How to solve big problems asking one small question

Critical thinking is a bedrock skill of the modern communicator. The ability to provide plans and advice based on clear, reasoned judgments is a core requirement as organisations strive to cope with increasing complexity and uncertainty. Here are some tools to help provide that critical thinking – writes Scott Guthrie.

As a professional communicator, how often have you been told things like: “You need to develop an intranet”. Or, “this should go out as a press release. Or “sales are down because of X; we need to do Y about it.” And you think: “is that the best channel to use?” Or, “is that the real reason behind the sales drop?” Or, just simply, “what are we really trying to achieve here?”

critical thinking from creative problem solving

Creative problem solving for communicators

Well, in this post, I’ll help you to find the root cause of issues, generate ideas, views and opinions and explore a deeper understanding of what’s being asked and what really needs to be done to achieve the right results. And all by asking one question with skills learned from my four-and-a half -year-old daughter.

My daughter asks questions. Constance asks a lot of questions. Why do we do this? Why can’t we do that? What does X mean?

It’s easy to fall into the dad trap; becoming slightly exasperated with this machine gun questioning. Especially when you know that, invariably, whatever answer you offer will be immediately followed by the further question: but why is that?

One day I sat back and thought about it. I then realised that although her questions are childish in delivery they are far from childlike in their intent to make sense of the world and to challenge it. At their core, they share a function that all communicators should have as a bedrock skill. That of critical thinker. An ability not to take things at face value.

By asking the question over and over again she causes me to think afresh about the subject; re-perceiving an issue by re-interpreting its context. Her ‘why, why, why’ questioning has a relentless quality that can help uncover unexplored depths and limits. Here’s what I learned from her.

Asking: ‘why’ to explore, gather and generate ideas

Thinking more about the function of these ‘why, why, why’ questions I realised that Constance is using them to explore, gather and generate.

  • Exploring: She’s trying to enrich her understanding of a particular issue through exploration
  • Gathering: She’s gathering information to make sense of the present situation
  • Generating: She’s generating ideas, views and opinions internally and with others

And with the ‘data’ from this exploration, gathering and generation process her questions can be used further as ways of:

  • Categorisation: sorting ideas into groups or categories
  • Causality: analysing and capturing patterns of cause and effect
  • Reframing: re-perceiving an issue by re-interpreting its setting

There are probably several types of repeatable question, here I’m going to focus on just two: repeatable and emptying questions.

READ ALSO: Intelligent naivety: Benefits of not knowing how we do things around here

Using serial questions to solve problems

Serial questions are Constance’s speciality. Her go-to for her exploration and my exasperation. These types of question can be repeated forever-and-a-day because the object of the question and its answer are the same kind-of-thing. Here’s an example of how these questions play out:

Why dialogue

You ask the question about something that happened (A) and the answer is another event (B), so the same question can be asked about that in turn and so on.

These types of questions are a great way for communicators to help explore deeper understanding about an issue and help discover a problem’s root cause rather than its presenting characteristics.

It is useful to think about four types of serial question:

  1. Cause
  2. Belonging
  3. Order
  4. Context


Here, the simple question: ‘why?’ can be expanded into ‘what caused this to happen?’ ‘What’s the reason for this?’ ‘What’s the consequence of this thing happening?’


Clustering ideas and issues: ‘Where does this issue belong?’ What other issues belong to it? What bigger thing is this part of? What are the parts of this?


These questions explore sequence and timing. What happened before X? What happened next, after X?


These questions deal with the idea that the meaning of something is most relevant when understanding its context. What’s the context of X? What is the context of that context?


“These types of questions are a great way for communicators to help explore deeper understanding about an issue, and help discover a problem’s root cause rather than its presenting characteristics.”

With a hat tip to Constance, I used this technique recently to analyse a suite of products. In the company, I was consulting for there were more than 200 sub products set across 20-plus price points. The company knew what the revenue associated with the overall product line was, and its associated costs. But they didn’t know which of the 200+ products sold, in what numbers and to whom.

Many of the processes were manual, too: “because we’ve always done it that way”. And, for example in the development pipeline lay 163 improvement suggestions.

However, by talking with:

  • Customers
  • Sales teams
  • Frontline guys in customer services
  • Backroom development team

I was able to ask a lot of ‘why’ questions:

  • Why are there 200+ products when only 22 sell in significant numbers?
  • Why are many of the processes manual – and therefore expensive?
  • Why are we producing this service when our customers have moved on and now expect that service?

Then, delving deeper, and deeper, probing the root of ‘why things were done this way’ and how they might be nudged into a newer, more effective, efficient and appropriate direction.

Again, repeating the ‘why’ questioning I armed myself with hard data and so was able to cluster the 163 improvements around six central tenets. And, provide clear, reasoned judgements as to the importance of these six groups.

If the improvement didn’t fit within one of these categories, it no longer had a place in the development pipeline.


Emptying questions as creative problem solvers

Unlike serial questions, emptying questions have a bottom; an end. I sometimes use these types of question to turn the tables on Constance.

mess dialogue

In the corporate context, unless you’re griping about a mess in the office kitchenette, you can better use emptying questions in:

  • Brainstorming,
  • Idea generating, or
  • Information gathering settings

Try asking questions such as:

  • And are there any other examples?
  • Could you try to list some more for me?
  • Can you suggest some alternatives?

Oh, and by the way, there was no Ruby or Lola. Only in Constance’s imagination.

Critical thinking is crucial to the modern day communicator. When asked to create, for example, we could either exclaim: “brilliant idea, what’s the cost code, I’ll get cracking on it” or, alternatively we could do a lot worse than to explore, gather, and generate ideas and opinions about what the real purpose behind this request is.

It might well involve asking questions to better determine the fundamental cause of the issue, rather than the problem it’s caused.

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IMAGE ATTRIBUTION: The above image: “creative-thinking”, is a derivative of ” More Questions Than Answers” by Tom, used under CC BY-NC 2.0 (some rights reserved).


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