Red Team Thinking for Change Leads
Helping leaders surface blind spots, test assumptions, and challenge groupthink without eroding trust.
Welcome: You Don’t Have to Have It All Figured Out
If you are leading change, you already know how hard it is to speak up when everyone else is nodding in agreement. You know what it feels like to see the risks no one wants to name, and to wonder if raising them will hurt your credibility.
That tension is exactly why this publication exists.
Red Team Thinking for Change Leads is written for professionals who want to improve decisions, reduce risk, and create durable change by asking better questions and making hidden assumptions explicit.
Each week, you will find practical tools and thought-provoking questions to help you:
Challenge assumptions constructively, not destructively
Identify groupthink before it undermines your initiative
Raise uncomfortable issues while maintaining credibility
Sustain your own energy and perspective as a change agent
These are not theoretical concepts. They come from my own experience leading change initiatives inside large, complex organizations, often while juggling competing priorities and personal constraints.
A Failure That Taught Me Something Valuable
Years ago, I stayed silent during a major planning session because I thought disagreeing would make me seem difficult. Months later, the very risk I saw materialized, costing the team time, money, and trust. That moment taught me that your role as a leader is not to be agreeable. It is to ensure the right conversations happen before it is too late.
A Success That Broke the Rules
When a project began drifting off course, I circulated a memo naming the underlying issues nobody had addressed. I fully expected pushback. Instead, colleagues thanked me for finally putting words to what they were all thinking. That memo created alignment and set the tone for a much more candid culture. Sometimes, saying the hard thing earns respect instead of resistance.
Three Practical Steps You Can Take Today
If you want to strengthen your ability to lead change and see blind spots, start small:
Write down three assumptions you are making about your stakeholders. Pick one and test it this week by asking a direct question.
Schedule 15 minutes to ask yourself, “If this initiative fails, what is the most likely reason?”
Draft one short email or talking point that raises an uncomfortable issue. Frame it as a question rather than a criticism.
These small actions build the habit of thinking critically while fostering trust.
One Question to Reflect On
Why do you care about leading change? Beyond career advancement, what is the personal reason you keep showing up and doing this work?
Take a moment to write your answer down.
If you are ready to improve how you lead change under pressure, subscribe now and join the conversation. Each week, you will get one actionable idea you can use immediately.
Subscribe now and start leading with greater clarity and courage.