Who likes the annoying person asking for something? No one—not you, your boss, nor your client.
However, sometimes it’s worth it to be annoying. Such as when it’s really important or really urgent, and people are getting in your way of doing what needs to be done. Then, you can be annoying.
But there’s a middle ground. Not quite that important, but also not unimportant. Or someone is blocking you from doing what you need to do, and no matter how nice and courteous you are, it’s just not happening. What to do?
My preferred strategy is to start at a low level of annoyance and just be calm and nice, giving the other side extreme benefits of the doubt. I remind myself, every moment—in work and life—that no one else will have the exact same priorities I have. For this reason, no one else will choose to do what I want them to do at the exact speed and exact ways that (in the ideal world in my mind) I’d love them to do. There’s no need to be an asshole on day one.
The “on day one” is key to that phrase. Here’s my strategy: I start out calm, and get increasingly annoying, only then (if important enough) my annoyance and pressure knows no bounds.
You probably do the same, instinctively, for the issues that are important to you. You’ve probably had a client who hasn’t paid his invoice. You remind him two weeks after the deadline. Then two more weeks. Then two more weeks. And at some point, you start reminding him every two days, and write the emails in increasingly strong language, or stop engaging in the work, or something like that. This is a variation of that strategy.
So, you do that, in this natural way, for issues that are important to you, like getting paid. But what about doing the same to help you achieve what you’re trying to do for your client? Imagine that same strategy, but geared towards bugging the partner who won’t give you the piece of information you need to move forward? Or geared towards that designer who isn’t delivering the needed collateral? Or geared towards the boss himself, who is putting off making a difficult but increasingly important decision? Let it go at first, but increase the pressure.
The alternative here is to not do this and let the issue die. Time will solve it, the way time solves everything in the world, by killing it. Oh, Chronos, you child-eating monster! So, what it boils down to when people aren’t doing what they need to do is that you have to be annoying to make sure what needs to happen for your client does. That or you let time gently put it out of its misery. Your choice!
There’s a variation of this point that is particularly important when you’re at the higher level, but important enough and different enough to be worth noting. If you’re inspired by these chapters and you are ready to start a new job or project and rock the boat, don’t rock the boat too much on day one. For the same reasons here but let us reframe this example usefully: you need others within the company on your side, to best achieve what the client needs. To the minimum degree necessary, you need to be political with the others on the ground in the company. The first rule of politics is, don’t make people hate you on day one (unless doing that is an explicit part of your strategy.) Being the asshole on day one may make the boss appreciate you, but it will make the people on the ship deck hate you, and you need them. So, you may want to start out more positive and charming and if they’re not doing what they need to, turn up the annoyance knob. But only after you’ve charmed them.
