
Maintenance
Part of Why your own first hundred days rarely go in a straight line
How to ask the right first hundred days questions in the right order
First 100 days questions grouped by who you ask: the customer who stayed, the one who left, the record, and yourself, with how to score each answer.
Questions in the first hundred days are cheap and answers are not. The difficulty is that the four groups you can ask know completely different things, and most teams ask all four the same question and average the results.
So these are sorted by who is being asked. Each comes with what a useful answer looks like and what a worthless one looks like, because at this stage a bad answer is more dangerous than no answer.
What to take away
- The people who stopped hold the information about your ceiling. They are available for about a week.
- Every question here asks about what happened. None asks what someone would do, because a prediction from a person with no stake is not evidence.
- Score answers against your written expectation, not against how the conversation felt.
Ask the customer who stayed
They are the friendliest group and the easiest to learn nothing from. Keep the questions about behavior.
Five questions for staying customers
- What were you doing before?
- What nearly stopped you paying?
- When last used, and what for?
- Who else has seen this?
- What would you stop doing?
What were you doing about this before?
What nearly stopped you from paying?
When was the last time you used it, and what for?
Who else in your organization has seen this?
What would you have to stop doing if you kept paying for this?
Ask the customer who left
The hardest group to contact and the only one that can explain the limit. Ask within a week, ask once, and make it short.
Exit interview in three questions
- Ask within a week, once, short
- What did you hope it would do?
- Back to old method or something else?
- Was there a moment you decided?
- Make canceling easy
What were you hoping this would do that it did not do?
Did you go back to what you were doing before, or find something else?
Was there a moment you decided?
Canceling has to be easy for any of this to happen. Where billing recurs, that is also what the rule on negative option offers is about, and a person who gives up and disputes the charge answers nothing.
Score these by whether the reasons cluster. Three people saying the same unexpected thing is worth investigating. Three people saying three different things means you do not have a pattern yet, and saying so is a legitimate result. Separating a price reason from a value reason takes one follow-up, and the method is in the pricing questions.
Ask the record
The question log, the arrival record, and the cancellation file will answer questions nobody has asked them.
| Question | What you are looking for | The trap |
|---|---|---|
| What is the largest group of questions? | The place the product or page is unclear | Answering the loudest question instead |
| Is the question rate per customer falling? | Comprehension improving over time | Reading total questions, which rise with customers |
| Which route produced customers who stayed? | A repeatable channel worth more effort | Ranking routes by volume rather than by who remained |
| Do cohort one and cohort three have the same shape? | Whether anything actually changed | Reading the whole population, which the newest cohort dominates |
| How many leavers were asked why? | Your own discipline, which you control | Reporting how many answered instead |
The last row is the only figure on this page you fully control, and it is the best single indicator of whether the hundred days will produce anything. The counting rules underneath these are in the market metrics.
Ask yourself
Written answers, dated, in the same file as the weekly notes.
Four written questions for yourself
- What did I expect, what happened?
- What am I avoiding?
- What would make me stop?
- Which claims can I support?
What did I expect this week, and what happened?
What am I avoiding?
What would I have to see to stop?
Which of my claims can I still support?
Am I fixing or flinching?
Questions that sound rigorous and are not
Would you recommend this to a colleague? A prediction, given free, by someone with no stake. Ask instead whether they already have, and to whom.
Rigorous-sounding questions to replace
Don't ask
- Recommendation
- Would you recommend?
- Renewal
- Likely to keep paying?
- Features
- What features do you want?
- Price
- Is the price fair?
- Yourself
- How is it going?
Ask instead
- Recommendation
- Have you, and to whom?
- Renewal
- The renewal date
- Features
- What did you do last time?
- Price
- A real decision with a number
- Yourself
- The four written questions
How likely are you to keep paying?
What features would you like?
Is the price fair?
How is it going?
Common questions
How many people should I ask?
Everyone who left, and five or six of those who stayed, per cohort. The completeness matters more for leavers because they are the smaller and more informative group.
By email or on a call?
Leavers by email, one question, because a call is a large ask from someone who just stopped paying. Current customers on a call, because follow-ups are where the useful part lives.
What if nobody replies?
Record the ask rate anyway. A file showing thirty asked and four answered is still a record, and the four are still the best evidence you have.
Can I use a survey?
For the record questions, yes. For the leaver question, no: a form with options gets you the option list back, and the wording of the options will do most of the work. Open text, short, one question.
Should I offer something for answering?
It changes what people say and, if you then quote them, it is a connection that has to be disclosed. Better to ask smaller and accept fewer answers.







