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A Comprehensive Checklist For Running Design Workshops

Slava is a design leader from Ukraine. He has over 12 years of multidisciplinary experience: from graphic design in his early years to digital products, UX, …
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The more workshops you organize, the better you realize how similar they actually are, regardless of the methodology or tool used. I would like to share a comprehensive checklist that will help you prepare for any workshop and take care of all the tiny details (i.e., enablers of the workshop’s success).

You can jump directly to the topic you’re interested in or browse through all the steps. Enjoy!

What problem are you trying to solve?

Don’t skip this step while striving to come up with a robust solution. If you notice a workshop goes sideways at some point, you can always say, “Wait a minute. What problem are we trying to solve?” and refer to the agenda where it’s written.

Remember to formulate the problem negatively (risk of…, lack of…, low…, prefixes ‘un’ and ‘in’). Otherwise, it might not be a real problem but rather an attempt to push your preconceived solution.

Is a workshop the right choice?

Workshops are a tool. They require much preparation but help tackle problems where conventional methods — presentations or discussions — won’t help. Here is what workshops are capable of:

If you want to share fully reliable and accurate information, there is no need to arrange a workshop; a simple meeting will do.

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What information is already available?

You don’t want people to write known information again from scratch (it’s just wasting their time) or hear such complaints as:

What information can you prepare in advance?

Starting from an empty canvas rarely works in actual business conditions, and here is how you can prepare:

What deliverable will you produce at the end?

Depending on the problem defined in the previous step, you may want to prepare a certain artifact after the workshop, for example:

Note: There might be an immediate deliverable right after the workshop and a more elaborate one to be created later.

Who and how will use this deliverable?

Think of it in advance not to produce something people won’t find useful (even if it’s objectively great). A few things to consider:

What long-term effect can this workshop have on your team?

In other words, with what feeling should participants leave the meeting room or Zoom call? For example:

What other initiatives can build on the achievements of this workshop?

This is an optional point. If you skip it, nothing terrible will happen, but you might overlook an opportunity. Questions to answer here:

What expertise do you need to be present in the workshop?

Depending on the subject, you’ll need to involve people with suitable knowledge and skills:

For example, you need to involve software engineers if you’ll talk about the feasibility and business logic, you need to go for customer support and operations specialists, researchers, product managers, and designers if the topic is about user experience, or you need all of them if you are going to identify problems and search for holistic solutions.

Who exactly should participate?

When it comes to choosing particular people, you need to take into account their connection to the subject:

Do you need decision-makers or knowledge-keepers? Or both?

There are workshops for gathering and structuring new information and workshops for decision-making with known data.

Depending on participants’ positions and experience, they can be inclined to certain workshop activities. Of course, this is quite simplified, but it narrows down to the following:

Do you need a co-facilitator, and who can it be?

If your team is large and enthusiastic about workshopping, you might need help with facilitation. Below are several examples of what a co-facilitator can help you with, depending on the workshop format.

Online workshops:

Offline workshops:

An optimal co-facilitator is a trusted team member who has participated in workshops before, understands workshop basics well, and is proficient with the tool (if you collaborate online).

How many representatives of one role or function do you need? How will you ensure equality?

When the list of expertise to involve is ready, it’s time to think about the number of people from each side. In a narrowly focused workshop, one expertise can prevail (for example, three-fourths of engineers for a technical feasibility workshop or more than half of product managers for product roadmap alignment).

But if the workshop goal is to co-create a new solution to a large problem, you’ll need an equal representation of product management, design, UX research, software engineering, operations, marketing, customer support, data analysis, and others.

Will you collaborate all together or split into working groups?

Efficient collaboration where everyone contributes equally is possible in groups of 3–5 people. When the team is larger, you’ll need to split it into workgroups. You can organize their work in two ways:

The number of workgroups also depends on how many representatives of essential roles participate in the workshop. For example, if one of the exercises is sketching potential solutions, it would be helpful to have at least one designer in each workgroup. If the exercise is about mapping pain points on a journey map, having at least one customer support or operations specialist makes sense.

✅ Format: online, offline, or hybrid? Several hours or full-day?

Many factors impact the format choice, for instance:

And here are the main workshop formats:

✅ A digital tool or paper canvas?

The format influences other workshop parameters, including how people accomplish exercises.

✅ How to inform people so that they attend and know what to do?

Satisfaction is a matter of expectations. That’s why it’s essential to set the right expectations. If team members lack awareness and alignment, even a perfect workshop is destined to fail before it even starts.

The best approach is to blend in and use channels that people check regularly. If people don’t read emails, don’t spend time on them and better write a Slack message or compose a Google document.

Information to share in advance:

What will participants do in the workshop?

Formulate the plan on a high-level first, without diving into individual exercises. Try to fit it into one sentence.

It may sound like this: “Vote for the previously discovered (pre-filled) UX issues, take three top-voted items for brainstorming, generate solution ideas, vote for the strongest ideas, make sketches of the top-voted ideas, vote for the most promising sketches for further prototyping.”

Another example: “Write feedback about team collaboration in a matrix, group positive and negative feedback pieces by topics, rank the issues from minor to major ones, and assign people to solve five major issues.”

Note: Feel free to check a comprehensive anatomy of design workshops where I dwell on typical ‘atomic’ activities all workshops consist of.

✅ What will each exercise be like?

When the general plan is ready, it’s time to think about the way you’ll organize each exercise, for example:

How much time will participants need for each exercise?

Usually, the simplest exercise requires 15–20 minutes, while more sophisticated ones may take 40–50 minutes. And don’t forget to include a few minutes to instruct the participants before each activity and summarize their contributions afterward. Besides, you cannot immediately dive into the workshop since people are a few minutes late and need to switch to a workshopping mood.

However, every team has its own dynamics, that’s why accurate estimations are possible only after you conduct a couple of workshops and witness your teammates’ actual speed and engagement.

Will you need to break the ice at the beginning and keep people energized during the workshop?

Unlike the main workshop activities, these ones play an auxiliary role and help you keep the team spirit high:

Input: where will participants get the information for each exercise?

Every exercise should be based on the previous one. You need to check if there are no logical gaps between the workshop stages.

For example, if you want people to vote for the most critical problems with your digital product, you must get a list of problems first. In this case, ask people to write them down in the previous exercise or add them to the canvas yourself in advance.

Output: how will each exercise feed into the next one?

This is just a double-check that each next exercise will build upon the findings from the previous one. If the information from a previous step doesn’t go anywhere further, the team will be naturally curious about why you even asked them to share this data.

Canvas: what visual structure will help the team to contribute?

Information is clearer and more useful when it’s structured and visualized. Besides, participants can submit better data if you guide them with a relevant canvas. Depending on the workshop goal and expected outcome, you might choose one of the following structures:

Prevention is always better than a cure. When you involve many people in any activity, there will always be an element of ‘chaos’. But, like a seasoned standup comedian always finds a way out when they forget a joke or when a microphone stops working, the workshop facilitator should also have a trump up their sleeve just in case.

⚠️ Some people are skeptical and resist the workshop idea.

How to prevent it:

When it has happened:

⚠️ You are about to exceed the planned timeline.

How to prevent it:

When it has happened:

⚠️ The online workshop tool stopped working.

How to prevent it:

When it has happened:

⚠️ The key people are absent.

How to prevent it:

When it has happened:

⚠️ In the middle of a workshop, you suddenly discover the actual hidden problem that changes your initial plan.

How to prevent it:

When it has happened:

⚠️ People get distracted during the workshop.

How to prevent it:

When it has happened:

Design workshops are no rocket science. In the ideal world, there would probably be no workshops: people would just have common sense by default. Maybe, that’s why small, close-knit teams usually don’t need special workshop preparations because they share the same values and already speak the same language.

However, in most cases, workshops are inevitable. They help build trust if it doesn’t appear between team members naturally and align people of different backgrounds who haven’t collaborated a lot before. That’s why you should plan workshops with people in mind. And if I had to choose one point that contributes to the workshop’s success the most, it’s involving the right people.

Meanwhile, here is a short version of the checklist:

Problem framing

Participant selection

Workshop format

Agenda and canvas

Risk management: what can go wrong

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