CUSTOMER SUCCESS & NRR
Stop Selling Against Yourself
I hear it from founders and sellers all the time. “I don’t want to grill the customer.” “They won’t want to expand.”
Every time, I ask the same question: what did the customer say?
Nothing. “I didn’t ask, I assumed”.
Assume…we all know what that means.
Asking Is Not Grilling
The #1 response I hear is “I feel like I’m grilling the customer.”
Here is what I think is happening. Most founders are strong technologists and the new world of sellers are used to getting information without real live conversations (how much detailed info do you get in a zoom meeting vs. a 1:1 or in person meeting?). Asking open questions about someone else’s world is a different skill, and nobody taught it to them.
The customer sees it differently. Someone who gave you their time and their budget usually wants to be asked what is working, what is not, and what they wish you would build next. Being asked is a form of respect.
Writing the Customer's Objection for Them
Sellers do a version of this. They look at an account that bought last year. The first deal took longer than expected. Procurement pushed back. The champion changed roles. Then the list grows: budgets are tight, the team is busy, now is not the time.
Every item on that list came from the seller. The customer hasn’t said a word.
A hard first deal is not evidence against the second one. It is a map of what to prepare for.
Getting Rid of the Guesswork
Two things change the conversation:
Ask, then let them answer. Make the request and let the customer decide. “Would 20 minutes next week be useful?” is a fair question, and the answer belongs to them. Founders, start with their world: what they were trying to do, what got in the way, what they do today. Product feedback follows naturally.
Turn the assumption into a question. When you catch yourself writing the customer’s objection, ask it instead. “I assume budget is tight” becomes “How are you thinking about investment in this area next year?”
What to Do This Week
Pick one customer you have been hesitating to call. Write down the reason you haven’t. Now turn that reason into one open question and send the invite.
Then pick one account where you have assumed the answer is no. Ask the question you were afraid of. Whatever they say, you now know something you didn’t before.
The Right Question
Don’t ask “what will the customer say no to?” Ask “what haven’t I asked them yet?”
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If your team keeps finding reasons not to ask, let’s talk.