Why Strategy Breaks Down in the First 90 Days
If there’s one thing I’ve learned after working with hundreds of strategy and operations teams, it’s this: most strategic plans don’t fail because the plan itself is bad.
In fact, most plans are thoughtful, ambitious, and well-intentioned. Teams spend months debating priorities, aligning on goals, and pressure-testing assumptions. By the time the plan is approved, everyone feels a sense of relief. The hard part is done.
And that’s usually where things start to go sideways.
This was the heart of our recent Ask a Chief of Staff workshop on the first 90 days of strategy execution. The Chiefs of Staff in the room weren’t struggling with vision. They were struggling with something much more familiar: how quickly momentum fades once kickoff meetings are over and reality sets in.
The first 90 days are where strategy either becomes a living discipline or slowly turns into a document everyone agreed with but no longer uses.
📉 The Execution Gap Shows Up Faster Than You Think
One of the biggest misconceptions we talked about is the idea that failed execution means the strategy was flawed from the start. In practice, that’s rarely true.
What we see far more often is an execution gap: the distance between what the organization agreed to focus on and how people actually spend their time once the year gets going.
January starts strong. There’s energy. There are town halls and kickoff decks. But as the weeks pass, people put their heads down. Day-to-day demands pile up. Cross-functional collaboration becomes more siloed. Decisions get made without clear reference back to the strategy.
As a Chief of Staff, you usually feel this before anyone names it. You’re sitting across departments. You’re hearing the questions behind the questions. You can sense when priorities are drifting, even if the plan itself hasn’t changed.
🚨 The 3 Pitfalls That Kill Strategy Execution
After working with hundreds of organizations, we've identified three patterns that consistently derail even the best-laid plans. The good news? Once you know what to look for, they're surprisingly fixable.
Pitfall #1: Accountability Exists in Theory, But Not in Practice
The first place execution tends to break down is accountability.
On paper, everything is owned. Every initiative has a name next to it. Everyone raised their hand during planning and said “yes.”
But once execution starts, the clarity fades. Leaders lose a shared understanding of what should take priority when everything feels urgent. Teams say yes to too many initiatives because they don’t have the context to say no. Accountability still exists, but it’s theoretical.
What’s missing isn’t effort.
✨ The Fix: Build a regular rhythm where commitments stay visible and leaders are expected to come back, month after month, and talk about what's moving, what's stuck, and what needs to change. Without that rhythm, strategy slowly drifts into the background.
Pitfall #2: “Status Theater” Takes Over Leadership Meetings
This naturally leads to the second pitfall we discussed, what we jokingly call “status theater.”
It’s the leadership meeting where everyone goes around the room reading updates. There’s a lot of information shared, but very little progress made. The meeting ends, everyone nods, and the same issues show up again next month.
These meetings are expensive. They bring together the most senior leaders in the organization. And yet, they’re often optimized for reporting, not decision-making.
The shift isn’t complicated, but it does require discipline. Status updates should be shared ahead of time.
✨ The Fix: Reserve meetings for the things that need intervention:
- What’s blocked?
- What’s at risk?
- What decisions need to be made for execution to move forward?
When meetings are designed this way, they stop being about optics and start becoming a real lever for progress.
Pitfall #3: Data Loses Its Meaning
The third breakdown happens more quietly, but it’s just as damaging.
Over time, teams stop trusting the data. Updates are inconsistent. Context is missing. What’s being reported doesn’t quite match what people are feeling on the ground.
Eventually, leaders start asking themselves whether these updates are worth the effort at all.
✨ The Fix: Separate strategy execution from performance management. Strategic metrics aren't personal report cards. They're signals. Their purpose is to help the organization learn, adapt, and intervene earlier. When leaders feel safe saying something is off track, the organization gets smarter. When they don't, problems stay hidden until it's too late.
What Strong Execution Actually Looks Like
After naming the pitfalls, we spent time on what great execution looks like in practice.
The organizations that execute well don’t treat strategy as a project. They treat it as part of how the business runs.
1️⃣ Alignment Turns Into Real Commitment
Not just agreement in the planning room, but a shared understanding that this work will show up in leadership meetings, decision-making, and tradeoffs throughout the year.
2️⃣ Strategy Runs Like an Operating System
There’s a consistent cadence. Expectations are clear. Meetings are designed to drive decisions. Follow-through is non-negotiable.
3️⃣ Ownership Is Unmistakable
If no one is willing to own an initiative, it’s worth asking whether it’s truly a priority. Focus matters. Most teams see the best results when they’re driving three to five strategic initiatives at a time, not ten.
⏰ Why the First 90 Days Matter So Much
The first 90 days set the tone for everything that follows.
This is when operating rhythms are established. This is when leaders signal what truly matters. This is when the culture around accountability, transparency, and adaptation is formed.
The goal isn’t to lock in a plan and never change it. In fact, the best strategies evolve over the year as markets shift, assumptions get tested, and new information emerges.
The goal is to create a system that makes those adjustments intentional instead of reactive.
Chiefs of Staff are uniquely positioned to make this work. You see the whole system. You connect the dots others can’t. You help translate vision into day-to-day decisions.
When strategy execution works, it’s often invisible. When it fails, it’s painfully obvious.
The work you do in those first 90 days is what keeps strategy alive.
💭 Final Thoughts
If this feels familiar, you’re not alone. Almost every organization struggles with the same question once the kickoff energy fades: How do we keep strategy alive once the real work starts?
If you’re heading into the year thinking about how to set the right rhythm early, we’re always happy to compare notes. Whether it’s pressure-testing your operating cadence, rethinking how leadership meetings run, or figuring out how to close the execution gap in those first 90 days, sometimes a quick conversation is the fastest way to get unstuck.
And if you want to see how we think about supporting this work in practice, we recently put together a short product overview that walks through how teams move from plan to execution with more clarity and less overhead.
Either way, the goal is the same: fewer plans that collect dust, and more strategies that actually shape how work gets done.
Following our recent workshop with the Ask a Chief of Staff community, Brooks Busch, Co-Founder and CEO of Elate, shares key takeaways about why most strategic plans fail within the first 90 days, and what Chiefs of Staff can do differently to keep strategy alive well past January.
