Best Exercises for Problem-Framing

Discover our favorite exercises to help you untangle any problem and frame it for success. Workshopper is the #1 resource for facilitation and workshopping advice.

Defining just the right problem to tackle and framing it right is the groundwork of the effective problem-solving process. Without taking the time to carefully define your challenge you run the risk of focussing on all the wrong things, scattering your attention, and ultimately - solving no problem at all, or worse yet – realizing after the challenge that you should’ve focussed on a different challenge altogether. What makes things worse is that problems are rarely (if ever!) straightforward and transparent.

But not to worry, there are effective tools and exercises that will help you get to the bottom of the tangled mess that problems are.

These exercises are our personal favorites (that we use when working with clients!) for getting to the bottom of the challenges and framing them for success.

1. How Might We

How Might We is a great note-taking technique that allows you to reframe your challenge in a more positive, solution-oriented statement. At its core, every problem is an opportunity for improvement, and the How Might We method allows you to switch the gears into the solution mode, rather than dwell on all the things that are not going your way. This exercise will help you look at your challenge from a different angle and tap into unseen before opportunities. 

For example, “We don’t have enough sales” is not a challenge or an opportunity, it’s just a negative statement. So how can you transform it into an opportunity instead?

  1. Begin by identifying and jotting down your main challenges and pain points.
  2. Now, reframe these insights into questions by starting each note with “How might we…”, or by simply writing “HMW” at the top left corner of your note.
  3. Write out as many “How Might We” as you can come up with! The HMWs you can gather, the more opportunities you’ll have for solution exploration.
An example of a How Might We (HMW) exercise

*You can run this exercise with the challenges you already know exist, or combine it with the next exercise on our list–Expert Interviews–to uncover bottlenecks and unearth problems you weren't aware of.

Pro tip: Make sure that your HMW is neither too broad, nor too narrow. Something like “How Might We save the business” encompasses too many areas and makes it hard to ideate a specific solution. In contrast, “How Might We increase sales by leveraging our affiliates” is too narrow, and already implies a solution.

2. Expert Interviews

Time: Approximately 30 minutes

You can’t solve a problem you don’t fully understand. But here’s the thing: getting to the nitty-gritty of each and every problem can be time-consuming. Why not take advantage of the experts who already know their domain? Expert Interviews are a great way to leverage the existing knowledge in a time effective manner.

When we talk about experts in this setting, we are referring to a person who knows more than everyone else about the whole product or parts of the product we are most interested in.

They could be talking to us about customers, legal issues, UX ideas, company considerations, finance and budgeting, AI...you get the gist.  

Whatever their role may be, they are telling us something important about what we are going to do and what they tell us will prompt ideas, challenges and questions and will help us define the challenge more clearly. 

This exercise is super easy to run:

  1. Invite all your selected experts to your problem-solving session, describe the challenge at hand, and let them share their views and expertise on it.
  2. Have your other team members listen to what the Experts are sharing, and as they talk, urge your participants to think about the implications this shared information has for your business or challenge. Everything that might influence the challenge you’re working on has to be noted down!
  3. Tell your participants to note 1 challenge per sticky note to make working with these challenges easier in the follow-up exercises.
  4. After you’re done, these notes can be turned into challenges to be worked on, and will help you get more clear on the angle of the challenge you need to tackle, where exactly you need to focus, and some underlying issues you might not have been aware of. 


Pro tip: Combine the Expert Interviews with the How Might We note-taking technique to double the efficiency! All you need to do is explain the HMW method to your participants beforehand and tell them to reframe the challenges on the fly as they listen to the expert.

3. The Sailboat

The sailboat is a nice metaphor to help teams figure out what’s moving them forward, and what’s holding them back when it comes to the challenge they’re trying to resolve. It also is a great tool that will allow you to see any emerging repeating themes that you might not have been aware of before. 


As the outcome of this exercise, you’ll have a categorised list of challenges and issues to work on.

Here’s the step-by-step process of running this exercise:

  1. Start by drawing a sailboat on a white board, or in a digital whiteboard, just like so:


Sailboat exercise step 1: drawing the sailboat
  1. Set the timer to 5-10 minutes and tell your participants to silently note down the things that they feel are moving the team forward when it comes to the challenge they are  working on. They should write simple statements, one per sticky note. 
  2. Once the time is up, you as the facilitator will ask each participant, one by one, to stick their sticky notes to the top part of the Sailboat drawing and read them aloud to the group. The goal here is not for each person to explain each sticky in detail, simply read what's on the sticky note. Give each person 1 minute to stick up and read all their sticky notes. Once everyone is finished presenting, this part of the exercise is complete and the Sailboat will look something like this:
Sailboat exercise: what's moving us forward


  1. Now you’re moving onto the more negative part of the exercise and the rules for presenting change here, too. In fact, there will be no presenting at all! This is a completely anonymous round which will allow people to be more honest!
  2. Set the timer for 8-10 minutes and ask the team to write as many sticky notes as they can on "What's holding us back" in terms of solving the challenge you’re working on. Clearly state to the participants that their stickies will be anonymous this time, so they should write whatever they like.
  3. Once the 8 minutes are up, ask everybody to stick their stickies to the bottom part of the Sailboat. They should do this fast and randomly without discussion. If there isn't enough space underneath the sailboat, simply have them spread them out.
  4. As quickly as you can, remove duplicates from the board. Just you, no-one else, and no discussion. Once Step 2 is complete, you now have a visual overview of the challenges that the team is experiencing.
Sailboat exercise: What's holding us back
  1. The final step here is to tidy things up and categorize the challenges. You could skip this step if you’re short on time, but it is a great way to give everyone a super clear overview of where most of the challenges lie.

And just like that, you have a visual categorized overview of the most pressing challenges that you can tackle!

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4. The Map

The Map is a great exercise for when the challenge you’re trying to tackle is complex, multi-faceted, and you just don’t know where to start.

This exercise is all about creating a high-level overview of the challenges our product or service is facing. Having a high-level overview of the challenge not only helps us to visualize where the bottlenecks are, it also helps us to choose an area of maximum impact to focus on!

Often, when teams are presented with a host of different challenges for a product or service, it might be hard to pick the right one to ficus on first. Mapping out your challenge gives you a nice visual overview of where in the workflow your challenges are. A good rule of thumb to follow is to tackle the bottlenecks that are more upstream - it’s likely that solving them will solve a couple of other challenges down the flow.

To properly run this exercise, you either need to be a subject matter expert on the topic of your challenge, or conduct prior research on the subject (Pro tip: you can combine this with the Expert Interview exercise!)  

Once you have all the information you need to understand how the product works, it’s time to get down to business.

  1. Create an outline of the Map on a whiteboard (or in a digital collaboration tool of your choice). On the left-hand side, create a column headed  ‘Actors’: these are all the people who interact with the product. Later you will list all your Actors under this heading. On the right-hand side, write out the end goal, the objective you have for your actors after they’ve gone through the whole Customer Journey.
  2. Write the different stages of the Customer Journey  across the top from left to right: Discover, Learn, and Use. Your outline should look something like this:
The Map exercise: Map outline

  1. Now it's time to fill in the Map. The easiest way to start is by defining the start and the end of the Map, because you usually know who your product is for, and what your goal with it is!
  2. Start jotting down the ‘Actors’- all the people who interact with your product, service, or process. To keep it high-level, try to keep the number of Actors to four max, and group them if necessary (i.e. Customer Service team). After listing all relevant Actors, choose the main one - the user of this product or service that you want to focus on most.
  3. Define the end goal for your main Actor. What is their end target action you want them to make? What do they want to get done? This can be as simple as “completes the check-out process”, or “subscribes to a newsletter”
  4. Now fill in the Discover column.  Include  a few points about how your main Actor might first find out about your service. For example, if you’re working on a music streaming app, you might jot down things like “saw a Facebook ad” or “typed in a query into the App store”  
  5. Continue filling out the Map, transitioning into the ‘Learn’ phase. Think of the steps your Actor might take once they have discovered your product or service.  How do they learn more about it?  Is there an onboarding process? How and where does the learning process take place? Jot down  a few bullet points of how your Actors find instructions, or product info.
  6. The last step of the Map is called ‘Use’. This one is usually where discussion and debate breaks out, because the usage part is often the most complex. Remember to keep the Map high-level and don’t get too bogged down by the small details. Once your entire Map is filled out, it will look something like this:
The Map exercose: filled out map

Now you have a full overview of the flow of the challenge you’re working on and can use it with other tools to choose problem areas, create solutions and commit to experiments and changes.

Pro tip: If you ran a How Might We session, you could take your notes and start placing them on the respective parts of your worflow. This will allow you to visualize where most of the challenges concentrate, and what the most upstream challenge is.

5.  The Empathy Map

The Empathy Map is yet another great exercise that will help you enhance a user-centric point of view and solve challenges that are important for your users. It’s also a great tool for revealing blind spots in your user data!

  1. Sketch out the Empathy Map on your (digital) whiteboard. The centre of your map is the user, surrounded by 4 quadrants, labeled with “Says”, “Thinks”, “Does” and “Feels”. Draw two rectangles under the square and name them “Pains” and “Gains”. You should have something like this:
Empathy Map exercise outline
  1. Each Empathy Map is centered around one user, so if you have multiple Target Audiences, draw a separate Map for each group and run the exercise in lop until you fill out all of the Maps.
  2. Name the first user or customer group you’ll be analyzing with this map.
  3. Go through the four sections and explain to your team what you want to collect in each quadrant:

In the “says” section the participants will put all the things users actually said in interviews, product tests or reviews. An example would be “My favourite thing about this product is that there’s always new things to discover.”

In the “thinks” section they can also put in things they heard the users say in interviews, but also things they just assumed that the user thought. One example could be that a user raises one eyebrow when asked if the price is too high, politely says “there will be different opinions on this” but seems to think that the price is too high.

In the “does” section they put everything they can observe users do, e.g. switching between tabs all the time.

In the “feel” section they can put the emotional states of users, e.g. “I'm worried that clicking this button will delete all my previous actions”.

  1. Set the timer to 10 minutes and let your team come up with as many ideas as they can. The exercise is done ina  together alone manner, and that means that there’s no discussion or sharing going on during these 10 minutes. Your team will be silently noting down things on their (digital) sticky notes. 
  2. After the ten minutes are up, ask everyone to put the sticky notes up in the respective sections at the same time. Your Empathy Map will know look something like this:
EMpathy Map exercice step-by-step process
  1. Now’s the time to synthesize your learnings from filling out the 4 quadrants into the pains and gains. Set the timer to 5 minutes and let your team read all of the sticky notes that you gathered on the map to make sure they got insights form other team members.  
  2. Introduce the pains and gains to the group: The "pains" are the biggest frustrations of the user when using the product and challenges for the product. The “gains” are the goals and motivations of the users when using the product.
  3. Set the timer to 10 minutes and let them come up with as many pains and gains on their sticky notes as they can. Again, you’re jotting one idea per sticky note, and you’re working together alone! 
  4. After the time is up, let everyone stick up their insights for both sections one by one and read them aloud to the group.

And there you have it, you now have more insight into both the pain points that you need to solve for your audience, plus the benefits you need to emphasize for them. Once you know what really drives your audience it’s that much easier to spot the right challenge to tackle.

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6. Draw Toast

Draw Toast is a quick and fun exercise that will get your team out of their usual thinking patterns and will allow them to take a fresh look at their mental models. 

Now, while it’s not an exercise that will help you get to the bottom of your problem per se, it’s a great launch pad for further discussions, because the exercise reveals how diverse the thinking models of the group are, priming the group to be open-minded and think laterally while discussing the challenge at hand. It works as a great warm-up before a problem-solving session. Try it out and see for yourself!

Here’s how to run the exercise: 

  • Gather all your participants in the same space (whether in-person or remote), and explain the scope of the problem you’ll be working on. Set the expectations with the group and tell them that the kick off exercise will be centered around getting a clean slate for looking at the problem with fresh eyes. 
  • Set the timer to 3 minutes, and tell the participants to draw out  the process of making a toast. Reassure them that their sketch doesn’t need to be a work of art, and tell them to concentrate on the sequence of the steps rather than on the aesthetic aspect of the task. 
  • Remember to emphasize that the exercise is done in a ‘together alone’ fashion–meaning no conversations or discussions should be taking place between the participants as they get on with their sketches.
  • Once the time is up, tell your participants to reveal their drawings to the group. Once aöö drawings have been put up on display, take the time to reflect as a group on how different each sketch is.
  • Point out that while every drawing is different, they are all fundamentally correct, opening up your participants understanding that one problem can have different solutions.
  • Play the original Draw Toast TED talk that explains the ideas about system thinking. Alternatively, you can  watch the video on your own and relay the main ideas to the group!
  • Now that you’ve done the priming, it’s time to move on to your actual challenge! Set a timer to 3-5 minutes and tell your participants to draw schematically how they see the challenge you’re currently working on. Again, the exercise is done in together alone mode, so watch out for any conversations sparking up
  • Once the time is up, let the group present their sketches. Compare the diagrams they’ve created: find the differences and point out the similarities.  

This is a great foundation for not only understanding the challenge deeper, but getting the entire tema aligned on a common understanding of the challenge.

7. The 5 Why’s

The 5 Why’s is an easy exercise out of the Design Thinking toolbox. It’s great for exploring the cause and effect of the problem, and getting to the core of the issue you’re working on.

Running the exercise is as simple, as starting with the most obvious effect of your problem, and asking “why” 5 times, until you get to the ultimate cause of it. 

The repetitive nature of the exercise allows you to build off the cause and effect relationship, and uncover the underlying issues quickly. 

For example, this is how the exercise might unfold: 

Why don’t we reach our sales targets? – Because not enough people convert from discovery calls into paid services. 

Why aren’t enough people switching to our paid services? – Because they don’t understand or see the extra benefits of our services.

Why don’t they understand the extra benefits we offer? – Because they don’t read through our promotional materials.

Why don’t they read through our promo materials? – Because the materials are too long and not interactive.

Why are our promos too long and not interactive? – We’re limited by the legal constraints of our industry.

The root cause, in this case, are the legal requirements that you are bound by. Your problem statement would likely focus on balancing marketing persuasion and legal requirements of your industry.


8. Problem Framer Workshop

And there you have it, this concludes the list of our all-time favorite exercises for problem framing and definition. Now, if you're looking at the list of exercises and don’t know where to start, or how to combine them for best results–don’t worry. Combining workshop exercises together is actually harder than you might think! 

They need to flow into one another seamlessly, and complement each other. It’s a hard balance to strike! So if you’re looking for a plug and play workshop that you can implement right away to frame the right challenge to tackle, Problem Framer is just what you need. 

The workshop builds on several exercises from the list above, is easy to facilitate and run. You’ll just need 30 minutes of your time.

Check out how to run the workshop here. 




Anastasia Ushakova

Brand Strategist, Digital Marketer, and a Workshopper.