Be tangibleTue 18 September 2018
Something that I see again and again is mistaking imprecision for wisdom. For instance, if I asked you: "go out and get 10 more users", that's a tangible, easy to understand goal. If I tell you, "we need to increase penetration of our software", then you have to add a translation step to try interpret the meaning of what I'm saying (do I mean add more users or add more time per user?). If I tell you, "our mission is to take over the world", you would be very justified is asking what the hell I was talking about.
I get it - we have ideas in our minds and sometimes words can only capture the overall sense of what we're trying to communicate, not the specifics. Language cannot perfectly convey ideas. And big thinkers, like the CEOs and leaders we all hope to become someday, tend to have so much experience (or think they do) that they shrink from describing a specific instance, and instead try to extract whatever fundamental idea they believe sums it up. These phrases are almost always universal truths that no one can deny but have no useful, actionable meaning. Life is short. Be kind. Don't be evil. Etc.
If you're trying to communicate something specifically, say it. I think we underestimate how many of our words are lost in translation.
My brain -> my words -> your ears -> your brain
You need to make this journey as easy as possible.
Unfortunately, because leaders tend to speak in generalities, people who want to become leaders speak the same way - except worse. They don't have the background to know how to abstract meaning from experience. And good speakers can intercalate their general propositions ("healthcare is a right!") with specific examples ("Jim had prostate cancer, and wasn't insured, so he couldn't get his medication in time to prevent his death"). Novices don't have the anecdotes; the generalities are just shallow truth-speak and there's nothing deeper.
So what you end up with is a terrible word salad - a bunch of conceptual mumbo jumbo that no one, including the speaker, actually understands. The only thing I grasp from such moments is: 1) this person probably doesn't know what they're talking about, and 2) they want to look like they do.
One of my favorite examples of this is from Richard Feynman, who describes reading a paper by a sociologist afflicted with the same syndrome:
So I stopped at random and read the next sentence very carefully. I can't remember it precisely, but it was very close to this: "The individual member of the social community often receives his information via visual, symbolic channels." I went back and forth over it, and translated. You know what it means? "People read."
I see smaller forms of this pretty much everywhere. People will have a bickering, long discussion about, ultimately, the definition of a sophisticated sounding word. Sometimes they'll even invent the word! There's nothing like a neologism to make you sound clever. And because it hasn't been defined yet, you get to bend the language to the actions you want to take, rather than the other way around.
My solution to this is to always add a translation step whenever I think someone is being unclear, and repeat it back to them. Here's an example of a typical dialogue:
Them: We want to build a structured mechanism by which users can ingest their own data into the existing infrastructure
Me: Gotcha, so you want to create a form that can add rows to this dataset.
Them: Not only that, but we also want to productize the workflow so that other people can easily compound on it.
Me: Ok, agreed, we need to make the form easy to use.
As you see, I keep a specific example, ideally of what we plan to do in the short term, constantly in discussion. If we're begin to veer off and talk about what this will look like in the next 6-9 months, I stop the conversation, politely. I don't mind planning, but most people are terrible at planning and really good at playing out vague fantasy escapades. It would be one thing if the fantasy escapades had even a 50% likelihood of coming to pass. They never do. People who have the diligence to plan out a new project a year in advance don't have the foresight to realize how much will change after the first 2 months. Planning is less and less useful the farther out you project, and at some point your variance in outcomes is beyond what can be feasibly predicted. No plan survives the first battle, as they say.
What I've found is, conveniently, once I've translated from vague nonsense to understandable language, people can begin to engage and provide feedback. They poke and prod and iterate. In other words, we can actually build the thing. Victory.
 Feynman, "Surely You're Joking Mr. Feynman!"