“When you compared the options, what made you choose this one?”
From April Dunford · Author of Sales Pitch and Obviously Awesome
Why it works
Dunford's central argument in Sales Pitch is that buyers don't fail to choose because they lack information — they fail because they can't confidently weigh their options. As she puts it, 'customers are overwhelmed with information and starved for insight… buyers need to ensure that they have the right purchase criteria and have fully explored their options.' This question reconstructs the criteria the buyer landed on after that struggle: not the feature checklist, but the trade-off that actually settled it. Because they're describing a real comparison they already made, the answer reveals your true differentiated value — the dimension on which you genuinely beat the alternative in their eyes. Lead your positioning with that, and you stop fighting on criteria where you're merely adequate.
When to ask
After a buyer has chosen you over real alternatives — a won deal, a recent purchase, a switch from a competitor. Reach for it whenever you suspect your pitch is leading with the wrong strength; the gap between why you think you win and why buyers say you win is where positioning quietly leaks.
Good follow-ups
- Of everything you weighed, which single thing tipped it?
- What was the closest alternative, and where did it fall short?
- Was there a criterion you cared about that none of the options handled well?
Watch out for
Hearing a generic answer ('it just seemed best') and stopping. That's the pre-insight fog Dunford describes, not the real reason. Press for the comparison: 'best compared to what, on which dimension?' The opposite trap is steering them toward your favorite feature — if you supply the criterion, you learn nothing. Let them name the trade-off in their own words, even when it's a dimension you'd rather wasn't the one that mattered.
Where to ask
- User interviewgreat
The gold is in the ordering — live, you can ask 'and which of those mattered most?' until the one criterion that actually decided it separates from the nice-to-haves.
- Sales callgreat
On a win-loss call this is the whole point: you learn the real purchase criteria the buyer used, which is rarely the one your pitch was built around.
- In-product surveyworkable
Asked just after purchase, a single open field captures the deciding factor while it's fresh; answers cluster into the criteria your positioning should lead with.
- Long-form surveypoor
A fixed list of factors imposes your frame and lets people tick what sounds reasonable; you lose the buyer's own words and the relative weight that makes the criteria useful.
Stage: Consider · A question popularized by April Dunford
Source: https://aprildunford.substack.com/p/a-buyer-centric-approach-to-competitive