9 Ways to Think More Obliquely and Develop Your Ideas

Tom Barrett
Startup Grind
Published in
9 min readSep 24, 2016

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A pencil saved my life

In “The Rules of Genius, Rule #9: Approach answers obliquely”, Marty Neumeier outlines a range of thinking strategies to explore a challenge in new ways. These strategies are always great to have in your toolkit when exploring a new project.

In an effort to build on Neumeier’s thinking I have expanded on his suggestions by adding some additional thoughts and links to help you take a comprehensive approach to thinking obliquely.

1) Think in metaphors

A metaphor is a link between two dissimilar things: “The world is a stage.” By equating the world with a stage, you can more easily imagine that we’re all actors playing a part an insight you might not have had without the metaphor.

There are some great further ideas on this post about metaphorical thinking:

“When you use a metaphor to link two ideas together, you are combining elements that have little or no logical connection. By breaking the rules of logic in this way, metaphors can open up the creative side of the brain — the part that is stimulated by images, ideas, and concepts.”

Here is a great example of how you might use metaphorical thinking to explore the concept and challenge of collaboration.

Doug Belshaw recently shared how as part of his work with We Are Open they used metaphors to help explain the Creative Commons.

2) Think in pictures

Visual thinking can strip a problem down to its essence, leading to profoundly simple connections that language by itself can’t make. The ability to draw stick figures, arrows, and talk balloons is all you need to think visually.

Visualising your ideas in a simple way is a strategy I regularly use when working with groups. I encourage them to draw their initial idea on a post-it note and share it quickly with a colleague.

This quick sketch and share, precludes us from investing too deeply in a given idea and does force us to be open to hearing how to make it better from our peers.

As we don’t have all the answers, and our idea is only roughly formed we are more likely to be open to advice. Take a look at this introduction to the “Basics of Visual Note-taking” for some other info.

You could also follow the “5 Sketching Secrets of Leonardo Da Vinci”: Look for new combinations; Engage your imagination; Collaborate with others when you sketch; Use annotations in your sketches; Sketch your ideas out 4–5 times.

3) Start from a different place

When you grab for the “correct” solution, brilliant solutions will elude you. You’ll get stuck in the tar pits of knowledge, unable to free your mind of what you already know. The easiest way to escape this trap is by rejecting the correct solution — at least temporarily — in favor of the “wrong” solution. While the worst idea can never be the best idea, it will take your imagination to a different starting place.

Typically when we are exploring new solutions we have an invisible filter that is usually marked “safe”. Even with encouragement it is very hard to break that safe set and come up with a new set of ideas beyond the realms of feasibility.

We rarely spend time in this fanciful place and so find it very difficult. But coming up with your 5 Worst Ideas to solve a problem is a great way to let the pressures go a little.

It often leads to lots of laughs and by inverting some of those negative elements there is often a kernel of something great there. There are some nice little activity steps in this post about it.

4) Steal from other domains

If you steal an idea cleverly enough, the theft will go unnoticed. While stealing is not the same as pure imagination, it does take a mental leap to see how an idea from one industry or discipline could be adapted to another.

One of my favourite stories that illustrates this method is from the reform work that occurred at Great Ormond Street Children’s Hospital in London.

“Recognising the similarities with the handover disciplines (in emergency care) visible in the pit of a Formula One racing team, they invited the McLaren and Ferrari racing teams to work with them to examine how their processes could be more structured and effective. They went out to the pits of the British Grand Prix, met Ferrari’s technical managers at their base in Italy and invited some of them to come and observe their handovers at Great Ormond Street…The input of the Formula One pit technicians resulted in a major restructuring of their patient handover from theatre to the ICU.”

It is a fine example of a group being able to see beyond their own discipline in order to seek out innovative ways to solve existing challenges.

5) Arrange blind dates

Great ideas are often two ideas that haven’t previously been introduced. Using a technique called “combinatory play,” you can throw unrelated ideas together to see if the create a new idea. Look for combinations that have a natural fit.

Maria Popova shares a post on Brain Pickings about the elemental work of combinatory play in the creative process, of course referring to Einstein’s take on it: “Combinatory play seems to be the essential feature in productive thought.” However Popova shares a lovely introduction to the concept herself:

“For as long as I can remember — and certainly long before I had the term for it — I’ve believed that creativity is combinatorial: Alive and awake to the world, we amass a collection of cross-disciplinary building blocks — knowledge, memories, bits of information, sparks of inspiration, and other existing ideas — that we then combine and recombine, mostly unconsciously, into something “new.” From this vast and cross-disciplinary mental pool of resources beckons the infrastructure of what we call our “own” “original” ideas.”

6) Reverse the polarity

Write down as many assumptions about the problem as you can think of. Reverse them. Think about what it would take to make the reversed assumption true. Some of these may lead to new ideas.

Assumptions are often the baggage that we bring along on a journey of change.

The way things have always been “done” has a powerful influence on the decisions we make and the ambition we have. Give assumptions too much leeway and they can stultify organisational change.

When I am working in schools there are often many assumptions being made because the challenges are often deeply complex. We need to be open enough to Name them and Challenge them.

“Human nature is such that when we assume we know how to do something, we perform the act without much thought about the assumptions we make. History is replete with thousands of examples of what happens when people don’t challenge assumptions.”

This is taken from What Monkeys Teach Us about the Assumptions We Make, by Michael Michalko the author of Thinkertoys: A Handbook of Creative Thinking Techniques. Make sure you explore the post and read the great story of where assumptive practice can blindly lead us.

7) Ask simple questions

What else is this like? Who else believes this? What if I changed it slightly? What can I eliminate? What can I substitute? Is this the cause or the effect? What if I changed the timing? What if I made it bigger? What would happen if I did nothing?

No doubt this is linked with our ability to challenge those assumptions we hold, asking questions is, in my humble opinion, the pre-cursor to any creative process, rarely are they missing.

We could look to people like Da Vinci for his insatiable curious mindset that set him apart from his peers. Also you should look at the work of Eleanor Duckworth and her work on “Critical Explorers” which encourages us to use simple questioning to get out of the way of children’s thinking.

Additionally I would highly recommend reading Alex Quigley posts about questioning in the classroom, this popular post on strategies will help with the practical side of things.

Furthermore his blog post: “’Question Time’ and Asking ‘Why’” is an:

“exploration of one of the simplest, but most fundamental, aspects of how students learn and how students display their learning in lessons: higher order questioning. It is simply about getting students to ask ‘why‘ and an exploration of the crucial value of such deep questioning.”

8) Watch for accidents

You can sometimes make the best discoveries when you’re searching for something else. Pay attention to anomalies, surprises, or feedback that confounds your expectations. These can open up exciting new areas of inquiry.

In this lovely exploration of accidental discovery in science on Brain Pickings, Alan Gregg is quoted:

“One wonders whether the rare ability to be completely attentive to, and to profit by, Nature’s slightest deviation from the conduct expected of her is not the secret of the best research minds and one that explains why some men turn to most remarkably good advantage seemingly trivial accidents. Behind such attention lies an unremitting sensitivity.”

9) Write things down

Not all your ideas will be worthwhile, but they might trigger new ideas. Make a list of your thoughts as you work through any problem. Keep a notebook, a sketchbook, a scrapbook, or an idea file. A pencil can be a crowbar for lifting ideas from your subconscious.

I like that description from Neumeier of the pencil being an idea-crowbar. In this particular field Da Vinci has set us some incredible precedent.

Thomas Alva Edison has much to offer as well in this particular note-taking technique. In a post that explores Edison’s creative process in further detail it suggests that historians have discovered over 3500 detailed notebook belonging to him. In those books there are over four million pages of ideas, sketches and notes he made.

“What is immediately apparent is that Edison’s mind wandered through a vast spectrum of unrelated projects in an apparent free flow of associations. This is a critical point to understand. The mind grows through the number of connections it can make. Genius finds relationships between the most diverse things….Frequently, one of Edison’s inventions would spawn another in an unrelated field, which in turn would give rise to another in a different area of interest. It’s as though by pushing, experimenting and thinking in one direction, Edison simultaneously benefited in all the other projects that he was working on. This points to the concept of the holographic mind. Affect one part and you affect all the parts. Nothing is wasted.”

Whether we are exploring a period of curriculum enquiry with our students, tackling a challenge in our organisation or embarking upon creative development of some kind, our thinking, and the tools we use to do it, need to engage and provoke as much as possible.

Typically we need to be able to see complex themes or challenges from as many different angles as we can. These nine strategies or cues certainly will help to ensure we are being as thorough as we can be.

This type of multi faceted thinking strategy not only provides us a more comprehensive creative approach, it also gives us all the best possible chance to break new ground and reveal opportunities that have yet to be discovered.

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Since writing this I have made this handy little graphic of the nine strategies for thinking obliquely and divergently. I hope you find it useful.

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Tom Barrett
Startup Grind

Re-discover the curiosity you had when you were 6. Learning, Leadership, Innovation. Join Medium to support my writing https://buff.ly/3RtxqpE << Affiliate link