Ask the Right Question

Last updated on May 13th, 2019 at 02:36 pm

Want to test your own organizational savvy? Solve the following sales case.

After nearly a year-long sales cycle, Eric, a veteran financial software salesperson, sold a huge deal to the chief financial officer at one of his key accounts. The two had celebrated closure of the sale via dinner with their spouses. And the CFO had made all the appropriate announcements inside the buying company.

A week into the installation of the software, a very embarrassed CFO, tail between his legs, called Eric with some devastating news: the company had decided to cancel the purchase and would de-install the components that had already been installed. It seems the chief information officer, who hadn’t been very involved in the buying process, killed the deal. According to the apologetic CFO, the CIO had cited some esoteric technical issue for rejecting the software.

Oh, this one’s a no-brainer – Technology Sales 101 says you have to involve the CIO!

You’re right, obviously. But are you right for the right reason? Let’s find out.

Start by factoring this into the mix: the CIO reports directly to the CFO.

In the real world of corporate life, there is no way that an executive would allow a subordinate to give him such a black eye as occurred here. After making such a public display of his decision to buy the software, the CFO would simply tell the CIO – in so many words-"Make it work!"

What makes this case even more unusual is that the purchase in question is financial software. Who should be more influential on such a purchase than a company’s CFO? And then to be upstaged by a subordinate, no less? What’s wrong with this picture?

One really good political question

When Eric related the story to me, the situation was still warm. So I gave him one question to ask his lower-level contacts about the players involved in this decision. That question was: How long have the CFO, the CIO and the president been with the company?

A few days later Eric called me back. The bottom line: The CFO had been with the buying company for 20 years. The president had been with the company for about a year, the CIO had been hired six months ago, having come from the same company as the president.

Is it getting a little clearer? Sure, it’s obvious by now. The CIO, while officially reporting to the CFO, actually carried more influence in the company – and not just on I/T matters – than his own boss.

This insight was critical to the outcome of the sale, but Eric had not bothered asking the one question that would have yielded such insight. He had relied, like too many salespeople would, on the title of the executive buying his financial software. Eric was, after all, talking to the "CFO," and on financial software for crying out loud. By most measures, Eric was in the catbird seat.

Unfortunately for Eric, he failed to ask the one question that all salespeople should ask but few do: "How long has ‘so-and-so’ been with the company?" While there’s more to a sound political analysis than just this question, knowledge of how long contacts have been with the company, or in their current positions, can reveal a lot about the level of influence of those contacts.

Every sales cycle is profoundly influenced by political factors, whether we like it or not. Salespeople must remember that, in the real world of corporate life, political reasons trump business reasons for any decision, including a buying decision.

That’s why we need to, as I like to say it, put on our political glasses, so that we can peer deeper into customers’ organizations than just the org chart.

One really bad political question

There’s a good chance Eric had, earlier in the sales cycle, also asked the CFO the classic traditional question: "Who else should I be talking to?" To which the CFO probably responded with something like, "There’s no need to talk to anyone else, this one’s my baby."

Who’s going to argue with that?

Why is, "Who else should I be talking to?" such a bad question? First, what if – as in this case – the contact says, "Nobody?" You’ve just boxed yourself into a corner. Second, if the contact does give you a name, it’s almost certainly going to be a low-influence contact, and often a gatekeeper, at that.

You can put on your own political glasses starting tomorrow by asking the innocuous question, "Gee, how long has so-and-so been with the company?" and by avoiding one of the most popular questions in selling: "Who else should I be talking to?"

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