What I’m learning playing games with companies

One of the most enjoyable parts about my day job is helping companies come up with new product ideas or ways to enhance existing products. While coming up with new ideas is definitely enjoyable, the most fun part of the ideation process is inventing or adopting new methods for helping others create their own ideas, seemingly out of thin air.

In my world, the way these ideas often come to life is through some kind of “strategy workshop.” Before I became a facilitator of these strategy workshops, I participated in them as a client or product stakeholder. My first exposure to one of these workshops was through a company called Gravity Tank (they’ve since been acquired by Salesforce). I spent two days in the GT office sketching on Post-It notes, arguing about business objectives, eating chocolate, and pounding espresso.

The workshop with Gravity Tank felt immersive, engaging, and actionable. The team (there were about 15 participants) left with a feeling that anything was possible — opportunities were at our finger tips, ready for the taking. And, as a novice workshopper, I attributed the perceived success of the workshop to the workshop itself.

Said another way, I believed that the simple act of having a workshop was the critical factor in driving new ideation. I believed that workshops — regardless of the content or the activities or the snacks — were imbued with certain magical properties that, by the very fact that people were taking a business vacation from their day jobs, elevated participants to a new level of genius that was impossible to achieve elsewhere.

Over the years, I’ve learned (through experimentation and failure) that workshops are merely the medium, nothing more. Workshops can be wildly successful or colossal failures. They can be meticulously planned or they can be improvised. They can create deliverables, answer questions, or help participants make decision. Sometimes, they create more questions than participants began with.

In my experience, the best strategy workshops create a comfortable environment that activates the genius of individual participants. When I facilitate workshops, the content and the activities are rarely the same. I rely on resources and games developed by others and feedback from my teams about what will work and what will flop. But, most of all, I rely heavily on the workshop retrospectives our teams conduct following every session. Here are some of the core truths about how to run successful strategy workshops I’ve picked up over the years.

Facilitator Preparation Starts with the Audience

Strategically minded people like to develop roadmaps. We like to outline and sketch. We like to develop content and watch our creations unfold in real life. When tasked with facilitating a workshop, these “maker” tendencies drive us to start preparing by developing the content of the workshop. We ask questions like:

• What ice-breakers will spark the most energy or stretch participants’ minds the best?
• What games can we play to motivate people to “unlearn”?
• What teaching do I need to provide to help center people on the core objective?
• What physical materials do I need to bring and how will I distribute them?
• How should I involve critical stakeholders during the workshop definition stages?

These are all valid questions to ask, and they should be answered before you begin a workshop. But they are not the most critical elements to facilitating a successful workshop. In every workshop, there will be participants who can’t get behind an activity or who will suggest a different way of solving the problem. These organic pivots can make or break a workshop based on how facilitators react to them. Whether you believe a workshop should stick to a script (e.g. put participant suggestions in a “parking lot”) or shift based on the room’s dynamics, you need to be confident in your position when pivots arise. This means that, before you ever plan the content, you have to know who will be in the room and what attitude they’re bringing to the workshop.

Workshops tend to reveal the hidden agendas of participants. This can be an amazing thing, especially if participants don’t frequently collaborate with one another. It can also create a disaster if one participant uses the workshop as a forum to push an agenda rather than allowing the group’s shared genius to lead discussion.

Lead Workshops in Locations Unfamiliar to Participants

Talking about workshops conjures visions of grand rooms covered in whiteboards, Legos, and Post-It’s. Whatever your vision for the place of your next workshop, one thing is absolutely true: the space needs to allow for organic creativity to happen.

Do you know where that doesn’t happen? In your own office.

By their nature, strategic innovation workshops break the daily routine and enable participants to create something new or solve problems that have become difficult to solve during the average workday. Hosting workshops at a client’s office is one of the most damaging mistakes a facilitator can make. That’s because the office brings with it the baggage of participants’ daily routines.

Being in the office means you are reachable by others. Being in the office means carting your work computer with you and feeling entitled to open it whenever you please. Being in the office means the workshop you’re expected to participate in fully is just another meeting that can be multi-tasked through.

The office is distracting. If your audience is comprised of high-level leaders, this is even more true.

Hosting workshops at offsite locations empowers you — the facilitator — to create ground rules that participants cannot object to because the space is not their own. Offsite workshops also create a sense of camaraderie between the facilitators and the participants, which is necessary when one of your objectives is to create enough trust among participants to enable open idea sharing.

Bring a Backlog of Games and Ideas with You

No matter how detailed you get with your workshop time boxes, it’s highly likely that you’ll either over- or under-shoot your projections. Sometimes, conversations become so fruitful that it’s worth extending the time of an exercise to ensure the highest value is generated. Other times, participants are fully capable of realizing a sessions’s value well before you planned.

In these cases, it pays to have a backlog of activities ready to be deployed in any situation. This has multiple benefits. First, if you’ve sold a full-day workshop, you need to execute a full-day workshop. I’ve heard stories of companies who felt like they got the short end of the stick because the workshop didn’t last as long as promised. Even if the value generated is high, some participants will still walk away disappointed if you don’t fill the whole day.

Second, if you bring activities with you that are untested or unproven, you can use the group to validate the activities and work out implementation and facilitation quirks.

One of the most important things to remember about improvising the flow, however, is that the activities you insert ad hoc still need to feel organic. When preparing for workshops, I often identify 5–6 activities or games that I would like to try, which fit with the desired outcomes of the workshop, and also span multiple group scenarios. For instance, if we’re exiting a brain-writing session where participants have been working silently alone, it may be a good idea to deploy an activity that includes large-group discussion or small-group collaboration. The opposite can also be true.

And, it’s never a bad idea to have a few games with you that can be completed quickly, but have not relation to the workshop outcomes, as a way to lighten the mood or create a boost of energy in the mid-afternoon.

Final Thoughts

Many UX design firms offer templates workshops that follow a standardized process. Making use of these services can be beneficial for some companies, but you’ll need to come to the table with a particular type of problem in most cases. In the majority of scenarios, though, problems are rarely as easy to solve as a process seems to imply. When preparing for a workshop with my clients, it helps to see myself more as the creator of an experience or an environment where creative problem-solving is possible rather than the inventor of a process where results are guaranteed.

I’m curious to learn how other workshop facilitators approach this process. Let’s start a dialogue.

If your company is at a cross-roads, let me know. I’ll be delighted to help you figure out next steps.