Why new manager struggles are more common than you think

A founder’s lesson on leadership resets, emotional blind spots, and what most startups still get wrong.

We made the promotion in a celebratory Slack thread. She was our top performer, our culture driver, the one who always stepped up before being asked. Promoting her to team lead felt like a no-brainer. Three months later, she was burnt out. Her team was frustrated. And I was trying to figure out how we’d gotten it so wrong. This is the part no one warns you about: the scariest leadership mistakes don’t explode. They erode. Quietly. In plain sight.

We thought being great at the job meant she’d be great at managing the job. What we didn’t realize? Management isn’t a promotion. It’s a role change. A complete psychological reset.

According to Professor Peter Cappelli, 59% of managers receive no training before stepping into leadership. Most are promoted from within—and suddenly have to supervise the same people they shared war stories with the week before. This isn’t a skills issue. It’s an identity one. And it hit us fast. She didn’t know how to give hard feedback. She tried to stay “relatable.” She overexplained every decision and said “sorry” too often. The team got confused. They started testing boundaries. She started doing the work herself again.

When we finally sat down, she looked tired in a way I hadn’t seen before. “I feel like I’m letting everyone down,” she said. She wasn’t. We were the ones who failed to prepare her.

Most new managers aren’t walking into a new team. They’re walking into a new power dynamic—with people who remember what they were like before. That transition is delicate. And dangerous if you get it wrong. We expected her to draw boundaries. But how do you set authority with the same people you went to karaoke with last week?

Cappelli puts it plainly: pretending you can be the boss by day and a buddy by night is a fantasy. In his words, “It’s a division that’s impossible to sustain.” And I’ve seen it firsthand. She still joined casual chats. Still laughed along with inside jokes. Until the moment someone missed a deadline. Or came in late. And then it got weird. She wasn’t sure when to step in—and they weren’t sure if they had to listen. That ambiguity cost us more than time. It cost us trust.

Here’s the part I hate admitting: I made the same mistake years earlier. When I became a founder, I didn’t understand what real management looked like. I thought it was about direction. Output. Performance charts. It took me years—and multiple team resets—to realize the hardest part of leadership is emotional clarity. Not just for others. For yourself.

New managers struggle because we ask them to change their behavior, without changing their internal story. We don’t tell them what the new role really demands: authority, boundaries, vision—and the discomfort of being misunderstood sometimes. We don’t say, “You will lose certain friendships. You will have to say no. You will feel isolated. And that doesn’t mean you’re failing. It means you’re adjusting.” If you skip that conversation, you’re not onboarding a manager. You’re abandoning them with a new title and a blurred identity.

When her team started slipping, I noticed she hesitated to confront it. “Maybe they’re just tired,” she offered. “It’s been a long sprint.” But the truth was, she wasn’t tired. She was scared. Scared that giving feedback would ruin relationships. That asserting expectations would make her look like she’d changed. But that’s the point. She had changed. The role had changed. If you don’t name that out loud, your team won’t follow the shift. Instead, they’ll keep treating their “buddy” like a peer—and expect her to behave like one. Until things fall apart.

Cappelli’s advice here is gold: managers should tell their team how they operate, what they’re responsible for, and what they expect in return. Don’t make your team guess whether you’re a buddy or a tyrant. Set the frame clearly.

We did this retroactively. She sat down with her team and said: “I care about every one of you—but I also have to advocate for the team’s performance. I won’t micromanage. But I will step in when things need fixing. And I expect us to be honest when that happens.” That one conversation bought back more clarity than any title ever could.

The other piece we missed was how emotionally draining early management can be. We assume new managers will naturally filter what to share, how to respond to gossip, when to hold confidentiality. But that’s not instinct. It’s skill. And it’s one they’ve never been taught. One day, she confided in me, “They expect me to explain every decision. Even when it involves someone else. I don’t know what I’m allowed to say.”

That’s when it hit me: we gave her accountability without equipping her for discretion. Managers aren’t just task allocators. They’re buffers, filters, and protectors of emotional and legal boundaries. It’s not enough to tell them “don’t overshare.” You have to coach what that looks like. What you can say when someone asks about another person’s raise. How to redirect when team members complain about each other. When to bring in HR—and when to just listen without absorbing the pain.

This isn’t common sense. It’s leadership hygiene. And if you don’t train for it, you get resentment, silence, or burnout. And in Southeast Asian teams—especially in places like Malaysia or Singapore—those feelings don’t surface as direct conflict. They show up in withdrawal. Quiet compliance. Deferred feedback.

A team member might say “Okay, noted” while silently disengaging. Or continue smiling in meetings while privately searching for another job. It’s not deception. It’s social self-protection. And if you don’t train your new manager to spot those signals—shifted tone, delayed replies, reduced initiative—they’ll miss the cues entirely. That’s when founders complain about a “vibe change” without knowing where it came from.

It’s easy to say, “Well, they’ll figure it out.”

But here’s what usually happens instead:

• The new manager avoids confrontation.
• Deadlines slip.
• Team members grow passive-aggressive or disengaged.
• The founder has to step back in.
• Trust in internal promotions declines.

All because we wanted to “move fast” and assumed the transition would work itself out. It doesn’t. The scariest part? Some of your best people will never say they’re struggling. They’ll just perform harder. Until they can’t anymore. And by the time they raise their hand, it’s often too late.

I’ve rewritten our internal playbook for first-time managers. It’s simple, but it works:

1. Coach before the crown.
Before we promote anyone, they get two weeks of shadowing, expectation-setting sessions, and boundary-setting coaching.

2. Reintroduce them to the team.
We make the transition visible. Not just a Slack ping. A real team announcement that frames their new role and what it means.

3. Equip them with scripts, not theory.
We don’t hand out articles. We role-play. We give them lines to use when giving tough feedback or holding boundaries. The goal is comfort in execution, not just understanding.

4. Normalize growth, not perfection.
We tell them: “You will mess up. You will feel awkward. That’s not failure—that’s rewiring. And we’ll walk through it with you.”

5. Culture-specific coaching.
If the team is based in KL or Jakarta, the emotional calibration is different. We teach new managers how to balance authority with cultural humility—how to be clear without being cold, firm without causing shame. That’s what builds true trust.

Because the truth is, most new managers don’t need more pressure. They need more permission—to lead imperfectly, to draw new lines, to grow without pretending they’ve got it all together.

If you're about to promote someone, pause.

Ask yourself: Have I had the hard conversation about what this new role really is? Have I named the identity shift? Have I created a support system they can lean on—not just performance reviews, but actual coaching?

If not, you’re not promoting a manager. You’re handing them a title and hoping for magic. I’ve been there. It’s a painful way to learn. But it’s also fixable. And the moment you fix it—when you see your former IC own a room, set boundaries with confidence, and coach their team like it’s second nature—it’s worth every awkward retro and reset.

Because now, they’re not just doing more. They’re becoming more. And that’s the kind of growth we should actually be celebrating.