When Should You Stop Trying For VP?

Maya Grossman
Nov 25, 2025
4 min read

"I've been trying to become a VP for a year.

When should I stop trying for it?"

A client inside my program asked me this recently.

And it stopped me for a second - because that's not really a tactical question. It's an emotional one.

It's what people ask when they've tried everything they think they're supposed to do… and it's still not working.

It's the moment when ambition meets exhaustion.

My honest answer?

If this milestone matters to you - never.

Not because I believe in endless hustle.

But because the right question isn't "When should I stop?"

It's "What do I need to do differently?"

The Hidden Truth About "Trying"

My client wasn't chasing VP for the title or salary (though she deserved both).

She had a 10-year vision - she wanted to build her reputation inside corporate first, then transition into consulting.

So when she said "nothing's working," I asked a simple but uncomfortable question:

"What exactly have you tried?"

We made a list.

She networked… with about five people - all year.
She had a few "fun" coffee chats, but no real plan.
She posted occasionally on LinkedIn - mostly random thoughts.
And she had one recruiter interview for a role she didn't even want.

If you've ever been in this situation, you know how frustrating it feels. You're doing things. You're putting in effort. You're technically trying.

But without the right strategy, all of your effort doesn’t get you the right results.

Let’s change that.

What a VP Strategy Actually Looks Like

Getting to VP isn't a waiting game - it's a campaign.

And like any good campaign, it needs a plan, clear positioning, and consistent action.

Here's what I told my client to do instead:

Step 1: Turn Networking into a Strategy

Talking to five people a year won't move the needle. You need consistent, intentional outreach.

Reach out to 20 VPs every month. Not for favors - for insight.

These conversations are where you learn how people actually made the leap.

Here's how to make those calls count:

Listen more than you talk. Spend 80% of the conversation understanding their path, the shifts they made, and what leaders looked for when promoting them.
Ask smart questions. "What do you think made leadership see you as ready?" "What skills mattered most?" "What advice would you give someone preparing now?"
Build momentum. End every call by asking, "Who else would you recommend I talk to?" - and keep the chain going.

Within a month, you'll have real data - not assumptions - about what it takes to reach VP in your company or industry.

Plus, a hot network of VPs who would think about you when opportunities open up or when they are leveling up.

Step 2: Know Your Value

If you can't clearly articulate who you are and the unique value you bring, it will be hard to stand out and explain why you are the best person for the job. Avoid the trap of trying to be good at everything and focus on highlighting one thing that matters.

Your positioning statement should answer three questions:

What problem do you solve?
What impact do you create?
Why does that matter to the business?

For example:

"I help product organizations turn customer data into strategic decisions that drive growth."

Now you're not just a Director who's great at execution - you're a strategic operator with a business lens.

Once you're clear on your message, make it visible.

Use LinkedIn to share insights, results, or patterns from your work that reinforce your value narrative.

Visibility builds credibility.

Step 3: Create Your Own Opportunities

Most people wait for the perfect job description or for recruiters to DM them.

But that's how you end up waiting years.

Instead, make a dream list of companies and CEOs whose problems you can solve.

Then, reach out directly - not with a resume, but with a short message that articulates your value proposition.

Something like:

"I've been following your company's growth, especially your recent expansion into [X].

I specialize in helping teams operationalize that kind of scale efficiently.

Would you be open to a short conversation about how I could help?"

That's how senior hires happen. Quietly. Through proactive, thoughtful outreach - not job boards.

(If you are a Director, just swap CEO with VP and voila!)

Why Quitting Your Dream Isn’t The Answer

Here's the hard truth: most people give up right before things start to move.

When a few months pass without progress, they assume they're not good enough.

That maybe they don't have "it."

But that's rarely true.

They don't lack potential - they lack a process.

Just because you know the ingredients - hard work, networking, visibility - doesn't mean you know how to bake the cake.

It's the same with your career.

You need to know how to combine your skills, relationships, and visibility in the right order to create results.

That's the strategy I used to land my second VP role - and the same one that helped two of my clients get promoted to VP this year, despite a tough economy and fewer opportunities than ever before.

No magic. No shortcuts. Just the right ingredients, in the right order.