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When doing more stops working

  • Writer: Rachel Windzberg
    Rachel Windzberg
  • May 1
  • 3 min read

What made you exceptional at your current level can quietly become what holds you back at the next one:

  • Your attention to detail becomes micromanagement, and suddenly your team stops thinking for themselves and everything runs through you.

  • Your bias for action means you keep solving problems instead of framing them, and leadership never sees you as someone who sets direction.

  • Your reliability makes you the person everyone depends on, which makes you very comfortable to keep exactly where you are.

To summarize, what got you to where you are might not be what makes you great at the next level - your deep expertise becomes a crutch, and instead of building the cross-functional trust that gets you promoted, you stay in the weeds where you feel safe.


The transition to the next level isn't about doing more of what worked. It's about doing something fundamentally different. And most people don't find that out until they've been stalled for a year wondering what went wrong.


This is also true for transitioning from startups to big tech and vice-versa: Your skills at a startup focused on execution, problem solving, leaving very little time to longer term thinking. Your skillset in big tech focuses a lot more on alignment, risk-management, and navigating organizational and cross-organizational stakeholder management. In many cases, without adaptation, the response can be similar to an organ rejection.


A few weeks ago I ran my first session of my Promotion Blueprint cohort. Before getting into any frameworks, I had everyone do a 5-minute exercise: score yourself across six dimensions (scope, strategy, influence, ambiguity, manager relationship, visibility) from three perspectives: Your view, your manager's view, your skip's view.

The data that came back showed a perception gap: Self-ratings averaged 3.8 out of 5. Manager ratings: 3.3. Skip-level ratings: 2.9.


But the number that gave me pause was the "I don't know" response - Nearly half of all skip-level scores came back as "I don't know."

Participants couldn't estimate what their skip-level thought of them across scope, influence, visibility. Not because they were underperforming, but because they had no read on it at all.

This is the gap nobody talks about. You can be executing well, getting strong performance reviews, and still have your promotion stall, because the person who matters most in that calibration room doesn't know what you do.

There's a concept I keep coming back to with clients: what got you here is not what keeps you here. The skills that made you exceptional at your current level (deep execution, attention to detail, delivering on a roadmap) are exactly the skills that can hold you back at the next one.

What changes at the senior-to-principal or director transition is not the volume of your output. It's three things:

  • Relationships: You're not looking to be liked. You need to be trusted with the real problems, and having sponsors who advocate for you in rooms you don't yet have a seat in. The data showed most people couldn't name what their skip-level manager thought of them, and more importantly, in the later conversation, couldn't articulate what the main focus of their skip was. That's a relationship gap, not a performance gap.

  • Execution: Shipping things and even moving the metrics isn't enough. The "so what" test is simple: if you're not showing how you identify the right problems to solve and set direction for your org and outside of it, you're not playing at the next level.

  • Influence: A promotion is ultimately a signal that you can move people and decisions beyond your immediate team. It means someone is willing to advocate for you unprompted. And when calibration conversations happen without you in the room, the question isn't whether you worked hard enough. It's whether you made the right things visible to the right people, early enough for it to matter.

The shift I kept coming back to in that session: you stop being managed and start managing up. Your stakeholders become your features. Each one has strengths, bugs, and the ability to unlock or block what you need.

That's where most strong performers stall. Not because they can't do the work, but because nobody prepared them for the part where the work is the relationships.

 
 
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