The Perfect Compromise
A hard call is not one you haven’t solved yet. It’s one where every direction is problematic. And still, your job is to tell which of those is the best.
About twenty years ago, in my first product role, there was a feature in our product that engineering kept asking to rewrite.
They were right. It was written poorly and the code was a maintenance hell. But I said no.
I also knew no one was using that feature, because it was so bad that had anyone used it we would have heard them complaining.
So they asked to kill it instead.
I said no to that either, because I knew customers were asking for this feature and it impacted sales even though they weren’t really using it afterwards.
I left it in the product in its bad shape, and promised that if we ever saw customers actually starting to use it, I would make the time in the roadmap to rewrite it the way they originally asked.
I wish that hadn’t been the decision I needed to make. It would have been much easier if there was a simple and clean solution. But none of the alternatives was optimal, and I needed to make a creative trade-off.
I’m really proud of that, actually. Not just because it was the right call in a non-trivial situation. Three years later, when I left the company, still no customer had used that feature, and having it available had helped us win significant deals, or at least not lose them.
I’m proud of it because I didn’t freeze in front of complexity. I found my way in, and out.
Here is how you can do it too.
Nobody is coming to simplify it
When people tell me about a decision they’re stuck on, they rarely describe it as too hard to make. They describe it as too messy to get into.
So they don’t get into it. They stay at the edge of it, waiting for someone to hand them a simpler version. The CEO will decide. The data will settle it. Someone with more context will make it obvious.
But think about how many decisions you make every day. You don’t experience most of them as decisions at all. You see what needs to happen and you do it. You don’t spend the afternoon wondering whether you should answer that email, move that roadmap item, or ask another question in the meeting.
You just act.
The ones that stay with you are different because every option leaves something important behind. There is no perfect or clear answer.
That’s not a bug, it’s a feature. The simpler decisions are no-brainers. It’s the hard decisions that they brought you in for. If you wait for someone else to simplify them for you, you are simply not doing your job.
There is no black and white to find
Once you accept that the problem is yours to figure out, you hit the next thing immediately. You still don’t understand it.
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Nobody is going to make that part clear for you. Product leadership is navigating chaos, not waiting for it to settle.
So you go in. But most people go in looking for the wrong thing.
They go in looking for the answer. For the version of the situation where one direction is clearly right. That is still the search for black and white, just conducted more thoroughly.
You are not going in to find black and white. You are going in to find the shades of grey.
Which means, for example, being willing to hold two things that contradict each other, and accepting that both are true.
That feature was written badly enough that it should not have been in production. True. It also could not be removed. Also true. Those two facts sat next to each other the whole time, and neither one cancelled the other.
Then, once you can see the shades, name the price of each direction you could take. Not in general terms. Explicitly.
Rewrite it, and I spend roadmap time on something nobody uses. Kill it, and I lose deals. Leave it, and I carry bad code and keep saying no to people who are right.
Three directions. Three real costs. None of them free.
When perfect is not an option
I don’t think those decisions ever become easy. And yet making them is exactly what you need to do.
Once the prices are on the table, the question changes. You are no longer choosing between directions. It’s not good vs. bad. You are choosing which cost you are willing to carry.
Not all costs are the same.
Some can be undone. If you are wrong, you go back and pay the other price later. Others close a door behind you, and no amount of budget next quarter reopens it.
Some are paid now. Others compound quietly over time.
Some carry high risk, but also a potential high reward. Can you afford it?
None of that produces a right answer. It produces a shorter list.
That is what the call actually is. Not finding the option without a downside. Choosing the downside you can live with, on purpose, knowing what the others would have cost.
And while we are always proud of great decisions, sometimes you need to be proud of making a decision at all.
Our free e-book “ Speed-Up the Journey to Product-Market Fit” — an executive’s guide to strategic product management is waiting for you at www.infinify.com/ebook
Originally published at https://infinify.com on September 2, 2026.
