Most people don’t like repeating things too much. You feel like you’re being annoying when you have to say something a million times. (Exception: people who don’t mind being annoying!)
But there are a few things that are really important to say again and again and again.
One of those items is this: whenever you’re doing something that has a risky outcome, it’s best to reassure your boss that you know it’s a risk, but you’re taking steps to minimize that risk. Even if you’ve said this a thousand times before. Some things you can never say too many times, especially from the point of view of your boss or client, who above all, wants to make sure nothing major goes wrong.
Here are a bunch of different examples.
- If a client gives you his credit card number to use, you should notify him every time you use it and say, “By the way, I’m keeping the credit card number in my encrypted password protection app on my local computer, so it can never be hacked.” You can never say it too many times to them.
- If you’re talking to a big potential customer of your client—and your client is worried that you talking about politics could turn off that potential customer—repeat endlessly to the client, “By the way, I’m not going to mention politics when I’m talking to him!” (See my previous chapter recommending you don’t discuss politics at all!)
- If you’re about to send out an email blast, and your boss is really worried that some unhappy people we can’t email are on that list and asked you 4 times to double-check their email addresses are removed, you can tell him, “Oh, by the way, I just checked for a 5th time that the email addresses are removed,” before you send it out.
What all of these have in common is soothing a fear, to minimize the appearance of a risk from your client’s eyes. The value of this is so high, it’s worth it to be annoying and repeat it. Remember, humans value lowering the downside much more than they value the equivalent but inverse potential upside; we get sadder about losing $10,000 than we get happy from earning $10,000.
On a related but slightly different note, you can repeat qualifications as often as needed, for any sort of qualification for which you worry there may be any risk. Take, for example, situations in which you may need to point out something not perfect about your manager; when you need to do that, you can repeat, “I know you’re trying to do [positive intentioned thing ABC]” as often as needed.
The meta lesson here is that this is a reminder that there are many situations where it’s perfectly fine to be annoying.
There’s also an important implication here: you shouldn’t only repeat to them that you’re minimizing the risks, you need to actually be minimizing the risk. Don’t just tell them you checked it five times, but actually, check it five times!
