The Wanderer

Manager at the first start-up. Solid guy. Significant experience. I know that I can learn from him. No doubt. All the correct operational 1:1 hygiene is there. We meet every week like clockwork; we fill the time, and I often leave with a healthy sense of productivity.

But sometimes… he talks. And wanders.

He’s a talker. He likes stories. He thinks out loud. Often, these stories are related to a topic he or I brought up, but often, they are entirely unrelated to the company, our work, or my job. Or are they? I’m not sure. He’s still talking, and while it’s a compelling tale, I think it’s for his narrative enjoyment rather than our collective professional well-being.

The failure case and the reason you are reading this is that once during storytime, I was seeking guidance, I was looking for answers to essential questions, and I was working to figure out how to make progress. I forgot the story he was telling, but I discovered a question, jumped in, and asked, “You mean I should do this?”

“Yes. Yes! Exactly. Do that — great call.”

So I did.

Two weeks later, I received an urgent and irate Tuesday night email from my manager, “Hey, what are you doing here? Why are you doing this?”

“You told me to.”

“No, I didn’t.”

I don’t yet have a deep analysis of why storytime guidance differs from work guidance. I suspect that because he was lost in the narrative, he is in a different part of his brain, which isn’t work; it’s the story. I do know that receiving contradictory guidance from leadership drives me bonkers. As a leader, your job is to illuminate, not obfuscate.

My solution in this scenario, which I’ve now used for over a decade, has three simple steps:

Prepare for the 1:1.

Capture thoughts in writing in real-time.

Post-mortem (document) the 1:1 immediately.

Preparation Artifact

Sometime before the 1:1, I spend five minutes writing down what I need from my boss this week. This can be a low-prep exercise where I yolo scribble my current set of worries, concerns, and questions. The content is less important than the fact that I’m preparing my brain for the 1:1. We are going to meet. This is what is important to me. With the initial concerns out of my head, I will then take a pass through my to-do list. Anything that I need to discuss that isn’t front of mind? Jot it down.

Do I share this list with my manager beforehand? Depends. My move is always to share any larger, complicated, or political topics the night before so that they can be pre-processed. I don’t always share all topics because it’s a conversation, it’s organic, and I want to give the conversation room to breathe. More on this in a moment.

Back to Reality

With my artifact in hand, my job is to steer the conversation towards these topics. I do this before storytime starts by declaring, “Hey, I have three topics I’d like to cover at some point.” This is easier if I’ve pre-sent the topics. Sometimes we do them right then and there (sweet), but sometimes they happen later organically as part of the 1:1. Read the room.

Now for a power move—it’s subtle. First, I bring the Preparation Artifact as a reminder of the topics or questions I have. I make sure he sees this act. Second, and here’s the move, when he says anything that sounds like a decision, task, or essential — I write it down.

This practice is for me, but it’s also for him. See, he might be in storytime mode, and while storytime might be his chosen means of delivering wisdom, he wanders. When I hear an essential thing, I pick up my pen, and I write it down. He sees this and remembers this isn’t a clever yarn told at the bar, this is work. This is reality. We are at work doing work things.

This practice is not a replacement for having a conversation. This does not absolve me from seeking real-time clarification; this is a quick reminder that we are doing work here. Infrequently, he sees me capture the decision and realizes what I might have heard, so he comes back to reality and clarifies, “This isn’t relevant to that topic. This is just a story.”

Oh.

The Tides of Trust

All done? Great, take three minutes to glance at my notes. Did I cover what I wanted? No? It goes on this list for next week unless it’s urgent. Did I capture all to-dos, thoughts, and next steps? No, write them down. Right now, I’m heading to another meeting, which is where I’ll forget critical bits the moment someone asks me a deliciously complex question.

This last step is essential because once I’ve written everything down, I often discover that what I heard is different from what I wrote down. The act of passing the thought through my fingers and onto the page forces structure onto the thought. Brains. I know, right?

Professional trust is like the tides of the oceans; it comes and goes. When trust was low between my boss and me, I’d send my read-out of the conversation as a mail or message. I am surprised how often the words he said differ from what I captured, and during low trust, he’ll respond and correct. This response means I need to send these follow-ups post 1:1. Three times with no response? The tide has returned along with truth. Good job.

Do That — Great Call

“You told me to.”

“No, I didn’t.”

In your career as a human working for other humans, this moment will stand out. You believe you did precisely what they asked, but upon completion, they question your work. The work you thought was precisely what they asked. For this specific scenario, I think my boss believed he’d figured it out, so it was OK to wander into story land.

At some point in your senior leadership professional growth, you’ll start to feel like you’ve got it figured out. The circumstances vary, but many years into your career, you’ll start to feel like you have satisfying answers to most questions, your projects will appear drama-free, and previously complex problems will appear familiar.

Good job. You’ve never figured it out. Ever.

Stories. Good stories are fun to write and to tell. You’re reading one right now. Stories can inspire you, point you in the right direction, but the leadership we need day after day is a conversation.