When Being Nice Stops Being Kind
Written by Sheryl Raphael Whitaker, Founder & CEO
Sheryl Raphael Whitaker is a leadership transformation expert, founder and CEO of EdenAnthony LLC, and author of It Starts with Joy. With 35+ years spanning Fortune 100 and executive leadership, she helps organizations strengthen the human foundations that lasting excellence is built on.
There is a particular kind of leadership meeting where everyone is pleasant, nobody says anything especially difficult, and the real conversation happens afterward. The concern comes out in a hallway, a private message, or a conversation with someone who cannot actually resolve it. Meanwhile, the person who most needs to hear it leaves believing everything is fine.
We can call that keeping the peace. But whose peace are we keeping, and who is paying for it? In my work, I call this respectful avoidance: withholding the honest thing in the name of being polite, professional, or considerate. It can look remarkably like care. The difference becomes clear when we ask whether our silence serves the other person's growth or protects us from an uncomfortable moment.
What niceness can cost the people we lead
There is nothing wrong with being pleasant. I am not suggesting that leaders need to become harder, sharper, or more intimidating to be effective. Most workplaces do not need another person confusing bluntness with bravery.
The trouble begins when being liked becomes more important than being useful. We praise someone's potential while avoiding the behavior that is limiting it. We keep correcting work ourselves instead of explaining what needs to change. We reassure a team that a decision is settled, then quietly allow it to be reopened because holding the line might disappoint someone.
The immediate conversation stays comfortable, but the work gets harder. Colleagues compensate for a problem nobody has named. Expectations become something people have to guess at. Eventually, a person may receive feedback about a serious performance concern that could have been addressed much earlier, when there was more room to learn.
That is a steep price for a pleasant exchange. When we withhold useful truth, we also withhold someone's opportunity to respond to it.
I have needed the kind truth too
Years ago, I asked a leader I trusted for feedback. She initially told me I was doing great, but I pushed a little further and asked about a blind spot. Her answer was, “You're awfully self-sufficient.”
I was proud of being someone my leader did not have to worry about. If I said I could handle something, I wanted her to know I meant it. What I had not fully understood was that always being able to handle it could also keep me from letting anyone help me.
She saw something that praise alone would not have helped me see. The feedback did not erase my capability, it asked me to examine how I was using it. That is the kind of care I want us to practice as leaders. We can appreciate a person's strengths and still help them recognize where a familiar way of operating has become a limitation.
Challenge with care begins before you speak
The alternative to respectful avoidance is not an unfiltered opinion. It is a conversation prepared with enough care that the other person has a fair chance to understand you, disagree with you, and participate in what happens next.
Start by getting honest about your intention. Are you trying to help, clarify an expectation, or address an impact on the team? Or have you waited so long that what you really want is relief from your frustration? If it is the latter, give yourself time to settle before you turn accumulated resentment into somebody else's feedback.
Then separate what you observed from the story you have attached to it. “You don't respect the team” is a conclusion about someone. “In our last two meetings, you interrupted before your colleague finished explaining her recommendation” gives both of you something specific to examine. Explain the impact without pretending you know the person's motives, then ask what you may be missing.
The question matters only if you are willing to hear the answer. Perhaps you misunderstood. Perhaps an expectation was never clear. Perhaps there is a problem you still need to address. Listening is how you find out, not a courtesy you perform before returning to your original verdict.
Before the conversation ends, agree on what happens next. What needs to change? What support is needed? When will you revisit it? Kindness includes following through rather than leaving someone to interpret a difficult conversation alone.
Timing matters, of course. Pausing to gather facts or choose a private setting is responsible. Waiting indefinitely for a conversation to become comfortable is something else. If you are delaying it, be able to name what you are preparing for and when you will return to it.
Your response teaches people what honesty costs
Leaders also need to examine the other side of this. It is easy to say we welcome candor while making the person who offers it regret speaking.
When someone challenges you, notice the urge to explain yourself before you have understood them. Ask for an example. Reflect back what you heard. You do not have to agree with every interpretation, but you do need to make it possible for someone to bring you information you would rather not hear.
On It Starts With Joy LIVE, I return to two kinds of accountability: personal and cultural. Personal accountability asks what is mine to own. Cultural accountability asks what my way of operating is teaching the people around me. If I avoid every uncomfortable conversation or punish the person who starts one, I am helping create the very culture I say I want to change.
Where joy belongs in the hard conversation
When I talk about leading from joy, I am talking about alignment and integrity, not keeping everybody happy. A difficult conversation can be an expression of that alignment. I can value your dignity, believe in your potential, and still tell you that something needs to change. I can also care about our relationship enough to examine my own part in what is not working.
This week, choose one conversation you have been postponing and give yourself a respectful avoidance audit. What needs to be said? What am I protecting by not saying it? What would it sound like if I cared about this person's growth more than my own comfort?
Prepare for that conversation and make time for it. You do not need a perfect script or a guarantee that it will land easily. You need to be clear about the issue, curious about the person, and willing to stay in the conversation. Respect should make the truth possible, not keep it out of the room.
For more conversations and practices on leading from joy, join me at It Starts With Joy LIVE on YouTube.
Read more from Sheryl Raphael Whitaker
Sheryl Raphael Whitaker, Founder & CEO
Sheryl Raphael Whitaker, MBA, is a leadership transformation expert, bestselling author of It Starts with Joy: The Inner Shift That Changes Everything, and founder and CEO of EdenAnthony Elite Talent Solutions LLC. Through her JoyShift™ method and leadership philosophy, Joy is my COO™, she helps executives, teams, and organizations move from disconnection and overload to clarity, authenticity, and lasting performance. With 35+ years spanning Fortune 100 organizations, including State Farm, AIG, and USAA, her conviction is simple: lasting excellence is built on human foundations, and joy is the infrastructure most organizations are missing. Connect with Sheryl here.
