How to run Design Sprints and Workshops like a Pro, with Jonathan Courtney (Part 1)

Jonathan Courtney is founder and CEO of Berlin-based global product design agency AJ&Smart. In April of this year, he released his first book, titled The Workshopper Playbook— a guide to workshopping and decision making– and distributed 1,500 copies in less than a few hours, with a waitlist of 35,000. How did him and his company gain such an immense following? Well, for one, he has a great marketing team and an interesting personality (which you’ll hopefully see a bit of through this interview, too). But it’s what he’s marketing that has really grown his following– Jonathan has mastered the art of Design Sprints and “Workshopping”, and more importantly, how to teach these skills to others. 

Originally created by Jake Knapp at Google Ventures and published in his book Sprint (2016), the Design Sprint is traditionally a 5 day workshopping process focused on rapid ideation and prototyping. It was first adopted by Jonathan Courtney as part of his digital product design practice, and later as freestanding consulting and corporate educational service. 

We interviewed Jonathan a few weeks before his book release to find out how he came to be so interested in Design Sprints, how he convinces people of their benefits, and what he sees in the future for Sprinting and workshopping. As it turns out, Jonathan had so many interesting insights to share that we had to split this into two blog posts. In Part 1, we will cover how Jon got started using Design Sprints, how he sells them, and the personal tips and lessons learned through seven years as CEO of a Product Design and Design Sprint agency. In Part 2 to find out more about his shift from Design Sprints to Workshopping, sticking to the fundamentals, and why the Design Sprint isn’t (necessarily) the answer.

We’ve broken down this blog into a few different sections:

• From Product Design to Design Sprints
• Pitching Design Sprints and Workshops
• Preparing for Design Sprints and Workshops
• Facilitating Like a Pro

From Product Design to Design Sprints

Neuromagic: So how did you first get started with Design Sprints?

Jon:  Well AJ&Smart was a Product Design agency first. I’m sure if you’ve worked on products before you’ll know this– after six months people just forget what the thing was all about in the first place. We’ve been on projects– it’s crazy– we’ve been on projects where we’re getting paid X dollars and one year into it a new person joins the team and doesn’t know what it’s about, and we have to start from scratch again. And we get to keep charging, but I didn’t like that feeling. It felt pointless.

So in 2016 when the Sprint book came out, and even a couple of years before that, we figured out that workshops were just something we needed to do to get everyone on the same page before we did a design project. It wasn’t that we wanted to do workshops–  it’s just that we figured out that if we didn’t do workshops, the projects sucked. So, when the Sprint came out we were super happy that there was like, this really big, step by step workshop that we could use to get everyone on the same page.

I think that the missing piece of the puzzle is that people don’t know how to start projects. 

Jonathan Courtney, CEO, AJ&Smart

And I went from hating the product world– really, I really hated it– I wanted to shut this place down because I could not stand working with these companies anymore– to really enjoying it again. And I think that the missing piece of the puzzle is that people don’t know how to start projects. 

Neuromagic: So when you started out bringing workshop methodologies into your regular UX practice, was it intimidating to go to a client and say “okay, you know we’re going to try this new thing, where you have five days of post-its and timeboxing”?

Jon: The truth was I was super nervous because I didn’t know yet if the stuff would work. I didn’t know if the theory that workshops were a good way to align teams was true. But even when I was nervous, even when it was a bad workshop, it was still 100 times better than doing the normal process– which is no process, which is everyone talking at the same time. So I did, I very quickly believed that having a facilitator and a system was better than not having a facilitator and a system. 

Pitching Design Sprints and Workshops

Neuromagic: At this early point, how were you able to sell this new idea to product design clients?

Jon: Well, I think I was pretty nervous about it because I know that, I mean, our clients are big old corporates. I was more worried about it than they were. I was the one who felt nervous that they wouldn’t like to do it, and it was true that they didn’t like to hear about creativity and brainstorming and these things.　One thing that my co-partner and I did really well at the beginning of starting our company was get rid of all of the UX vocabulary and replace it with business vocabulary. For example, I would want to change, lets say, the landing page of a booking website or something– I would actually want to change it because I want it to be a better user experience, and for, lets say, one year I tried it this way around, and I always got shut down. And  then I was like, wait a minute, what if I say I want to increase the conversion rate? And then I would get my way.

Neuromagic: Can you give us an example of how you really pitch a Sprint or Workshop?

Jon: There’s a lot of different explanations but I’ll just try one of the ones I would use on a sales call…

I’d say: Okay, let’s say there are two teams working on the same product. Team A is using what you usually use, Team B is using a Design Sprint at the start to get things moving. And let’s just make it really fair, and say at the end, both have the exact same quality product. Let’s just say that’s the case, even though it isn’t going to be true. But, to make it really fair. 

Now, I can tell you that Team A, who is not using the Design Sprint is going to take six months just to figure out what everyone’s talking about, just to get everyone on the same page. Just to really even start the project it will take six months of people misunderstanding each other. That six months will make everyone hate each other, it will bring up a lot of frustration, and people will no longer enjoy working on the project by the time it gets to the point of actually creating it.

Now, a year goes on without a product even being shown to users, and maybe then they show it to users and they realize, “oh maybe this is not what people wanted,” but they’ve invested so much time and energy and hate into the project that they are going to bring it out anyway. So that’s team A. Team B has the opportunity, in the space of two weeks (we usually do a Sprint and a Duration Sprint) to get six months of chaos out of the way and crushed into two weeks– a very intense two weeks– but it basically means that at the end of the two weeks, you kind of know what you should build. 

Preparing for Design Sprints/Workshops

Neuromagic: I’m curious about AJ&Smart’s workshopping process. I know Design Sprints and other workshops are meant to be fast, but there must be some work that you do before that to prepare? We certainly do.

Jon: Well two years ago we didn’t do any prep, and now we do a loooot of prep. A lot. An entire week. We call every stakeholder who’s going to be on the project, just to really understand their reason they are joining this workshop, to really understand the project. 

…The crazy thing is– you know what we do? We finish, we do a first draft of every exercise. We have the How Might We’s, the map, the target, the Can We Questions, the long term goal, so when the client walks into the room these things are already up on the walls because of all the discussions we’ve had with them, and then instead of starting from scratch we just ask them to add whats missing. So actually, we essentially do our own sprint the week before the sprint starts. I was totally against this two years ago, because I was like, “no the whole point of the sprint is that it’s fast and blablabla” and actually I think I was wrong. So it turns out it was better to prepare.

Neuromagic: Was there a particular moment you were like “ok this is  not working…(in terms of diving into the Sprint with no prep)?”

Jon: It was just the thing of feeling like it was unbelievably stressful every Monday morning and not being able to sleep on Sunday night because I was worried about how the sprint would turn out, and just A/B testing, how much calmer does it feel if you do a full week of prep work. And for some clients, we even do two weeks of prep work if we’re worried about it. So we do a lot of prep now. 

Facilitating Like a Pro

Neuromagic: When you have international clients do you change your methodology depending on the region you’re working with, or do you find that the same things kind of work all around?

A big part of being a workshopper is being able to improvise.

Jonathan Courtney, CEO, AJ＆Smart

Jon: For us it’s not about where the client is based, it’s about who they are. For example, in January I was working for one of the big four consultancies, management consultancies, and a few weeks before I was working for Novartis, the pharmaceutical company. And I was doing the same workshop for them, but I ran it completely differently. And it’s just because they have different needs and different company cultures. Because the companies we work for are international, as in they all fly their employees in from everywhere, we have the problem that we can’t just say “this is an American crowd” or this or that, so we think more about the specific company culture more than anything else. And you know, a big part of being a workshopper is being able to improvise, and being able to work even if the names change. At the pharmaceutical company, I used the term “decider” and this is something from the Design Sprint– so I was like this person is the “decider”. At the management consulting firm, they don’t like the term, because they don’t have a clear hierarchy system, so I called the “decider” the “project-responsible.” 

Neuromagic: And in general, how much say do you give yourself as a sprint facilitator– you know, you’re also a designer so you have your own input– so how much do you allow your own opinion to enter the Sprint?

I think that a really excellent facilitator understands that they are a guide and not a hero.”

Jonathan Courtney, CEO, AJ&Smart

Jon: I think that a really excellent facilitator understands that they are a guide and not a hero, so they understand that it is their job just to bring people from step to step. And tries to avoid steering people unless they see it going really horribly wrong. So for example, I won’t give my opinion on my concept, but I will give my opinion if the target on the map is too wide. So I’m here as a best practices person rather than saying “this is the best concept, you’re an idiot for choosing this one.”  

I do create my own concept because I like to do that. I don’t tell them whose  concept it is. We all at AJ&Smart add our own concepts in, but I don’t steer it and I don’t feel bad if they choose the wrong thing because the Sprint itself will reveal whether it was right or wrong. 

Neuromagic: Any other tips for facilitators?

Jon: The confidence and extroversion is absolutely not required. Some of our best facilitators started and still are extreme introverts. Coder types who don’t like looking you in the eye and don’t like talking and don’t like small talk. Even they can captivate a pretty big group during the workshop just because they know the steps and have facilitation training. So it’s really, really scalable as well. 

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Phew! A lot of great information packed in the first half here. Here are some key points we took from the first half of this interview with Jonathan about on Sprinting, Facilitating, Workshopping, and showing their worth: 

• Pitching Sprints and Workshops to clients or stakeholders means being flexible— using terminology that they are comfortable and familiar with, and adjusting activities to custom suit needs.
• Prep is important! So important that Jonathan and his team run a full Sprint before the Sprint with their clients.
• As an international firm, adjusting to different national cultures isn’t nearly as important to adjusting to different company cultures— different companies in the same country can still require entirely different styles of work. 
• Facilitators are guides and not heroes— helping when things go too far off track, but not interfering with ideas they may not think are the best.
• You don’t have to be an extrovert to be a facilitator!

Please head to Part 2 to find out more about his shift from Design Sprints to Workshopping, and the future of Workshopping in business.