Design Thinking: The Secret Decoder Ring to Transformative Enterprise Technology Deals

Last week I went to a panel discussion in Palo Alto on “Design Thinking”. To be honest, a good friend was on the panel and going was one of those things you do to support your friends. I had a vague sense of Design Thinking – in my mind it was for people with stylish glasses and perfectly unkempt hair who work at Apple and churn out cool consumer products.

Two hours later, I walked out with one of the most compelling approaches I’ve heard in a long time for doing big, strategic deals.

What is Design Thinking?

How many designers does it take to change a lightbulb? Does it have to be a lightbulb?

In simple terms, Design Thinking is an approach for solving problems and creating solutions.

The core is a focus on the user and finding the right problem to solve. In doing so, the process allows for multiple different solutions to come to the surface. The spirit is to identify new ways of looking at the problem. You don’t truly get to the answer until the end of the process – all proposed solutions get reviewed, tested, torn apart, and re-conceived into better forms before being executed.

Sounds interesting…. but what does that have to do with enterprise technology sales?

My Favorite Deals

If you don’t have time to do it right, when will you have time to do it over – John Wooden

As I listened to the panel talk about design thinking I was struck by the parallels to the experience of some of my all time favorite deals.

In enterprise technology most transactions are roughly the same: the prospect has a clearly defined set of requirements and views the salesperson with a wary eye. The salesperson is motivated to sell what the customer wants to buy as quickly as possible, and for sure no later than the end of the quarter.

From time to time it works differently.

Last year I worked with Paul, one of our EMEA reps, on a deal with a Danish company. Originally, the company approached us to purchase a small number of licenses to solve an important but tactical performance issue. A nice deal and straightforward to complete that quarter.

To his credit Paul sensed that there was something bigger. Over the next month, he met with multiple people at the company and learned about a planned re-architecture of their data center. We were not part of that concept, but as Paul talked to people at the company, they began to identify a very different way to conceive of this re-architecture. It wasn’t obvious – only through talking to the product owner, finance, and IT did the broader opportunity emerge.

I still remember the conversation two weeks before the end of the quarter where Paul and I discussed our options. I’d like to say that we both had the foresight to know for sure that a bigger opportunity was coming, but in the end the decision to hold off on the tactical sale and focus on the bigger, more uncertain opportunity led to several sleepless nights.

Fast forward 6 weeks later, and Paul had progressed with the customer to the point where our product was a core part of the proposed architecture. Now all we needed was the CEO’s signoff. We waited, and waited and waited. The feedback we received was that while it all made sense on paper, the CEO was concerned about the risk of the new approach.

Paul went back to the first principles question “what problem are we trying to help them solve?” In doing so, he identified a number of different challenges for the CEO, including his desire to build their brand in other markets. Leveraging this, Paul modified the solution to include joint marketing, something we had never thought of before.

One month later, our deal closed – the largest deal ever in EMEA. The CEO of the company proclaimed it game changing for his company.

For Paul and for me, it held the honor of being the most fun deal we worked over several years of working together. Twists and turns, clarity and uncertainty, it was selling in the best sense of the profession.

What does this have to do with Design Thinking?

Design Thinking Applied to Enterprise Sales

If I had an hour to solve a problem I’d spend 55 minutes thinking about the problem and 5 minutes thinking about solutions – Albert Einstein

Listening to the Design Thinking panel, I was struck me by the parallels to this deal and other similar ones:

  1. Substantially more time than typical on discovery
  2. Synthesizing perspective from multiple stakeholders into a new framing of the opportunity
  3. Patient, iterative approach
  4. Transformative solutions

I both love this approach and also believe it’s not practical all situations – sometimes the best answer is to pick the low hanging fruit.

When and how to apply the Design Thinking approach

Here’s my four suggestions for enterprise technology sales professionals:

  1. Everyone should have a couple deals in their funnel where they’re applying this approach. They’ll take longer, be less predictable and look different than everything else. Sales management: make that OK & expected.
  2. Figure out the pattern for when a transformative deal is worth pursuing. It could be a new market opportunity for the prospect, a champion looking for a personal win, a competitive threat, and so on. Understand what matters to the CEO or relevant business leader.
  3. Don’t rush the discovery process for these deals. Modern sales management drives towards reducing time from step A to step B. Take time to touch different parts of the prospects organization before framing the problem you’re trying to solve.
  4. Have someone take the role of “out of the box questioner” in reviews of key deals. Their role is to look at situation and see opportunities and challenges otherwise not apparent. My experience is that particular individuals have a knack for this – pull them into the process.

I’m interested to hear from others out there who have intentionally or unintentionally applied “Design Thinking” to their sales process.


This post originally appeared on LinkedIn by Ted Stinson.

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