When Giving the Benefit of the Doubt Backfires
Over the past year, I’ve heard more and more founders and design leaders tell eerily similar stories:
Over the past year, I’ve heard more and more founders and design leaders tell eerily similar stories:
In 1949, a crew of elite smoke-jumpers parachuted into Montana’s Mann Gulch to fight what looked like a routine wildfire. But within hours, the fire turned deadly. As the flames roared up the slope, their leader, Wagner Dodge, made a radical move: he lit a fire of his own. By burning the grass ahead of him, he created a patch of scorched earth the wildfire couldn’t cross. He lay in the ashes as the main fire swept over.
A lot of designers, especially those with a strong systems-thinking mindset, pride themselves on being rigorous problem-solvers. We stress-test ideas. We poke holes in weak assumptions. We say things like “That won’t work because…” or “The problem with that is…” and we think we’re doing our job — helping move the team forward, protecting users, flagging risks.
But let’s be honest: a lot of the time, we just come across as… difficult.
Starting a company is a crash course in humility. You’re juggling 100 decisions a day, half of which you’ve never faced before. You’re trying to build a product, grow a business, and stay sane—all at once.
Here are seven principles I’ve seen trip up first-time founders (myself included). If you're just getting started, I hope this saves you some scar tissue.
It starts, as these stories often do, with a bold vision.
A founder has an idea — one they’re convinced is going to change the game. It’s innovative. Disruptive. The kind of idea that turns heads and opens investor checkbooks. Before long, there’s money in the bank, a team in place, and the runway to bring this vision to life.
From the founder’s perspective, the stars are aligning. The idea has been validated — after all, someone just put money behind it. Now it’s just a matter of execution.
But this is where things often go wrong.
The end of the year is a natural time for self reflection. It’s an opportunity to take stock and consider the accomplishments you made over the past 12 months. The big things are usually obvious. You made these hires, you worked on these projects, you shipped these features and, if you're lucky, have some positive stats to show for the work. However the details are always a little bit fuzzy.