Here is a stat that should stop every CEO and CHRO in their tracks: 60 percent of new managers fail within their first 24 months. Not because they aren’t smart. Not because they don’t care. According to CEB Global research, the primary reason is that they were never properly equipped to manage people in the first place.
We promote our best performers and hand them a team. Then we cross our fingers. We assume the skills that made someone excellent as an individual contributor will somehow transfer into leading other people. They don’t. Not automatically. And if you’re a CEO, this is your problem to solve—not theirs.
The first 90 days set the tone for everything that follows. The new managers who struggle most aren’t the ones who make bad decisions in those early weeks. They’re the ones who never have the right conversations. Not status updates. Not kickoff meetings. Coaching conversations. The kind that builds trust, surface real information, and set the conditions for a team that actually performs.
Here are the five conversations your new managers need to have—and what you can do to make sure they happen.
1. The “Tell Me What’s Really Going On” Conversation
New managers often spend their first weeks projecting confidence. The instinct makes sense. They want to establish credibility fast. But credibility built on the illusion of knowing is fragile. The managers who earn trust quickly are the ones who lead with curiosity, not answers.
This is a one-on-one conversation with every person on the team. Not a performance check-in. Not a “here’s what I need from you” kickoff. A genuine listening session. The new manager isn’t gathering data to report up. They’re learning how the team actually works, what people care about, and what they’ve been carrying.
Prompts that open this conversation well:
“What do you love about your work? What drains your energy?”
“What’s one thing I should know about you that’s not on your resume?”
“What does a great manager look like to you?”
When a manager remembers a month later that someone mentioned wanting to grow in a particular area, and brings it up unprompted, it signals something powerful: you were actually listening. That’s the foundation everything else is built on.
Your role as a senior leader: Don’t assume your new managers know how to run a listening session. Model it. Share the questions. Better yet, tell them what you learned when you started doing it yourself. Make it part of the onboarding expectation—not a suggestion buried in a slide deck.
2. The “What Does Good Look Like?” Conversation
Unclear expectations are one of the most common drivers of early manager failure. Not because new managers don’t set expectations, but because they assume everyone shares the same definition of success. They don’t.
This conversation is about co-creating clarity. What does high performance look like on this team? How will it be measured? How does each person’s work connect to the bigger picture? New managers who skip this conversation spend months managing to a standard they never actually communicated.
The question that anchors it: “What would ‘great’ look like to you at the end of this quarter?” Let the team answer first. The new manager may be surprised by what they hear.
Your role as a senior leader: Make sure your new managers have clarity on what success looks like from above before they try to define it for their teams. If you haven’t told them what you expect in their first 90 days, they’re guessing. And their teams are guessing, too.
3. The “How Are You, Really?” Conversation
This one makes a lot of new managers uncomfortable. It feels personal. It feels risky. They’re not sure where the line is between caring about someone and overstepping.
Here’s the line: you don’t need to be a therapist. You need to be a human being. There’s a difference between probing into someone’s personal life and simply making space for them to show up as a whole person. When a team member knows their manager actually cares how they’re doing—not just what they’re producing—everything changes. Trust builds faster. Problems surface sooner. Disengagement gets caught before it becomes turnover.
The approach is simple. “How are you?” followed by a pause long enough to actually hear the answer. Not a transaction. An invitation. If someone says “fine” and clearly doesn’t mean it, try: “I appreciate that. I ask because I value your perspective, and I notice you’ve been a little quiet lately. Is there anything going on I can help with?” You don’t have to solve it. You just have to show you noticed.
Your role as a senior leader: Have this conversation with your new managers first. They’re adjusting too. They’re carrying the weight of a role they’ve never done before. When you model that it’s safe to be honest about how things are going, you give them permission to do the same with their teams.
4. The “Where Do You Want to Go?” Conversation
Most managers wait too long to have this one. They figure it’s a six-month or annual review topic. But research is clear: people disengage when they don’t see a path forward. And by the time you get to month six, you’ve already lost the window to shape that path alongside them.
New managers don’t need a formal career development plan to have this conversation. They need two things: genuine curiosity and a willingness to advocate.
Three questions that open it well:
“When you think about your work a year from now, what do you hope looks different?”
“What’s one skill you’re working to build that you want more opportunity to use?”
“Is there anything about your current role that feels like it’s holding you back?”
People don’t leave bad companies. They leave managers who never asked.
Your role as a senior leader: Give your new managers the organizational context they need to actually follow through. If someone on their team wants to move laterally, or take on a stretch project, or build a skill set that lives outside their current role, the manager needs to know that’s supported. That signal has to come from you.
5. The “How Am I Doing as Your Manager?” Conversation
This is the one almost no one has. And it might be the most important one on this list.
New managers focus so much energy on evaluating their teams that they forget to ask how they themselves are landing. Are they communicating clearly? Giving people enough autonomy? Too hands-on in some areas and too absent in others? They will not know unless they ask. And the longer they wait to ask, the harder it becomes to course-correct.
This conversation takes courage. Most people aren’t going to tell their manager the hard truth unprompted, especially in those early months when the relationship is still being established. The manager has to make it safe. Something like: “I’m 60 days in and I want to make sure I’m showing up in a way that’s actually working for you. What’s one thing I could do differently that would make your work easier?”
Then listen without defending. Whatever they say, the job is to thank them, reflect on it, and act on at least some part of it. That single act—asking for feedback and changing because of it—builds more trust than months of strong performance reviews ever could.
Your role as a senior leader: Normalize this at the organizational level. If asking for upward feedback is treated as a sign of weakness, your new managers will never do it. But if it’s something your leadership team models openly, it becomes part of how your culture works. That’s how coaching cultures get built—from the top, one conversation at a time.
New managers who spend the early months talking build teams of followers. The ones who spend them listening build teams of leaders. That gap shows up in performance, retention and culture. It shows up in whether people bring problems forward or hide them. It shows up in whether your teams grow or stagnate.
But here’s the part that doesn’t get said often enough: the responsibility for whether these conversations happen doesn’t sit with the new manager alone. It sits with you. The CEO who sets the expectation. The CHRO who builds the infrastructure. The senior leader who makes coaching a priority and not a platitude.
None of these five conversations requires a leadership certification or a perfectly worded script. They require showing up with genuine curiosity and a willingness to let what you hear actually change how you lead. That is, at its core, what coaching is. Not something you do to people, but something you do with them.
And if your new managers aren’t having these conversations? That’s not a training problem. That’s a culture problem. One that starts at the top—with you.
