Someone posted in r/humanresources this week asking a simple question: at what point does leadership stop feeling intimidating? They'd been in HR for three years, most of that in employee relations, and they were still asking. No formal training. Everything learned on the job, one uncomfortable conversation at a time.
That question is the real story behind most new managers right now. Nobody sits them down and teaches them how to lead. They find out by getting it wrong in front of their own team, then trying to do better next time.
CEB's research on this is blunt. Sixty percent of new managers underperform or fail within their first two years, and 85 percent get no training at all before stepping into the role. Gartner's numbers explain why that matters beyond the manager themselves: employees who report to a struggling new manager are 20 percent more likely to disengage or leave. The manager isn't the only one paying for the gap. Their whole team is too.
Why Confidence Takes So Long to Build Without Training
Confidence in leadership doesn't come from tenure. It comes from doing hard conversations enough times that they stop feeling hard. A new manager who's never practiced giving direct feedback, setting a boundary with a peer who's now a direct report, or sitting across from someone during a tough performance review is going to feel every bit of that discomfort the first ten times it happens — live, with a real employee watching.
Without practice reps in a lower-stakes setting first, new managers build confidence the expensive way. They make the mistake on a real relationship, then spend months repairing the trust it cost them.
Without practice reps in a lower-stakes setting first, new managers build confidence the expensive way — on real relationships, with real consequences.
What "Learning on the Job" Actually Means
It sounds efficient on paper. Skip the training budget, let people figure it out through experience. In practice, it usually means the new manager's own team absorbs the cost of that experience. A missed conversation about a performance issue lets a problem grow for months. An overly harsh correction damages trust that takes a year to rebuild. None of this shows up on a training line item, but it shows up in turnover, in engagement scores, and in exit interviews that mention "my manager" as the reason someone left.
This is what we call the Habit Tax at Groveland. Every organization pays it one way or another — either up front with real development, or on the back end through attrition, disengagement, and managers who never quite figure it out.
What Actually Builds Confidence Faster
A single workshop doesn't fix this, and most HR leaders already know it. A day of role-playing scenarios feels good in the room and evaporates within a few weeks, because a skill that isn't practiced repeatedly doesn't turn into a habit. It stays a nice idea from a training day.
What works is closer to how athletes train. Reps, feedback, more reps — in a cohort with peers who are working through the exact same transition. New managers need somewhere to practice the hard conversation before they have it for real, and someone checking in on whether the habit is actually sticking three months later, not just whether they showed up to a session.
That's the model Groveland builds around. Not a one-day workshop. A structured, ongoing program that turns leadership skills into habits before a new manager is relying on guesswork with their own team.
How Long Should It Take to Feel Like a Real Leader?
Most research points to the first 90 days as the window that sets the trajectory, with the full transition from individual contributor to confident manager taking closer to a year without structured support. That's a long time to leave someone exposed, especially when the people reporting to them are watching every decision in real time.
The Reddit post that started this piece never got a clean answer to when leadership stops feeling intimidating. Three years in, they were still figuring it out solo. That's not a personal failing. That's what happens when a company hands someone a title and calls it done.
Frequently Asked Questions
Most new managers start finding their footing within the first 90 days, but the full transition to feeling genuinely confident tends to take closer to a year without structured coaching or practice built into the process.
CEB research found that 60 percent of new managers underperform or fail within their first two years, and 85 percent receive no formal training before moving into the role.
Training budgets often get cut first, and organizations frequently assume leadership skills develop naturally with time in the role. In practice, skills that aren't practiced deliberately rarely improve on their own.
It can be taught, but only through repeated practice — not a single session. Confidence comes from doing the hard conversations enough times in a supported setting that they stop feeling unfamiliar.
The Habit Tax is the cost every organization pays when managers aren't properly developed — either through upfront investment in real training or later through turnover, disengagement, and the slow damage of managers learning by trial and error on real employees.
A workshop delivers information once and hopes it sticks. A habit-based program builds in repeated practice and follow-up over months, which is what actually turns a skill into something a manager does automatically under pressure.
Source data: CEB/Gartner research on new manager training gaps, cited via Forbes.