What I Wish I Knew Before Becoming a VP¶

The day I got promoted to VP, I went out to dinner with my wife to celebrate. We ordered a nice bottle of wine. I felt accomplished. Validated. Like I'd finally "made it."

The next morning, I woke up terrified.

I had no idea what a VP actually did. I'd been a director. I knew how to run teams, manage projects, and deliver results. But VP felt different. The scope was bigger. The stakes were higher. The expectations were unclear.

Nobody prepares you for the shift from director to VP. Everyone assumes it's just "more responsibility" or "a bigger team."

It's not. It's a fundamentally different job — with different skills, different pressures, and different emotional challenges.

Here's what I wish someone had told me before I took the role.

1. Nobody Prepares You for the Loneliness¶

As a director, I had peers. People at my level who understood my struggles. We'd grab coffee, vent about our bosses, commiserate about tough projects.

As a VP, that camaraderie disappeared.

Why Senior Leadership Is Isolating¶

You can't vent to your team. They look to you for stability. If you're anxious, they're anxious. You can't share doubts the way you used to.

You can't vent to your peers. The VP layer is small and competitive. Admitting struggles feels like showing weakness. Everyone is managing up and protecting their territory.

You can't vent to your boss. The CEO doesn't want to hear about your self-doubt. They want solutions, confidence, and results.

You can't vent at home (as much). Your partner is supportive, but they don't understand the nuances of your business problems. "Just tell them no" doesn't work when "them" is the CEO.

I spent the first six months as VP feeling completely alone. I had no one to talk to who truly understood what I was navigating.

What Helped¶

1. External mentors I found two former VPs outside my company who'd been through this transition. We met monthly. They became my sounding board.

2. Peer groups I joined a VP roundtable — 8 VPs from different companies, different industries. Confidential. Candid. We shared struggles, advice, and support.

3. Executive coaching I resisted this for a year. Felt like admitting I couldn't figure it out myself. Best investment I ever made. My coach gave me tools to navigate the emotional complexity of leadership.

The reality: Senior leadership is lonely. You need to intentionally build support structures outside your organization. If you wait until you're struggling, it's too late.

2. Your Job Is Now 80% Politics, and That's Not a Dirty Word¶

I used to think "politics" meant manipulation, backstabbing, and playing games.

I was wrong.

At the VP level, politics is how work gets done.

What "Politics" Actually Means¶

Politics is: - Building coalitions to support your initiatives - Navigating competing priorities across departments - Managing relationships with executives who have different goals - Influencing without authority when you need resources you don't control

As a director, I could mostly operate within my function. I had a budget, a team, and clear deliverables. If I executed well, I succeeded.

As a VP, execution alone doesn't cut it. You can build the best solution in the world, but if you don't have executive buy-in, it won't ship. You can have a brilliant strategy, but if you can't get cross-functional support, it won't happen.

The Skills Nobody Teaches You¶

1. Reading the room Understanding who has influence, who has veto power, and who will block your initiative if you don't bring them along early.

2. Building alliances before you need them The time to build a relationship with the CFO is not when you need budget approval. It's six months earlier, when you're just getting to know their priorities.

3. Framing initiatives in terms of others' goals I used to present projects based on what I wanted to accomplish. Now I frame them in terms of what the CEO or the board cares about.

Example: - Old framing: "We need to rebuild the billing system because it's fragile and hard to maintain." - New framing: "Rebuilding the billing system will reduce revenue leakage by $2M annually and cut our month-end close time by 2 days, which directly supports our path to IPO."

Same project. Different framing. Night-and-day difference in buy-in.

4. Knowing when to push and when to let go As a director, I fought every battle. As a VP, I had to learn that some hills aren't worth dying on. You have limited political capital. Spend it wisely.

3. The Shift from Execution to Strategy Is Brutal¶

I got promoted because I executed well. I shipped projects on time. I hit targets. I solved hard problems.

Then I became a VP, and the CEO said: "I need you to think more strategically."

I had no idea what that meant.

What "Strategic Thinking" Actually Means¶

Strategic thinking is: - Zooming out from day-to-day execution to think about what the team should be doing six months or two years from now - Seeing patterns across projects and recognizing systemic issues, not just individual fires - Saying no to good ideas because they don't align with the top priorities - Making decisions with incomplete information because waiting for certainty means missing the window

For me, the hardest part was letting go of execution. I was good at execution. It was comfortable. It felt productive.

Strategic work felt slow and uncertain. I'd spend three hours thinking through a problem and have no tangible output to show for it. That was uncomfortable.

How I Learned to Think Strategically¶

1. I blocked two hours a week for "thinking time" No meetings. No email. Just a whiteboard, a notebook, and space to think through big questions: - Where are we headed? - What are the biggest risks? - What should we stop doing?

2. I started reading more Books on strategy, case studies, industry trends. I needed frameworks to structure my thinking.

3. I learned to ask different questions Instead of "How do we fix this problem?" I started asking: - "Why does this problem exist?" - "Is this a symptom of a larger issue?" - "If we solve this, what's the next constraint?"

4. I practiced saying no This was the hardest skill to develop. Every request that came my way felt important. Learning to say "not now" or "not ever" based on strategic priorities was a muscle I had to build.

4. You're Now Responsible for Outcomes You Can't Directly Control¶

As a director, I could roll up my sleeves and fix problems myself. As a VP, I couldn't.

My scope was too big. I was responsible for outcomes across multiple teams, multiple systems, and multiple functions. I couldn't be in all the details.

This was terrifying.

I was accountable for results but had to trust other people to deliver them. If they failed, I failed — even if I'd done everything "right."

The Control Paradox¶

The higher you go, the less direct control you have, but the more accountability you carry.

As a director, I controlled most of the variables that determined success. As a VP, I controlled maybe 30% of them.

The other 70% depended on: - Decisions made by other executives - Performance of teams I didn't manage directly - External factors (market conditions, vendor reliability, regulatory changes)

How I Learned to Let Go¶

1. I hired people better than me If I was the smartest person in the room, I was the bottleneck. I started hiring people who were better than me in specific domains and trusting them to own those areas.

2. I defined outcomes, not processes Instead of telling teams how to do something, I told them what success looked like and let them figure out the how.

3. I built feedback loops I couldn't be in the details, but I could build systems that gave me visibility. Weekly metrics, monthly reviews, and quarterly deep-dives kept me informed without micromanaging.

4. I accepted that some things would fail Not every project would succeed. Not every hire would work out. I had to get comfortable with that uncertainty.

5. Imposter Syndrome Doesn't Go Away—It Just Looks Different¶

I thought that once I became a VP, imposter syndrome would disappear. I'd finally feel like I belonged.

Nope.

It just took on new forms.

The New Flavors of Imposter Syndrome¶

"I don't know what I'm doing" Especially in the first six months. I was in meetings with C-suite executives making decisions I barely understood. I felt like a kid sitting at the adults' table.

"Everyone else seems more confident than me" Other VPs seemed to have it all figured out. They spoke with authority. They commanded the room. Meanwhile, I was drowning in self-doubt.

"I got lucky" I convinced myself my promotion was a fluke. Right place, right time. Eventually, they'd figure out I wasn't actually qualified.

"I'm not technical enough anymore" I wasn't writing code. I wasn't in the weeds. I started wondering if I was still a "real" engineer.

What Helped¶

1. Realizing everyone else feels this way too I started asking other VPs (in safe settings) if they ever felt like impostors. Every single one said yes. Some were just better at hiding it.

2. Reframing the narrative Instead of "I don't know what I'm doing," I started telling myself: "I'm learning a new skill set. It's supposed to feel uncomfortable."

3. Tracking wins I kept a "wins" document. Every time something went well — a successful project, positive feedback, a good decision — I wrote it down. On hard days, I'd read it to remind myself I wasn't faking it.

4. Accepting that confidence comes from reps, not revelation I wasn't going to wake up one day feeling like a "real VP." Confidence would come from repeatedly doing the job and seeing that I could handle it.

6. You're Now "The Company" to Your Team¶

One of the strangest shifts: my team started treating me differently.

The Perception Gap¶

As a director, I was close to my team. We'd grab lunch. We'd joke around. I was "one of them."

As a VP, that changed.

My team became more guarded. They'd self-censor in meetings. They'd hesitate to share bad news. They'd interpret offhand comments as directives.

I said something like, "It'd be nice if we automated this process someday."

Two weeks later, someone had dropped their current work to build the automation. When I asked why, they said, "You told us to."

I didn't. But they heard a VP say something, so they treated it as an order.

What I Learned¶

1. Everything you say carries more weight than you think Casual comments become mandates. Questions become priorities. You have to be way more intentional with your words.

2. You can't be friends with your directs the way you used to This hurt. I valued those relationships. But the power dynamic had changed. They couldn't be fully candid with me anymore because I controlled their careers.

3. You have to actively create space for dissent I started asking explicitly: "What am I missing?" "What would you do differently?" "Tell me why this is a bad idea."

Even then, some people wouldn't push back. But it helped.

7. The Pressure to Have All the Answers Is Crushing¶

As a director, I could say "I don't know" and go find the answer. As a VP, I was expected to know.

At least, that's what I thought.

The Trap¶

I felt like I had to have an answer to every question. If I didn't, people would lose confidence in me.

So I'd make up answers. Or give answers I wasn't confident in. Or avoid situations where I'd be asked questions I couldn't answer.

This was exhausting and counterproductive.

What I Learned¶

1. "I don't know" is a valid answer As long as it's followed by: "Here's how I'll find out" or "Here's how we'll figure it out together."

2. Admitting uncertainty builds trust The best leaders I've worked with are the ones who say, "I'm not sure. Let's think this through together." That honesty creates space for real problem-solving.

3. Your job is to make good decisions, not to know everything You don't need to be the expert on every topic. You need to know how to gather the right information, ask the right questions, and make informed decisions.

8. Success Is No Longer Measured by What You Accomplish¶

As a director, my success was clear: did I hit my goals? Did I ship the project? Did my team perform?

As a VP, success became fuzzier.

The New Success Metrics¶

1. Did you make the CEO's job easier? Are you solving problems before they escalate to the CEO? Are you freeing up their time and mental bandwidth?

2. Did you position the company for future success? This isn't about this quarter's results. It's about whether you're building the foundation for next year's results.

3. Did you develop the next generation of leaders? Are you building a team that can operate without you? Are you creating opportunities for others to grow?

4. Did you influence the direction of the company? Are you shaping strategy, not just executing it?

These metrics are hard to measure. They're subjective. They're frustrating.

But they're also the reality of senior leadership.

9. You Can't Fix Everything Anymore¶

As a director, if something was broken, I'd fix it. That's what made me successful.

As a VP, I had to let some things stay broken because I didn't have the time or resources to fix everything.

This was a painful lesson.

The Triage Mindset¶

I had to learn to categorize problems:

Critical: Actively causing harm. Needs immediate attention.

Important but not urgent: Should be fixed, but the business can tolerate it for now.

Nice to have: Would make things better, but not a priority.

Not worth fixing: The cost of fixing outweighs the benefit.

As a director, I fixed everything in the first three categories. As a VP, I could only fix the first one — and maybe some of the second.

The rest? I had to document them, acknowledge them, and move on.

That felt like failure at first. Over time, I learned it was just reality at scale.

10. The Title Doesn't Make You Ready—The Job Does¶

I spent the first six months thinking, "I'm not ready for this. I shouldn't have been promoted yet."

Eventually, I realized: no one is ready to be a VP before they become one.

You learn the job by doing the job. You make mistakes. You course-correct. You get feedback. You iterate.

The title doesn't make you qualified. The work makes you qualified.

The Bottom Line¶

Becoming a VP was the hardest career transition I've made. Harder than my first management role. Harder than any technical challenge I'd faced.

Here's what I wish I'd known going in:

1. Senior leadership is lonely. Build external support systems before you need them.
2. Politics is how work gets done. Learn to navigate it without losing your integrity.
3. The shift from execution to strategy is brutal. Give yourself time to develop new muscles.
4. You'll be accountable for outcomes you can't control. Learn to let go.
5. Imposter syndrome doesn't go away. Confidence comes from reps, not revelation.
6. Your words carry more weight than you think. Be intentional.
7. You don't need to have all the answers. You need to ask the right questions.
8. Success metrics become fuzzier. Get comfortable with ambiguity.
9. You can't fix everything. Triage ruthlessly.
10. The title doesn't make you ready. The job does.

Two years in, I still don't have it all figured out. I still make mistakes. I still doubt myself sometimes.

But I'm also learning to trust my judgment, lean into discomfort, and lead from a place of authenticity instead of trying to be someone I'm not.

That's the real work of senior leadership.

Not pretending you have it all together. But showing up anyway, doing your best, and learning as you go.