. I’m a risk,” asking questions can root them out and prevent them from accumulating. Woulda-coulda-shoulda! We’ve all said it. As one VP of Sales told me, “Experience is something you get after you need it.”

Your organization’s future depends on asking questions because the questions your sales force asks—or doesn’t ask—have a huge impact on enterprise risk. But most CXO’s don’t have a clue about what gets discovered throughout the sales cycle. “It’s the sales rep’s job to qualify leads!” Wrong-a-mundo. If others in your organization don’t influence discovery, or if you’re leaving those decisions completely up to Sales, you’re adding risk by the bucket load every minute. Want proof? Next time you’re in a staff meeting, jot down (or type) a note for every comment related to:

“The forecasts sales sends us are way off.”
“Marketing sends sales useless leads.”
“We have a warehouse full of slow-moving inventory.”
“Our financial and production planning stink because Sales never hits their number.”

Words you hear when risks come home to roost. So knowing how closely your product meets a prospect’s requirement, whether your sales team has access to decision makers, whether your prospect has sufficient financial resources to buy from you, and when they’re motivated to purchase, matter. They matter to your business and financial strategy. They matter to your planning processes. They matter for your financial performance. And the answers are all uncovered through asking questions.

Go to the location where your company’s sales conversations take place, listen (or read, as the case might be), and you’ll quickly learn the starting point for risks and how they amplify. Sprint got a painful lesson in 2008 when the company decided to grow its subscriber base, and nixed “ability to pay” from its qualification process. The discovery failure cascaded, and nearly sank the company. The math: $29.45 billion loss equals (“Can you fog a mirror?”) minus (“Can you pay your bill?”). Down in the trenches. One transaction at a time. I can imagine the CFO’s expression when he or she learned for the first time that prospects became customers even when ability to pay was unknown. Woulda, coulda, shoulda. Questions matter. Especially the ones that uncover risks and opportunities. Today, I’d wager that Sprint’s CFO can recite from memory every sales question in the call center script, or the route each branch takes out of a flowchart decision box.

Sprint’s confusion isn’t unique. Many questions that sales organizations use are inconsistent from rep to rep, unfocused, or too limited. Ryan asks questions centered on discovering his risks and opportunities, and those of his prospect. Jennifer’s are a meander around disparate issues. When Suzanne, the CFO looks at their sales forecast rolled up into a single cell on her spreadsheet titled Pro-forma Cash Flow, does she know the insight, assumptions, and knowledge that comprise the consolidated number? Frequently, issues relating to which questions are asked—and how they’re asked—bubble to the surface only after months of misguided activity. Part of Suzanne’s job is to control her organization’s financial risk. Time for her to have a seat at the table for the monthly sales meeting.

Some recommendations for Suzanne and her senior management colleagues:

1. Develop an understanding of risk capacity in the context of the organization’s goals and objectives. Sometimes referred to as risk appetite, this understanding serves as the basis for deciding which sales opportunities are targeted, how they’re vetted, and how resources are committed to the sales process.

2. Seek input from a cross-functional team of executives to understand how their risk goals match the discovery processes used in the sales organization (what would Sprint’s receivables manager have said about the company’s customer intake processes?).

3. Understand as clearly as possible the sales opportunity characteristics that portend a successful outcome, or conversely, the characteristics that must be avoided.

4. Learn the risks that have the highest likelihood and the highest impact for successful sales outcomes.

5. Direct the questions your sales force uses toward exposing the greatest risks and the best opportunities, not only for your sales organization, but for your prospects as well.

6. Adapt the questions as emerging trends and forces change the risk exposure and risk capacity for your organization and for your prospect’s.

7. Embed key questions into your sales process and forecasting methods to ensure consistency across the organization, and to enable early identification and mitigation of risks.

8. Obtain feedback. Develop metrics that expose which risks to manage as they’re developing, and ask the sales force which questions work best, and which ones don’t.

Which sales questions are most useful? There are plenty to choose. Today’s search for “best sales questions” yielded 135,000 links—more than I have time to read. But the most valuable questions for salespeople are those capable of discovering risks and opportunities. It’s time for senior executives to pay attention to what they are.


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