The Blessing and Curse of Being a Truth-Teller 🤫

At nearly every review I’ve had in my career, I’ve been told some version of this contradiction:

“You don’t communicate enough.”
“You communicate very well—you provide a lot of valuable feedback.”
“Your feedback tends to be a little critical.”
“You push for clarity, which is helpful—but you can be adversarial.”

In other words: people want communication—just not that kind. 🤷🏽‍♂️

My therapist once told me: “The truth is a medicine. Some people can take a full dose. Some need it diluted. For others, it’ll feel like poison.” That stuck with me.

Because being a truth-teller sounds noble in theory. In practice—at work and in life—it often sucks. 😅

The Pros of Being a Truth-Teller

✅ You tend to see things others miss—risks, gaps, poor assumptions, wasted effort, false victories.

✅ You help teams avoid costly mistakes—or at least give them a chance to consider other perspectives.

✅ You build trust with people who value honesty. Over the years, plenty of engineers, designers, and PMs have told me they appreciate that I speak up when others stay quiet.

✅ You often say what others are afraid to voice. In one review, my manager wrote:

“You challenge assumptions in a good way. You elevate conversations and push for real clarity.”

✅ Over time, you earn a reputation for integrity—someone whose words actually mean something.

The Cons of Being a Truth-Teller

🚫 People say they want honesty—but not everyone wants it from you, or at that moment, or in that tone.

🚫 The culture of a team or company makes a huge difference. In “don’t rock the boat” cultures, truth-telling is punished—even when done politely.

🚫 I’ve heard many times:

“You’re too adversarial.”
“You can come off as combative.”
“You ask ‘why’ too much.”

What they don’t always see is my intent: I ask why so we can do better—not to attack. 🤷🏽‍♂️

🚫 Even when your feedback is valid, it can backfire: you risk being labeled negative, difficult, or “not a team player.”

🚫 I’ve also been told:

“Sometimes you push so hard for understanding the why, you frustrate others.”

In other words—seeking the truth too persistently can get you in trouble.

🚫 Too much honesty? You’re “too critical.”
🚫 Not enough honesty? You “don’t communicate enough.”

🚫 You’re constantly having to gauge timing, tone, and dosage of truth—just to be heard. And honestly? It’s exhausting. The energy it takes to “package” the truth well sometimes makes me want to say nothing at all. 😩

🚫 In personal life, honesty can be even trickier. People often want empathy—not correction. I’ve had to learn this the hard way.

When Truth-Telling Has Cost Me

🟥 I’ve been passed over for leadership opportunities because I wouldn’t play the politics. One review even said:

“Sometimes you don’t understand how much others are driven by politics and relationships.”

🟥 I’ve faced resentment from PMs who didn’t like their plans challenged—even when I was offering constructive alternatives.

🟥 When I switched from manager back to IC, one former teammate soured toward me the moment I started offering direct technical feedback—something I’d intentionally held back from as a manager.

🟥 I’ve been asked to “be more positive” in situations where I thought a dose of realism was needed far more than another round of enthusiasm. 🥴

🟥 And sometimes, I’ve held my tongue—then later regretted it when the team ran straight into an avoidable problem. 🤦🏽‍♂️

Lessons I’ve Learned

I’ve had to accept this: telling the truth is not enough.

How you tell it—matters.
When you tell it—matters.
Whether the other person is ready to hear it—matters.

Sometimes, it’s better to ask questions that lead someone to their own truth.

Sometimes, it’s better to stay silent—for now.

Sometimes, it’s worth choosing words carefully so the truth builds, instead of breaks.

And sometimes, the best you can do is speak the truth clearly and kindly—and be willing to accept whatever response comes.

Final Thought

Being a truth-teller is not for the faint of heart.
It can feel isolating. You won’t always be liked. Some people will quietly resent you.

But I’d rather live with the discomfort of honesty than the regret of silence—or the betrayal of lies.

I’m still learning. The truth matters. But so does kindness. So does timing. And sometimes, so does knowing when to let things go.