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How might we...

How might we...

build on something more than a hunch?
Weekly-ish from 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
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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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