The Emotionally Uncomfortable Work That Drives VP Promotion for Directors in Tech

Maya Grossman
Jan 8
5 min read

If you’re a Director in tech aiming for VP, this scenario may feel uncomfortably familiar.

Six months from now, someone with less experience and fewer deliverables lands the promotion you wanted. Not because they worked harder, but because they did the emotionally uncomfortable work you avoided.

This post breaks down why working harder doesn’t lead to VP promotions, what actually creates executive leverage, and how Directors get promoted to VP by building visibility, influence, and strategic courage before the title ever changes.

I was reminded of this while listening to a podcast with Itamar Marani (former special-ops commander turned performance coach).

He shared a question that hit like a gut punch:

“Could someone else with your exact skill set achieve more than you are right now?”

If the answer is yes, your problem isn’t skill.

It’s a strategy and some emotional courage.

I see this every day in tech. Directors who are brilliant operators, drowning in deliverables, and assuming performance alone will translate into a VP promotion. Meanwhile, the person who looks less “ready” on paper moves up because they tolerate more discomfort: they ask for visibility, make a business case, get sponsors, say the hard thing in the important room.

At the VP level, promotions aren’t rewards for output.

They’re decisions about trust, scope, and perceived executive readiness.

Let’s make this practical.

Today’s newsletter will help you start your reset for 2026 with a simple but powerful assessment. If you hit an “ahha” moment after you take it, hit reply and let me know.

An executive coach explaining the emotionally uncomfortable work that gets Directors promoted to VP

The Special Ops Drill: 3 Moves to Accelerate VP Promotion for Directors

After listening to the podcast I immediately wanted to figure out how these tools can be applied in every day situations, not just under cover ops. So here is the revised version meant to help you develop mental fortitude to win in your career and life.

Take ten minutes for this — it’s short, but it’s the kind of reflection that gives people a breakthrough.

It helps you see exactly why you might be stuck and what would truly move you forward.

This is where you start to build executive presence, by doing what others avoid and showing up in high-stakes moments

1) Run the Six-Month VP Scenario

Borrowed from the podcast adapted for corporate reality.

It’s six months from now. Someone who doesn’t work as hard as you — two kids, new mortgage, a full plate — just landed the VP role you wanted.

What must have been true for them to get promoted to VP—beyond raw performance?

List 1–3 actions they took that you didn’t, especially the ones that make you squirm.

Examples to jog your brain:

They asked a senior VP to sponsor their business case and got a yes.
They ran a crisp monthly executive update that tied work to revenue, risk, and runway (not tasks), creating strategic visibility that senior leaders notice.
They made the ask with a clear promotion business case: scope, outcomes, impact, and why now.

If you’re thinking, “I could have done that,” exactly.

2) Identify the Habit That’s Blocking Executive-Level Impact

High achievers don’t stall from lack of effort; they stall from comfort habits. Pick the one that’s costing you the most.

Avoiding Uncertainty: You stick to “safe” execution and avoid ambiguous, political, or high-stakes rooms.
Optimizing for Approval: You won’t move until everyone is happy. (Everyone is never happy.)
Seeking Validation: You wait for permission or “proof” before you ship, ask, or lead.

Circle one. That’s your constraint. We’re not judging it; we’re managing it.

3) Do the VP-Level Move You’ve Been Avoiding (This Week)

Pick one move a VP would do anyway and schedule it in the next seven days.

Starter list (steal one):

Sponsor Ask: “I’m building a business case for expanding X. Would you be open to advising and, if you see merit, sponsoring it for the Q1 promotion cycle?”
Strategic Update: 1 slide, BLUF first: outcome → impact → decision needed. Send it before the meeting.
Promotion Business Case: Draft it. Scope, metrics, org impact, timing. Put a date on the calendar to review it with your manager.
Skip-Level Signal: Request 15 minutes with your skip to sanity-check priorities and surface risk. (Executives love risk mitigated.)
Priority Reframe: Push back (respectfully) on a low-leverage ask with a better, business-aligned alternative.

Will this feel awkward? Yes.

Is the point awkward? Also yes.

Why Working Harder Doesn’t Get You Promoted to VP

So many high achievers fall into the same trap — working harder to compensate for uncertainty or discomfort.

There’s a reason. Doing more gives you a sense of control. You can measure tasks. You can check boxes. You can stay busy and feel productive.

But real success requires a different muscle: tolerating uncertainty while you influence outcomes.

That’s why hard work alone isn’t enough for VP promotions, executive courage and strategic action matter more.

You don’t get ahead by doing more of the same, you move up by doing what feels uncomfortable and strategic: picking bets, aligning power, making decisions, owning impact.

That’s what one of my clients discovered after ten years at the same level. Three managers came and went, and he was never considered for promotion.

When he joined my program, he already knew the playbook — be more visible, build relationships, shape direction. But knowing isn’t doing. And he wasn’t doing any of it because it was uncomfortable.

It wasn’t a strategy problem. It was a courage problem.

So we started small — self-promotion in 1:1s with his manager. Then, networking with senior leaders. Eventually, direct communication with the CEO.

That was the year everything shifted. The executive team finally saw his potential (including a shout-out from the CEO), and he was promoted to Senior Director.

Here’s what that story proves: