When Speaking Up Changes How You're Seen - by Tarun Kohli

There's a brutal paradox in organizational life: stay quiet too long and you're checked out, speak up too often and you're the problem. The line between being seen as an owner who cares and being labeled as negative is far thinner than anyone admits. What starts as trying to protect the long-term health of the organization can quietly become a reputation issue, where your commitment reads as negativity and your caring looks like complaining.

The timing problem is real and unforgiving. Organizations say they want leaders who think like owners and speak their mind, but that honesty is usually welcome only in small doses, and only when it fits what people are already comfortable hearing. If you don't point out where culture or structure is breaking down, you might be seen as lacking a complete view. If you do point it out, you risk being seen as pushing a personal agenda, even when you're offering real solutions. A lot depends on who you're talking to - not every leader looks at organizations through a design lens, and structural misalignments can feel trivial to someone who hasn't spent time building organizations.

The author admits to being on both sides of this dynamic, quietly labeling someone as "too focused on problems" not because they were wrong, but because really engaging with it would mean slowing down or changing course when it felt easier to keep moving. The practical approach that emerges is to say something, watch how it's received, and adjust. Pay attention to whether the response is curious or defensive. Over time, you start to sense what the organization can handle and what it's not ready to hear yet.

What weighs heaviest isn't the uncertainty of when to speak - it's watching good leaders pay a price for trying to fix organizational problems. People who genuinely cared and wanted to belong, who weren't scoring points or pushing agendas, spoke up because they believed in the company and ended up paying for it. Leadership becomes learning how to live with that credibility risk, how to speak clearly without making yourself the problem, how to keep caring even when it might cost you. And wisdom isn't about knowing exactly when to speak, but sensing how much truth the moment can really take.