Questions and curiosity as a growth strategy.
Could the answer to cookie cutter marketing lie in questions and listening?
When I started at my current role, I was staring at a blank screen, lost.
I just spent the first month running a variety of pilots on the customer base.
The idea was to test various hypotheses on what would unlock expansion (up-sell + cross-sell) growth in the high-velocity segment.
I tested free trials, extended trials, discounting, (turns out; they all were terrible ideas) (that warrants a separate post) referrals, among other approaches.
I ended up finding an answer to a question I did not ask. What’s an effective communication strategy? Turns out, this was the “why” that needed figuring out first.
I knew, regardless of the tactic, channel, or offer; I'd figured out a scalable over-arching communication strategy to unlock growth.
I summarized it as,
Start a conversation.
Talk to customers like we know them and they know us.
For example, instead of asking do you know about <Product X>, I took the liberty to ask, why are you not using <Product X>?
Do not start the conversation with discounts, prices, or an offer.
I distilled all this learning into one piece of actionable, tactical advice for me and the team I would build.
"Can we lead with a question in every piece of communication we put out?"
Can questions be an answer to unlocking growth? Especially with an aggressive eight-figure target?
I'm not even talking about the conversational marketing babble; this wasn't about the channel or technology.
This was about going back and ripping apart the SEO-driven, product-obsessed, inside-out drivel and replacing them with genuine questions with curiosity.
As is common in marketing, you just keep discovering the most basic things over and over again. Just with different levels of vigor and clarity.
Digging into questions
The Surprising Power of Questions published by HBR under Managing People may well have been published under marketing.
"Questioning is a uniquely powerful tool for unlocking value in organizations: It spurs learning and the exchange of ideas, it fuels innovation and performance improvement, it builds rapport and trust among team members. And it can mitigate business risk by uncovering unforeseen pitfalls and hazards."
What’s the power of questions in sales? Gong studied 500,000 business-to-business sales conversations—over the phone and via online platforms.
It found a strong connection between the number of questions a salesperson asks and his or her sales conversion rate.
The data also shows that top-performing salespeople tend to scatter questions throughout the sales call, which makes it feel more like a conversation than an interrogation.
Chris Voss, the ex-FBI negotiator, knows a thing or two about asking the right questions. In his book Never Split The Difference, he digs deep into the power of questions in a negotiation.
Asking people "why" can put them on the defensive and force them to defend their position. It's a good way to be assertive without being aggressive.
Replace "why" questions with "what" and "how" questions. They are the best words to start a question. "Does this look like something that would work for you" becomes "how does this look to you?"
"How am I supposed to do that?" is one of the most powerful questions, it's asking for help while moving them in the direction you want.
Closer to home, Dave Gerhardt's 1-line cold outreach email is a great example of a question done right.

Back to my experiment.
While my pilots validated the power of the strategy; I still had to put it into action, get results, and achieve scale.
I was mainly concerned about three things
I was worried that customers would face question fatigue
I had to orchestrate questions into campaigns (the funnel nonsense that comes with it plus to pick the right channels)
I also needed a response strategy.
As marketers, we're wired to drive the customer to take action. Sending them off to blogs, landing pages, sign up pages, calendars, etc. But, we, typically, don't have a response strategy (that more sales' territory). But, having a conversation means both sides are listening and engaging. I set aside marketing bandwidth to listen and respond to customers.
Converting questions into dollars
In early 2020, I wanted to put this into action in a big way.
My first big-bet campaign, now prophetic, asked our customers, Share Your Pain with us in 2020; what's the biggest challenge you're looking to solve in 2020?
The answer did not have an option for a pandemic or a recession.
By early March, it was clear that it would be insensitive to continue asking this question.
So much for a grand plan. What a dud.
But it did give us an opportunity. We genuinely wanted to know how our customers were doing.
So, we went back to the same strategy, and asked our customers, two simple questions,
“How are you doing?” & How can we help?
That resulted in an outpouring of responses.
Businesses that were shutting down told us their horror stories. Some were doing fine. Some wanted monetary relief. Some grew their business 4x overnight.
We found out who was doing well, who wasn't, and who needed help. This helped us save a significant dollar number in churn.
Buoyed by the responses, I was celebrating my first win. And a measurable dollar number to boot.
With that momentum, I went back to the entire customer lifecycle and mapped out questions for each part of the life cycle.
Top 10 customer life-cycle marketing questions:
What is the one thing you're looking to accomplish with our product?
Why did you not upgrade? What did we miss?
Did you consider any other product besides us? If so, which ones?
Why did you choose to buy from us as opposed to from our competitors?
What's the one thing we can improve in the upcoming year?
What's the one thing that impressed you the most in the last year?
Which product aligns with your business need, and you would be interested in trying it out next?
Can you write us a review?
Would you like to be a sales reference for other prospects?
Can you refer a friend or business to us?
Insight: The power of questions compound; we got 4 times the number of responses than we would normally, whenever the question followed an action by the customer. Signup, a download, a page visit, etc. Follow up immediately for the best results.
Action: I see your trial expired and you did not upgrade.
Response: What did we miss?
Action: I see your NPS promoter response
Response: What other products are you interested in?
Action: Web activity or competitor web page visits
Response: Are you evaluating X?
For demand generation, we aligned question packs to each product.
For example, if you’re selling an email marketing software, your question could be,
What are your key email marketing priorities in 2020?
I want to send trigger-based or personalized emails based on web activity
I want to improve my deliverability and email engagement
I want to improve lead nurturing through email automation
Other <type in your response>
You’ll have a set of similar questions aligned to email marketing that’s ready to use across channels.
The other side of this strategy is; what questions are our customers asking?
This is a key focus area for 2021. Can we go back to all your customer interactions and pull out 25 of the most asked questions by our customers?
Then, spend the entire year answering these questions with honesty and depth. (save us the SEO-driven, product-obsessed, inside-out drivel)
I'm headlining this for the upcoming year; ask the right questions; answer the right questions.