Challenging the Challenger Sale

Can you challenge your customer’s thinking on what they need to buy – while still building warm, empathetic rapport?

About 13 years ago, I was bumbling through the airport of Little Rock, Arkansas, home to the grandfather of teach-a-man-to-fish organizations, Heifer International. I did not see the Clintons or the Waltons, but I was not alone. With me from my organization (Blackbaud) was the CTO, the VP of something, the VP of something else, the Director of something something, and me.

None of us had the term “sales” in our titles, yet together we were a de facto sales team. And for three days we met, lunched, dined, and talked with an even bigger team of people from the “client side”. 

That’s a sliver of what complex, 7-figure software and services selling looks like, at least with a first-time engagement.

After the contract is signed and the first installment paid, the selling keeps happening, through “services”, whose job is to help the client maximize the value of its purchase by deploying a blend of consultative expertise and custom implementation, as most of us do at our smaller firms. ((Owners of Salesforce implementation and consulting firms need to prepare the for the growing, inevitable competition from Salesforce’s own internal client services team – it’s a lucrative business for an enterprise cloud software platform to enter.))

At numerous points before and after such a deal is inked, both sides teach the other what they know, challenging assumptions, and sparking new ideas.

A thought has been rolling around in my head about a book I read 8 or so years ago, The Challenger Sale. In a sign of its worthiness, it looks as though the book has given rise to an eponymous consulting firm, along with dozens of blog and video reviews. 

But skip the reviews, I can compress the book into one sentence: in corporate B2B sales, the most successful salespeople adopt a consultative approach that challenges the buyer to reconsider what/how they need to buy.

If you view your work as consulting, this is sort of a “captain obvious” statement and a pretty flimsy premise for a book ((And here I have to think of Seth Godin’s recent #mikedrop assertion: non-fiction books should only have to be read for about 10 pages, which is about 3,000 words. Which is to say that the basic concept should be clearly conveyed such that – litmus test – the reader can tell someone else what the entire book is about. This is based on Kindle data)). But for many bearing the job title “sales” or similar, I suppose it’s been quite a revelation. 

To be clear, the Challenger Sale is a good book and worth reading.

But it’s written for the enterprise, for the corporate world “insider”. That world hasn’t fallen apart yet – maybe it never will – but it’s being infiltrated like never before by the independent B2B tech and creative firms. In 2018, VCs invested 251 billion in startups around the world. And for every venture-funded business, there are a dozen more independently owned ones selling software and/or services that solve the same kinds of problems.

And on that note, I’m going to get meta and challenge the Challenger Sale’s premise. Or at least, what the premise implies: that you can’t be the type of person who builds rapport and makes an emotional connection.

You see, the book describes 5 alleged archetypes:

  1. The Relationship Builder creates connection and maintains relationships over time
  2. The Reactive Problem Solver is detail-oriented and a bit OCD
  3. The Hard Worker is a manically hard worker (hard to accept that this is a “type”)
  4. The Lone Wolf is psychotically self-assured and effective…. but not ultimately effective
  5. The Challenger debates and pushes customers and deeply understands their business – which makes this the dead-giveaway winning type.

As if you had to emulate just one. 

Again, these are thought-provoking allegations. You don’t have to be as self-assured and polished as Italian marble to be the challenger that wins big deals. You don’t even have to a smooth talker. Interesting. Nor do you have to be a worker bee. Or detailed oriented, like a good project manager. Or even personable.

In the context of enterprise complex sales.

Why not – why don’t you have to be all these things? Because whatever quality you lack as a challenger will be made up for by your teammates. Because you always have teammates. So you can be even more of a challenger. In other words, even more of a consultant.

Like other indispensable business books (The Million Dollar Consultant, SPIN Selling, Ogilvy on Advertising, Positioning), we have to take the lessons learned from analyzing the enterprise world with a grain of salt when we apply them to the world of the independently-owned business.

Yes, we may challenge assumptions about what and how our customers need to buy, based on a keen understanding of their business and our own. But because we work in smaller teams ((Counterpoint: stop working in smaller teams while keeping overhead low, whatever that means to your business/process)), it’s also possible essential to do so in a way that builds authentic connection based on curiosity, empathy, and goodwill. After all, maybe it is empathy that gives you the finest-grained understanding of how you can help your customer?

On that note – it’s Friday and I imagine that like me, you have worked hard this week catching up after the holidays. Have a restful weekend 🙂