I was in a funny situation yesterday. A friend, a designer, had been following my advice and writing everything down, as I recommend. Yet, his CEO would ignore what he said and what he wrote, engaging in tactics like asking him the same question 16 times (even though he told him the answer, and put it in writing.) When people ask the same question again and again, we remember the famous Einstein quote and think the asker must be insane. But what happens when the asker isn’t insane and is, in fact, particularly smart? What is going on here?
To unwind the dynamics, we need to remember two important things:
The first is, when someone repeats a question, it does not necessarily mean they didn’t understand the first answer. (Maybe Einstein was wrong—or, more likely, his quote applies in some situations but not in other situations, such as acting or confusion.) Rather, it’s a way that a lot of people convey that they don’t like the initial response. In particular, they want to apply light pressure to you to change your answer. This can depend on the frequency with which they ask, or maybe it is high pressure they are applying! The answer means nothing more and nothing less than that. If you tell me, “Morgan, I’ll have the design by next Thursday” and then I ask you every day between now and Thursday, four times per day, if it’s ready, that just means I want it sooner than Thursday.
As a result, trying to respond literally, “As I told you on the phone and in such-and-such email and in such-and-such Google doc, it will be ready by Thursday EOB” will only increase frustration in all directions. He doesn’t want or need the deadline repeated to him again; he is indirectly asking you to change it. And yes, this is a form of passive-aggressiveness.
But knowing that answer wasn’t enough to solve the problem. How do you push back to a boss—or a client—that, upon agreeing to something, applies annoying, passive-aggressive pressure to change your answer?
One key part of the answer not only can stop this passive-aggressor but is even better used beforehand to preempt him. It is this: don’t just write everything down (as we’ve recommended in a previous chapter) but write everything down in a format commensurate with its importance.
How anything is written down changes—often drastically—its importance. For an extreme example that makes the point, using the metaphor of a different type of relationship: compare a drunken text message “u marry me?” to a formal proposal with an expensive ring when you’re on one knee in front of a magnificent mountain view. The same point, but the change of format changes everything. Importantly, note that one reason why divorce papers have such power to them isn’t just the legal ramifications behind them, but because, by dint of what they are, it means a lot of thought, planning, and preparation went into them (in a way that didn’t go into your drunken email.)
In short, the levels of writing communication down are something like this, from weakest to strongest:
- Written in a one-on-one chat that vanishes quickly (SMS)
- Written in a one-on-one chat that’s archived (Google chat)
- Written in a Slack channel
- Written in email
- Written in a Google doc or MS Word doc
- Written in a doc and signed
- Written in a doc, signed and notarized
- Written in a doc, signed with everyone’s lawyers together, and then notarized
The key to this is: the format doesn’t just change the importance but, as you go down the list towards greater and greater importance, the requisite documents you’ll create should have increasing detail, granularity, and thought in them. (Just like how the divorce paper delivery has more thought into it than the drunken email you sent.)
So, compare the following situations. Situation A: you tell your client, “Hey Mike, the Invision mockups will be ready 4 weeks from tomorrow” versus Situation B: “Hey Mike, check out my Google doc I made for you, linked here, that includes my estimate for when it will be ready, how I came to the estimate, and the various risk factors associated with this estimate and a likelihood I associate with each risk factor of happening. The key point of the doc is that, if all goes well and only the least-likely risk factors happen, it should be ready 4 weeks from tomorrow.”
In other words, the same point, delivered in a different format, sounds not only stronger but more professional as well. And this can be done once the client is annoying—or even better—to preempt the annoyingness.
Now, there are a few key nuances here that we need to remember when we implement this.
First, it’s not a coincidence that in my hypothetical, detailed example, the doc includes risk factors and probability estimates you’ve made to the best of your abilities. All clients ever in the history of the universe since time immemorial love both of these. (There may be one or two exceptions.)
Second, document creation is one of the hearts of good management (firm people management is probably the other heart of this two-hearted beast, but that’s the subject for another chapter.) One key difference between “the good employee” and “the good manager” is the good manager thinks through complex issues, and then puts the results of this thought, as well as an outline of his thought process, into documents for the relevant people to review. And you don’t want your client to manage you—you want to manage your client.
