Emotional Discovery: Feel Bad Like the Customer
On customer calls, dig until you feel the exact emotion the customer wants to avoid, then build to remove it
- Difficulty
- Advanced
- Time to result
- ~weeks to results
- Steps
- 3
- Confidence
- 95%
In saturated markets the goal-oriented, jobs-to-be-done insights are already picked over by every competitor's PMs. Nan Yu's edge is finding emotional hooks — the specific moments a user feels bad during their workday. Rather than running the analytical five-whys, he keeps a customer conversation going long and deep enough to reach the emotional valence behind a request, aiming to feel bad in the same way the customer does, then designs the product to ensure that bad feeling never recurs.
Origin
Nan Yu's discovery method, informed by his time in hyper-competitive industries (Everlane, Mode, Linear); references Paul Graham's concept of 'schlep blindness' — being blind to the daily drudgery you've normalized.
Core principles
- 01In competitive categories, the rational goal-oriented insights are already exhausted; emotional hooks are the under-explored angle
- 02PMs and engineers are 'thinky' people who avoid the touchy-feely, which is exactly why the emotional angle is open
- 03People will not directly tell you how they feel; you reach it only through a long, deep conversation where you level with them
- 04Users are often blind to their own recurring bad feelings (schlep blindness); an outsider must map the rhythm of their emotions across the day and week
- 05The insight is not the request itself but the emotional moment that motivates it
How to run it
- 1
Take the request but treat it as a symptom
When a customer says 'we want X,' recognize something emotional is motivating it. Do not stop at the literal feature or the surface goal.
Watch out The standard analytical path (five-whys, 'as persona X I want outcome Y') can miss the real reason they feel bad about not having the thing.
- 2
Keep digging until you reach the emotional valence
Ask from angles that surface the actual feeling — go past 'what's your goal' to 'what happened, and how did that make you feel.' Keep the conversation long and deep enough that they start to level with you and open up.
Pro tip Aim explicitly to feel bad in the same way the customer felt bad — that shared feeling is the signal you've reached the real insight.
Watch out Vague framings like 'marketing and I never align' are not the insight; keep going until you reach the concrete moment (e.g. the specific miscommunication) that produced the bad feeling.
- 3
Build to eliminate that specific bad feeling
Once you know the emotional moment, design the feature so the user never has to experience it again — solving the emotion, not just the stated request.
Pro tip Look for recurring weekly/daily bad moments users have normalized ('I hate Mondays because I have to gather data for a report') — a single button that removes the drudgery removes the dread.
In the wild
A user set a project ship date of December 30 (a Q4 project) and their marketing team lost it — nobody ships when everyone's on vacation. The user felt so bad they vowed never to put dates on things again. Digging into that feeling revealed the real problem was false precision causing miscommunication.
→ Linear lets you set a target date at any granularity — a December project, a Q4 project, a second-half-2024 project — so users commit only to what they're comfortable promising and never feel forced into false precision.
Some users manually routed and tracked cross-team tickets and felt underwater from the constant attention it demanded; others let tickets get thrown 'over the wall' and felt everything was out of control with no expectation of response. Both bad feelings shared one root cause: no automated, organized way to handle a triage queue.
→ Linear built triage management, which parks cross-team issues in a special zone, notifies the right people on rotation, and organizes responses.
Common mistakes
Stopping at the rational goal
Running only the analytical five-whys yields the same insights every competitor already has and misses the emotional reason the user feels bad.
Accepting a vague description of the pain
'We never align' tells you nothing actionable; without the concrete emotional moment you cannot design the specific relief.
Is it for you?
Best for
PMs and founders in crowded categories doing customer discovery who need a differentiated angle beyond jobs-to-be-done
Not ideal for
Early greenfield markets where basic goal-oriented insights are still unexplored, or research that cannot support long, trust-building one-on-one conversations
From the transcript
“my goal is to feel bad in the same way that customers feel bad right”
“what is the actual sort of emotional veilance that is motivating whatever you're telling me”
“he calls it schle blindness right”
“the thing that we did specifically to solve this uh was we you know on projects in linear you can just specify um of Target…”
From the episode
Linear’s secret to building beloved B2B products
Nan Yu (Head of Product)