Questions, Not Answers: Keeping Marketing On Track

Posted on Oct 20, 2016
Reading time: 5 minutes Tags: Strategy Planning


Real progress comes from clearly defined obstacles or problems. Challenging working assumptions with fundamental questions on a regular basis is an incredible way to stay focused._

There’s nothing uniquely 21st century about innovation, or technologically- driven efficiency. Even hockey-stick growth has been around for over two centuries.

Graph via OurWorldInData

And while there was a less espresso involved, the type of people behind innovation hasn’t changed. The industrial revolution, which kick-started global growth, wasn’t primarily driven by scientists like Isaac Newton. It came from people in the factories, not laboratories, contending with real-life problems.

According to Matt Ridley, during the industrial revolution, “ scientists were the beneficiaries of new technology, much more than they were the benefactors.”

Yarn prices fell through the roof because of the spinning jenny, which was invented by a weaver. The steam engine, invented to remove water from tin mines, was created by four developers, three of whom had zero scientific background.

Entrepreneurs look at obstacles and see a sign that says “ fix me “. There’s a glaring problem that they encounter in their day-to-day work…and they know that something can be done about.

“If I had an hour to solve a problem and my life depended on it, I would use the first 55 minutes determining the proper question to ask, for once I know the proper question, I could solve the problem in less than five minutes.”

Albert Einstein

Working at a startup, means plugging away alone. Despite all-hands meetings and regular discussion sessions, at the end of the day, you do you. You decide what works, what to prioritize and what to change. And then you go at it full steam. Stopping yourself and asking the right questions is critical – it puts up a big f**king stop sign that screams “why?!”.


Dropbox’s legendary referral program was the result of three questions.

Question #1: Drew Houstan at Dropbox looked at user acquisition cost and asked “ is this working“? At $300/user for a $99/year product, it wasn’t.

Question #2: Then THEY looked at their user base and asked “ when do prospects actually look for us “? Since this was a new product category, customers weren’t actually looking for them – they were hearing about Dropbox from friends.

Question #3:How do we tap into that “? Friends hear about Dropbox from friends. So Dropbox incentivized people to tell their friends about how awesome Dropbox was.

It worked.

In 15 months, Dropbox shot from 100,000 users to 4 million. 55% of those signups came from viral features.


I regularly schedule a 30 minute window into my week to challenge myself on both high and low level issues. The steam engine was the result of a concrete issue. With digital marketing, you need focus to identify those concrete problems. Here are some of the questions that I try to regularly ask myself:

  1. Who is my target? Who am I going after? What is the buyer persona? Am I going after the right audience? Is it defined? Am I selling a solution to high-level managers when it’s really a landswell effect led by actual sales teams that will help me penetrate the market (ala Yammer)?
  2. What does my target want? Do I understand their needs?
  3. Where is my target? Do I have the right channels? Am I messaging right on those channels? What’s the best way to get to him?
  4. How am I helping him? When I look at his needs and my marketing efforts, am I ensuring that I am helping him at every step of the way? Does my content provide value? Am I pushing him into a funnel for something he doesn’t want?
  5. How does my target conceptualize my product? Do I understand how they conceptualize their own need. We spent months at Freightos trying to sell “instant freight quoting technology” to freight companies. When we asked our best sponsor at a huge company what he was looking for, he called it “freight rate management” technology. Right buyer, right value, wrong language.
  6. What am I tracking? How am I ensuring that what I’m doing is working? What am I tracking? Is the KPI that I found actually representative of what I’m trying to measure? For years, I was tracking homepage visits as a mark of brand visibility (a notoriously difficult thing to track regardless). Over time, I shifted over to earned press mentions and branded organic traffic search terms. I’m still working on it.
  7. What can I cut out? It’s tempting to constantly add more acquisition channels, content ideas, events…anything. At some point, you lose focus. For us, social media wasn’t converting into a huge pipeline…challenging ourselves into honestly assessing the channel meant less time wasted on it. There’s a reason Superhuman is constantly cutting out one channel.


I adore reading about marketing online. I love GrowthHackers,Inbound.org and – my new personal favorite – zest.But a so many articles today are quick solutions ( “10 ways to optimize CRO” or “5 awesome email subject lines” ). The front three pages of those sites alone offer 505 tips, tricks, examples and templates, based solely on the headlines with numbers.

That’s 505 answers that are being viewed without specific questions in mind. Which is totally fine for casual browsing or random strokes of inspiration. But it’s not how you methodically scale a marketing machine.

Asking the right question ensures that you’re consuming the right content. It ensures that your team is aligned on the correct metric. It guarantees that you relentlessly pursue a target and make it happen. That you don’t rest until you get that steam engine, spin that cotton or pick the field.

Questions and obstacles changed modern commerce, gave us cellphones, the Bunny Rabbit wine opener and – yes – the spinning jenny. And they can make sure you’re working right.

What questions do you ask yourself?