Ideation: Leveraging the Worst Possible Idea

Ideation is the first stage of Contour’s innovation funnel, and the phase where we generate ideas about what we can innovate on for Contour. As a relatively new lab, we wanted to spend some time engaging with our internal Contour experts to inner source some innovation ideas. We believe that inner sourcing combined with customer engagement and market research are good ways to ensure that we are capturing the best possible ideas in our innovation backlog.

That said, we decided to leverage the Worst Possible Idea ideation technique to get things started.

What is the Worst Possible Idea technique?

The Worst Possible Idea is a Design Thinking technique that enables creative thinking.

It involves:

  1. Brainstorming on the worst possible ideas

  2. Evaluating why they are bad

  3. Flipping them so that a bad idea becomes good by doing the opposite

  4. Mixing/matching/combining the ideas to see what happens.

For more information, this page has some useful guidance and background info on this technique.

Why did we select this technique?

We selected the Worst Possible Idea technique for Contour’s inaugural innovation day because:

  • We wanted to kickstart our ideation activity with a technique that allowed us to think differently, challenge assumptions and traditional boundaries. This is particularly important within trade finance, which is an industry that has no shortage of innovation ideas, but has struggled to put them together and commercialise appropriately.
  • We wanted to create a space where our internal experts could feel safe coming up with a diverse set of ideas. What better way to do this than by specifically asking them to come up with the worst possible idea that they could this of?

How did we implement it?

In order to implement this technique we took the following steps:

  • Mobilised 10 internal participants (largely self-nominated) with diverse skillsets and differing levels of Contour experience.
  • Set the scene with a challenge question about “What’s the simplest feature that would drive our members to log on to Contour?”
  • Set some ground rules for the workshop. Key rules were to declare a judgement/executive free zone, and to respect all ideas.
  • Gave some starter ideas and encouraged our workshop participants to think about ideas that were bad, terrible, stupid and illegal(ish).
  • Took the bad ideas raised through the Worst Possible Idea process (bad idea creation → evaluation → flipping → good idea creation). Note that we separated out into two breakout groups of 5 (to encourage more focused collaboration), and allocated approximately one hour for this exercise.

So what happened?

In all, we got around 40 new ideas (of differing sizes) that we have added to our innovation backlog, which is not a bad outcome for a brainstorming exercise.

In terms of the session itself, after some initial hesitation, the bad ideas started to flow. Taking the bad ideas through the Worst Possible Idea process seemed to work quite well.

For example, one of the most popular ideas that may become a feature that you may see in an upcoming release of Contour, had the following origin story…

Bad Idea – we could entice members onto Contour by providing functionality similar to a popular dating app. This dating app, that shall remain nameless, allows you to log on to identify prospective matches in your close vicinity at the time when you are keen to meet new people.

Why is this bad? While it is good to connect via Contour, our current product offerings do not include dating options…

How can this be flipped to a good idea? Thinking about some of the elements that make dating apps so popular, another way of framing it could be to think about using the platform to find suitable partners for trade finance opportunities that meet your criteria, at the time that you’d like to transact with them.

Good Idea – within Contour, we could provide a “matchmaking” service for our Contour members, where we provide a service for members to find and match with each other for specific services, e.g. Letter of Credit Confirmations.

Key learnings

The Worst Possible Idea technique did help us in achieving our initial goals of getting our teams to think differently, and providing an environment for them to express their ideas in a safe space.

From this exercise, we did learn the following:

  • It is absolutely critical to ensure that the workshop participants have a safe space to express their ideas (without judgement), else you run the risk of not getting many new ideas. We kept our C-suite out of the sessions deliberately, though we were happy to bring them in at the end of the session when we published the results to them.
  • Having a starting set of bad ideas can help stimulate thought. It also gives the team “permission” to go down the bad idea route, which in turn gives them more confidence.
  • Having the team focus on genuinely bad ideas allowed them to think beyond the usual trade finance innovations. Their focus was on using their imagination to make the bad ideas stupid, terrible and illegal(ish). That said, as we explored why these ideas were bad, and how to flip them to good ideas, it was easier to tie these back to more practical trade finance ideas.


Facilitator tips

Prepare a set of tips and suggestions – As a facilitator, you also need to be confident that even the worst idea can be flipped in some way. What can help is to have some worst idea examples and their flipped counterparts ready, as well as a list of suggested ways to flip an idea, e.g. thinking of the opposite idea, removing/doing the opposite of the worst attribute of the bad idea, etc.

Do a dry run – Grab your co-facilitator to do a dry run of the activity so that you ensure that the instructions are clear and that stipulated timelines are appropriate. Dry runs also help you to foresee any potential issues during the actual workshop itself so that you feel more confident during facilitation.

Practice flexibility – Some of our workshop participants struggled to come up with bad ideas (sometimes it’s hard to break habits). While we could have “forced” people to come up with bad ideas, we took the position that the objective of the exercise was to come up with good ideas, so exercised some flexibility with the process.


In summary, I would recommend this ideation technique to those who are looking to break away from traditional thinking and to encourage a free flow of ideas. Just make sure you have a safe space when implementing this!

If you like this article and would like to share your thoughts with us, reach out to our innovation team at .

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