The most dangerous moment in a project is when you win it.
Everyone exhales when the client says yes. Joy, relief, validation for the effort and time spent chasing. The win is addictive and unifying for any team, but it’s also the moment you’re most exposed.
For a lot of independent creative companies, the space between the yes and project kick-off highlights a huge accountability gap: often no longer prioritised by the deal-maker but not yet fully with the delivery team. Nobody’s name is naturally on it. The ground feels solid because you’ve won, but beneath the surface: the contract is unsigned, the brief is evolving, the scope’s soft and procurement (professional buyers who do this five times before lunch and have no emotional connection to the work) are about to hit you with additional asks, pricing scrutiny and the request for a three-month interest-free loan disguised as payment terms. The moment is a potential sinkhole.
Your buyer has their maximum leverage at the moment you want the deal the most. In your head, you have already won and so it’s too easy to fall into the sunk cost fallacy and make last-ditch concessions to secure the win. If allowed, the Win Sinkhole can be the single greatest source of gross-profit leak across the whole engagement. And if the deal sets the precedent for work that rolls on for months or years after, it can make or break the entire account.
But who should own it? Look around at who’s seated on your side of the table, and their natural, competing motivations. New business people’s remuneration often incentivises converting revenue, regardless of terms. Client services are programmed to validate the client’s genius decision to hire you - you’re easy and frictionless to work with, after all. Creatives are on a high, pushing everyone to make the best possible work. Production is already stressing the delivery, on top of everything else they’re juggling. Perhaps the founder is holding it all together. Not because they’re best placed or going to stay close to the work, but because unowned things default to them. That’s a symptom, not a solution. And they are often the worst person to navigate the Win Sinkhole, as they’re the most emotionally invested out of anyone.
Everyone’s doing their job brilliantly, but nobody’s sole focus is protecting the money. And if you’re flying solo or a small shop, every seat at this table might be yours, and that brings its own unique challenges.
There’s a quieter, more personal tension too… nobody wants to be the office fun sponge. Interrogating scope and payment terms an hour after the team earned the win lands as a buzz-kill, or worse, as not being a team player. But it’s precisely when scrutiny and detail matter most.
From my conversations with peers and founders, accountability for the Win Sinkhole often defaults to whoever’s standing closest. Or, even more quietly, whoever turns out to be good at covering it.
For thirteen years across production, creative services, and agency operations, I was the person standing closest to that sinkhole. Regardless of how my role evolved, protecting the money stayed on my desk because I was good at it. I enjoyed it. And for a while it looked and felt like a solution, rather than a symptom. But a sinkhole capped by one person’s aptitude and stamina isn’t a sustainable fix, it’s a hidden dependency, and a solve that lasts exactly as long as they do.
At one point, I (half) joked with the team that all celebrating was banned until we were sitting on a pile of cash. But that too would have been half a fix - a solution relying on discipline when the problem was structural.
The real fix was not only giving one person sole focus for protecting the money from proposal-to-kick-off, but building out the entire commercial architecture in service of gross profit, so it never depended on any one person pushing back against, or corralling, everyone else’s natural instincts. The entire journey from proposal, to signed contract, to project kick-off moved inside our formalised commercial architecture: non-negotiable profit targets, hard milestones on when work could start, clarity on what we would and wouldn’t accept in negotiation and, crucially, a shared expectation of what a project set up for success truly looked like. Nothing was truly won until the framework said it was - and everyone could see it.
So don’t ban the celebration. Don’t even delay it. Celebrate twice.
The first toast belongs to the yes: the energy and creativity required to win. Most teams are already brilliant at that one. The second belongs to the official Green Light - contract signed, POs in, first invoice out. This deserves to be at least as big. This one toasts to the genuinely solid ground: the project live, and the entire company connected to the commercial success they have worked together to create. And in doing so, you’ll retire the need for a fun sponge.
Chances are, your team already throws the first party. When’s the second?