
The “Start Strong in Your New Role” Method Map Workshop — A practical, technology-leader-specific system for making the most of your first 90 days in a new role.
A Five-Step Framework for Your First 90 Days — Diagnose the situation, agree on success, protect the time to lead, pick wins that count, and win over the skeptics.
The Complete Companion Workbook — The workbook you’ll write in during the workshop, including your situation read, conversation planner, power map, calendar defense plan, early wins, and stakeholder strategy.
The Full Workshop Presentation — Every card and framework from the session, so you can revisit the method and run it again when your next leadership transition arrives.
The Workshop Recording — Watch the complete session on your own schedule if you can’t attend live or want to revisit the material later.
A Personalized 60-Minute Working Session with Robert Castle — A follow-up session focused specifically on your transition, your organization, your stakeholders, and the game plan you need to move forward.
Your First Situation Read — A weighted, dated first assessment of the organization, its challenges, opportunities, people, and culture—so you’re working from evidence instead of assumptions.
The STARS Evidence Worksheet — A practical tool for assessing the situation you’re walking into and identifying the type of leadership approach it requires.
The Five Essential Questions Card — The exact questions to ask your boss, peers, direct reports, long-tenured employees, and customers to uncover what’s really happening inside the organization.
A Clear List of What You Still Need to Learn — The specific questions that remain unanswered, along with the people who can help you find the answers.
The Five-Conversation Planner — A step-by-step guide for conversations about the situation, expectations, leadership style, resources, and personal development.
A Draft of What Success Looks Like at Day 90 — A written definition of “winning” that you can use to align expectations with your boss and avoid being judged by standards nobody ever explained.
The Diagnosis-Window Script — The exact language you can use to buy yourself time to understand the situation before being pressured to make decisions too quickly.
A Power Map of Your Organization — A practical template for identifying advocates, neutrals, likely opponents, and the key people who influence whether you’re seen as credible.
A Calendar Defense Plan — A framework for protecting the time you need to lead, rather than allowing day-to-day demands to consume your entire first quarter.
The “What You Will Stop Doing” Workbook Exercise — A way to decide what must come off your calendar so you can make room for the transition work your new role requires.
An Early Wins Scoring Sheet — A simple system for evaluating potential early wins based on business impact, speed, available resources, long-term value, and the behavior change they create.
Your Three or Four Early Wins — A focused shortlist of achievable wins that can be completed inside the 90-day window and build credibility for the bigger changes ahead.
A Stakeholder Map for Winning Over Skeptics — A framework for understanding who may resist you, why they may be holding back, and how to turn resistance into cooperation.
The “Three Skeptics—and Why” Workbook Exercise — A guided process for identifying the people whose confidence you need to earn and understanding their goals, fears, incentives, and concerns.
Technology leaders stepping into a new role — especially those responsible for leading teams, initiatives, or organizational change.
Newly hired executives and senior leaders who need to establish credibility quickly.
Technology professionals who have accepted a new role but have not started yet and want to prepare before the clock begins.
Leaders in their first 90 days who want a structured approach for diagnosing the organization, aligning expectations, and choosing early wins.
Leaders who have been in their role for less than a year and want to strengthen their transition plan or reset their approach.
Anyone moving into a role with high authority but low credibility who needs to understand the organization before making major decisions.
Leaders who need to clarify what success looks like with their boss and avoid being judged against expectations that were never clearly defined.
Leaders who need to build relationships with stakeholders, skeptics, peers, direct reports, and potential opponents.
Leaders who want to identify and complete three or four meaningful early wins that build credibility and support longer-term initiatives.
Technology leaders who want a practical, hands-on method for creating a personalized 90-day plan.
Anyone stepping into a new leadership role who wants a proven framework for understanding the situation, protecting time to lead, and earning the trust of the people who matter most.
This workshop is for technology leaders stepping into a new role—or within their first year—who want to build credibility, align expectations, choose meaningful early wins, and create a practical 90-day plan.
No — it’s for anyone preparing to start a new role, already within their first 90 days, or in the role for less than a year.
Yes — especially if you’re preparing for a new role, leading a major transition, or need to reset your approach and build stronger alignment, credibility, and momentum in your current position.
It's happening on Wednesday, September 23rd at 6pm EDT. The workshop will be hosted virtually on Zoom. You will get the link after you register.
Yes, you'll get access to it shortly after the workshop - whether or not you actually attend. You will also get a clean transcript in PDF format..

If you attend the workshop and don’t feel you received practical, actionable value you can use in your first 90 days, email me directly at [email protected] and I’ll issue you a full, prompt refund — no questions asked and no hard feelings.