The Design Partnership Playbook

Not what you typically hear when you ask founders about their ideal design partner.

Most chase their biggest believers - a mistake. Skeptics can make for far better design partners.

Here’s why:

Supporters tell you what you want to hear. They're excited about your vision. They see the potential. They give you energy. But they don't push your thinking.

Skeptics tell you what you need to hear. "We're building this internally already." "I don't see how this is different." Such challenges make your product bulletproof.

On top, when skeptics become believers, they’re your strongest advocates. They've thought through every objection and challenged every assumption. When they say yes, it’s a very strong yes.

So, how do you run effective design partnerships?

Most startups start chaotically:

No real structure. Loose timeline (often 3-6 months). No clear payment expectations. Just bi-weekly calls with passionate users.

This can work for product development but doesn’t for monetization.

Awkward conversations emerge when design partners must become paying customers. Some negotiate hard, some stall, some ghost you entirely.

Here's what most founders get wrong:

• Optimizing for quantity over quality: 10 deeply engaged skeptics beat 50 polite supporters. You need people who use the product daily, break it, complain about it, and push you to make it better.

• Hiding from commercial conversations: It's awkward to talk pricing when the product barely exists. Do it anyway. Even broad ranges help set expectations. "Somewhere between $30-50K annually" beats surprising them later.

• Building in isolation too long: Typically, two months is the sweet spot. Longer and you're building features nobody asked for. Shorter and you haven't built enough trust for honest feedback.

• Focusing only on product feedback: Design partners should also teach you about buying processes, budget cycles, and organizational dynamics (i.e. GTM).

Try this instead:

• Clear timeline: Two months. Not three, not one. Two months gives urgency without rushing. Long enough to build trust, short enough to maintain momentum.

• Explicit expectations: "At the end of two months, if you want to continue, you'll need to pay." Said upfront. No surprises. No awkward transitions.

• Structured engagement: Bi-weekly 30-minute calls. Dedicated Slack channels for daily feedback. Up to x users per company. Enough to get real usage, not so many that it becomes unmanageable.

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Enjoyed reading this?

Then check out my conversation on the focal podcast with Alexa Grabell, Co-founder and CEO of Pocus ($23M raised from First Round, Coatue, Pear, Box Group, GTM Fund).

Youtube | Apple Podcast | Spotify

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