My First 90 Days – What I Learned the Hard Way

If you’ve ever transitioned into a leadership role, you know how tough those first few months can be. You step in full of ideas and excitement, but reality hits fast. Today, I want to share my personal story—what I expected, what actually happened, the struggles I faced, and the lessons I learned the hard way.

Before we get started, if you haven’t yet, I highly recommend checking out my previous episode, “The First 90 Days – Leadership Framework for Success.” In that episode, I covered the structured framework for navigating the first three months in leadership. Today’s episode will be much more personal—what I personally learned through trial and error.

Whether you’re about to take on your first leadership role or just want to reflect on your own journey, this episode is packed with real experiences, honest reflections, and some advice I wish I had when I started.

Grab your coffee, get comfortable, and let’s dive in!

Expectation vs. Reality

Before I took on my first leadership role, I had this vision of what leadership looked like. I thought I’d be guiding my team, making strategic decisions, and driving impact. And while all of that is true to an extent, I quickly realized the reality is very different from the expectation.

What I imagined was control, structure, and influence. What I got was ambiguity, unexpected challenges, and a steep learning curve. Let me break down what I struggled with the most and what I learned the hard way.

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The Struggles & Adjustments

Letting Go of the Expert Hat

One of the biggest shifts I had to make was letting go of being the go-to expert on everything. Before stepping into leadership, I was known for my technical expertise, and people came to me for answers. But in my new role, I had to shift from solving problems to enabling my team to solve problems.

At first, I kept getting involved in everything—reviewing every detail, double-checking work, and stepping in too much. I had to learn to step back, trust my team, and focus on the bigger picture. It took time, but when I finally embraced delegation, I saw my team step up in ways I hadn’t expected.

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Coping with a Different Work Rhythm

Previously, I could measure my productivity by what I personally got done. Now, my job was more about coordinating, guiding, and making sure my team succeeded.

Suddenly, my days were filled with meetings, coaching conversations, and strategic planning. I had to redefine success—not by how much I got done, but by how well I empowered my team to get things done.

At first, I felt like I wasn’t accomplishing much. It was frustrating. But over time, I learned to celebrate my team’s wins as my own.

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Mastering Soft Skills (Coaching, Mentoring)

I quickly realized that technical skills were no longer my main value. What really mattered were coaching, mentoring, and communication.

I had to learn how to provide constructive feedback, handle conflicts, and motivate my team. And trust me, this was a steep learning curve. It required patience, self-awareness, and a whole lot of trial and error.

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Navigating Organizational Politics & Bureaucracy

One of the unexpected challenges was navigating internal politics and bureaucracy. As an individual contributor, I could focus on my work. But as a leader, I had to deal with approvals, policies, and internal dynamics I had never faced before.

At first, it frustrated me. But then I realized—understanding how the system works is part of leadership. Instead of resisting it, I learned to navigate it effectively and use it to my team’s advantage.

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Redefining Relationships with Former Peers

Stepping into leadership meant I was now leading people who used to be my peers. This was awkward. Some colleagues still treated me as one of them, while others distanced themselves.

I had to redefine my relationships—balancing professionalism with authenticity. The key? Clear communication and consistency. Setting expectations early and leading with empathy made a huge difference.

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Dealing with Leadership Loneliness

Leadership can be lonely. The dynamic changes, and suddenly you can’t share everything with your team. Your words carry more weight, and people watch your reactions closely.

I had to build a support system outside my direct team—mentors, peer managers, and trusted advisors who could offer guidance and a safe space to talk. Finding a leadership community was a game-changer.

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Finding New Ways to Measure Success

With fewer hands-on tasks, I needed new ways to feel productive. I started doing weekly reflections—asking myself:

• What did I enable my team to accomplish?
• Where did I help clear roadblocks?
• How did I support individual growth?

This shift in mindset helped me find fulfillment in my new role.

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What I Would Do Differently

If I could go back, here’s what I’d change:

• Get a mentor sooner – Learning from someone who has been there makes all the difference.
• Focus on relationships first – Leadership is about people, not just results.
• Let go of perfectionism – Done is better than perfect.
• Prioritize self-care – Leadership is demanding. Taking care of myself made me a better leader.

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Lessons Learned from This Coffee Journey

To sum it up, transitioning into leadership is tough, but it’s also one of the most rewarding experiences. If you’re stepping into a new leadership role, here’s my advice what I learned the hard way:

• Expect the unexpected—leadership is different from what you imagine.
• Focus on empowering your team, not just doing the work yourself.
• Build relationships—with your team, peers, and mentors.
• Be patient with yourself—it’s a journey, not an overnight transformation.

And if you want to dive deeper into structured frameworks for success in your first leadership role, don’t forget to check out my previous episode, “The First 90 Days – Leadership Framework for Success.” It’s packed with practical strategies to help you start strong.

If you’re about to start your first leadership role, I’d love to hear from you! What are you most excited or nervous about? Let’s chat in the comments or on social media.

Thanks for tuning in to The Coffee Journeys Show! Until next time—keep leading, keep learning, and keep growing.

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Useful links

• Your First Step to Engineering Leadership
• The First 90 Days – Leadership Framework for Success
• How Mentoring Can Inspire You to Become an Impactful Leader
• Leadership begins at home – strengthening relationships that matter the most