One of my favorite questions is: “What’s wrong with this idea?” It drives the conversation away from why the idea is great, and toward finding its flaws. That is invaluable in technology.

Question: “What’s Wrong With This Idea?”

I learned this idea from Paul Arden:

“If, instead of seeking approval, you ask, ‘What’s wrong with it? How can I make it better?’, you are more likely to get a truthful, critical answer."― Paul Arden, It’s Not How Good You Are, It’s How Good You Want To Be

People don’t like to criticize. They’d rather agree.

Add in power dynamics such as boss-subordinate or junior-senior. Engineering leaders have both working against them. On top of that, criticizing an idea requires emotional safety.

Less-experienced folks often won’t even think to challenge the idea. They might have good reasons to doubt based on life experience, or reasoning skills. But the thought won’t enter their heads unless invited.

Asking this question invites challenge. It’s signaling: “I care the most about getting the right answer.”

And that feedback is incredibly valuable. We want to hear it now from our team. Not from a customer or competitor when the product is failing in production.

Ask this about your ideas, not others. You’re being vulnerable and modeling that.

Here are three mental models that have helped me think about this question.

Mental Model: Crossing a One-Way Street

They say that a programmer is a person who looks both ways when crossing a one-way street. This question is a way of “looking both ways.”

People get hit by cars going the wrong way down a one-way street. Do this job long enough, and you’ll see it happen.

Mental Model: “How am I going to lose this case?”

I watched a legal procedural where the lead prosecutor asked, “How am I going to lose this case?” Another version of this question.

Her team of lawyers listed a bunch of problems: the defendant was too likable, the victim had a complex past, and no witnesses. And then, the team started attacking these flaws.

Contrast that with a prosecutor who says: “Open-and-shut case; we don’t need to waste resources on this.” Which team do you want to be on?

Mental Model: Inverted Thinking

Another way to think about this is through the lens of inverted thinking.

With inverted thinking, we can think through the full implementation of our idea and ask, “We built this and it failed. What happened?”

Some possible answers:

  • We missed a use case
  • We didn’t know what the customer wanted (no acceptance criteria, or bad acceptance criteria)
  • We didn’t deliver what the customer wanted (failed to meet the acceptance criteria)
  • It took too long to deliver (the competition beat us, or we ran out of funding)
  • The customer churned

Asking “What’s wrong with this idea?” can surface these hazards early on.

Conclusion

The next time your team is considering an idea, break through the positivity with the question: “What’s wrong with this idea?”