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Oliver Buchannon
Skipper Warson

I'm Skipper, facilitating better product strategy & design work at How This Works co

tense

+9

The question is always about the past

May 12, 2026

•

3 min read

The question is always about the past

The answer to the future lives in what your customer has already tried

Skipper Warson
Skipper Warson

startups

+7

When your pipeline stalls, check which conversation you're having

May 4, 2026

•

3 min read

When your pipeline stalls, check which conversation you're having

Sales down 23% over 18 months — not for lack of customer contact, but for lack of the right kind of contact

Skipper Warson
Skipper Warson

startups

+7

The difference between a discovery conversation and a sales pitch is one question

Apr 27, 2026

•

4 min read

The difference between a discovery conversation and a sales pitch is one question

The moment you pitch, most conversations are over

Skipper Warson
Skipper Warson

startups

+7

"Um, shit," I said

Apr 18, 2026

•

2 min read

"Um, shit," I said

On echo chambers and the 1-pager I should have updated a year ago

Skipper Warson
Skipper Warson

product-market fit

+5

While I was gone... and then I realize I've been running experiments this whole time

Mar 29, 2026

•

7 min read

While I was gone... and then I realize I've been running experiments this whole time

On coming back, a domain detour, and the detective agency I never opened, but kinda did

Skipper Warson
Skipper Warson

bullseye customers

+4

The confidence that comes after dressing up in a giant hoop skirt

Dec 22, 2025

•

8 min read

The confidence that comes after dressing up in a giant hoop skirt

Two (2) months for 15 minutes of fame

Skipper Warson
Skipper Warson

AI

+5

82 responses, three (3) interviews, and a single wasted week

Dec 1, 2025

•

9 min read

82 responses, three (3) interviews, and a single wasted week

When your data tells you one story and humans tell you another

Skipper Warson
Skipper Warson

product-market fit

+8

Why that feeling of "almost right but not quite" matters more than the perfect prompt

Nov 24, 2025

•

9 min read

Why that feeling of "almost right but not quite" matters more than the perfect prompt

AI is inevitably part of the conversation, here's what I've learned about when it actually helps — and when to trust your gut instead

Skipper Warson
Skipper Warson

facilitation

+6

Bound by time: the forcing function behind the Bullseye Customer Sprint

Nov 10, 2025

•

8 min read

Bound by time: the forcing function behind the Bullseye Customer Sprint

Why the timeline isn't about speed — it's about limiting how much you can invest in being wrong

Skipper Warson
Skipper Warson

bullseye customers

+4

How I've been able to turn 80 customer interviews into clear insights

Oct 27, 2025

•

11 min read

How I've been able to turn 80 customer interviews into clear insights

Using Redact and Claude to systematically extract insights without drowning in hours of transcripts

Skipper Warson
Skipper Warson

How might we

+6

How might we... prompt AI tools like we're actually thinking

Oct 21, 2025

•

9 min read

How might we... prompt AI tools like we're actually thinking

Why the way you frame questions to AI determines whether you're thinking or just following instructions

Skipper Warson
Skipper Warson

fishing

+4

The fish that swam away

Oct 14, 2025

•

7 min read

The fish that swam away

Sometimes you have to hold something to feel it, to understand it

Skipper Warson
Skipper Warson

startups

+5

Your customers aren't who you think they are

Oct 6, 2025

•

8 min read

Your customers aren't who you think they are

The gap between what you're building and who actually needs and wants it

Skipper Warson
Skipper Warson

bullseye customers

+5

The prep work before bullseye customer interviews to make them go off without a hitch

Sep 28, 2025

•

11 min read

The prep work before bullseye customer interviews to make them go off without a hitch

People often ask me what's different between a bullseye customer interview and a user interview

Skipper Warson
Skipper Warson

brain science

+5

Why your brain isn't built for typical meetings (and what to do about it)

Sep 24, 2025

•

6 min read

Why your brain isn't built for typical meetings (and what to do about it)

The cognitive research that changed how I think about collaboration

Skipper Warson
Skipper Warson

facilitation

+4

"What am I even doing here?" — the meeting problem we all recognize

Sep 23, 2025

•

5 min read

"What am I even doing here?" — the meeting problem we all recognize

Starting How This Works co taught me meetings are really just design problems

Skipper Warson
Skipper Warson

Sesame

+1

The WeWork common floor conversations that saved Sesame's launch

Sep 22, 2025

•

5 min read

The WeWork common floor conversations that saved Sesame's launch

What we learned bribing strangers to look at our half-built product

Skipper Warson
Skipper Warson

Innovation

+5

Gustave Whitehead's dilemma: to build engines or to chase flight?

Sep 21, 2025

•

6 min read

Gustave Whitehead's dilemma: to build engines or to chase flight?

What his story can teach us about focus when markets barely exist

Skipper Warson
Skipper Warson

customer interviews

$2M insight hiding in 10 conversations

Sep 11, 2025

•

4 min read

$2M insight hiding in 10 conversations

Why subject matter expertise and market research isn't the same as customer insights

Skipper Warson
Skipper Warson

customer interviews

Teams swear they know their customers like the back of their hand

Sep 8, 2025

•

5 min read

Teams swear they know their customers like the back of their hand

But the reality is that they haven't talked to one in weeks or months — if ever

Skipper Warson
Skipper Warson

TIL

+3

How one lie created a 30-year feud

Sep 7, 2025

•

8 min read

How one lie created a 30-year feud

What it teaches us about truth, positioning, and the history of innovation

Skipper Warson
Skipper Warson

How might we...

test what we think we know. How might we... stop building on assumptions we haven't tried out yet. How might we... know if what we're building is for the right person. Sensemaking at its finest from inside the work and sometimes from home.

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