(Some of what I am sharing here will shock you.)
TL;DR: Most executives blow their first 100 days by moving too fast, trusting too quickly, or getting sucked into operational quicksand. Here's the framework I developed after watching dozens of leaders crash and burn (including myself once or twice). This isn't about making friends—it's about setting yourself up, actually, to deliver the transformation you were hired for.
Remember that scene in The Godfather where Michael says, "It's not personal, it's business"? That's basically your first 100 days as an executive. Except it's actually incredibly personal for everyone involved, and pretending otherwise will get you eaten alive.
I've stepped into executive roles five times. Twice, I crushed it. Three times, I learned expensive lessons that I'm about to save you from repeating.
The Brutal Truth About Executive Transitions
Here's what nobody tells you: The moment you walk through that door, you're not just taking a job. You're stepping into a complex web of relationships, hidden agendas, and unspoken rules that have been years in the making.
Your predecessor didn't just leave you a team. They left you their baggage, their alliances, and their failures. And everyone's watching to see if you'll be different or just more of the same.
The data backs this up. Research from the Center for Creative Leadership shows that 40% of new executives fail within their first 18 months (Dai et al., 2011). Not because they lack skills, but because they misread the landscape.
The FORTRESS Framework: Your 100-Day Battle Plan
After my third executive transition (the one where I almost got politically assassinated by my own team), I developed what I call the FORTRESS framework. It has saved my bacon ever since.
F - Feel Out Your Direct Reports (Days 1-30)
O - Observe Without Acting (Days 1-45)
R - Replace Strategically (Days 30-100)
T - Time Your Changes (Plan by Day 30, Execute by Day 180)
R - Resist Operational Quicksand (Days 1-100)
E - Evaluate Pace Expectations (Days 1-14)
S - Stay Silent on Promises (Days 1-365)
S - Seek External Validation (When needed)
Let me break this down with the messy details.
Feel Out Your Direct Reports: The Protection Test
In your first 30 days, you need to figure out one critical thing about each direct report: How much does their team protect them?
I learned this the hard way. At one company, I had a VP whose team would practically form a human shield around him during meetings. Red flag? You bet. Turns out he ruled through fear, and his team was terrified of what would happen if I discovered their actual performance metrics.
Here's my quick assessment technique: Schedule skip-level meetings and watch the reactions. If the team seems relieved to talk to you, that's healthy. If they're nervous and keep looking over their shoulders? Houston, we have a problem.
Document everything. Create what I call a "Team Health Matrix" - rate each direct report's team on fear vs. appreciation. You'll need this data later.
The Sacred Rule: Never Promote in Year One
This one hurts people's feelings, but I don't care. Not. One. Promotion. In. Your. First. Year.
I violated this rule once. Promoted a "superstar" in month four. By month eight, the rest of the team had turned against both of us, and by month twelve, she'd left for another company. Why? Because I promoted based on initial impressions, not proven performance under my leadership.
Promotions should only happen for one reason: role readiness. Not as rewards. Not for heroes who swoop in to save the day but never document anything or share knowledge.
McKinsey's research on leadership transitions supports this - premature personnel changes increase team dysfunction by 47% (Keller & Meaney, 2017).
The Replacement Reality Check
Now for the part that'll make you uncomfortable. If you're replacing an executive who failed to drive change, you probably need to replace most of your direct reports within 100 days.
My rule? If they've been there more than five years, they go. Harsh? Maybe. Necessary? Almost always.
These long-timers aren't bad people. But they're conditioned to protect the status quo. They've survived multiple leadership changes by keeping their heads down and resisting transformation. They're organizational antibodies, and you're the foreign invader.
Check this out 👇
I once inherited a team where every direct report had been there 7+ years. By day 90, I'd replaced all but one. The survivor? She came to me on day 15 and said, "I know you're going to clean house. Here's why I deserve to stay." She laid out a transformation plan better than mine. She stayed and became my secret weapon.
Timing Your Transformation
Your boss hired you to deliver results. The question is: how fast?
Map out expectations immediately. If they want transformation in 12 months, you need to make all major changes in the first six months. The second six months? That's for stabilization and proving the changes work.
Think of it like surgery. You can't keep cutting forever. At some point, you need to let the patient heal.
Dodging the Operational Quicksand
This is where most executives die. They get sucked into day-to-day operations and never emerge to think strategically.
Your team will try to drag you into every crisis. "We need your input on this vendor decision!" "This customer is upset!" "The system is down!"
Stop. Breathe. Delegate.
Your job in the first 100 days is to observe patterns, not fight fires. Let your team handle operations while you build a mental model of what's actually broken. If you jump into operations too fast, you'll make decisions based on symptoms, not root causes.
The Complaint Parade
In your first few team meetings, everyone will line up to badmouth their colleagues, other departments, and probably your predecessor. It's like organizational speed dating, except everyone's trying to recruit you to their side of various wars.
Smile. Nod. Take notes. Trust no one.
The loudest complainers usually have the most to hide. People confident in their value don't need to trash others to look good. They know you'll figure it out.
When to Call in the Consultants
Sometimes, rarely, you'll realize you need to replace your entire direct team. This is DefCon 1 territory.
When this happens, bring in external consultants. Not because you need their advice (though it helps), but because you need political cover. "The consultants recommended these changes" plays a lot better than "I decided to fire everyone."
The Communication Dance 👇
Throughout your first 100 days, communicate your willingness to learn. Not weakness—curiosity. There's a difference.
Say things like: "I'm studying how we've gotten to where we are," instead of "I don't understand why you do things this way."
This openness gets you better data. People share more when they think you're learning, not judging.
The Burnout Connection
Here's where this connects to burnout: Most executives flame out because they try to do everything at once in their first 100 days. They make promises they can't keep, trust people they shouldn't, and exhaust themselves trying to prove they deserved the job.
The FORTRESS framework isn't just about political survival—it's about pacing yourself for the marathon ahead. You can't transform an organization if you're burned out by month four. Strategic patience in your first 100 days prevents tactical exhaustion in your first year.
Your First Move
Your first 100 days set the tone for your entire tenure. Don't waste them trying to be liked. Use them to build an unshakeable foundation for the transformation ahead.
Start tomorrow: Create your Team Health Matrix. Schedule those skip-levels. Begin documenting everything.
Most importantly, remember: You weren't hired to maintain the status quo. You were hired to drive change. The FORTRESS framework gives you the strategic patience to do it right.
Want to dive deeper into executive transition strategies? I work with leaders navigating these exact challenges. Book a consultation at https://book.drdegnan.com and let's build your 100-day battle plan together.
Trust yourself. The game is already in motion.
Cheers, my friend!
—Oliver
