Registration deadline: Tuesday October 27th @ 11:59pm EDT Loading timer…

How to Get The Backing You Need For Your Next Promotion — Without Looking Pushy, Political, or Entitled.

A 90-minute live workshop for technology leaders who are tired of receiving glowing performance reviews while their title, scope, and trajectory remain stuck in place.

Robert Castle

From the desk of Robert Castle

Right now, the decisions that determine the rest of your career are being made in rooms you aren’t invited into.

While you keep your head down delivering great work…

A group of senior executives sits around a table deciding who gets the next VP title, the expanded team, and the strategic budget.

Even worse yet, you might think you have your boss’ support…

But behind closed doors they’re not willing to stick their neck out for you to their boss…

Polite compliments on your annual review don't turn into executive promotions.

In fact, being reliable at day-to-day execution makes you dangerous to replace…

So your manager fights to keep you right where you are.

I’m here to help you fix that.

Advancing to the executive tier doesn't require sucking up or playing slimy office politics…

It requires a repeatable system to turn your manager from gatekeeper into your #1 career backer.

You can spend another year keeping your head down…

Hoping your work magically speaks for itself while another promotion cycle passes you by…

Or you can spend 90 minutes with me and leave with the exact strategy, scripts, and power map to turn the relationship above you into your greatest competitive advantage.

Here are the details:

Managing Up: Get the Backing You Need From Above For Your Next Promotion

  • When: Wednesday, October 28, 2026 | 6:00 – 7:30 PM Eastern
  • Where: Live on Zoom (Interactive session + full recording included)
  • Price: $197
  • Special Bonus: Every ticket includes a private, post-workshop 1:1 strategy call with Robert Castle to troubleshoot your specific manager and review your plan.

Here’s What You’ll Learn

  • Does your manager support you privately but doesn’t go “to bat” for you with their higher ups? I’ll show you how to fix that step-by-step.
  • How to get your manager to actively speak up for your work and ideas, rather than assuming the work will speak for itself.
  • The four currencies you can earn with my “managing up” method — and how to maximize each.
  • The eight most common mistakes technology leaders make, and how to ensure you don’t fall into any of them.
  • The single most powerful diagnostic question you can ask your manager to uncover their true priorities.
  • The exact word-by-word script to establish alignment with your boss so they can get what they want -- and you can get what you want.
  • How to establish regular communication rhythms when your boss does not hold regular one-on-ones.
  • How to shift a micromanager from inspecting your work task by task to reviewing it project by project with agreed checkpoints.
  • The single most powerful question you can ask your boss to get backing for your promotion -- and what you must be ready to provide so you don’t become "too valuable to promote".
  • The 3-options framework to make it easy for your boss to say yes to your strategic initiatives — even if your boss is indecisive or is too tactical.
  • How to present technical requests as commercial business opportunities to arm your boss to defend your requests higher up (and simultaneously signals you are operating at the executive level).
  • This counter-intuitive “argue the opposite” method goes against everything you’ve been taught but it will ensure all objections are accounted for when it comes time to presenting your ideas.
  • The exact script to use when an executive says no (this will uncover the hidden calculus and context behind their decision).
  • How to set boundaries with your boss (without ruining your relationship) using a simple 4-step “positive no” formula
  • The exact 5-line script for delivering bad news early and simultaneously building trust.
  • How to construct an organizational "power map" who can say yes or no to your promotion.
  • What to do when backing isn't there, plus the six objective signals indicating it is time to leave.
  • Plus much, much more

Who This Is For

This workshop is specifically for technology leaders who:

  • Consistently deliver strong results, but are frustrated by a title, scope, and salary that haven't kept pace.
  • Have a manager who agrees with them behind closed doors, but caves the moment other executives push back.
  • Are tired of being micromanaged or waiting weeks for simple decisions to get approved.
  • Remain completely invisible to the decision-makers on the executive floor who actually control promotion calibrations.
  • Want to advance their career with confidence and integrity—without ever having to suck up or play manipulative corporate games.
The "3 New Breakthroughs" Guarantee

The "3 New Breakthroughs" Guarantee

I don’t believe in theoretical fluff or generic HR platitudes.

Join us live (or watch the replay). If you don’t walk away with at least 3 concrete, high-leverage strategies that fundamentally improve your autonomy, executive standing, and career trajectory, you shouldn't have to pay for it.

Simply send an email to [email protected] within 7 days, and I will promptly refund every penny of your $197. No interrogation, no hoops, and no hard feelings. You keep the workbook and the replay anyway.

Lock In Your Seat & Private Strategy Session

Stop leaving your career trajectory in the hands of an indecisive boss or an annual review gamble. Turn your manager into your strongest sponsor and get the executive backing your work deserves.

Registration deadline: Tuesday October 27th @ 11:59pm EDT Loading timer…

What You Get Today:

  • 90-Minute Live Zoom Training with Robert Castle on Wednesday, Oct 28
  • Full Session Recording to revisit whenever you change roles or report to a new manager
  • The Managing Up Companion Workbook packed with Robert’s scripts, templates, and frameworks
  • Complimentary 1:1 Strategy Call with Robert Castle to tailor the method to your exact boss and promotion goals