How Workshops Changed My Career, An Interview with AJ&Smart’s Jonathan Courtney

We sat down with AJ&Smart CEO Jonathan Courtney to delve into the history of AJ&Smart, the story behind Workshopper, and learn why facilitation could be the key to your next promotion...

To celebrate the launch of Workshopper, AND AJ&Smart’s 8th birthday, we sat down with our very own Jonathan Courtney, AJ&Smart’s CEO & Founder, to delve into the history of AJ&Smart, the story behind, and to learn why being able to run a workshop could be the key to your next promotion…

You started AJ&Smart 8 years ago (today!). For those that don’t know, tell us how you ended up starting the company…

Jonathan: Ok it’s a long-winded story, but people do ask quite a lot, so here we go!

I moved to Berlin in 2008 to be a filmmaker, after studying a course called ‘digital media production’ in Darmstadt, Germany.

My course was a mixture between design, filmmaking, photography, audio engineering, coding, illustration, game design, and a bit of everything really! Filmmaking was the part I liked the most at the time, so I followed that path.

My goal was to be a filmmaker or director, so to start out I was working on film sets, from like 6 a.m. until midnight. I was really paying my dues – setting up lights, packing up sets, cleaning toilets, I won’t go into detail about that though! Generally speaking, I was doing anything and everything – just kind of making myself as useful as possible and I did this for about six months. While I was doing that I needed to make some money, because I couldn’t afford to live anywhere, so I started doing looking for design work on the side.

My mom had a wedding planning service and I designed her website, and I was also in a band at the time, so I designed our website for that too. I finally realised it was time to to get a job, or else I wouldn’t be able to afford to live in Berlin anymore, so I looked for a full-time job and stuck to filmmaking in the evenings.

I then actually ended up getting a job at an old-school tech company in Berlin as a designer. If I’m honest I kind of bluffed my way in there because I didn’t have a portfolio, so I’m very thankful that they gave me a chance. What I had to do in the next six months was f***ing learn how to design a product, and even though I studied design psychology, I didn’t know what UX was because it wasn’t really a thing back then. I started learning a lot and got really into the idea of being a Product Designer.

Then I met a guy called Michael Smart, who was freelancing as a designer at my company. One of his clients wanted to do a much bigger project with him. Michael told me about it one day and immediately I was like, “let’s pitch for it”. We then called my friend Alex, the bass player in my band, who was learning to code at the time and got him involved. The three of us pitched for the project and, to our surprise, we managed to get it.

After that, myself and Michael quit our other jobs to go all-in with this project because it paid pretty well. It turned out that the project was crazy stressful – we basically worked until 5:00 a.m. every day. At the end of the project we were exhausted, but we loved the buzz of working on something like this together, so myself and Michael decided we’d work together on projects again, and so AJ&Smart was born!

So AJ&Smart started with you, Michael, and Alex tackling freelance projects together?

Pretty much! Actually one of the only real reasons AJ&Smart became a proper business is because the client we were working with wouldn’t pay us three different invoices as freelancers, so we had to come together as a company. We then decided to see if we can get other projects as ‘AJ&Smart’ because we had set it up already. It seems weird saying it now, 8 years later, but AJ&Smart being a company was a full accident.

It seems AJ&Smart started as a classic Design Agency – executing design work for clients. How and why did you transition from doing design work for clients to running workshops with/for clients?

For the first six years we were, as you said, a relatively traditional design agency. We did manage to focus on product design and UX design, but we were doing the usual projects where we would go in and do a little kick off session with them to collect all the information. We’d then go away, do the work, and come back to them, and in many cases they would be disappointed because it wasn’t exactly what they wanted.

Then we would go away again to do some iteration work, then go back and then they’d give us more things to change, and the cycle went on and on.

It always felt really unsatisfying because, even if it was really fun at the start, it always became misaligned and frustrating for both parties after a while. It took us so long to get to the execution work because we kept having to redo everything all the time, which I now know is very common in the agency world.

Flash forward a little and myself and Michael (my co-founder) are at a conference in Portugal. I’m not going to mention the name, but it was a really bad summit and was poorly organised, however there was one talk there that stuck out to me there. It was one guy showing us how to plan out a development cycle properly. Afterwards myself and my co-founder went for a drink and spoke about how we could use something like that to align with a client at the start of a project. And so we put together a version of this ourselves called ‘applied user story mapping’.  

We used this when we did some work with eBay, who was our client at the time. They loved it and we were like “f**k maybe that on its own could be something we can sell”. So we started Googling and learning about Design Thinking, and we went to a Design Thinking workshop at IDEO which we loved. We then immediately started selling Design Thinking workshops – the first one we sold was to Bundesliga. This marked the start of us transitioning into a more strategic design firm.

For the first six years we were, a relatively traditional design agency. Our projects always felt really unsatisfying because, even if it was really fun at the start, it always became misaligned and frustrating for both parties after a while.


How long into AJ&Smart’s life did this happen?

This would have been around 2015. So from 2011 to 2014 we were really traditional in how we worked, and in 2015 we were still somewhat traditional, but were starting to learn about workshop methodology. Then in late 2015 we started reading Jake Knapp’s blog because our workshops were selling better than our other services, and we were looking for any resources or inspiration we could find. When Jake started posting about things like ‘note and vote’ and all these different workshop exercises we just started collecting exercises to add to our toolbox to use with clients, we didn’t care what they were.

Eventually Jake started talking about this thing called the Design Sprint and we got super excited about it. We tested selling it to our clients, and they started buying! We were still in the midst of some traditional design work with clients, and kind of slowly transitioning to consulting. Soon after we first learned of the Design Sprint, the Sprint book came out – I read it on a plane and was blown away. We made the decision then and there to stop doing these frustrating really annoying circular projects where we start to hate each other, and we went all in on the Design Sprint!

What was that transition like? What did it mean for you and the company?

We were already moving in that direction and were getting interested in workshops, but it was still a big change for us and took about 8 months from the decision to go all-in, to getting to a place where this new way of working was fully integrated. It was a bit painful, as most transitions are, but of course it paid off massively.

Interview with a workshopper Jonathan Courtney

How did you manage that change with existing clients?

We started to make workshops an integral part of our work, to get them used to this way of working. So for example, instead of doing kick-off meetings we would now always do kick-off workshops, and we would always use workshops whenever we’d get stuck on something.

Essentially we were making the workshop part of working together mandatory. The transition was difficult because some clients said “no we don’t want to work like this. We’re looking for a normal agency. We’re not looking for someone to just do strategy.” But after a while, because we made it clear that we’re here to do the start of projects and to kick things off for them, they accepted it.

It is difficult to transfer your current clients, but we made the decision to go all-in and stick to our guns. It paid off and most clients stuck with us and came back time and time again!

Were there any short-term losses?

There was a period where we lost some good long-term clients. But the result was that we ended up with more, short-term projects, which is better for revenue. Every person who’ll consult you on running an agency always says ‘make sure no client makes up 50 percent of your revenue’. Almost every agency breaks this rule. Almost every agency has one client that makes up 50-60 percent of their overall revenue. And with the Design Sprint and the way we were selling it, none of our clients even would have the option to make up 15 percent.

Today we’re launching Workshopper (on AJ&Smart’s 8th birthday!) Can you talk a little about the motivation for launching Workshopper? Why do you think it’s important?

Internally at AJ&Smart for years we’ve been trying to define what the job title of someone who runs workshops at AJ&Smart is. We realize it’s a very special and unique role: a person who can just pull out different types of workshops for almost any scenario and facilitate them very well. We started, almost colloquially, calling ourselves workshoppers, instead of saying facilitator.

Looking back, it was so life-changing for us to find workshop information online, but also so hard to find the right stuff, so we wanted to create the best, easiest, free place to find all of the best workshop materials and information. It’ll essentially become 6 years of our tried-and-tested workshop learnings and knowledge, all in one place.

For us it’s about creating an amazing free resource on the Internet for workshop people. Companies often like to keep this stuff secret, their secret sauce, but we want to have a public, free place to present all of this material because it’s served us so well over the years.

Join our free community of facilitators, where you'll have the opportunity to learn, connect, and grow

Can you explain what it means to be a workshopper?

A workshopper is somebody that can help teams do valuable, meaningful work by removing the pointless busy-work.

So for example, relating to a new project, busy-work for me would be trying to figure out what systems and what processes to use right at the get-go. Teams spend way too much time thinking about the process. A workshopper would come in and give a framework to a project so that people can work on the real challenges and the real work without having to think about the processes and argue about the systems.

For me a workshopper is a guide who can bring people through projects with the least amount of friction, helping people do the most valuable work and the least amount of busywork.

Jonathan Courtney on why running workshops is the next step in getting your promotion

What do you wish more people knew about running workshops?

I wish people knew that the default way of working – having no structure – is fundamentally a bad way to do meaningful work and innovate.

I wish people knew that, without having a set of tools and processes in place, you’re just doing busy work.

I wish people knew that there’s a workshop for every type of project, and that it’s not difficult to get good at being a workshopper.

Finally, I wish people knew that there was an available role for a workshopper at companies. I think it’s coming, but there’s still a way to go, but the good news is that if you’re ahead of the curve and are already looking into these things, then you can set yourself WAY apart from everyone else.

What would you say the most important components of a successful workshop are?

First and foremost it’d be using the right workshop format for the right problem. Basically having the right set of exercises for the challenge at-hand. Secondly, having/being a facilitator that’s confident in bringing about a peace treaty between peers during conflict, which very often will arise when establishing a workshop culture – you need to be pretty confident and have some tactics at the ready to make this happen! Lastly, having a tangible, clear outcome and next steps to present to the other participants, so that it doesn’t feel like a waste of their time and they can see progress being made.

How can people start implementing workshops in their everyday work life?

I would always start small. I wouldn’t recommend starting with trying to solve big huge problems through workshops. How I’ve seen it work really well is trying to replace certain meetings with workshops.

So for example, a great workshop to experiment with is a retrospective or an improvement session, and running in a workshop like the Lightning Decision Jam instead, which is easy to follow and should only take an hour and a half. You don’t even need to call it a workshop, instead you can just call it ‘structured meeting’, which gives people a feeling for the power of workshops, and will likely give you confidence and practice that’ll come in handy when it comes to running larger-scale workshops.

To summarise, I think the best place to get started is looking at what meetings are happening in your company currently, and offer to facilitate one of these, using a workshop like the Lightning Decision Jam as your structure.

Tell us about a time you’ve seen a workshop go WRONG – what happened and what would you have done differently?

Any time things have gone wrong in workshops it always goes back to us not knowing which exercises to bring to solve the problem at-hand.

There’s one example I can remember where we were working with a client and at that point we hadn’t run many workshops before, so we just filled the session with random exercises, like persona building and business model canvassing. We realized halfway through day one that we weren’t going to be able to pull all of it together, and there were 18 people in the room with us participating.

Aside from not having the right workshop format ready, what also went wrong is we realized that we let everyone in the room have an opinion in the format and exercises, without us properly guiding them.

The way to avoid these issues would have been having a bigger toolbox of exercises and workshop formats that we could have pulled from and changed on the fly, and also by being better of guides and making sure that people know exactly what’s coming up.

I wish people knew that the default way of working – having no structure – is fundamentally a bad way to do meaningful work and innovate. I wish people knew that there’s a workshop for every type of project, and that it’s not difficult to get good at being a workshopper.


Tell us about an AMAZING workshop you’ve experienced or ran? What made it so great?

Funnily enough, some of the worst experiences I’ve had running workshops actually turned out to be the best and most memorable. For example, the situation above: even though we didn’t guide people through it and it wasn’t nearly as smooth as it could have been, it was still better than not doing workshop. The outcome of those two days ended up solving a BIG problem that the client had for years and that they hadn’t been able to solve themselves. At the end the CEO even came up to us, telling us how amazing the workshop was and blown away he was at how much we managed to get done. I think that was the first moment where we realized that, even if it goes bad, doing a workshop is still better than not doing a workshop.

If you could give ONE piece of advice for someone running their first workshop, what would it be?

My biggest advice is to just get started. If you don’t think your colleagues will be open to it initially then just say that you’re going to run a meeting in a different style, so you don’t have so much pressure on yourself and you won’t feel so overwhelmed if it doesn’t go well.

I know you said one piece of advice but I’d also like to add something that was really helpful for me. It’s that when starting out you should use something that’s already been clearly established, like the LDJ workshop, for example. This means you don’t have to think about what type of workshop to design and you can just follow an already-existing process and focus on practicing facilitation to build your confidence.

What do you wish you could go back and tell yourself 8 years ago, while you were starting AJ&Smart?

If I could go back eight years and try to get my career to the same place it is now, but faster, I would try to become a strategic partner to clients much earlier. Basically I’d focus on  being seen as the person who can coordinate and align, rather than being the person in the team executing the work.

One of the things that makes AJ&Smart special is that we’re not a company that focuses on execution. We’re a strategic partner, and being a strategic partner is always better than just being one of the millions and millions of companies who are just seen to be executers.

If I had known that one of the best ways to become a strategic partner with our clients is to become the facilitator, the workshopper, then I would have done this from day one.

So there you have it – facilitation and workshopping are the skill of the the future!

If you were ever wondering about the back-story of AJ&Smart, or why we focus so much on being excellent workshoppers, then hopefully this interview answered your questions and gave you some inspiration!

And in the spirit of getting started, if you’re looking for a great workshop to try with your team, to get you started in the workshop world, then check out our Lightning Decision Jam – it only takes 1.5 hours and you’ll be blown away by how easy it makes team collaboration – take our word for it!

Are you looking to future proof your career and learn a skill that will make you irreplaceable for ANY team? Then we have just the right thing for you!  The Workshopper Playbook* is an entire that will teach you how to level up your career using workshops, AND will show the step-by-step method for creating and running custom workshops.

*We’re giving away copies of The Workshopper Playbook for FREE for a limited time, you’ll just need to cover shipping. Hot off the press, get it here, only while stocks last.

AJ&Smart Team

A team of pro workshop facilitators with 9+ years of experience.