How to ask questions in person, by email and online

A good question can still fail on its wording, its timing or where it is asked. These sets are for anyone who wants better answers: how to ask without leading, how to fit several questions in one email, how many is too many, and how to find the nerve. Some cover Snapchat, forums and ChatGPT.

29 sets · 928 questions · each with a note on why

A few to start with

How do you like to spend a day with nothing planned?
The open cousin of 'Do you have any hobbies?', which a lot of people answer with 'not really' and then feel dull. A free day is easier to describe: the long breakfast, the hardware store, the nap nobody admits to. Ask about whichever detail they lingered on, since that is the part they enjoy.
From: Open-Ended Questions to Ask
What are you working on right now that you find most interesting?
A way into a one-on-one or a coffee that skips the status report. People talk longest about work they would have chosen, so you find out where their energy is going. If you manage the person, a long pause before the answer is worth noticing.
From: Open-Ended Questions to Ask
How did you arrive at that estimate?
This draws out assumptions, and those are where estimates usually go wrong. Ask it of numbers you like as well as numbers you doubt, or people will learn that the question means trouble. A strong answer names what was left out.
From: Open-Ended Questions to Ask
How does a decision like this usually get made on your side?
The blunt version, 'Are you the decision maker?', can put people on the defensive, and tends to get a yes whoever really decides. Asked this way you hear about the partner, the board, the spouse or the budget cycle. Then ask what each of those people will want to see.
From: Open-Ended Questions to Ask
What have you already tried?
It stops you from proposing the thing that failed last year. The detail to listen for is why each attempt was dropped: cost, effort, a person who left. Those reasons are the objections you will meet later, stated early and without heat.
From: Open-Ended Questions to Ask
How did you get into that?
Have it ready for the moment someone mentions a job, a hobby or a team they follow. 'Have you done that long?' gets a number of years; this gets the uncle with the darkroom or the summer job that never ended. If they say they just fell into it, 'fell into it how?' tends to bring out the longer version.
From: Open-Ended Questions to Ask

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