The Basics

Before we start, let’s go over the basic rules I follow regarding one-on-ones :

• Hold a one-on-one the same time each week: When you become a manager of people, an odd thing happens. You’re automatically perceived as being busier. Whether you are or not is irrelevant; folks just think you are. Consistently landing your one-on-ones at the same time on the same day is a weekly reminder that you are here for them—no matter how busy.

• Always do it: OK, so you are really busy. You’re running from meeting to meeting. It’s easy to deprioritize a one-on-one because, unlike whatever meeting you’re running to or from, a one-on-one doesn’t represent an urgent problem that needs solving. I’ll beat this perceived-lack-of-value opinion out of you later in this piece, but for now, understand that each time you bail on a one-on-one, the person you’re managing hears, “You don’t matter.”

• Give it 30 minutes, at least: Another favorite move of the busy manager is to schedule a one-on-one for 15 minutes or less. It’s the best I can do, Rands. I’ve got 15 people working for me. First, those 15 people don’t work for you; you work for them. Think of it like this: if those 15 people left, just left the building tomorrow, how much work would actually get done? Second, if you’ve got 15 people working for you, you’re not their manager, you’re just the guy who grins uncomfortably as you infrequently fly by the office, ask how it’s going, and then don’t actually listen to the answer.

Having a meaningful conversation with anyone takes time. As you’ll see in a moment, you start with an opener where you figure out where everyone is mentally, which builds momentum into having a conversation of consequence. In your 15-minute one-on-one, all you learn is that you don’t have time to care.

How Are You?

It’s a softball opener. I recognize that, but I lead with a vanilla opener because this type of content-free question is vague enough that the recipient can’t help but put part of themselves into the answer, and it’s the answer where the one-on-one begins.

What’s the first thing they say? Do they deflect with humor? Is it the standard off-the-cuff answer? Or is it different? How is it different? What words do they choose and how quickly are they saying them? How long do they wait to answer? Do they even answer the question? Do you understand the answer isn’t the point, either? The content is merely a delivery vehicle for the mood, and the mood sets your agenda.

As I’m listening to the answer, I’m discerning your mood, and I’m throwing you into one of three buckets regarding the type of one-on-one we’re about to have:

• The Update (all clear!)

• The Vent (something’s up . . .)

• The Disaster (oh dear . . .)

The majority of the one-on-ones fall into the first bucket. The answer to my softball opener is pleasant and familiar. We’re going to walk through the facts, dig a little bit here and there, wander, and then it’ll be over. Great. The other two buckets are trickier to assess with a single question. Your answer to my question is . . . off. You either state this up front with the alarming, “We need to talk” proclamation, which immediately throws you in the Vent bucket, but this could also easily be a Disaster. By far, the worst answer to the opener is the quiet one, the answer that contains something hidden and insidious. Oh dear.

The Update

You get exactly what you expect from the Update—it’s status. These are my projects and these are my people and this is how it’s going down. I believe most folks consider this type of one-on-one to be a success, and they’re wrong.

A one-on-one is not a project meeting. A one-on-one is not status report. See all those project managers scurrying to and fro? Their job is the maintenance of the facts and the discovery of project truth. If you’re drawing the line for success in your one-on-one as the discussion of data you could find in a status report, you’re missing the point. A one-on-one is an opportunity to learn something new amidst the grind of daily business.

When a one-on-one starts and is clearly an Update, I start listening twice as hard for a nugget of something that we can discuss, investigate, and explore. It’s not that I don’t care about status, it’s just that we’ve got 45 minutes here, and if we fill that time with data I can find scrubbing the bug database and the wiki, we’re both wasting our time.

So, I listen, I take it on myself to find a meaty conversation, and if I don’t find it in the first 15 minutes, I’ve got three moves:

• Three prepared points: While I believe part of a good organic one-on-one is improvisation, I usually have three talking points in my back pocket that have shown up over the past week regarding you or your team. If we can’t find a good thread of conversation in the first 10 to 15 minutes, I’ll start with one of these points and see where that takes us.

• The mini-performance review: You read that right. If we’re 15 minutes into a lifeless, redundant, status-based one-on-one, and I don’t have anything sitting in my back pocket, I’m going to turn this into a performance review. It won’t be your actual performance review; it’s one aspect of your review that somehow strikes me as more appropriate conversation than an update on your bug counts. I see you’ve got a handle on your bugs, but one thing we talked about at your last annual performance review was getting a better handle on the architecture. How’s that going?

• My current disaster: Chances are, in my professional life, something is currently off the rails. It’s selfish, but if you’re leading with status and I can’t find an interesting discussion nugget, let’s talk about my current disaster. Do you know how many open reqs we have that we can’t hire against? Who is the best hiring manager you know and what were their best moves? The point of this discussion is not to solve my Disaster; the point is that we’re going to have a conversation where one of us is going to learn something more than just project status.

Business is noisy because there is always stuff to do, and the process of doing stuff is called tactics. It’s tactical work, and while tactics are progress, the real progress is made when we get strategic. A productive one-on-one is one where we talk strategically about how we do stuff, but more importantly, how we might do this stuff better.

The Vent

A really good Vent starts with a disarmingly long period of silence. I’ve just asked my soft opener and you’re quiet. Really quiet. I can see you mentally gathering steam. I take this time to ground myself, because while I know a Vent is coming, I likely don’t know the content or the severity. Vents vary from a semi-tense “I can’t stand QA today” to a full-on explosion: “If I have to listen to Thomas grind his goddamned Fair Trade–Certified Peruvian coffee beans in his office one more time, I might lose it.”

When the Vent begins, you might confuse this for a conversation. It’s not. It’s a mental release valve, and your job is to listen for as long as it takes. Don’t problem solve. Don’t redirect. Don’t comfort. Yet. Your employee is doing mental house cleaning, and interrupting this cleaning is missing the point. They don’t want a solution; they want to be heard.

A Vent does have a conclusion. There is a point where you need to jump in, but these conclusions and your actions vary.

• It’s done: The Vent starts to lose steam and the venter finds themselves panting and staring at you with nothing to say because they’ve said it all—probably a couple of times. It’s in this moment that you begin your triage. Great, now we start talking . . .

• It’s a rant: A Vent can repeat itself. The same facts and content might be thrown at you in a couple of different ways. I see this repetition as healthy way of chewing on the problem, but there’s a point where this Vent becomes a rant. After a couple of Vent cycles, you might try grabbing hold of the conversation and starting with triage, but brace yourself—the venter might not be done. My suggestion, in the face of resistance, is to give them the benefit of the doubt and let ’em go another round.

• The Vent that wants no help is a rant. The ranter somehow believes that the endless restatement of their opinion is the solution. Perhaps they have no clue what a solution might be or how to find it, or perhaps they’ve been stewing on the topic so long that they’ve lost all sight of logic.

• Whatever the backstory, the ranter is finding some weird mental satisfaction in the endless restatement of the problem, but they have no interest in solving the actual problem at this point. Annoying. When you’ve got a confirmed rant on your hands, it’s OK to jump into the middle of the Vent—you’re saving everyone a pile of time, and you’re teaching the ranter that the incessant restatement of the rant is not progress.

• It’s a disaster: You’re listening carefully to the Vent. It’s moving forward and it’s not repeating itself, but . . . something is up. Perhaps it’s their demeanor or maybe it’s the topic, but your radar is pinging. The venter is not standing on their usual soapbox. They’re out of character and, as time is passing, they are becoming less themselves.

At its core, the Vent is motivated by emotion. That’s the key difference between the Update and the Vent. The topic has triggered an emotional response, and the venter’s therapy is the verbal statement and restatement of the situation. Emotion is a slippery slope, and what can start as a Vent has a chance of spiraling into a Disaster. It’s rare in business, but it’s a risk when you’re dealing with emotionally slippery human beings.

The Disaster

If a Vent feels like a speech, a Disaster feels like an attack. What started as an emotional conversation has transformed into a war, and you’re suddenly and unexpectedly on the battlefield.

Until you’ve seen the Disaster once, it’s hard to predict how you’re going to react to the perception of being attacked. For better or worse, it’s happened enough to me that when I see the Disaster approaching, I carefully tuck all of my emotions in a box, lock the box, and magically transform into a Vulcan.

When the Disaster arrives, the absolute worst response is any semblance of emotion. See, in this case, the venter wants to fight. They literally want to go a couple of rounds on this particular topic. What was a high degree of frustration has transformed into pure aggression and if you so much as blink improperly, you’re contributing to the escalation of this situation.

Here are some tips on recognizing and handling the Disaster:

• The person you’re talking to isn’t him- or herself. As you’re sitting there weathering the Disaster, remember that you are experiencing an anomaly—a bizarre emotional version of the person that only shows up when they’re on the edge. The person you’re familiar with will show up . . . eventually.

• Shut up. Really. Your primary job during the Disaster is to defuse, and you start defusing by contributing absolutely nothing. If you’re a logical, reasonable management type, you’ll be tempted to ask clarifying questions—to try to shape the problem. Don’t. Be quiet. Let the emotion pass. Here’s why . . .

• It’s not about the issue anymore. You’re no longer experiencing the problem. You’re experiencing the employee’s emotional baggage regarding the problem. Sure, there’s the core issue, but that’s not what you’re currently observing. You’re seeing the extreme negative reaction to the issue, and that’s the first order of business.

As with the Vent, success comes with traversing the emotional explosion. There will, hopefully, be a point when the majority of the emotion has passed, and the aggrieved will be willing to having a rational discussion. Unlike with the Vent, the discussion won’t be about the core issue. It will start with the Disaster, with understanding the intense emotion surrounding the topic.

A Disaster is the end result of poor management. When your employee believes totally losing their shit is a productive strategy, it’s because they believe it’s the only option left for making anything change.

Assume They Have Something to Teach You

The cliché is, “People are your most valuable resource.” I would argue that they are your only resource. Computers, desks, buildings, data centers . . . whatever. All of those other tools only support your one and only resource: your people.

People mentally wander. It’s in their nature to make off-the-cuff observations—“Why does Phil get the choice features?”—and to let those observations fester, mutate, and sometimes transform into a Disaster. I’m not suggesting that every one-on-one be a tortuous affair to discover deeply hidden emergent disasters, but that they offer a weekly opportunity for you to see where dissatisfaction might quietly appear. A one-on-one is your chance to perform weekly preventive maintenance while also understanding the health of your team. A one-on-one is a place to listen for what your employee isn’t saying.

The sound that surrounds a successful regimen of one-on-ones is silence. All of the listening, questioning, and discussion that happens during a one-on-one is managerial preventative maintenance . You’ll see when interest in a project begins to wane and take action before it becomes job dissatisfaction. You’ll hear about tension between two employees and moderate a discussion before it becomes a yelling match in a meeting. Your reward for a culture of healthy one-on-ones is a distinct lack of drama.