Below is a general outline of how I prefer to approach an opportunity. To be clear, this process is pretty fluid with lots of side iterations and re-attempts to drive at the fundamental needs, pains and goals of my customer or user. Every situation is different and so I utilize methodologies as a part of a toolkit rather than relying on one prescriptive application. 

When first starting out with new challenge, I like to ask a lot of questions that aim at different aspects of the problem. Questions like:

-What is the user doing now?

-Where are they now?

-If we solve for X and get Y – What does that mean for the user? for your business?

-Who does something like this now? What is the perception of this?

-What business are we in? it’s usually an obvious answer but sometimes it gets interesting results.

EX: Personal Insurance – We’re in the business of protecting what people care about the most. OK – fair…

But consider the question in the context of an auto insurance claim:

A customer is in an auto accident and their vehicle cannot be repaired. They no longer have a way to get to work, take the kids to daycare, get groceries. They are now deeply affected in their life. They need to get back on their feet and they need help.

So now, what business are we in?

Taking the customer’s perspective empowers me to go through different thought progressions, uncovering new possibilities.

Questions allow me to frame the challenge and also start unearthing some competitive intel. I will sometimes call “best in class” businesses and ask what’s on the rep’s screen or go to their sites and play around. Of of this gives me some context to guide the starting direction.

With some clarity, I like to get timelines, budgets and expectations of deliverables squared away. Then, I like to exit the building and go see what’s going on in the wild.

I interact with customers to understand what jobs they want to be done and the pain points that the current solution is giving them. Depending on the situation, I use the following methods to empathize with the customer and develop a profile:



-Card sorts


-5 whys

-Chat bots

Discovery allows me to map, categorize and rank insights; leading to a customer profile.

Once the data is collected and the challenge more narrowly defined, I begin to ideate around specific points in this customer’s journey. I like to evaluate both the most troubling pain points and the nagging ones that can amount to a bad experience (a lot of times you see a pattern of small missteps that create one big issue).

When ideating I like to use a series of divergent and convergent questions to help open and close the thought with my team.

I then storyboard the idea into scenes that will allow us to visualize the prototype. Storyboarding is great because it allows me to:

-focus back on the customer and their experience,

-makes the prototyping easier and

-helps to better define the test.


Prototyping varies by situation. If I am designing a new process, I need to think more about a team, logistics and props. If it’s a digital product or service, I use Sketch and InVision to create a facade for the test.

If it’s a digital product or service, I start by getting some inspiration boards and colors together. I then make some low fidelity layout mockups. I will pencil out the boards and sequences to make sure I’m not missing major concepts. Once acceptable, I quickly dive into the pixels and create a high-fidelity prototype.

Running a test is so much fun! I like to get the immediate reactions and feedback from my conceptual prototype. It’s awesome running tests in this way because its low cost, less time and if the customer loves it or hates it – we learn something.

I try to do testing as low cost as possible. Usually, I will go into one of our call centers, talk to random people on the street or orchestrate a craigslist ad to get targeted users to try the prototype.

Once the test is completed, distilling the feedback with my team is important. Getting other perspectives on the outcome is helpful. It keeps me from anchoring my thoughts to the customer’s interpretations. Once this is all distilled – rinse and repeat!