Michael Sippey

Line up 30 meetings with potential customers before you write a single line of code. You get much better at your pitch after the first five meetings. After the first 10, you start to see patterns. After 20, you really understand segmentation of the market. After 30, you have a really good understanding of what it is that you actually need to go build.

Matt Lerner

When you can understand and articulate your customers’ goals and struggles and anxieties in simple, precise language, your developers and product teams will not have to guess at what to build.

Anne Raimondi

Trust = (Credibility + Reliability + Authenticity) / Perception of Self Interest

Julie Zhuo

Can you say with confidence that each report would want to be on your team again? If you aren’t sure that the answer is yes, it’s probably no.

Sean Twersky

“I trust you, make the call” might be the six most powerful words you can hear from a manager.

Annual Planning Sucks — A CPO, CRO, CFO, and COO Share Advice on How to Make it Better

Four top execs reveal their annual planning secrets from Notion, Stripe, Vanta, Linear, Linktree and more. From addressing AI to adjusting org charts, this COO, CFO, CPO & CRO share insights so startups at any stage can build effective, realistic plans.

Kevin Fishner

After OKRs are set, there’s no ritual for reviewing them, so they quickly get out of date. Then employees start resenting them because the effort to actually create the goals was a waste of time — and OKRs slowly die because no one looks at them anymore. Expectations aren’t enough. It’s the ritual that keeps the priorities top of mind and folks focused on what’s … [ Read more ]

Nate Stewart

What I’ve found is that it’s not necessarily the way you ask for feedback that matters. It’s how you show up when you receive that feedback that increases your chances of getting high-quality insights.

Matt Wallaert

For interpersonal [feedback], I’m a big fan of a simple formula: “When you A, I feel B, because C, and what I’d really like is D.” Specific behavior, specific emotion, specific cognition, specific alternative behavior.  And I think a variant can be used for delivering performance feedback as well: “When you A, it causes B, because C. One thing to try could be D.” Specific … [ Read more ]

Jonah Berger

If we only focus on the monetary barriers to adopting a product, we miss out on a lot. There are also time, effort and energy costs — ones that we are often unaware of. Consider when the real cost of change occurs in a transaction, and solve for that uncertainty.

Jonah Berger

Show people what they are losing by not doing something, and help them realize that even if the moment-to-moment costs are harder to create change, even over a short period of time, the cost of inaction is higher than the cost of action.

Jonah Berger

A startup’s biggest competition isn’t an established player, it’s inertia.

David Hsu

[A cold outbound strategy] gives you a very good sense of how something resonates. On the other hand, if you get a warm intro, people will take the call and maybe ask for a demo. It’s very non-committal and vague, and I actually think that’s harmful to startups because it can make them think they have product-market fit when they don’t.

David Hsu

If you want to launch a startup, you need to have differentiated beliefs about the world. If your beliefs are the same ones that everyone else has, there’s no reason why you’re going to find success when others didn’t.

Sara Clemens

At large corporations, making decisions is often not a matter of getting somebody to say yes, it’s getting nobody to say no.

Sara Clemens

The key thing that leads people to feel like companies are slowing down is when decisions don’t get made, when there is an opportunity or an issue and it just drifts on. Not knowing who can make a decision is the curse of large organizations.

Russ Laraway

Ask the question: Which quarterly goal does that workstream support? If you keep finding that the work that you’re doing isn’t reflected in the quarterly goals, it’s time to rethink how you’re approaching those OKRs, or get them right the next time.

Annie Duke

There’s no problem with tackling low-hanging fruit. Eventually, you have to. But you better make sure that you solve for the bottleneck first — because every bit of low-hanging fruit you tackle creates an illusion of progress and sunk cost problems.