Take Your Own Shoes Off
Empathy fails at the removal step, not the entry step — drop your agenda before entering theirs.
- Difficulty
- Moderate
- Time to result
- ~ongoing to results
- Steps
- 5
- Confidence
- 85%
The cliché is 'put yourself in someone else's shoes.' Adriel Frederick's correction is that the hard part is taking your own shoes off first — clearing the thing you walked in wanting before you can genuinely understand the other person's motivations, fears, and goals. Only after that removal can you put both pairs on at once and find the common objective. This is the skill he names, alongside organization design, as the one he most had to grow moving from IC to VP.
Origin
Adriel Frederick, describing the transition from senior IC to product leadership at Lyft and Reddit; sharpened by his experience as a leader who 'looks different, talks different, comes from somewhere else' and must overcome an unconscious 'this guy isn't one of us' reaction.
Core principles
- 01Empathy for users is a different (and easier) skill than empathy for peers and cross-functional partners.
- 02The blocker is not entering their perspective; it is releasing your own agenda first.
- 03Understanding what someone fears and what excites them is the raw material for finding common ground.
- 04Sometimes the honest output of the exercise is 'you're good, I'll leave you alone.'
- 05Once the shared objective is explicit, most conflicts dissolve.
How to run it
- 1
Name what you came in wanting
Before the conversation, articulate your own agenda explicitly — the thing you walked in to get.
- 2
Take your own shoes off
Deliberately set that want aside and clear your mind. This is the step everyone skips, and skipping it means you 'listen' entirely through the filter of your own goal.
Pro tip Treat it as a discrete act, not a mindset: 'I wanted X. I'm getting rid of that now.'
Watch out You cannot fake this. If you're still holding your agenda, the other person hears negotiation, not understanding.
- 3
Get into their head
Understand what's going on with them, what they care about, their life goals and motivations, what they're scared of, what they're excited by, and how you might be able to help them.
Pro tip Ask about their goals and fears, not just their position on the issue at hand.
- 4
Put both shoes on at once
Now reintroduce what the organization broadly needs to achieve, and hold both perspectives simultaneously. Look for the common objective that serves both.
- 5
Decide: push, or leave them alone
Sometimes the honest conclusion is that your concern is already handled and the right move is to back off entirely. Other times you push. Both are legitimate outputs — but only after the empathy step, never before.
Pro tip Making 'I'm going to leave you alone' a real possible outcome is what makes the whole exercise credible to the other side.
In the wild
Frederick describes being 'a guy who looks different, talks different, comes from somewhere else,' where the unconscious first reaction from a counterpart may be 'this guy isn't one of us.' His method is to make the shared objective explicit — we're about the same thing, and I want to know what's going on with you so I can help you achieve what you want to achieve.
→ Once the common objective is established, in his words, the problems go away.
Frederick had internalized the idea that the smartest, most technically competent, best individual contributors rise. That belief was disabused: the leadership job is building a great team, setting the right context, unblocking, guiding, and helping people work efficiently. He identifies organization design and empathy as the two skills he had to grow most, and the empathy piece is where the shoes framing lives.
→ He reoriented from doing the work himself to designing the culture, skills, people, and processes so others could — recognizing that nothing meaningful gets done by a single person, 'even though people like to make you think that in their hustle porn.'
Common mistakes
Entering their shoes while still wearing your own
You end up performing empathy while running your agenda in the background. The other person can tell, and the conversation becomes a negotiation dressed as a listening session.
Assuming user empathy transfers to peer empathy
PMs are trained to empathize with users, but doing it for a peer, another function, or someone on your team is a different and harder skill — their motivations and fears are personal, not segment-level.
Entering the conversation with the outcome predetermined
If 'leave them alone' isn't a possible result, you haven't taken your shoes off and no shared objective will be found.
Is it for you?
Best for
Newly-promoted product leaders and anyone doing cross-functional influence without authority, especially outsiders to the dominant culture of the company.
Not ideal for
Situations demanding immediate directive action (incidents, safety issues) where deliberation on shared objectives is a luxury.
From the transcript
“the hardest part is taking my own shoes off”
“try to understand what's going on with them what they care about for like their life goals and motivations what they're scared of what they're…”
“I'm then able to think about what we as an organization broadly want to achieve and try to put the two shoes on at the…”
“there's nothing meaningful that gets done by any single person even though people like to make you think that in their hustle porn that they…”
From the episode
Humanizing product development
Adriel Frederick (Reddit, Lyft, Facebook)