Early on in your mastery of a complex thing you are going to catastrophically overestimate your ability.

Your confidence is going to be artificially high. This new job, hobby, or sport is going to appear magically easy. You’re going to feel gifted. Those watching your miraculous aptitude keep saying, “beginner’s luck”, but that’s neither what you’re hearing nor what they’re saying. What you’re hearing them say is, “We are jealous that you are gifted at this thing you totally don’t understand”, but what they’re actually saying is, “We understand it’s intoxicating to instantly feel like an expert and we will most certainly bite our tongues when you painfully discover how much you have to learn.”

Learn schmearn. I’m a genius.

The gift of the enthusiastic beginner is blissful and empowering ignorance. They are not burdened with the depth and complexity of understanding; they shine brightly with enthusiasm… until the Fall.

Wallace Hates Me

I wasn’t even a manager. I was a lead of two engineers, but titles don’t matter. It was the change in attitude of one the engineers that got my attention. Harold didn’t miss a beat after I became his lead. He was in my office on Monday morning: “Where do we start?”

“Maybe we should, uh, fix error handling in the test framework? Maybe?”

“It’ll be done by Wednesday”. Cool. I can so do this.

Wallace was indifferent. I waited until Wednesday to walk into his office to ask, “Hey, I was wondering what you were working on?”

“Same as last week. Endless bugs.”

“Ok, great… super. Uh, holler if you need anything, ok?”

Silence. Ok, fine. I’ve never really gotten Wallace, he’s done his own thing and he seems to do it well, so let him do it, right?

Besides, I was a lead. Look at Harold — he bolts into my office every morning in his bright orange Philadelphia Flyers jersey and asks the same question: “What’s next?” He and I were cranking, so much so that three weeks after I became a lead, they added Stan to the team. Stan was a Boston Bruins fan, but he and Harold were birds of a feather. They grabbed coffee together in the morning, argued about hockey, and then darted to my office: “What’s next?”

I can so do this.

Three weeks turned into three months and Harold, Stan, and I were nailing it. Yes, I’d dutifully check in on Wallace each week, but the action was with the three of us. I figured when Wallace was ready to climb out of his shell and join the productivity party, he would.

Three months to the day, my boss walked in my office with a paper in his hand. “Wallace has been keeping a daily log of every interaction with you and claims, outside of meetings, that you’ve collectively spent 30 minutes with him in the last three months. Is that true?” He handed me the paper:

• 3/21 — Asked about bug status — 47 seconds.
• 3/22 — Question about performance — doesn’t know what he’s talking about and/or asking for — 1 minute 12 seconds.
• 3/23 — No interaction.
• 3/24 — No interaction.

Six pages of meticulous, single-line entries documenting every single minute of my managerial incompetence. My thought: “I thought he didn’t care.”

It’s called the Fall because in an instant the normally predictable floor upon which you stand vanishes and you enter a mental free fall where you feel like throwing up because you no longer know which way is up.

The Fall is Not the Lesson

The sensation of the Fall is disproportionate to the size of the lesson. You experience not just the sense of failure, but also the colossal irrational disappointment that you are no longer an expert at this task with which you have no previous experience — which is goofy. Here’s the kicker — you now have just enough experience to understand the actual work involved in becoming proficient at a task you previously thought you could magically improvise.

A Wallace-class Fall is common with freshly minted leaders and it’s one exacerbated by the commonly introverted tendencies of engineers. It’s the discovery that not only is someone you lead not following, but that there is a complete and total personality disconnect with this person. None of your usual networking moves work. They stare blankly at your witty repartee and when they do talk, it’s as if they haven’t heard a single word you’ve said.

It’s a frustrating discovery because part of the reason you became a leader was due to your natural and proven people skills. But it’s an enviable discovery because on a planet full of people most of them aren’t like you and your first Wallace will not be your last.

Your Instincts are 100% Wrong

A complete personality disconnect with someone you intend to lead, like in a Wallace situation, is rare, but for the sake of figuring how to tackle it, let’s assume this is the worst case scenario.

In a normal getting-to-know-you situation with an employee, the first question I want to be able to answer is: “What do they want?” What is their core motivation with regard to their current gig? Are they working on a promotion? Are they just figuring out the gig? Are they adrift? Are they ok with being adrift?

Understanding core motivation does not give me a complete picture of a person, but it gives me a place to start. When I know where they want to be, I can start to figure out how to get them there. Unhappily adrift people want immediate action. Those seeking promotions are eagerly seeking opportunity and will own anything to get it. However, this is Wallace and Wallace stares blankly when I blithely ask, “What floats your boat, Wallace?”

Give up on the idea that you’re going to finesse Wallace into telling you his secrets. Nothing that comes to you naturally is going to work with someone who honestly believes you are an alien. Your first job isn’t understanding core motivation, it’s basic communication.

In any situation where communication is suspect, I rely heavily on clarification. Whenever I say something that might be ambiguous, I ask, “What did you hear?” In return, when I’m listening and the topic or intent is not abundantly clear, I restate, “Ok, what I heard was…”

It sounds like this:

Me: “… and new requirements came in this weekend, but Jennifer still wants to see an initial spec by Thursday. Wallace, what did you hear there?”

Wallace: “Jennifer wants a spec on Thursday.”

Now, if this was Harold or Stan, we’d be done. A verbal commitment was made and we’d move on, but this is Wallace and I can assume nothing.

Me: “Yes, a spec on Thursday. And what does that mean for your work?”

Wallace: “I was planning on finishing doc review on Monday and building out test data on Tuesday and Wednesday. I won’t get to that if Jennifer needs a spec on Thursday.”

Me: “What I’m hearing is that you’ve got a pile of work that will need to be rescheduled, right?”

Wallace: “Right.”

Me: “And if we do that, do you think you can have the spec done?”

Wallace: “Maybe.”

I know it feels like the passive aggressive Olympics, but I swear this is how Wallace thinks. In his world, a work commitment is never implied and must be verbally stated. We need to go back and forth until he states, “I will reschedule all of my planned work from this week until next week. I’ll relay the implications of these changes to the docs and QA teams and I have moderate confidence there will be no issue in delivery of a first draft of the revised spec by close of business on Thursday.”

It’s pedantic, annoying, and inefficient, but when personalities are disconnected, you don’t know how to communicate, so that’s where you start. With practice, you’ll learn the unique rules of engagement. You’ll discover the words and the ideas they use to describe both their happiness and their displeasure. You’ll learn the visual and verbal tells they employ when they have no idea what you’re talking about. In time, you’ll develop a mental map of this person who is decidedly not you.

The sensation of interacting with these aliens will never feel natural. It will always feel deliberate and foreign, but practice will provide you with a guide into how they think and a map that might provide insight for you into what they want.

The Size of the Lesson

It took months. It took months of conscious and intentional conversations with Wallace for us both to subconsciously agree to a communication peace treaty. It was painful — each time Wallace and I would drop into that primitive conversation dance, Harold and Stan would stare at each other and shake their heads — This nonsense again?

The nonsense was the essential lesson I learned from my first managerial Fall: when communications are down, listen hard, repeat everything, and assume nothing. The Wallace situation was the first of many Falls, and the beginning of understanding something fundamental to make future Falls less catastrophic: that people are the best puzzles you’ll never solve.