To Succeed As an Intrapreneur: Ask the Right Questions

To Succeed As an Intrapreneur: Ask the Right Questions

Gray Somerville

Gray Somerville

Einstein once remarked that if he had an hour to solve a problem and his life depended on it, he would use the first 55 minutes determining the proper questions to ask.

This comment highlights a key insight into the creative process: if you want to have better ideas and insights, ask the right questions.

An excellent illustration of this principle comes from the cargo shipping industry. In the early 1950s cargo shipping seemed to be dying. Costs were rising and delivery times were getting worse due to port congestion. Meanwhile, air freight was getting faster and more efficient.

At first, the industry responded by answering the question, how can we make shipping more efficient? They built faster ships. They built more fuel efficient ships. They built ships that could operate with a smaller crew. However, despite these efforts, the improvements were insignificant.

After failing to solve the problem, the industry asked a new question, how can we make loading the ships more efficient?

The answer that emerged was the now familiar cargo container – an elegantly simple innovation that resulted in a four fold increase in shipping throughput, the salvation of the industry, and dramatic acceleration of the global economy.

Let's look at three more examples of how asking the right questions focused creativity and changed the outcomes.

So again, as all of these examples illustrate, the key to more and better insights is to ask the right question, but how do we do that? To ask the right questions, we need to apply the following three basic principles:

  1. Define the question that is currently being asked.
  2. Identify the assumptions that the current form of the question contains.
  3. Restate the question without the unnecessary assumptions.

For example, if we had been part of the NASA “space pen” team, applying this process might have looked like this:

Simple, right? And yet most individuals and organizations fail to ask the right questions. I’m not exactly sure why this is, but I suspect that it’s because both schools and employers tend to reward our ability to answer questions more than our ability to ask them. Whatever the cause, we all have room for improvement when it comes to asking the right questions. Following are three simple things we can do to elevate our game.

Say it Back – Develop the active listening skill of “saying back” the other party’s question. This will make you and them more aware of the current framing of the question. For example, when you’re in your next meeting, listen carefully and then say something like, “It sounds like the question we’re trying to answer is ….” Note that this technique works equally well in written communication. In fact, if you want to write a really good response to the next confusing email request that hits your inbox, just try starting your message with a message that reads, “Let me make sure I’ve understood your question before I offer a response.”

Probe for Questions – The Q&A portion of most meetings is shockingly weak. “Any questions? No? Great! Let’s move on.” Work to strengthen your Q&As by giving everyone a little more time to respond and also by really probing for good questions. For example, rather than just asking, “Any questions?” you might try calling out specific individuals (e.g. “How about you, Sam?) and zooming in on specific topics (e.g. “Does anyone have questions about the technical aspects of this project? What about regulatory issues?) One final tip is to end a Q&A session by asking, “What are the questions we haven’t asked but should have?”

Make Good Questions Part of the Job – A final suggestion for developing the habit of effective questioning is to add a “What Are the Questions We Should Be Asking?” section to the agenda of recurring meetings and status reports. Peter Drucker observed that “what gets measured gets managed.” By making good questions a part of the weekly report, we proactively manage the development of our questioning skills.

In summary, here are three key takeaways from this lesson:

  1. If we want to have more and better insights, we need to ask more and better questions.
  • Asking the right question is as simple as:
    • Defining the current statement of the question,
    • Identifying all of the unnecessary assumptions that are embedded in the current statement of the questions, and
    • Restating the question without the unnecessary assumptions.
  • We can develop the habit of asking good questions, by:
    • Saying back the questions we are hearing to make them explicit,
    • Probing for questions during Q&A sessions, and
    • Making good questions part of the job by including them in our recurring status reports.
Gray Somerville

Gray Somerville


Gray Somerville is a serial entrepreneur, innovation expert, and LaunchPath’s CEO. Besides LaunchPath, Gray has helped launch and lead three other successful startups including Telogical Systems and Adacus.