by Jesslynn Shepherd

“You’re such a laid back, go-with-the-flow type person,” said no one ever about me. I’ve always been an A-type adjacent individual – I like making lists and plans made out of more lists. Having a clear cut path has always been important in making me feel in control, whether in life or in a work project.

*2020 has entered the chat*, and all subsequent life plans essentially went to sh*t. But instead of feeling that dreaded sense of panic when I face uncertainty, I actually felt OK. Of course, that’s not to take away from the terrible loss and pain that the pandemic has inflicted on millions of people around the world, as well as a small sense of fear that comes with having a husband who is a healthcare worker on the frontline. But when it came to my very neatly laid-out 12-month plan, I was relatively cool about it falling apart.

What has led me to the sweet, sweet taste of that elusive laid-back feeling I often pretend to exude? It could be that the Capetonian way of life is finally rubbing off on my inner Jo’burg neuroticism, but I think it’s more down to the practice of learning to embrace uncertainty as part of the working process at dY/dX.

Uncertainty is a core component of design thinking and was probably the most difficult aspect I struggled with when I first started adopting a design thinking approach. I would often ask Nevo, one of the dY/dX partners who I work with, “Doesn’t it freak you out that this is such a big project and we don’t know what the end solution is going to be?” His answer was always a very casual “no”. My response would be an attempt at an equally chill, “Yeah, cool, me neither”. Like when you respond to an email with “no worries” when in actual fact you have very many worries.

It’s well documented that most people are averse to change and ambiguity – they may say otherwise in an attempt to be perceived as that free-spirited, nothing-phases-me-because-I’m-so-chill type of person, but when it comes to actual actions, you’ll find it’s very much true. But 5 years of design thinking later, I’ve accepted uncertainty as a key part of any successful project. And now, part of my everyday life.

Uncertainty is such a big part of the design thinking process because you learn to never start with a solution in mind. You put the user and the research at the centre, and that often reframes your thoughts and the subsequent process to allow for the best solution (if any) to take shape.

Take for example a project we worked on for a client that launched a budget hotel offering. The client had bought out a small hotel chain that offered accommodation known for its pay-by-the-hour business model, and was therefore associated with unwholesome services with the same flexi payment terms (no judgement here). We knew we wanted to reposition the brand and find out more about the customer, and had a hunch that it may be towards on-the-road business folk. But instead of our initial assumption where we were thinking along the lines of fancy Nespresso machines and Showmax VOD, the user research led us to a very different type of business requirement. One that favoured easier booking processes that allowed for customer accounts rather than paying upfront. Mind blown. This being a good example of what David Kelley, IDEO founder, promotes by saying “fail early to succeed sooner”.

From our user research, we identified 3 core user personas, with the largest opportunity being a business traveller that doesn’t book accommodation themselves, and doesn’t have access to a company credit card. For those who are familiar with the usual snail-pace in which corporates move, you know that payments are not quick and easy, and often have to go through a 30+ day payment process. But the problem is that these travellers often need to book accommodation last minute while on the road, and our client worked on an upfront deposit payment model. So the biggest barrier to booking accommodation with our client for this user group was that the traveller had to pay upfront rather than allowing the company to open a credit account. Had we not allowed for uncertainty within our process to give us the space we needed to identify new opportunities, we would have ended up with a bunch of expensive features that nobody really wanted. As a result, by making the service easier for businesses to use, we opened the door to allow for a whole new user market. 

Don’t get me wrong, design thinking isn’t about “winging it”. There is a process to design thinking and many tools that can be used to get things going. But it’s an inherently exploratory process that allows you to make unexpected discoveries along the way, and encourages you to dive into those discoveries should they challenge your initial assumptions and potentially lead to a more promising opportunity. These new avenues of possibility should lead to adjustments to any initial plan. And yes, it can feel a little chaotic to experience this type of open-ended, iterative approach, but things eventually come together and make sense over the life of the project. It’s really this design thinking approach to challenges that have made me feel comfortable with being uncomfortable, removing a lot of the stress of not knowing where I will be in a year’s time, and turning that into a feeling of excitement and curiosity. Plus, isn’t it kind of boring to know what’s coming next?

So when it comes to navigating the challenges of 2020, which has, and will continue to, essentially change the trajectory of most industries, the way we work, the way we shop and how we make decisions, I’m excited to find the opportunity in these challenges. So is design thinking the personal therapy I’m being paid to do? Maybe, my friends. Maybe.

Jesslynn is a project lead and consultant at dY/dX.