[Image created with ChatGPT (OpenAI) using prompts by Heather Smith.]
Is Your Kindness Mistaken for Weakness?
Are you an optimist like me, someone who almost always sees the glass as half full? Do people appreciate that quality about you, but then seem surprised when the optimistic, accommodating person they thought they knew puts on her skeptical cap, says no, or establishes a boundary?
I was once asked a question that really opened my eyes:
How do you think people perceive you before they really know you?
Hmm. That’s a pretty deep question, and honestly, it wasn’t something I’d ever really thought about.
I said that people sometimes perceive my positive demeanor as passivity. I’m optimistic. I’m empathetic. I like helping people. I give people the benefit of the doubt. But sometimes those qualities can create an impression that I will always accommodate others or won’t say no.
And then I do.
I disagree. I establish a boundary. I challenge an idea. Not because I’ve suddenly become a different person, but because kindness and agreement aren’t the same thing.
I kept thinking about that conversation afterward. In fact, I kept hearing Rihanna singing FourFiveSeconds in my head. There’s a specific power in part of the song when she’s had enough because her kindness has been mistaken for weakness.
I feel that deeply.
Not the getting drunk or going to jail part, obviously, but the emotion underneath it: that feeling of realizing that somewhere along the way, someone interpreted your kindness as permissive.
It got me thinking: How much of what we believe about another person comes from who they actually are, and how much comes from the story we’ve created about them?
Are You Seeing Me, or Your Idea of Me?
There’s something fascinating about the way we perceive other people. We meet someone, learn a few things about them, and start filling in the blanks.
I’ve written about this before in Are You Judging Me Because My Name Is…?, where I explored the assumptions we make about people based on surprisingly little information. A name. An appearance. A demeanor. A communication style. We take what we can observe and use it to construct a story about the person behind it.
Sometimes those assumptions seem harmless. Someone is warm, so we assume they won’t challenge us. They’re accommodating, so we assume they’ll always accommodate us. They’re calm, so we assume they won’t push back. They’re generous, so we begin expecting their generosity.
But assumptions can work in the other direction, too. We might decide someone isn’t assertive enough, strategic enough, technical enough, experienced enough, or ready to lead. Once we’ve formed that impression, it’s surprisingly easy to start interpreting new information through it.
How often do we decide who someone is first and evaluate the evidence second?
There’s a name for our tendency to favor information that supports what we already believe: confirmation bias. Once we’ve created a story about someone, evidence that supports that story can become easier to see, while evidence that complicates it becomes easier to discount.
Then something happens that doesn’t fit.
The kind person says no. The quiet person challenges the room. The person we didn’t initially see as a leader takes charge. The agreeable person disagrees.
And we think: That’s not the person I thought you were.
Maybe they’re not.
But were they ever?
There is an important distinction between knowing someone and knowing our idea of someone. People are more complex than the handful of characteristics we initially observe. Learning something unexpected about someone doesn’t necessarily mean they’ve changed. It may simply mean we’re seeing more of who they always were.
Kindness Has Boundaries
That original question eventually led to a conversation about something else I’ve been thinking about: the difference between being nice and being kind.
I have deep empathy for people. I genuinely care about people at their core. I mean, I’m a yoga teacher. Compassion, interconnectedness, and thinking about how our actions affect other people are quite literally part of my practice.
But I don’t believe being kind means abandoning boundaries.
I believe strongly in work-life balance, for example. I may choose to work after hours because inspiration strikes or because I want to finish something, but that’s my choice. I would never expect someone else to make the same choice. If I write you an email late at night, I’ll schedule it to arrive the next morning. If something is truly an emergency, I’ll pick up the phone. Otherwise, tomorrow is perfectly fine.
The same principle applies to professional boundaries.
If an organization hires me to manage its web experience, information architecture, accessibility, or digital strategy, I absolutely want feedback. In fact, I need it. Other perspectives make my work better, and I’ve learned plenty by listening to people who see a problem differently than I do.
But collaboration doesn’t mean automatically implementing every suggestion.
When I’m accountable for key performance indicators and organizational outcomes, part of that responsibility is exercising professional judgment. Sometimes that means advocating for a recommendation. Sometimes it means changing my mind because someone else has a better idea. And sometimes it means respectfully disagreeing.
None of those things are unkind.
In fact, sometimes disagreement is exactly what responsible collaboration requires.
I will also happily go out of my way to help someone. That’s part of who I am. But there’s a difference between generosity and obligation. Healthy teams should make room for people to contribute beyond their job descriptions without allowing every generous act to suddenly become a permanent expectation.
Maybe that’s part of the distinction I’ve been trying to articulate: kindness has boundaries.
You Teach People How to Treat You
My parents ingrained one rule in me growing up: Treat others the way you want to be treated.
Then one of my very first managers gave me another piece of advice that has stayed with me throughout my career: You need to teach people how to treat you.
For a long time, those might have sounded like two different philosophies. Now I think they’re actually the same philosophy.
I explored that lesson more deeply in Boundaries in Business: Learning to Be Comfortable in the Uncomfortable. I’ve come to believe that boundaries aren’t the opposite of empathy. They’re often what allow us to continue practicing empathy without resentment, ambiguity, or burnout.
I teach people how I want to be treated by modeling how I treat them. If I want you to respect my time, I need to respect yours. If I want you to value my expertise, I need to value yours. If I expect honesty, I owe you honesty. If I expect accountability, I need to be accountable.
I can’t hold someone else to a standard I’m unwilling to meet myself.
To me, that’s kindness. It’s thinking about the highest good for everyone involved, not simply doing whatever keeps everyone comfortable in the moment.
Sometimes Kindness Means Challenging the Room
I’ve spent years working in higher education and healthcare, particularly in digital experience, accessibility, and compliance. When you work in those areas long enough, you start seeing vulnerabilities everywhere.
Sometimes something technically “works,” but creates a terrible experience for the person trying to use it. Sometimes a content decision makes critical information almost impossible to find. Sometimes an accessibility issue prevents someone with a disability from accessing something everyone else can.
The comfortable thing might be to stay quiet, wait for consensus, and avoid stepping on anyone’s toes.
But sometimes the responsible thing is to say: we need to fix this, even if doing so requires an uncomfortable conversation.
One of the things I valued most during my nine years at Geisel School of Medicine at Dartmouth was the autonomy my immediate supervisor gave me. He trusted me.
If I identified problems with content, information hierarchy, imagery, nesting, taxonomy, accessibility, or the underlying technology, I was empowered to address them. I could collaborate with stakeholders when their input was needed while also making decisions within the areas I was responsible for.
That autonomy didn’t mean I could do whatever I wanted. Quite the opposite.
Trust creates accountability.
Being trusted to exercise professional judgment means being responsible for exercising it well. That includes listening to other perspectives, knowing when to change course, and being willing to raise an issue when staying quiet would be easier.
That’s the kind of trust I value, and it’s the kind I want to give other people when I’m leading them.
Sometimes You Have to Be Kind to Yourself
There’s another dimension of kindness I’ve been thinking about, too: being kind to yourself.
After nine years in one organization, I reached a point where I knew I needed to challenge myself in a different way. I believe growth sometimes requires becoming uncomfortable again: learning new systems, encountering different perspectives, and testing what you know in a new environment.
So I took a chance and moved outside my comfort zone.
Not every professional decision has to produce exactly the outcome we imagined to be worthwhile. Sometimes growth comes from making the move, learning something we couldn’t have learned by staying comfortable, recalibrating, and carrying that knowledge into whatever comes next.
I’ll take another chance. And probably another after that.
If at first you don’t succeed, try again, right?
Leadership Doesn’t Always Look Like Leadership
I’ve been told that I’m a natural leader since I was young, but the older I get, the more I’ve realized that leadership isn’t necessarily about being the loudest person in the room, having the most authority, or having a certain number of people reporting to you.
For me, leadership is about modeling the behavior I want to see. It’s asking hard questions. It’s challenging something when it doesn’t make sense. It’s being willing to have a difficult conversation when avoiding it would be easier. But it’s equally about listening, reconsidering your position, admitting when you’re wrong, and recognizing when someone else knows more than you do.
I learned that lesson early in my management career. When I was managing a team of group fitness instructors, I thought being the manager meant I needed to know everything. I thought I should understand every discipline and be capable of teaching every type of class myself.
My supervisor corrected me. He told me I didn’t need to know everything, and I certainly didn’t need to be able to teach every class. I needed to know how to hire the right people to get the job done.
That advice completely changed the way I thought about leadership.
A strong leader doesn’t need to be the most knowledgeable person in every room. In fact, if I’ve built a strong team, I shouldn’t be. I want people around me who know things I don’t know, who have strengths I don’t have, and who will see possibilities or problems I might miss. My responsibility isn’t to compete with their expertise. It’s to recognize it, bring the right people together, give them room to use it, and make sure we’re all moving toward the same goal.
That requires humility as much as confidence. It means being secure enough to say, I don’t know, but I know who does. It means asking questions instead of pretending to have answers. And it means creating an environment where someone can challenge my thinking without worrying that doing so will somehow diminish my authority.
Good leaders don’t need to have all the answers. They need to know how to bring together people who do.
If you ask for my perspective, I’m going to give it thoughtfully and honestly. If I’m hired to do a job, I’m going to care deeply about doing it well. I’ll help people whenever I can. I’ll share what I know. I’ll advocate for what I believe is right, and I’ll listen when someone challenges my thinking.
And I will always be the person who discreetly tells you when you have something stuck in your teeth.
Because that’s kindness, too.
Kindness Takes Strength
Maybe that’s ultimately the difference I’ve been looking for.
Niceness is often about preserving comfort. Kindness is about caring enough about another person, yourself, or an organization to be honest, set appropriate boundaries, and address what needs to be addressed, even when doing so creates some discomfort.
And perhaps part of kindness is allowing people to be more complicated than the version of them we’ve created in our heads.
Someone can be optimistic and skeptical. Empathetic and firm. Generous and boundaried. Collaborative and willing to disagree. Confident and willing to change their mind.
Kind and strong.
None of those things are contradictions.
Maybe the next time someone surprises us by behaving differently from the person we thought they were, the question shouldn’t immediately be, What happened to them?
Maybe we should ask ourselves: Did they change, or am I just seeing more of who they always were?
So yes, Rihanna, I understand the feeling.
I’m optimistic. I’m empathetic. I’m generous. I’m loyal. I’m kind.
Don’t mistake kindness for weakness because sometimes it takes quite a bit of strength to remain kind.