The Expansion Playbook Newsletter
Weekly frameworks to help expand your customers, company, and career. Read by 500+ CS & Sales leaders.
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Past Issues
Creating Customer Leverage
A friend told his teenagers something that changed their grades overnight: you're not getting good grades for me, these are your grades. That is the exact thing we get wrong with customers. Almost every ask we make is framed around our own metrics, and the customer can tell. Here are the four moves that tie the ask to what they already told you they have to achieve.
Everything Has Changed and Nothing Has Changed
A contact of mine has spent a year inside a company acquired by OpenAI, and I assumed he had seen the cutting edge of AI-powered customer success. He got no insight, no guidance, and nothing more advanced than what his team already had. I have now looked under the hood at several AI companies, and they all have the same problems we have been working on for 20 years. You are not behind. Nobody is ahead.
Know Your Customer's Business Better Than They Do
An onboarding specialist told me her customer had eight years more education than she did and had practiced medicine for twenty years, so who was she to tell them how to run their business. The answer is that you will never out-know them, and you do not have to. You have to out-model them on the two to five numbers that decide whether they make money, and that takes weeks of focused effort rather than a career.
Stop Waiting for Permission
A business law professor refused to give our class a rubric. Answer the question, he said, and that was the entire assignment. It turned out the arbitrary requirements were never the work, they were the packaging around the work. Most of the limits on your job are the same: rubrics you wrote for yourself, and they are standing between you and the outcome you are actually being judged on.
Six Problems Is Only Six Problems
A frustrated customer is rarely angry about a list. They are angry about a fog, because an undefined customer problem has no edges and expands to fill whatever space you give it. Put a number on it and six problems is only six problems, and usually only two of them are blocking the result they bought. Here is the Outstanding Needs play: capture every need, rank it against their outcome, and put an owner and a date on every row.
Would You Meet With You?
You can get the admin on a call any day of the week, but the executive who controls the renewal will not talk to you. The mistake is treating it as a persistence problem: more emails, more calls, until the contract quietly ends. The real question is the one you should be asking yourself. Would you meet with you? Here is how to earn an executive's time by doing the work and proving the meeting is worth taking before it is ever booked.
There's No Such Thing as a Stupid Customer
Every customer-facing team has a phrase that hangs over the hard accounts: the customer is stupid. But the customer was never the one with the expertise, and the act of buying your product is an admission that they need your help, not just your product. Every 'stupid customer' story is a failure you were supposed to design out. Here is how to stop blaming the customer and start engineering the successful path instead.
Name the Win
You can deliver $3 million of value and still lose the renewal, because value the customer never observed gets absorbed into everything else that happened that year. Name the Win is the discipline of calling your shot before the work starts, stating the result back the week the number moves, and repeating it continuously so the renewal becomes a harvest instead of a scramble. A result the customer cannot see is a result that did not happen.
Know Why You Miss
A streaky shooter chalks up an off night to bad luck. An expert knows why every miss happened, so every miss becomes a correction they can make mid-game. Customer success is the same game: define the fundamentals of a make, diagnose which one is missing, and fix it on the next shot instead of explaining the loss at renewal.
Two Sides of the Same Coin
Most teams run two motions: a customer success team watching a health score for risk, and an expansion team chasing more revenue. But risk and expansion share one core. Define what success looks like for one outcome in four parts, technical, behavioral, outcome, and time, and the same measurement, the Dual Signal, tells you both stories. All four met means the customer is ready to grow. Any one missing means they are at risk before the lagging numbers ever turn red. And there is really no such thing as retention.
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