User Testing with Senior Executives

You’re building an enterprise product, and have to get feedback from potential clients with high level titles. Can you really just show them a 30-minute prototype?

In enterprise services, we have this myth that being professional with your customer means acting like you have having under control.

Well, in practice, most of us already feel this way in most circumstances… But there’s an especially sharp way that it shows up in b2b — When we’re trying to sell into the VP or C level of a massive account, there’s incredible pressure to act like we Have The Answers.

So what does Building User Intimacy at 30% confidence look like when we’re talking to senior executives?

Case Study

Several years ago, we worked with this development studio, we’ll call them “Transara”. They previously custom-built solutions for the repair and servicing industry, and wanted to create their own standalone software product for HVAC companies because they saw an enormous opportunity among prior clients who didn’t have a comprehensive way to migrate from paper to digital.

Like many companies, they started at around 30% confidence. And their problem was that early on, they needed to test with CEOs of HVAC businesses to learn what was important — but but it was so early they had absolutely nothing to show them.

When “Navon”, the founder of Transara, came to us, he was stuck in a loop. He had nothing that felt professional enough to put in front of CEOs, but also couldn’t really build anything without talking to them.

We told Navon to just book calls with the 2 HVAC business owners that he could get ahold of through his existing network. (This took some pushing :D)

Then, he and his team build a quick outline of what they had in mind so far, including sketches of potential executive-facing dashboards and lists of features. None of it was beautiful or accurate: it was all about 30% confident.

But, the one thing it WAS, was clear.

When Navon’s team got into the calls, they were simply honest. They shared that they were a dev lab that had the opportunity to build a standalone backoffice HVAC solution.

They used the mockups to quickly communicate their overall goals and intentions, without implying or pretending that they already had any answers.

Then, most importantly, they asked the CEOs for help to work out a solution.

What happened was that the CEOs LOVED it.

They were living the exact same complex, uncertain, mess that the Transara team was stuck in. Except for them, it was their job day in and day out.

The owners were, in fact, over the moon that here came this team with technical development capabilities that their HVAC firms obviously didn’t have, determined to solve one of their biggest information management problems alongside them. And instead of being frustrated that Transara didn’t have answers, the team’s very willingness to be open about questions made actually made Transara look far more credible and trustworthy.

In other words, after being terrified for weeks of coming across as unprofessional, Navon instead established a rapport with these CEOs that he’d never had before.

Following that energy, they were able to leave the call with three things:

1) A request from the CEOs to be ongoingly looped in to the development process and commitment for future collaboration

2) A soft presale

3) Introductions to other HVAC business owners with similar problems

From there, Transara was on a roll, and launched their product the following year.

Techniques

The biggest mistake I see when people target large enterprise accounts is assuming that because the client is large and the deal size is large, then the relationship needs a commensurate amount of polish.

In practice, if you are tackling a messy problem, nobody feels the messiness more acutely than the client themselves. This is only MORE true when you move into senior leadership.

The purpose of senior leadership is to inhabit the biggest uncertainties. They KNOW there isn’t a simple one-step solution: if there was, a less senior person would already have handled it.

So the overall lower confidence level of the project does not reflect poorly on you.

Instead, you build user intimacy with the senior leader exactly the same way that you do it with any other user: show your hand, ask your questions, listen and adapt. The only difference is that you hold the conversation at the strategic level instead of the design level.

To be “professional enough” when user testing with senior execs, you DO need to:

• Come in when you’re at least 25%-40% confident
• Respect their time
• Communicate clearly
• Nail your basic writing & presentation etiquette
• Use a prototype that is visually clean and well formatted (it still shouldn’t be too polished, it just needs to not have uneven text boxes spilling all over the place at the beginning. You can still do ugly ad hoc changes)

You do NOT need:

• A complete idea that preemptively addresses all their concerns (it’s not a sales meeting!)
• A beautiful powerpoint (it will just make them think you are actually serious about that specific mediocre idea)
• To act overconfident or overestimate your capabilities too much. Do be confident, but they are used to tradeoffs and risky bets, and won’t give you accurate support if you imply you can easily pull off things that you can’t do

Other techniques for testing with senior executives:

- Be transparent — tell them what you have, what you need, and what you’re trying to achieve. They are used to partially complete solutions.

- Be succinct — avoid overpitching, and get quickly to the above.

- DO make real time changes in response to the conversation. There’s often a temptation to put this part aside due to being intimidated by the conversation, but don’t give in to it: they will appreciate the speed at which you modify, and it will make your progress 5x faster with the limited time you have.

- Generally, don’t use simulation testing, because they don’t have time for it — just jump to the purpose, show the prototype, and go to dialogue. Relatedly, don’t get bogged on details that you can get from less senior people.