Why The First 90 Days Are Harder Than We Admit

Think about the first couple of months of a new relationship. There’s a warm glow, everyone is on their best behavior and it’s easier to overlook minor annoyances—or downplay parts of yourself—because you really want things to work. Those early months feel good, but they also quietly set the stage for what comes next. Patterns form. Expectations take shape. Assumptions settle in.

The first 90 days in a leadership role are like that. The difference? In leadership, there’s no slow reveal, no “let's take it slow and see how it goes.” The stakes are higher, the audience is larger and you’re expected to perform with competence immediately.

If you’re stepping into a new leadership role as we head into a new year, congratulations. You’re probably feeling excited, confident and energized by what’s possible. That sense of momentum is part of what makes new beginnings powerful. And as the days unfold, it’s also likely that the work will feel more complex than it first appears—not because anything has gone wrong, but because leadership is learned in real time, not all at once. The challenge isn’t the optimism; it’s that optimism often collides with realities no one talks about ahead of time.

You’re not building a relationship with just one person. You’re stepping into a web of existing relationships, histories and dynamics you didn’t create. You’re learning how people work together, where tensions live and what’s been said out loud versus what’s simply been accepted as “the way things are.”

At the same time, you’re expected to keep the wheels turning—often while learning the systems, processes and politics that make the work possible. You’re not just getting to know people; you’re leading them. You’re not just observing; you’re deciding. And all of this is happening while everyone—yourself included—is finding their footing.

Let’s be honest—starting anything new comes with a learning curve. There’s the frustration of unfamiliar systems, the feeling that everything takes longer than it should and the mental load of constantly checking yourself as you figure out what comes next.

Layered on top of that is a quieter expectation: you should already know what you’re doing. After all, isn’t that why you were hired or promoted?

No one really talks about how disorienting this can feel. As a new leader, you want your team to trust you. You want to project confidence and competence. You want this to work. So it’s tempting to smooth over uncertainty, to avoid asking too many questions, or to tolerate behaviors and patterns you might address differently once you feel more settled.

That’s one of the real risks of the first 90 days—not failure, but unintentional precedent. Early coping strategies can quietly become long-term norms. Silence can be interpreted as agreement. What you overlook now may surprise people later when you decide it matters.

This is why the first 90 days are harder than we admit—and why they often catch us more off guard than we expect.

The mistake many leaders make is treating this time as a performance test: prove yourself, make your mark, hit the ground running. But the first 90 days aren’t really about proving yourself. They’re about orienting yourself.

No one walks in the door with it all figured out—and they shouldn’t. The work of this period is learning how to lead this team, in this context, within this organization.

That starts inward. Grounding yourself before you’re swept into the pace of decisions and demands makes a difference. Reflect on how you tend to show up under stress, how you make decisions, how you communicate when things feel uncertain. Clarify what success actually means in this role—and what authority you do (and don’t) have to pursue it.

It also means being intentional about support. Identifying peers or mentors who have walked a similar path gives you a place to test ideas and reality-check assumptions. Being willing to name missteps and ask your team what you’re missing builds credibility, not weakness.

From there, the work expands outward:

• Learning your team as people, not just roles

• Understanding the dynamics and history that shape how work gets done

• Seeing where your team fits into the larger organizational landscape

Only then does it make sense to begin shaping goals, expectations and rhythms that will last beyond the “new leader” phase.

None of this means the work should feel easy. It isn’t. The first 90 days are demanding precisely because they ask you to balance learning and leading at the same time.

If it feels hard, that’s not a sign you’re failing. It’s a sign you’re doing the real work of leadership—work that’s often invisible, rarely acknowledged and foundational to everything that comes next.

You’re not alone in that. And while you’re not expected to have it all figured out on day one, you’re more prepared than you think—because leadership, like any new relationship, is about learning people and context with intention over time.