The Journey: #63 I Wasn't Ready

There's a version of this story where I tell you I always knew exactly where I was headed and every step was intentional.

That's not this story.

This is the one where I wanted something badly, believed I had earned it, and was genuinely frustrated when it didn't look the way I expected. And where, years later, from where I sit now, I can see clearly that I wasn't ready. Not even close. Like, embarrassingly not ready.

But we'll get there.

The Title I Wanted vs. The Role I Got

When I made the jump from Senior Director to VP, I expected a broader scope. More oversight. A seat at a bigger table. I had put in the work. I knew the business. I was ready, or so I thought.

What I got was a VP title with a narrower scope. I was asked to oversee a specific discipline, Practice Development, rather than the expansive Customer Success leadership role I had envisioned for myself. The one I had definitely already planned out in my head in great detail.

I was annoyed. Honestly? I felt defeated.

Here I was, finally holding the title I had worked toward, and it felt like a consolation prize. Like someone had handed me a gift I didn't ask for, wrapped in paper I didn't pick. I smiled and said thank you, but inside I was spiraling. Very mature of me. Very VP behavior.

What I didn't understand then, what I couldn't see, was that the role I was given was exactly the role I needed.

What You're Good At Doesn't Always Travel

This is the thing nobody tells you when you're grinding your way up: the skills that make you exceptional at one level don't automatically transfer to the next. Shocking, I know. I was also shocked. Loudly.

As a Senior Director, I was good at being in the business. Executing. Driving outcomes. Managing teams toward clear goals. I knew how to operate. I was reliable, scrappy, and results-oriented. Those qualities got me the VP title.

But VP-level leadership requires something different. It requires you to work on the business, not just in it.

And I wasn't there yet.

When I look back now, here's what I was still developing, bless my heart:

Executive Presence. I had confidence, but confidence isn't presence. Presence is knowing how to command a room without dominating it. It's being composed when things are uncertain. It's making people feel steadied by your energy rather than anxious about it. Turns out, "loud and certain" is not the same thing. I had spent years perfecting loud and certain. Back to the drawing board.

Business Acumen. I understood my function deeply. I did not yet understand the business holistically, how CS connected to revenue, to product, to the market. I could speak to retention. I couldn't yet speak to the full financial picture or articulate CS impact in the language of the boardroom. Apparently, that matters when you want people to take you seriously. Who knew.

Cross-Functional Collaboration. I was good at running my lane. What I hadn't yet mastered was influencing across lanes I didn't own, working with Sales, Product, Marketing as a peer and a partner, not just as a stakeholder. That's a different muscle entirely. One I had very much skipped leg day on. For years.

Sales Alignment. Customer Success doesn't exist in a vacuum, and VP-level CS leadership requires you to understand the sales motion, how customers are acquired, what's promised, and what the handoff looks like. I had opinions about Sales. Lots of them. Strong ones. Largely unsolicited. I didn't yet have relationships or real fluency. Shockingly, opinions are not a strategy.

Strategy and Prioritization. At the Senior Director level, someone else sets the strategy, and you execute it well. At VP, you're expected to help build the strategy and, more importantly, make hard prioritization calls with incomplete information. That was deeply uncomfortable for me. I wanted more certainty than the role would give me. The role did not care. The role had seen my type before.

The Discipline I Didn't Want Was the One I Needed

Here's what I know now that I didn't know then: being asked to lead Practice Development wasn't a narrowing of my opportunity. It was a deliberate assignment.

I needed to go deep before I could go wide.

Leading a discipline forced me to develop rigor, structure, and strategic thinking in a focused context before I was handed the keys to a broader organization. I had to build frameworks. I had to think about scalability. I had to defend decisions to stakeholders who didn't report to me and didn't owe me anything. It was humbling. It was also exactly what I needed, even if my 30-something self would have rolled her eyes at that sentence.

It was exactly the training ground I needed, and I almost missed what it was giving me because I was too busy being annoyed about what it wasn't.

Readiness Isn't a Feeling. It's a Build.

If you're reading this and you're in that place, you've put in the time, you feel ready, and you're frustrated that the opportunity isn't materializing the way you imagined, I want to say this as directly as I can:

Your feelings are valid. And they might also be misleading you.

Wanting something badly is not the same as being ready for it. Tenure is not the same as capability. The title is not the point. The skills are the point.

Ask yourself honestly: Am I ready for this role, or am I ready for a promotion? Because those are not the same question.

The best leaders I know, the ones who've built lasting careers in CS, didn't just chase titles. They chased growth. They took the assignments that felt like a step sideways and wrung every lesson out of them. They built the skills, even when the path felt frustrating or indirect.

That's the work. And it's worth it.

I'm proof. Embarrassing early chapters and all.