Early in my career, I cut a boss in the middle of a status update.
One of my teams was running behind on a batch of instanced content. The lead designer gave me an update on where things were. While he was talking, I was running the production numbers in my head, and by the time he finished I’d made the call. One of the bosses had to go.
He pushed back. Fair enough. But his answer wouldn’t work either. He wanted to stay the course, and staying the course meant his team crunching to get there. It also meant signing up SFX and VFX downstream for crunch without either team having any input. They weren’t included or consulted. They’d just find out.
So I held firm, and the boss was cut.
I still think it was the right destination. I took the wrong route to get there.
The Blunt Instrument
I’d used a blunt instrument when it wasn’t needed.
Things weren’t critical enough that the call had to be made right then. There was time. Not much, but some. Enough to put the problem in front of the team and see what they came back with. I didn’t take that time, and what I walked away with was an understandably frustrated designer and less trust than I’d walked in with.
I think about that second cost a lot. Even today. A cut boss is one piece of content. Trust is what you spend in every hard conversation that comes after it.
Two halves of the same idea.
Looking back, the problem wasn’t that one of us was right and the other was wrong. He was all optimism and I was all skepticism. Neither of us was looking for a third option.
Both halves are useful. Neither works alone.
Skepticism on its own eliminates options. It’s the voice that looks at the schedule, sees the gap, and closes it the fastest way available. It’s usually right about the problem and often too quick about the answer. That was me.
Optimism on its own says yes to the impossible. It’s the voice that says we’ll make it work. And “we’ll make it work” usually means someone is going to work nights, and it isn’t always someone who got a vote.
What I needed was to hold both at once. I’ve come to call it optimistic skepticism, which, admittedly, sounds a bit like word salad. But it’s the stance I try to start from now, and the short version is:
“We probably can’t do what you’re suggesting. But there’s very likely something we can do.”
The skepticism is in the first half. You take the request seriously enough to say it won’t fit. The optimism is in the second. You assume there IS a solution, even if nobody has found it yet.
That assumption changes how you hear proposals. Most of the ideas that come at you mid-production are too big, too slow, or too risky. Skepticism alone treats those as things to reject. Optimistic skepticism treats them as pointers. A proposal that’s too big is still aimed at something, and the thing it’s aimed at is usually smaller than the proposal.
When It Worked
Some time later, a request came in to redo the quest flow and spawning for an entire region. It was a request to fix a playability issue without adding a ton more work to our already overworked artists. But, it was a big, costly, and time-consuming ask for the already over-worked designers.
Given everything else we had to get done, on its face, that’s a straightforward “no.” It was a big ask, and it moved cost from one team to another. The earlier version of me would likely have said so on the spot - or worse, simply taken the hit for the entire team and sign them up for the work.
Instead, we worked it through together. What we landed on kept the same environment layout. Art made some very small changes, mostly props. We changed the quest target locations, which we knew would be the easiest part of the original ask. And we only had to change mob spawning in a couple of areas to support it.
The request was too big. But it was pointing at something real - the feedback was absolutely valid, But the real thing solution was a fraction of the size of the ask. Nobody would have found it if the first answer had been no. And we we would have burned a lot of time for no reason if we’d just answered “Sure, we can do that.” Neither team would have found it alone, either. The solution needed a little from art and a little from design, and that kind of answer only shows up when both are looking at the same problem.
The Question I’d Ask Now
If I could go back into that first conversation, same designer, same update, this is what I’d say instead of making the call:
“So, let’s say we still need to deliver this on time, and we can’t PLAN crunch to make it happen. Can you work with me and the team to come up with ideas that still solve your requirements for the content, inside those constraints? And can you get me that plan by tomorrow afternoon?”
Each piece of that is doing a job.
It fixes the date. “We still need to deliver this on time” takes the schedule off the table as a variable. We’re not negotiating whether the milestone moves. We’re negotiating what goes into it.
It rules out planned crunch. Not all crunch. Planned crunch. Things go sideways, and sometimes a late night happens. What I won’t do is build it into the plan, and especially not on behalf of teams who weren’t part of the conversation.
It keeps his goal intact. “Solve your requirements for the content” tells the designer the thing he cares about is still the target. I’m not asking him to give up on the encounter. I’m asking him to find another way to get there.
It brings the team in. “Work with me and the team” turns a verdict into a shared problem. The people closest to the content know where the flex is. In that conversation, I didn’t.
It sets a short deadline. Tomorrow afternoon. Long enough to think. Short enough that if the answer is still “cut the boss,” I’ve lost a day, not a week, and the rest of the schedule isn’t at risk.
We’d probably still have cut a boss. But we likely would have found a better way to do it, and the team would have been part of finding it.
When To Skip It
None of this means every call goes to committee. Sometimes the blunt instrument is exactly the right tool.
If we’re finaling the game for certification and a request comes in to add a new NPC, the answer is a straight no. If we’re two days from tying off a demo for an event and someone asks to “just add in this one other level,” same answer. There’s no third option to find, because there’s no time for anyone to find it.
That’s the threshold for me. It isn’t how big the request is, or how senior the person asking. It’s whether there’s enough time left for the team to explore before the answer has to be locked. With the boss, there was. Not much, but some. That’s what made the blunt instrument the wrong tool.
Where I’ve Landed
Most of us have a default. Some reach for yes too easily (to be honest, despite the story here, this was actually my default). Some, reach for no.
Optimistic skepticism isn’t a midpoint between the two. It’s a different question. Not “yes or no,” but “what can we do?”
When someone hands you a plan you know won’t fit, what’s the first thing you say?
I'm building DriftWarden, a tool that helps producers see how their plan has moved and re-scope what's left while there's still time to steer. If that sounds like your week, I'd love to hear from you.