90 Days to Compounding Momentum
When a company brings in new product leadership, there's often a hope that the person will arrive with some framework or methodology that transform the company’s outcomes. The underlying assumption is that whatever problems the company is experiencing stem from a lack of knowledge and expertise: if only we knew the right way to do product, we'd be doing it and getting better results. I want to disabuse you of that notion. The frameworks aren't secret. The solutions to most product problems are well-documented, widely available, and intuitive enough to be implemented by nearly anyone with baseline competency. The question isn't what you should be doing. The question is why you haven't been able to do it already.
In my opinion, that's what the first 90 days of a fractional engagement are actually about. Not installing a methodology. Not reorganizing the team around your best practices. The job is to figure out what's blocking the company from implementing knowledge that's already readily available, and then remove that blocker. Then and only then can you start to make durable changes.
Why "Fractional" Changes Everything
Something interesting happens when you put "Fractional" in front of your title. People talk to you differently. They're more open, more honest, more willing to tell you what's actually happening rather than the version that makes them look good or protects their position. I've thought a lot about why this is, and I think it comes down to threat perception. When you're a permanent hire, especially a senior one, you're entering the org chart. You're going to be competing for resources, building a team, accumulating influence. People have to think carefully about what they tell you because you'll be around for years and it might come back to haunt them. But when you're explicitly temporary, there to help and then leave, that changes. You're not a long-term threat. You're not going to be their boss's boss in eighteen months. So they tell you the truth.
This dynamic is one of the most valuable things a fractional leader brings, and it's not something you can replicate with consultants who arrive, do interviews, and leave a deck behind. As a fractional, I'm embedded enough to see how things truly work, but temporary enough that people don't have to manage me politically. The result is that I often learn things in my first few weeks that the CEO has never heard. Not because people are hiding information maliciously, but because there's never been a safe channel for it to travel upward.
The Discovery Phase
The first two to four weeks of an engagement are almost entirely about talking to people. Not just the executive team, but everyone relevant, at multiple layers of management down to individual contributors. I'm looking for two things: consistencies and inconsistencies. The consistencies tell me what's actually true about how the company operates. The inconsistencies tell me where the gaps are between perception and reality, between intention and execution, between the CEO's mental model and the lived experience of the people doing the work.
What I typically find is that leadership has a curated version of how their company operates. This isn't dishonesty. It's the natural result of distance from the details. As companies grow, founders get further from the front lines. The information that reaches them is filtered through layers of management, each layer smoothing out the rough edges a bit more. What arrives at the top is a sanitized summary that emphasizes what's working and minimizes what isn't. Sometimes the CEO's mental model is based on how things used to work when the company was smaller and they were closer to everything. Sometimes it's based on how they want things to be rather than how they are. Either way, there's usually a meaningful gap between the story leadership tells itself and the reality employees experience daily.
When I surface these inconsistencies, I try to frame them as discovery rather than contradiction. "Here are some things I've learned that I think relate to the challenges you're facing" lands very differently than "here's what you’re wrong about." The goal is to expand the CEO's picture of what's happening, not to make them defensive. And I'm careful about validating sources. If I've only heard something from one person, I'll try to get other perspectives before reporting it as a pattern. By the time I'm bringing something to leadership, I've usually triangulated it enough to be confident it's real, not just one person's grievance. This makes it much easier for CEOs to receive the feedback as "that's not what I thought, that's interesting" rather than dismissing it as coming from someone with an axe to grind.
The Question That Actually Matters
Here's where things get interesting. After a few weeks of discovery, I typically have a pretty clear picture of what's not working and why. Time after time, the problems I uncover are not unique. They're the same patterns that show up at company after company. Unclear ownership, misaligned incentives, decision-making bottlenecks, teams optimizing for output rather than outcomes. And the solutions aren't secret either. There are well-established frameworks for all of this. Books have been written. Consultants have built entire practices around it. The knowledge of what to do is freely available.
So the next question isn't "what frameworks should we implement?" It's "these frameworks were available before I showed up, so why didn't you implement them?" This is the real diagnosis. The company doesn't have a knowledge problem. It has a blocker that's preventing it from improving itself. Until you understand what that blocker is, any solution you implement is going to run into the same wall that stopped previous attempts at change. You'll put a new process in place and watch it slowly get ignored. You'll hire someone to own a problem and watch them get frustrated and leave. You'll announce a new way of working and watch everyone nod along and then continue doing exactly what they were doing before.
The Usual Blockers
In my experience, the thing preventing improvement usually falls into one of two categories. The first is founder or CEO misalignment between what they expect to happen and what they actually allow or incentivize. This shows up everywhere: in business processes, decision-making frameworks, culture. The founder says they want the team to take ownership, but overrides every decision they disagree with. They say they want data-driven product development, but fund pet projects based on intuition. They say they want people to take risks, but punish failure. The organization learns to ignore the stated values and orient around the revealed preferences, and then leadership is confused about why the stated values aren't taking hold. This is the False North dynamic I've written about elsewhere: the team's compass pointing at what the exec wants rather than what's true.
The second common blocker is having the wrong skillset in a critical role, or lacking a critical skillset entirely. People without the right training or expertise end up making decisions they're not properly equipped to make. The junior PM who's expected to drive strategy. The engineer who got promoted into product leadership because they were the most senior person around. The founder who's still acting as head of product despite having no bandwidth for it. These gaps compound over time and create organizational scar tissue: workarounds and habits that form to compensate for the missing capability but that make it harder to operate correctly even after you fill the gap.
The Minimum Viable Change
Once you've identified the real blocker, the work becomes figuring out how to remove it. This is where I spend most of my time in the middle phase of an engagement, and it involves everything you'd expect: coaching, hard conversations, restructuring, sometimes hiring and firing. But my orientation is always toward finding the smallest possible intervention that will create the biggest shift. I'm not trying to overhaul the company or remake it in some idealized image. I'm trying to respect the existing culture and way of doing things as much as possible while removing the specific obstacle that's preventing improvement.
There's a reason for this beyond just being pragmatic. Change is hard, and organizations have immune systems that reject foreign objects. If you come in trying to change everything at once, you'll trigger resistance everywhere simultaneously and probably fail. But if you can find the one thing that, if it shifted, would make other changes possible, and focus all your energy there, you can create momentum. Once one thing changes and people see that it's working, the next change becomes easier. They've seen that improvement is possible. They've experienced what it feels like. They're less resistant and more curious. The goal of the early phase isn't to fix everything. It's to get that first win that proves change can happen here.
Often the hardest part of this is the conversation with the founder or CEO about what they personally need to change. It's one thing to restructure a team or implement a new process. It's another to tell the person who hired you that their behavior is the blocker, that the thing preventing the company from improving is how they make decisions, or how they communicate, or what they reward and punish. These conversations require trust built up over the discovery phase, and they require framing that makes it clear you're on their side. But they're frequently necessary. If the blocker is at the top, no amount of process change below will fix it.
The Click
Sometime around 90 days in, there's usually a moment where things click. That's enough time to have identified the issues, made some changes, and started seeing results. It might be a major insight that reframes how leadership sees a problem. It might be a critical hire that fills a gap everyone knew existed but no one had been able to address. It might be a product launch or initiative that succeeded specifically because it was done differently than before. Whatever form it takes, there's a point where the team experiences what it feels like to operate better, and that experience is more valuable than any framework or methodology I could hand them.
This is when energy shifts. People who were skeptical become curious. People who were going through the motions start engaging. There's a sense that things are actually going to be different this time, that the company is capable of changing, that the effort is worth it. This momentum is the real output of a successful engagement. Not a deck of recommendations. Not a new process document. A lived experience of improvement that makes further improvement feel possible.
The Fade
The end of a fractional engagement isn't when change is done happening. That would take years, if there even is a point of being “done”. It's when the team that's in place is equipped and empowered to continue making change themselves. They've seen how it works. They've internalized the questions to ask and the patterns to watch for. They've built the muscle for the kind of continuous improvement that used to feel impossible. My role shifts from driving change to advising on it, and the need for that advice naturally decreases over time. It's more of a gradual fade than a clean handoff, which is how it should be. A clean handoff implies a discrete transfer of something: a project, a responsibility. What's actually happening is more like a developing capability that no longer needs external support.
The sign that it's working is when the team starts solving problems I would have solved, before I even hear about them. When they're having the conversations I would have initiated, without prompting. When the CEO is asking the questions I would have asked. At that point, I'm not adding much value anymore. The system is running on its own. The momentum is compounding without external input. That's what a successful fractional engagement looks like: not just a transformed company, but a company that's learned how to transform itself.
