sending an email for the purpose of business communications can result in if vs whether grammar pitfalls

The following is a true story about if vs whether grammar pitfalls that can happen in business communications.

The First Email

A few weeks ago, one of the leaders of the company I work for sent all employees an email announcing an upcoming company event and listing possible dates on which it might be held. The leader also wrote this:

“Please let me know if you have any known conflicts.”

This sentence, being an “if statement,” is equivalent to the following:

If you have any known conflicts, (then) let me know.

This type of statement expresses a logical condition. If this, then that. Conditional statements say nothing about instances in which the condition is false, only about instances in which the condition is true.

I checked my calendar and ascertained that I did not have any known conflicts. Thus—according to the grammar of the sentence—the rest of the statement (about letting the leader know) did not apply. I figured that the leader did not want an inbox full of emails saying “I have no known conflicts.” The leader wanted to know only about cases in which there were conflicts, thus avoiding superfluous emails.

So I did not reply. I wasn’t—I swear!—just pretending not to understand the sentence, to prove what an awesomely fastidious grammar queen I am. I really thought I was doing what was wanted of me.

The Second Email

A week later, the leader sent out a second email:

“Just a reminder that we would like to know if you have any known conflicts. . . . If you’ve already replied – thanks and no need to send again.”

Like the sentence in the first email, these sentences, grammatically, indicate conditions:

If you have any known conflicts, (then) we would like to know.
If you’ve already replied, (then) there’s no need to again.

I did not have any known conflicts, so the rest of the first sentence did not apply to me. I also had not already replied, so the rest of the second sentence did not apply to me, either. Strictly speaking, then, there was no need to reply.

Analysis: Should the Leader Have Used If or Whether?

However, being the twenty-first-century English speaker that I am, I know that the word if is commonly colloquially used in place of the word whether. Unlike if, which indicates that there is a condition with only one option (only one “then” to follow the “if”), whether indicates that there are two options (and does not indicate a condition).

If the leader had, in fact, mistakenly used if instead of whether, the sentence in the first email would be equivalent to this:

Please let me know whether (or not) you have any known conflicts.

This statement is not conditional, and it indicates two options. No matter which instance is true—whether I have any known conflicts or don’t have any known conflicts—I should let the leader know.

The second email is trickier. If the leader had mistakenly used if instead of whether in both sentences, we would get this:

We would like to know whether you have any known conflicts (or not).
No matter whether you’ve already replied (or whether you haven’t), there’s no need to again.

The first statement expresses the same thing as in the first email when if was changed to whether (i.e., I should reply no matter what). The second statement does not make sense. If you have not already replied, it is not possible to do so again. This statement doesn’t make sense because the leader was expressing a condition, and so if was, indeed, the correct word choice. To avoid confusion, whether technically should have been chosen in the other two sentences—that is, if the leader did not intend to express a condition, but rather two options.

That was the conclusion I came to, anyway, upon receiving the second email. So I replied. I guess that was an appropriate response, since the leader wrote back to me with “Thank you!”

Note for the Record

I did not, while reading the emails and deciding whether to respond, have intricate thoughts about conditional statements, two options, and so on; my thoughts and actions happened more organically than that. It was only in writing this blog post that I was able to piece together the exact grammatical reasoning behind my comprehension (or lack thereof!) of the emails.

A Little If vs Whether Grammar Quiz

Here’s a little if vs whether grammar quiz. In the following grammatically correct sentence, what is the conditional statement? What is the statement that is not conditional and indicates two options?

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