How can Design Sprints foster creative confidence — Design at Pipedrive

Vanessa Mateus
Nov 26, 2020 · 7 min read
Pipedrive designers during a Design Sprint
Pipedrive designers during a Design Sprint
Pipedrive designers at a design sprint — photo credit Hannes Seeberg

Having the freedom and courage to fail/take creative risks and the knowledge that all of the ideas you create have value. — Unknown, at OpenIdeo

At Pipedrive, designers have long been adopting Design Sprints as a part of our Design Process. We understand the potential and have devised ways of tackling challenges at different stages of projects. Also, it is part of Pipedrive’s culture to focus on their people, even and especially while trying new things. We want to increase Creative Confidence in our teams regardless of their knowledge of Design and bring out the creatives in everyone.

Many of you probably know Design Sprints, their format, and their methodologies. For those less familiar, in a nutshell, it is a framework of activities and exercises that help to brainstorm and solving some sort of challenge. They can be used for all departments, not just Design and Product. Perhaps an epic in the backlog, a new strategic piece of work, or even a blocker.

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Design Sprint 2.0 by Aj&Smart

Jake Knapp was very clever when he coined Sprints. They are very efficient. But to be truly successful, they must be adapted, and thoughtful of the people attending them. What if there are one or more people with some sort of disability? Or even people that never participated before and are completely unaware of what they are getting into. What if there are people with higher degrees of anxiety? This is why it is important to have several moments (warm-up exercises) throughout the Sprint to help relax the self-censorship and introduce some fun, which is a lesser talked issue when we speak of Design Sprints as we tend to focus more on the results and outcomes.

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Pipedrive designers collaborating at a Design Sprint — photo credit Hannes Seeberg

In realizing the adaptability of Design Sprints we can think of which specific parts of the methods we need for different outcomes. Getting faster results and still aligning the teams in the process and thus increasing our Creative Confidence.

We actually end up splitting the Sprints depending on what we need to achieve, like doing Download Sprints, which we use for example at an initial stage of a new project. We get all the people involved that can divulge what data they know about a certain problem space. We bring in PMs, data analysts, researchers, and developers and try to answer the Why, How, What, Who, and Where questions. There are many ways of adapting Sprints depending on the challenge and the desired outcome and it is important to also adapt the warm-up exercises and to create more moments that increase the Creative Confidence of the people participating in these sessions.

Many times, whenever we have a new brief or a new project, we might have automatic thoughts such as do I know enough? Can I actually solve this challenge? To different degrees we all do, no matter how much experience we have. These are nothing but shared human fears we all share. And we are usually quite good at hiding them.

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Illustration by Pablo Stanley

We have been conditioned to censor ourselves. From really early on. Whether it was a harsh teacher that said something critical about a drawing we did, or the countless incredible things we see other people do on social media and we compare ourselves to.

In today’s society, there’s extra pressure to be a specialist, we obsess with success and being flawlessly good at what we do. The imposition of unrealistic goals frustrates us because we see that we’re far from achieving them. This, in turn only inflames the imposter syndrome, and not being mindful of the existence of these fears can hinder creativity.

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Ideo has done a fantastic job of exploring this thing called Creative confidence. In their book: Creative Confidence, they propose we are all creatives, not just the creative types, but that to bring out that innate creativity, teams must ensure everyone believes their ideas have value. No matter how seemingly daft they may sound at first. Creativity is available to everyone and can be accessed by freely letting people explore their individuality and it’s own series of thought associations.

  • Our own personal journeys, the memories — the things that we lived in any context
  • Knowledge of the processes — how familiar we are with a subject and the relevant tools
  • Feeling capable — do we believe we can have any impact or contribute
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Screengrab from the book Creative Confidence: Unleashing the Creative Potential Within Us All — by Tom Kelley & David Kelley

We need to foster an environment that helps people believe their ideas have value regardless of their experience, fear levels, and backgrounds, while we run adapted design sprints so that participants have fewer fears and self-censorship and give their contribution.

The answer is actually very simple.


Kids are great at it, they don’t have the self-censorship adults have been conditioned to. They can say the most nonsensical things, imagine without boundaries, and create worlds out of ordinary objects. As we grow up there’s a huge decrease in our imaginative thinking capacity, even just from years 5 to 10 there’s a 68% drop. This coincides with the beginning of school years. When we reach adult age, we are left at 2% imaginative thinking capacity.

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George Land’s findings in creativity decrease through the years

I found an author, Gianni Rodari, an Italian writer and journalist who wrote The Grammar of Fantasy in 1974. He worked mostly with kids and tried to find ways to answer their much-asked question: How are stories created?

In his book mentioned above, he collates a series of exercises that can be used as warm-ups during any design sprint because they prove to the participants they are creative regardless of their disbelief. He proposes that imagination is like observing a stone thrown into a pond, it creates ripples. So if we want to access imagination we need to provide prompts that trigger thought associations. The stone in this case is the trigger and the ripples are the free associations. Words, images, or sounds cause a sort of magical chain reaction through the symbolic accessed through our memory.

In doing these exercises we allow joy into the experience of invention and creation, which is one of the most important factors to creation itself as it relaxes the fears.

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Impossible objects — This exercise is inspired by Michael Michalko’s book Thinkertoys

I have used many of the exercises in Gamestorming. An aggregator for warm-up exercises for many purposes. And in collaboration with other designers, I many times steal and tweak their warm-ups. One of my favourites, Impossible objects, focuses on divergent thinking and it is great to run ahead of Ideation sessions as it lubricates the mind to problem-solving and thought associations.

In design, we try to find the narratives for challenges, to find a narrative, you have to try to find its story. To find the story it is important to know the characters and their prompts, what do they bring, what triggers them, etc.

To foster Creative Confidence we have to encourage a childlike sense of play, we can activate this through a series of exercises and experiments which in turn, means projects can be tackled faster and better, by keeping the energy levels up and relaxed and by making people feel included, heard and valued as well as adapting the frameworks to our needs.

The more we try a myriad of combinations and techniques, the more we become confident in our experience and the processes as well as improving our creative confidence individually and as a team. The more we include Sprints as part of our process, the more the process evolves and improves also. And all of this done whilst being inclusive and adaptive.

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