What’s a good Design Sprint Challenge?

3 Questions to ask yourself before you run a Sprint

Brittni Bowering
6 min readOct 30, 2018
Me being a total Design Sprint NERD

So you’re super excited to start running Design Sprints. You’ve got the perfect room, all the supplies and an eager team just waiting for you to say GO! You’ve got it all! Except… the right challenge.

This could quite possibly be the one question we get asked the most:

“What’s a good Design Sprint challenge?”

In any given company, there’s usually no shortage of problems that need solving. But should you Sprint on every business challenge you’re facing? Definitely not. Even with a quick 1-week process, that could take a while. So then how can you tell what’s an appropriate Sprint challenge and what’s a waste of your Sprint resources?

In this article, I thought I would get REAL. I’m going to outline three things you should ask yourself about the challenge, before you decide to run a Design Sprint on it. My hope is that it helps you and your team figure out what kinds of challenges you should bring to a Design Sprint, so that you can run it with the confidence that you’re putting your energy towards something worthwhile.

If you want a quick recap of what a Design Sprint is, that’s here.

Also, for the purposes of this article, I will be referencing the Design Sprint 2.0 (4-day Design Sprint).

Question 1: Would the project require significant budget to realise?

Stacks of cash, to represent stacks of cash.

The first thing you need to ask yourself is whether this project deserves a Design Sprint. Is it something that will require a large budget and/or time commitment? If so, a Design Sprint is a great way to validate the idea or solution to your challenge before you spend a hefty amount of money and resources only to find out that it’s a flop. Often after running a 1-week Sprint, teams are able to see quite clearly whether it’s worth pursuing. And if not, they’ll gain great insight into how they should pivot their idea or whether they should shift directions entirely.

One of my personal favourite Design Sprint metaphors (that was coined by Jonathan Courtney, CEO of AJ&Smart) describes this perfectly:

Imagine that at the beginning of the Design Sprint, you’re standing in a dark room and you have a dart in your hand. You’re not sure where the dartboard actually is (because you can’t see it), so you throw your dart somewhat randomly. At the end of the Design Sprint, it’s as if the lights come on and you can now see where the dartboard is, making it easy to pivot accordingly.

Question 2: Is there a risk that upper management might sabotage the project?

Dilbert is the best.

We’ve all been there. You’ve gone ahead and decided on a solution that you think will perfectly solve a challenge that your team is facing. But then, right after you’ve made a decision to move forward, it gets fully kiboshed by your manager. This is a great opportunity for a Design Sprint. Having your manager in the room, aligning with the team and participating in developing the solution is the best way to get (and keep) them on board.

If your manager is a busy person, it’s likely that they won’t be super excited about taking a week out of their schedule to participate in a Design Sprint. The good news is, with the Design Sprint 2.0, you will only need your decider (ie. manager) for the first two days of the Sprint week.

Question 3: Would it be valuable to have a variety of perspectives?

One of the beautiful things about the Design Sprint is that you’re able to work with a diverse team. In fact, it actually works best when you stack your team with a variety of perspectives and outlooks.

If you’re working on something that only requires knowledge from one facet of the business, you probably don’t need to run a Design Sprint. But if you’re working on something that would benefit from the marketing department, customer support centre and the product team, then a Design Sprint is your answer.

Alright, to really drive my points home for you I’ve provided an example of a “good” Design Sprint challenge versus a “not so good” challenge for you to reference.

Good Sprint Challenge

We are a healthy juice and smoothie company that has a good hold on the market share in our industry. However, we are aware that there are many competitors entering the market and are somewhat nervous that our current customer will jump ship as soon as something new and exciting shows up on the shelves. How might we engage with our customers in order to build a brand that they feel loyal towards.

This is a great Design Sprint challenge. Here’s why:

  1. Does it require significant budget to realise? Potentially yes. This would most likely be quite a large commitment from the company and could create an entirely new vertical within the business.
  2. Is there a risk that upper management might sabotage the project? Absolutely. This is a challenge that shapes the future of the company.
  3. Would it be valuable to have a variety of perspectives in the room? 100%. For this kind of challenge, you’ll probably want to talk to people from marketing, sales, customer relations and product.

Not So Good Sprint Challenge

We launched our app 6 months ago and have found that many users are complaining about the navigation. They aren’t able to find what they’re looking for and they generally find it difficult to use.

This is not such a good Design Sprint challenge. Here’s why:

  1. Does it require significant budget to realise? It might take some budget and resources, but it most likely won’t be a fundamental change to the actual product, meaning minimal resources.
  2. Is there a risk that upper management might sabotage the project? Probably not. Since the solution to this problem wouldn’t affect a lot of the other sides of the business, your CEO probably wouldn’t find it worth their time to get involved.
  3. Would it be valuable to have a variety of perspectives in the room? Not really. It might be good to hear exactly what the problems are from the people who are talking directly to the customer- but once you have that information, you won’t need their input to improve how the app functions. There are known ways to solve these types of challenges. We don’t need to reinvent the wheel since there are already known methods to solve navigation problems (ie. Card Sorting).

If you go through these three questions and are able to answer a resounding YES to 2 or 3 of them, I would suggest you try a Design Sprint.

I hope this helps demystify the daunting task of deciding on a challenge that’s well suited to the Design Sprint. If you have any other thoughts, things that you find helpful when debating a Sprint challenge, feel free to share them in the comments! Let’s discuss!

Thanks for reading.

Follow me on Instagram @brittnibow and say hi if you do!

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Brittni Bowering

I do standup comedy and I’m a brand & content strategist. I host the podcast “Happy Hour: Career Talk”, a show where we drink wine and talk about work.