Olivia: There are up to 500 million one-on-one meetings happening every single day across the globe. And get this, they cost businesses over a billion dollars. Daily. Jackson: A billion dollars a day? That's an astronomical number. That must be one of the most valuable business activities in the world. Olivia: You'd think so. But here's the kicker: research shows that for the team members actually in those meetings, nearly half of them are a complete waste of time. Jackson: Hold on, half? That’s a failing grade. You’re telling me we're burning half a billion dollars, every single day, on conversations that go nowhere? That’s not just an inefficiency, that’s a catastrophe. Olivia: It’s a communication catastrophe. And that's the exact problem that Steven G. Rogelberg tackles in his book, Glad We Met: The Art and Science of 1:1 Meetings. And if anyone can fix this, it's him. Adam Grant, the organizational psychologist, literally calls him the "world's leading expert on how to fix meetings." Jackson: The world's leading expert? Okay, no pressure then. So what does the expert say? Why are we so spectacularly bad at what seems like the most basic form of management: talking to our people? Olivia: Because, as one executive in the book puts it, there’s a “hole the size of the Grand Canyon” when it comes to this skill. And that’s where our conversation has to start.

Jackson: A 'Grand Canyon' sized hole. That’s a pretty dramatic way to describe it. What does that mean? Is it that managers just don't care? Olivia: It’s more subtle and, in a way, more dangerous than that. The research shows leaders have a massive blind spot. They consistently rate themselves as being highly effective at conducting 1:1s. But when you ask their team members, the scores plummet. There's a huge disconnect between a manager's perception and their employee's reality. Jackson: Wow, that is both hilarious and terrifying. So managers are walking out of these meetings thinking, "Nailed it!" while their employee is thinking, "I will never get those 30 minutes of my life back." Olivia: Exactly. And Rogelberg argues this happens because we fundamentally misunderstand what a 1:1 is for. It’s not a mini team meeting. It’s not a replacement for an open-door policy, where the burden is on the employee to interrupt the boss. As the author Angela Duckworth says in her praise for the book, these meetings are "the bedrock of relationships." Jackson: Okay, 'bedrock of relationships' sounds nice, but here's the pushback I feel from every manager listening: "I am drowning in meetings. My calendar is a nightmare. Can't I just meet when I have something important to say?" Olivia: That’s one of the key fallacies the book dismantles. It even has a chapter titled with that exact question. The answer is a firm no. If you only meet when you, the manager, have an agenda, the meeting becomes purely transactional. It signals that the time is for your needs, not for the employee's. Jackson: Ah, I see. So the consistency is the message. Having it on the calendar, week in and week out, says "This time is reserved for you, no matter what." Olivia: Precisely. It builds psychological safety. The employee knows they have a dedicated, predictable space to talk about challenges, career growth, or that weird obstacle with the finance department, without feeling like they're imposing. Without that rhythm, trust never gets a chance to form. Jackson: But what about the fear factor? I can imagine some people dreading that weekly calendar invite. It feels like being called to the principal's office. The book has a chapter on that too, right? "Won't Team Members Be Fearful of 1:1s?" Olivia: It does, and the key is in the framing. If the 1:1 is consistently used for ambushing people with negative feedback, then of course they'll be fearful. But if it's framed from the start as the employee's meeting—their time to set the agenda, to get support, to talk about what matters to them—it transforms from a moment of judgment into a moment of service. Jackson: The employee's meeting. That feels like a radical shift in ownership. Most people think of the 1:1 as a manager's tool to check in on work. Olivia: And that’s the Grand Canyon right there. It’s not a tool for surveillance; it’s a tool for development. When you see it that way, the entire dynamic changes. It stops being about "what have you done for me lately?" and starts being about "how can I help you succeed?"

Jackson: Okay, I'm sold on the 'why.' It's about trust, it's about development, it's the employee's meeting. But let's get practical. What do you actually do in these meetings to stop them from becoming that boring, soul-crushing status update we all know and hate? Olivia: This is where the 'Art and Science' part of the title really comes alive. The book offers a powerful antidote to the status update trap, and it comes from the foreword by the legendary coach Marshall Goldsmith. He calls it "feedforward." Jackson: Feedforward? What's that? Is it just a buzzword for feedback? Olivia: It's the opposite. Feedback, by its nature, is about the past. It's a critique of something that's already happened, which is why it so often puts people on the defensive. Feedforward is about the future. It’s asking for ideas and suggestions for what to do next. Jackson: So it's like being a coach for the next game instead of a critic of the last one. Olivia: That’s a perfect analogy. It’s collaborative and creative. Instead of "Here's what you did wrong in that presentation," it's "For the big client pitch next week, what's one thing I could do to help you feel more confident?" It completely changes the energy of the conversation from judgment to possibility. Jackson: I like that. It feels less confrontational. Olivia: It’s incredibly effective. And the book gives a fantastic case study of a manager named Sarah at a tech company, Innovate Solutions, who puts these ideas into practice. Her team was brilliant but totally disengaged. Their 1:1s were just lifeless status reports. Jackson: I know that meeting. I think I've been in that meeting a thousand times. Olivia: We all have. So Sarah decides to change things. She starts preparing for her 1:1s. She works with each team member to create a shared agenda before the meeting, focusing on their individual goals, their biggest challenges, and their career aspirations. She stops asking "How's it going?" and starts asking better questions. Jackson: Like what? What's a better question? Olivia: Instead of a generic "how are you," she asks things like, "What's one thing we could change about our team's process that would make your life easier?" or "When did you feel most energized at work last week, and how can we get more of that?" She even asks about their personal goals outside of work, showing she cares about them as a whole person. Jackson: That’s a huge difference. It’s specific and it shows you’re actually listening. So what happened to Sarah's team? Olivia: The transformation was remarkable. Over a few months, the team's motivation and productivity soared. The turning point was when her most senior, and most cynical, software engineer, Mark, told her that for the first time in years, he felt truly connected to the company's mission. He felt seen. And it was all because Sarah stopped treating their 1:1s as a chore and started treating them as the most important part of her job. Jackson: That's a great story, but it also sounds like a lot of work for the manager. How does someone like Sarah prepare for five different, deeply personal conversations every week without it becoming a second job? Olivia: That's why the book is so practical. It's filled with tools—agenda templates, checklists for giving feedback, and banks of powerful questions for different situations, like for remote employees or new hires. Rogelberg's point is that a little bit of intentional preparation on the front end saves you from hours of disengagement and problems on the back end.

Olivia: And that preparation is so critical, because the meeting itself is only half the battle. The real test of a 1:1 comes after everyone leaves the room. Jackson: Right. The dreaded follow-up. Or lack thereof. Olivia: Exactly. The book has a chapter titled, "The Meeting Is Done, Now What?" And this is where the trust built during the conversation is either cemented or completely shattered. An executive from Deloitte is quoted saying that a 1:1 can "make or break a person’s day, week, or even a year." Jackson: That’s a heavy thought. The long-term impact of these small moments. Olivia: It's huge. Because if a manager makes a promise in a 1:1—"I'll look into that promotion for you," or "I'll get you that training resource"—and then nothing happens, it's actually worse than if they'd never had the meeting at all. It tells the employee, "You are not a priority. Our conversation was just empty words." Jackson: So it's not just about having the meeting, it's about what the meeting represents. If you say you value your people but then blow off the action items, your actions are screaming much louder than your words. Olivia: You've hit on the book's final, and most profound, point. Ultimately, 1:1s are about values. They are the single most powerful and consistent way a leader demonstrates what they truly believe. Do you value growth? Do you value trust? Do you value your people as human beings? Your 1:1s will give the answer. Jackson: It’s where the rubber meets the road on corporate culture. You can have all the "people are our greatest asset" posters you want, but if managers aren't having meaningful, accountable conversations, it's all just talk. Olivia: That’s the core message. It isn't what we say or think that defines us, but what we do. And conducting a great 1:1, and following through on it, is one of the most defining actions a leader can take.

Jackson: You know, when we started, I was skeptical. It felt like a book about making meetings less awful. But it’s much deeper than that. Olivia: It really is. Ultimately, Rogelberg's argument is that fixing 1:1s isn't a management hack. It's a fundamental shift toward a more human-centered workplace. In a world of remote work, endless Slack notifications, and digital noise, this dedicated, focused, human conversation is one of the last, best tools we have to build real connection. Jackson: And it’s a skill. It’s not something you’re just born with. I find it fascinating that the book is so popular with leaders, but some reader reviews mention the ideas feel foundational. I think that just proves Rogelberg's point—this is a corporate training gap. Most managers are never taught this. Olivia: They're not. They just copy what their old boss did, for better or worse. This book provides the evidence-based blueprint that most of us are missing. Jackson: So the takeaway isn't just 'have better meetings.' It's 'be a better, more intentional leader.' For everyone listening who is a manager, or wants to be one, maybe the one action to take this week comes from that idea of the 1:1 being the employee's meeting. Olivia: What's the action? Jackson: Simply ask your direct report, "What would make this meeting more valuable for you?" And then, really listen to the answer. Olivia: A powerful question. And a perfect place to end.