Product Discovery at Would You Rather Be

12 Aug 2020

About the Author:

Phil Hewinson is founder and CEO of Would You Rather Be and can be found online at and @philhewinson.  Parts of this post were previously published on Phil’s personal blog, A Social Entrepreneur’s Journey.

Almost everyone on the planet spends the majority of their life’s energy working.  So it’s a tragedy that most people spend their careers doing something they don’t enjoy. That’s bad for them, their employer who isn’t getting the most out of them and bad for society as a whole.  Our mission is to help people discover, get into and flourish in their dream career.  Then people will start looking forward to Monday morning more than Friday afternoon!

Our web app,, helps people discover careers that are suited to their interests and passions.  We do this by asking them 100 questions to select their preferred career between two options.  We then show them top careers that match their preferred qualities, inferred from their answers.

We spent 10 weeks, between May and July, deep in the process of product discovery.  We spoke to over 50 users and potential customers to better understand their motivations, behaviour and pain points.  We then synthesised all of this information to figure out what products and features we should build next. In this blog post I’ll summarise the process we went through, our core user insights, the prototype we developed to test our biggest ideas and where we plan to go next.

Our approach

To generate broad insights, we needed to recruit a diverse group of subjects. We did this through our web app, by asking them some qualifying questions just before showing them their final results. We then sourced a wide range of people into our web app using Facebook ads. For a few hundred pounds, we were able to assemble a group of people with and without degrees, and at a variety of ages to help us understand multiple perspectives on this problem.

We then prepared a discussion guide to direct our conversation with them, so we could probe into their behaviours and motivations around trying to change careers.  We teased out their core struggles in this process to develop insights that would later inform our potential solutions for helping them with these struggles.  We also used the web tool Miro, which is a virtual whiteboard, to run a couple of “card sort” exercises with them so they could rank what services they would find most helpful and what they value most in a career.  We ran each interview remotely over Zoom, which gave us the opportunity to record them and watch them back later.

Through the CareerTech Challenge Prize, we’ve had access to one-to-one coaching with Livework, an international design studio who have helped us apply service design methods to synthesise our information into core insights.  For example, we built a customer value exchange diagram as well as a journey and opportunity map, to highlight the opportunities at each stage.

An example of a value exchange map

A value exchange diagram can help identify opportunities to engage with your users.

What we learned

Here are the core insights we gained across all of the users we interviewed:

  • People who struggled to identify the right career to pursue often talked to people they knew to explore further.  They were particularly attracted by work experience opportunities to try jobs out.
  • For people who struggled to find a way into a career, they’re often overwhelmed by the volume of generalised information available. Instead they want clear, personalised steps to follow that would guarantee them a job.
  • People struggled to identify open roles that matched their current skills, experiences and qualifications.
  • When it came to applying for jobs, the biggest frustrations people had were not hearing back from employers after investing time in a job application and dealing with a lot of rejections.

We also observed some unique struggles for people without a degree and working in precarious roles (who are the focus of the CareerTech Challenge Prize):

  • They often had certain constraints around pursuing different careers such as their physical health, having better hours than their current job gives them, and identifying more realistic options.
  • They were uniquely interested in unpaid work experience opportunities.
  • They demonstrated a greater struggle around finding suitable open roles based on their skills, experience and qualifications.

We identified four unique personas from the people we spoke with.  Let me give you a brief snapshot of one of our personas, frustrated Freddy…

Freddy works as a car salesman.  He’s always done this job.  And he wants a change.  He wants to do something he enjoys more.  Maybe something in marketing.  He’s applied for lots of jobs.  But he never hears back.  He’s not sure what steps to take really.  And he doesn’t even know if he’d like the jobs he’s applying for.  So he often falls back on sales, because that’s all he knows.  He’s quite good at it.  But the passion isn’t really there.

People in this persona are in their late 20s or early 30s.  They fell into a career without thinking too hard about it.  Now that they’ve been doing it for a while, they crave a new challenge.  The problem is that they don’t know what else they could do.  They feel a bit stuck.  They crave an opportunity to grow, which their job has never really given them.

What we did, and what’s next

We used these insights as fuel for our week-long design sprint, where we worked on answering this question:

“How might we help people get into a career they want to pursue and also create value for recruiters hiring for those entry-level positions?”

Our design sprint was based on Jake Knapp’s process captured in his book “Sprint”, which he invented during his time at Google.  Eight of us took part, and it involved us collectively sketching 120 ideas, using the method called “Crazy 8s”, and then discussing our favourites at length.

Screenshot of Would You Rather Be's initial prototype

Simple, visual prototypes can help bring your ideas from product discovery to life for user testing.

We then recruited five users to show the prototype to so we could see their reactions.  These insights then highlighted the most promising features, which we are feeding into a storyboarding session to create our initial minimal viable product (MVP).

We plan to build our initial MVP in early September and then iterate our way forwards towards a solution that best helps people get into a career they would enjoy.  This will help us make progress towards our mission of helping everyone discover, get into and flourish in their dream career.

About the CareerTech Challenge Prize:

The CareerTech Challenge Prize is a joint project between Nesta Challenges and the Department for Education, aiming to improve access to data-driven careers advice and guidance. You can read more about the other Finalists on the Prize website.