The Question is the Answer
Genuine Curiosity is a Secret to Selling and Serving any Customer
Welcome to the latest entry in The Workaround. You’re in good company with thousands of fellow entrepreneurs and innovators!
I’m Bob, your host. My mission here is to share personal, behind-the-scenes stories of the ups and downs of my career leading tech startups and corporate innovation.
I write to make you think, smile, and discover a shortcut to success or a trap to avoid.
Here we go…
Last week my friend Drew, a sales leader in a high-growth SaaS company, asked me to fly to Philadelphia to be a guest speaker at his team’s offsite event. Most of my guest speaking in the past few years has revolved around telling startup stories, so getting in front of a sales team forced me to come up with fresh material.
Oh, and I’ve never been a true enterprise seller in my career. So, what exactly did I have to offer…?
Drew assured me that inviting a typical sales trainer was the last thing he and his team wanted. Instead, they were looking for some outside perspective to help them develop new ways to overcome client challenges and close more deals.
This post is an overview of my talk. Whether you’re a veteran salesperson or a startup founder just learning the art of the deal, I think the message might be meaningful…
People are Amazing
While I’ve never been a full-time, commission-driven seller, I’ve done quite a bit of selling across my 30 years in business. Business leaders are often on the front lines with customers, and through multiple startups, I always got stuck with being the first seller. Damn, I wish I had learned to code…
For the vast majority of my career, my pitches have been to enterprise clients. In fact, in looking at the 100 most valuable brands list, I have presented to or worked with over 80% of them. That has brought me to a lot of fancy corporate campuses. Highlights include hanging at the firepit at Abercrombie, happy hour at Facebook, presenting my book at Google, and running laps around Nike’s Oregon HQ.
While I’ve had to teach myself the art of sales, one natural interest gave me a boost: I love to study people.
Studying people was one of the first interests I forged as a child. I closely listened to what my parents said, watched their interactions with friends and family members, and tended to hang with the adults instead of going off with the other kids. I was shy but watched carefully—curious to see how the real world worked and increasingly amazed that adults were often more childlike than I expected.
I was attracted to Marketing during business school because it offered the chance to make a living by better understanding people and providing them with valuable products and services. Startups lured me for a similar reason—with the bonus that I could create something new and retain significant ownership of what I built.
And like any skill, the more hours you put in, the better you tend to get. On my personal journey, a breakthrough happened sometime in my 40s when I dialed back on judging people and became more accepting. Credit goes to Robert Greene, the author of one of my favorite books: The Laws of Human Nature. He opened my eyes by quoting another brilliant mind on the topic, Arthur Schopenhauer:
“If you come across any special trait of meanness or stupidity . . . you must be careful not to let it annoy or distress you, but to look upon it merely as an addition to your knowledge—a new fact to be considered in studying the character of humanity. Your attitude towards it will be that of the mineralogist who stumbles upon a very characteristic specimen of a mineral.”
The bold is mine. This passage helps me overcome my tendency to judge. Truly, every person is interesting. My friends and co-workers still make fun of me when I use the “shiny mineral” quote. Whatever—it works!
A Customer Perspective
One of the best ways to study people and improve sales is to put yourself in the customer’s shoes.
For our recruiting business, we recently sought an alternative way to discover and reach out to talent. Lately, LinkedIn seems more interested in developing games and silly A.I. integrations than improving this core function.
I had heard about a software solution in the HR industry that a few other recruiters told me they used. I spent at least an hour looking at reviews on G2 and studying every page and product image on this company’s website. It looked promising, but I needed to see the output of an actual search to be confident that this was valuable for us. Naturally, you had to schedule a meeting to get a demo.
So, I hit the schedule button and was taken through a game of twenty questions, including every way of contacting me, our company size, team composition, revenue projections, and recent PSA test results. Finally, I got to pick a demo meeting time.
A few days later, as I logged onto Zoom to join this meeting, I actually felt a bit giddy. Sure, I was hopeful that this software would help us move our business forward. But mostly, I enjoyed the chance to be on the customer end of a SaaS pitch. This would be interesting…
Not one but two salespeople appeared on my screen. I learned that my meeting was a bit of a training exercise, with a sales manager and a newish hire joining in. We exchanged pleasantries about the weather in our various locations and were off to the races.
The junior seller began by asking me questions—the very same questions that I spent 15 minutes answering in their meeting request tool. After the third one, I stopped him and explained that I had hoped that they saw my responses. I reminded them that I was here to see a demo and a very specific use case.
That was the cue for the manager to jump in. I guess I’m a tough customer. He replied that they would be happy to schedule a demo. Ugh…
I took a deep breath and tried to say this in the most friendly way possible: “Guys, this is the demo meeting…If we’re not going to see your software today, there won’t be a second meeting.”
Five seconds later, they were screen-sharing a demo. I asked them to perform a talent search using a current project to evaluate the output. I immediately saw this was not right for us. But they didn’t pause to get my feedback or ask what specifically I might be looking for. I thanked them for their time and said that this was not the right solution for us.
I’d bet they were happy to be done with me, but I hope that the new hire learned something: Stop repeating the script and instead have a real conversation. Genuine curiosity is usually the first step.
Curiosity is the Key
Give this a try: The next time you go stand in line at Starbucks, walk through an airport, or have a meeting with your creative agency—take a deep breath and think of yourself as an alien who has landed on Earth for the first time.
You’ll see and hear things in a new way and be more present in the moment rather than swirling with thoughts in your own mind. It’s also a bit funny, as you’ll see how ridiculous most of us are most of the time. Just try not to laugh out loud.
Webster defines curiosity as “a strong desire to know or learn something.” Sales is about creating value for a customer, but you can’t create value until you know what’s valuable to them.
“Curiosity has led many a man and woman into the valley of serious wealth.”—Felix Dennis
There are so many reasons that curiosity is the killer app in customer conversations:
Good questions = Good discussion—Get the ball rolling on something a lot more important than the local weather and sports franchise.
Break the script—Clients are familiar with how software sales works by now. They gird against the onslaught of scripts and tricks (“You know, Bob…Good point, Bob”). But questions overcome their defenses and keep them engaged.
Unearth emotions—The secret to great negotiation is understanding the other side's feelings. Those feelings drive thoughts and decisions, but they can only be uncovered by asking good questions.
Curiosity communicates strength—People who are curious exude confidence, intelligence, and caring, which all add up to trust.
Let ‘em talk—People love to talk about themselves, so wind them up by showing interest and listening.
Get out of your head—Clever questions and careful listening help quell the unproductive voices in your head and get you into theirs.
In summary: Shift away from “I have to do my script in five meetings today” and instead think, “I get to have five interesting conversations with new people today.”
Less Why, More Warmth
Easy to say, but how do we start? What are the great questions?
It would be easy to trot out the “5 Whys” framework. We discussed this at the training event last week. And we all generally agreed that it’s too broad, makes the customer feel like you’re probing them, and is so commonly known that they think it’s more gimmickry. You risk losing trust, which is everything.
As an alternative, I take inspiration from 36 Questions to Fall in Love.
The 36 Questions was first popularized in the New York Times nearly ten years ago. Psychologists discovered that prompting couples with insightful questions can speed up the mating game.
Typically, you start with easy onramps like, “Given the choice of anyone in the world, whom would you want as a dinner guest?” and gradually accelerate to “When did you last cry in front of another person?” This is much headier stuff than swiping left and right! And if the date isn’t going well, taking a flyer with a big question might shake things up and allow both of you to be more “real”.
None of these questions feel scripted—although at one point there was an app that you could peek at under a restaurant table while with a date—but you can create your own favorite questions to unlock insight. Say, for example, that you work in enterprise sales for software that’s used for e-commerce. Some juicy questions might include:
What’s your top-selling SKU?
Are there elements from your current process or partner that you wouldn’t want to lose?
What’s different about the culture at your company?
What led you to your current role?
(And my all-time favorite) Of all the uses of your day and salespeople eager to speak with you, why choose me?
As I shared these examples with Drew’s sales team, they quickly turned away from me and toward each other. They began to trade ideas and share questions that worked well for them in the past. They smiled and laughed and seemed excited to use these new questions when back at their desks.
I still had several slides left to present, but I slowly eased down into my chair and just watched the show. For any training to stick, the students have to make it their own. Mission accomplished.
A Life of Curiosity
Have you ever played the computer game Civilization? A key part of this game is exploring a darkened map. Your character moves to bring light to the map, unveiling new land, rivers, mines, and other players’ cities. The outcome may be good or bad, and either way, we enjoy the challenge of dealing with it.
I increasingly feel like this each day in the “real world.” I’m often excited to see what emails will appear in my inbox, what new substack posts or podcast episodes will appear, and what our customers will say about our next proposal or creative presentation.
More recently, my curiosity led me to learn about mindfulness and “watching” my thoughts and reactions. So today, I have new questions—call it an “expansion pack”: “Why did I react that way?” “Where is this emotion coming from?” and “What made me answer this question as I did here!?” “Heck, where did this training idea come from?”
Life often feels like a game, with infinite results that will unfold and keep things interesting. Our curiosity drives us to keep playing and exploring the frontiers of our maps. It’s one of the marvels of being a human.
I’m excited to see what I write next week. I hope you are, too.
How we might work together…
Are you interested in launching your own consulting or service business or need help taking your current services business to the next level? Fleet is our holding company for services, and we’re actively looking to build business partnerships with winning leaders. Let’s talk!
My team and I lead Hearty, a boutique recruiting service that helps tech-forward companies hire proven talent. Our senior team of operators sources and screens, saving you time and money. When you need help, let’s chat.
Need help with a software project? Perhaps a product MVP, a project that requires outside help, or a fractional CTO for key strategic decisions? Our team at Shipwright Studio has worked together to build multiple successful startups, and we love helping leaders turn their dreams into reality. We're the team our clients trust for software built to last.
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Feel free to schedule a time during my Office Hours to discuss questions, feedback, networking, or any other topic!
BONUS: Cool Content of the Week
A little something I found meaningful. You might agree…
Leading with Questions
Learning to ask great questions and listen well is not only important for business development—it’s a winning strategy for leading people. And no one is better at making this point than Bob Tiede in his best-selling book, Leading with Questions. I was lucky to meet Bob through a random LinkedIn connection about a year ago. He kindly sent me his book, and I devoured it.
What I love most about asking my team questions as a leader is that it sends the message that “this is your business, and I’m just here to help.” It forces me to come into the discussion with a mentality of, “What can I ask that helps them get to the right answer?”
Two of my favorites are: “What do you think?” and “How can I help?” Try it! I guarantee you’ll have a productive discussion, and your co-worker will come out feeling better than before the meeting began—which is kind of the whole point…