If Not Could Not

Suppose you're hiring for a sales job. In the first interview, the candidate says: "I'm very good at selling things." Well, that's nice: the job is all about selling things, so someone good at selling things would indeed be a good fit.

In the second interview, the candidate says: "At my last job I increased sales by 47%, from $10k monthly sales to $14.7k monthly sales, over the course of six months."

Who should you hire?

I think it's obvious in this framing that the better person to hire is the second one. Anyone can claim that they're good at selling things, but (unless they're outright lying) not everyone can say they increased some specific type of sales by x% in y months.

Surprisingly, I constantly see people miss this insight when they're on the other side of the table. When helping friends with their CVs, I've often seen them write bullet points like

• Wrote posts that were read widely and received positive coverage

When they could have said:

• Wrote posts that were read by 20,000 people and got coverage on NPR

The test when writing such a bullet point should always be something like: if a person who didn't have my skills/abilities/interests/accomplishments were trying to spin their situation as positively as possible, could they say the same thing as I'm saying?

In this case, anyone can say they "wrote posts that were read widely and received positive coverage", since that's vague enough that it's not technically lying even if your facebook post was read by three people in different locations and your dad said he was proud of you.

But saying your work was "read by 20,000 people and got coverage on NPR" is a specific claim that couldn't be made by someone who hadn't actually done it: I'm going to call this an If Not Could Not.

Moving on to a different domain, in my life as a newsletter publisher I get a lot of cold emails that say things like:

Hello [my name]! I'm [their name], a writer from [place]. I am a massive fan of your work and platform. The quality is second to none! Just love it! 

I'm reaching out to ask if [favor the want from me].....

Notice the compliments are so vague and general that there's no evidence the sender has actually read my newsletter, and in fact you can automate this kind of email at scale and send thousands of people the same email with just their name and product swapped automatically into the sentence.

This seems so obvious to me that I assumed that 100% of emails that I received like this were automatically generated, until I snippily replied to one similar email and got a sad reply from a nice, confused person who said they'd hand-written the email and only contacted two of his truly-favorite newsletters with it.

This blew my mind (and I felt very bad). You can easily show that you're actually a fan of a specific newsletter: just say "I'm a massive fan of [newsletter] because of [specific thing it does], and I loved the thing you said recently about [specific thing mentioned in recent newsletter]." Or to put it another way: if you're a genuine fan of the newsletter you can do this, but if you're an automated system you can't. As a true fan, you can just do an If Not Could Not assessment in order to write an email that will stand out from the crowd. And it doesn't have to be deep or brilliant, it just has to be specific enough that an automation couldn't do it (yet).

One final example of an If Not Could Not I sometimes run into is during in-person conversations. It's weird to put it this bluntly, but in many conversations one hovering question is always: "did the other person actually understand what I just said?"

Certain kinds of answers don't obviously signal understanding: for example, if someone says "I agree!" or "you're totally right!" that might feel good in general, but they could easily say such things without actually grokking your specific meaning. There's a similar problem if they just repeat what you said as affirmation, or make vague ELIZA-like statements that could fit (at least grammatically) after almost any utterance.

By contrast, certain kinds of replies strongly imply understanding: if their response feels like it conceptually addresses the core of your argument, or if they mention an example that seems to perfectly illustrate the thing you were getting at, you can be pretty sure that (barring some improbable coincidences) you're both on the same page.

Of course, it's perfectly possible that someone 100% understood what you said but for whatever reason responds with "yeah sounds good" instead of an answer that properly signals their understanding; it's not possible or necessary to give a full If Not Could Not answer at every step of every conversation, but it's worth having the concept in mind so that when there's ambiguity you know what type of thing you can do to resolve it.

On the flip side, obviously the reason If Not Could Not works is that if you don't understand what the other person says then you can't signal that you do, no matter how much you want to – in that case, saying "oh, how interesting" or "couldn't have said it better" or "I just think it's important to acknowledge this is a very nuanced issue" is truly the best you can do.

The tragic outcome is only when someone who could have demonstrated an If Not Could Not doesn't realize that they should have, and therefore gets written off by their potential employer / email recipient / conversation partner unnecessarily. Since those who can't won't, those who can should.