The problem with “why wouldn’t you…?”

When I was only a year or so past graduation I had an opportunity to help define a new business proposition: finding ways in which malicious insider behaviour could be identified using the data already available to our client.

I distinctly remember the afternoon following our first half-day workshop with the client team in which we’d been figuring out how we could have spotted insider activity based on real historical cases. As I briefed back to my senior manager to show him where we’d got to, he jumped in with a “why wouldn’t you just do X?” question.

His proposal was a good one and I fumbled for a response as to why we hadn’t found that answer. I felt stupid and like I’d wasted my and our client’s time, but was frustrated because what we’d done that morning was collaborative, intellectually rigorous good work. We’d just found a different answer.

It was a form of phrasing often used by this manager and I quickly realised a very poor one. Fast forward to today and I still see this form used inappropriately all the time.

What’s wrong with it?

It’s a lazy and disempowering way to issue an intellectual challenge.

Firstly, it’s a proposal, not a genuine question. Most often in my experience it is meant as “what about doing X?”.

Second, because it’s a proposal, not a question, it can be quite disempowering, particularly from “senior” people. The time for this kind of proposal is before the team have to invested a bunch of work finding their own answer, not afterwards.

Thirdly, it’s aggressive. The framing of the proposition is essentially challenging the responder, in the short time it takes to comprehend the proposal hidden in the question, to find quality arguments against the proposal.

It’s incredibly easy to find yourself making proposals in this way (I certainly do). Should it exist as a tool in your toolbox? Of course, but use it judiciously.

And if you find yourself frustrated and on the receiving end of this kind of “question”, consider doing what I did: learn to spot the question and reframe it, with something like “I don’t know, that’s not what we came up with but I’ll be sure to fold it in to the next discussion”.