When Being “Thoughtful” Backfires and What to Do About It?

I once had a dear friend who also happened to be my roommate. She was incredibly thoughtful - always going out of her way to cook meals, clean the house, and generally make life easier for me. It was sweet, and I appreciated her intentions.

But here’s the thing…

Being thoughtful isn’t the same as listening.

The Cost of Anticipating Without Asking

Time and again, my friend would try to anticipate what I might want without actually checking in with me. She'd prepare meals I didn’t care for or organize our shared space in ways that made me feel more stressed than supported.

And when I tried to share what I actually did want - what would work better for me - she resisted. Because she was so busy trying to be thoughtful, she missed the mark on actually supporting me.

Eventually, this led to tension between us. I had to muster the courage to share, as kindly as I could, that what I really needed wasn’t for her to guess what might help, but to ask and listen to what I actually said.

When Good Intentions Go Wrong in Teams

This isn’t just something that happens in friendships or living situations. I see it all the time with the organizations and teams I work with.

People who care deeply about their coworkers, who pride themselves on being considerate and conscientious, often fall into the trap of assuming what others need instead of asking and listening.

And that’s where things get messy. Projects stall. Misunderstandings fester.People feel frustrated, overburdened, or dismissed. 

What’s worse, everyone thinks they’re doing their best to support each other so people start pointing fingers to place the blame elsewhere.

The Defensiveness That Keeps Us Stuck

What makes this dynamic even trickier is the way well-meaning people often resist feedback.

They’ve built their identity around being thoughtful. So when someone points out that their “thoughtfulness” is actually making things harder, it feels personal. Like their goodness is being questioned. Like you just told them they’re a mean, terrible, horrible, bad person.

But here’s the truth. This isn’t about being a good person or a bad person. It’s about being human.

We all develop patterns of behavior - some that serve us and some that don’t. And sometimes, the very thing we think is helping is actually causing harm.

This is especially confusing when that very behavior did serve as well at a point and time in our lives. It’s like that in the past, getting good at assuming and meeting someone’s needs was a way to maintain belonging and safety. And avoid getting shamed, humiliated or ridiculed.

Closing the Gap Between Intention and Impact

The real opportunity here is to close the gap between intention and impact.

To own the discomfort of hearing, “Hey, that thing you did to be helpful? It actually made things harder for me.”

To take a breath, lean into the conversation, and say,"I hear you. What I’m understanding is that next time, you’d like me to check with you first. Got it. I’ll do that."

It’s that simple.Not always easy, but simple.

The Gift of Genuine Listening

So here’s my invitation to you, especially if you tend to be the thoughtful one in your relationships or your workplace:

• Pause.

• Ask.

• Listen.

  
  

Create the space for others to share what they actually need. And be willing to adjust, not based on what you think is best, but on what they tell you they need.

This is how we build trust.This is how we strengthen relationships.This is how we navigate conflict and misunderstanding with grace.

Because when people feel heard, seen, and supported in ways that matter to them, everyone wins.

And that’s real thoughtfulness in action.

If you’ve found value in what I wrote here and you want to support me in continuing to create, guide, write, and make space for deeper transformation, I invite you to buy me a tea.

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