A good part of my career has been spent stepping into messy situations and helping turn them around. Sometimes by choice, sometimes by directive. I've seen these challenges in organizations with a few hundred people and in those with tens of thousands. The scale, complexity, and circumstances were different, but certain patterns kept showing up.
One of those patterns is how leaders approach change, particularly in their first 90 days.
The familiar playbook is to meet stakeholders, assess the current state, identify gaps, build a roadmap, and deliver a few quick wins. Nothing is wrong with this. In fact, much of it is necessary.
However, I've also learned that following this playbook doesn't necessarily put the organization on a better trajectory. You can spend months fixing what's broken without questioning what the organization should become. You can build a compelling strategy without the people needed to make it happen. And you can deliver impressive quick wins without changing much in the long run.
Looking back, three leadership mistakes stand out to me: assessing without aspiration, aspiring without coalition, and confusing quick wins with transformation.
1. Assessing Without Aspiration
Most leaders entering a new role start with a current-state assessment. They review performance, meet stakeholders, identify gaps, examine risks, and look for opportunities to improve. I've done this myself, and there's good reason for it.
But there's a trap. When we start by asking what's broken, we often end up with a plan to fix what's broken. That may improve the organization we inherited, but does it prepare us for the organization we want to become?
Imagine a business aspiring to double in size over the next three years. A conventional assessment might identify inefficient processes, technology debt, and organizational gaps. All worth addressing. But the more important question is whether the current operating model can support a business twice its size. The answers could lead to a very different set of priorities.
Or consider a new CISO who discovers a growing backlog of security findings, slow triage, and remediation delays. The natural response is to improve prioritization, add automation, and accelerate remediation. These improvements are necessary, but the backlog shouldn’t define the ambition. Suppose the business wants to expand its digital services without multiplying reviews at every step. The CISO’s assessment must then ask whether identity, access, and decision-making practices can support this growth, rather than focusing simply on whether findings are being cleared quickly enough.
I believe aspiration should come before framing the assessment. That doesn't mean walking in with a grand vision or ignoring urgent problems. It means first understanding what the organization is trying to achieve, challenging assumptions about what's possible, and helping sharpen that ambition.
Only then can we meaningfully assess the distance between where we are and where we want to go.
The purpose of assessment isn't simply to understand the present. It's to understand what must change to create the desired future.
2. Aspiring Without Coalition
A compelling aspiration is a good start, but it doesn't take an organization very far on its own.
I've seen leaders put considerable effort into crafting a vision, defining strategic priorities, and communicating them across the organization. Yet months later, very little has changed. Often, the problem isn't the quality of the strategy. It's that the people needed to make it happen were never truly part of shaping it.
Building the coalition and shaping the aspiration need to go hand in hand.
The right people bring perspectives that challenge assumptions, expose blind spots, and make the ambition more grounded. More importantly, they develop a sense of ownership in what the organization is trying to accomplish. This ownership becomes real when people commit resources, make trade-offs, and accept responsibility for the outcome.
However, coalition-building isn't about getting everyone into the room or seeking consensus on every decision. Too many stakeholders can dilute ambition just as easily as too few can undermine execution.
This is where I find the concept of a Minimum Viable Coalition (MVC) useful: the smallest group that collectively controls the critical decisions, actions, and dependencies needed to achieve an outcome.
MVCs are goal-specific. For example, product, design, and engineering may form the MVC needed to build a product, but not necessarily the coalition needed to sell it or build a successful business around it. That requires a different set of capabilities and decision-makers.
The coalition may start with a few leaders shaping a shared ambition and evolve as the path becomes clearer. The key is to identify who can commit the resources and make the decisions the outcome depends on, not simply who has an interest in it.
A leader doesn't need everyone to agree. They need the right people committed to making something happen.
3. Confusing Quick Wins with Transformation
There's enormous pressure on new leaders to demonstrate results quickly. And understandably so. Quick wins build credibility, create momentum, and reassure stakeholders that things are moving in the right direction.
The trap is confusing that momentum with transformation.
One of the products I inherited in my portfolio, as part of a transformation charter, was struggling with a large backlog, quality issues, and unhappy customers. Those were the problems presented to me, and the obvious response would have been to increase engineering capacity, accelerate backlog reduction, and improve quality processes.
But as I dug deeper, I realized the real problem was upstream. Professional services had been delivering extensive customer-specific customizations that the core product organization was then expected to support. The backlog and quality issues were symptoms of a much larger problem in how the organization operated. Clearing the backlog might have delivered a quick win. But unless we changed how customization decisions were made and how responsibilities were shared, the same problems would keep coming back.
This is something I've come to recognize in transformations: the most visible problem is not always the real constraint. And solving the wrong constraint can make us more efficient at doing the wrong things.
Quick wins are important, but transformation requires us to look beyond the immediate problems, trace them to their underlying causes, and change the conditions that keep producing them. Sometimes that means rethinking processes, sometimes decision matrix, and sometimes how different parts of the organization work together.
A useful test is whether the improvement will persist when the leader stops intervening, and whether the organization can repeat it without another extraordinary effort.
That's the difference between improving today's performance and changing what the organization can consistently deliver, at scale, tomorrow.
The First 90 Days Are Just the Beginning
None of this means assessments are unnecessary, quick wins don't matter, or leaders should spend months building consensus. All three have their place.
However, the first 90 days are an opportunity to establish something more important than a roadmap or a list of accomplishments.
I would encourage leaders to ask themselves three questions:
- Aspiration: Are we clear about what we want the organization to become, or are we simply fixing what isn't working today?
- Coalition: Have we brought together the people who can shape that ambition and make it happen?
- Transformation: Are we addressing the underlying conditions that limit our progress, or just getting better at managing their symptoms?
You won't transform an organization in 90 days. But you can establish a shared direction, build the commitment to pursue it, and begin changing the system that determines its future performance.
In Beyond Posture, I explore the distinction between understanding where a system stands and governing where it can go. I believe the same distinction applies to leadership.
The real measure of your first 90 days isn't how much you've fixed. It's whether you've put the organization on a path to achieve something it couldn't before.