Jeff Weinstein

Effective executive communication requires a personal, authentic voice rather than a sanitized corporate tone.

"I remember writing the first draft... and he wrote back, 'This doesn't sound like you yet.' ... I rewrote it completely, and I made it sound like me, and I've tried to make things sound like me since."

Low-fidelity, high-vision storyboarding aligns teams on the 'perfect' outcome before getting bogged down in technical constraints.

"Storyboard some solution visually with a Sharpie and not a pencil, not Figma initially... What is the unconstrained perfect solution to this burning problem? That's Pixar-style storyboard."

A lack of customer outrage during a service outage is a strong indicator that your product is not solving a mission-critical problem.

"I missed a huge moment that I should have pounced on, which is that during those 20 minutes, our customers weren't furious. They weren't emailing us like crazy... I didn't realize at the time that was..."

Feedback from friends or non-paying users is often polite noise that distracts from the needs of the actual target customer.

"I just set a rule, which is, 'We discount all of that feedback from our friends to zero.' That is not of interest to us... We are only interested in Sarah, our target customer, and can we get her to s..."

Building a diverse and effective team requires intentionality at the very top of the recruiting funnel, not just at the hiring decision stage.

"The candidate poll must match where you want the team to go. It's not a down funnel problem, it is an up funnel problem. And where you have to just make sure that for each role you're comfortable with..."

Immersive role-playing as a customer helps teams overcome internal 'expert blindness' and identify hidden product friction.

"Study Group... Rule one is you do not work at Stripe and rule two is we're not here to solve any problems. This is just about practicing empathy for the customer. ... We show up four to eight people t..."

The best metrics measure the successful delivery of value from the customer's point of view, rather than internal activity.

"What was the value that we're trying to produce for the customer and can we measure it from their perspective? ... We suggested this metric to ourselves, companies that have no support tickets through..."

The naming and aesthetic presentation of a metric determine its cultural adoption and motivational power within a team.

"Picking metric titles that make you feel something... 'companies with zero support,' that's it. And the brevity and the focus and the customer mindset built into the chart name can become currency ins..."

High-performing leaders often default to clearing easy tasks (3-100) instead of tackling the most difficult, existential problems (1-2).

"You are one of the best people I've ever worked with at solving problems three through 100, but I need you stuck on problems one and two."

Direct, high-speed communication with a small group of highly engaged customers provides more valuable signal than large-scale aggregate data.

"The moment the customer felt compelled enough to go out of their way to talk about some problem, that's a unbelievable gift. I will leave a meeting to just get one message back to them. If you're text..."

Pitching during a research call anchors the customer and prevents them from sharing their actual burning problems.

"You have to carefully listen and not pitch your customer... people don't want to be pitched. I'm sometimes on a UXR call... and the first thing that they start talking about when we get on the call is..."

Specific, open-ended prompts about a customer's daily life reveal the 'first problem' they are desperate to solve.

"I'll prompt our customers, I'll say, 'Hey, do you mind just opening up your email? What's in there?' Or, 'If you weren't talking to me right now, what would you be working on?' Or, 'Hey, last week, wh..."

The gap between 'willingness to pay' and actually 'paying' is massive; forcing a $1 transaction validates the product's core utility.

"I will have them practice charging me. I'll just say, 'Hey, I'm just a friend. I'm trying to help you out... send me an invoice or a payment link for $1 right now, right now. That way, when it comes t..."

Tracking every instance of user friction as a 'bad day' event creates a prioritized backlog of quality improvements.

"If you are unsure what to measure... just make a user having a bad day chart, emit a log line and count it as a bar chart. ... It's like, oh, I'm working on making this chart go up and it feels good t..."

A single working prototype or 'proof of existence' is more persuasive than any theoretical argument or slide deck.

"I find proof of existence to be an incredibly powerful proof, rather than proof by theory or proof by debate. It's like, 'Look, we did it one time. Hey, I'm holding the piece of paper.'"