9 Classic Compliments from Boomers That Often Miss the Mark: Understanding Generational Gaps in Kindness

Crafting a compliment involves some skill. Get it right, and you make someone’s day. Get it wrong, and you might leave them feeling awkward.

Recently, I’ve noticed that many compliments from older generations often miss the mark with younger folks. Baby Boomers usually mean well, but sometimes their words don’t connect as intended. Here are nine common compliments, why they can fall flat, and how to improve them.

1. “You’re so articulate.”
   This phrase can come off as surprising, almost as if the speaker didn’t expect someone young to be clear and concise. Many young people have been giving presentations for years—clear communication is a norm for them. Instead, try saying, “I loved how you explained that idea—very easy to follow.” This appreciates the skill rather than assuming it’s unexpected.

2. “You remind me of my grandkid.”
   While this might sound sweet, it can inadvertently undermine someone’s authority or professionalism. Instead of turning someone into a family anecdote, say, “Your energy kept everyone engaged.” This keeps the focus on their professional presence.

3. “You’re fearless.”
   Labeling someone as fearless can dismiss the hard work and courage that comes from preparing for challenges. Organizational psychologist Adam Grant suggests that rethinking situations is both a skill and a mindset. Instead, you might say, “I admire how you took on that challenge despite the risks.” This recognizes their effort and bravery.

4. “You have your whole life ahead of you.”
   While meant to be encouraging, this can minimize the real struggles people face today, like student loans or job market challenges. Instead, say, “Today’s market is tough, but you’re building valuable skills.” This way, you’re looking to the future while acknowledging current realities.

5. “Good for you for chasing your passion.”
   On the surface, this sounds supportive. However, it can also imply that a more traditional job isn’t as valuable. Say instead, “It takes courage to freelance full-time—what’s been your biggest win?” This shows interest and recognizes the hard work involved in pursuing passions.

6. “You’re lucky to work from home.”
   Remote work comes with its own set of challenges, like blurred work-life boundaries. Instead of attributing it to luck, acknowledge their effort by saying, “You’ve structured your workday really well—any tips?” This shifts the focus to their achievements.

7. “You’re so tech-savvy.”
   Complimenting someone for basic tech skills can come off as patronizing. Instead, try saying, “The way you automated those reports saved us so much time.” This recognizes their skills in a meaningful context.

8. “It must be nice you don’t want kids.”
   This compliment can seem judgmental, overlooking the deep personal values behind such choices. Instead, say, “I respect how clear you are about what a fulfilling life looks like for you.” This focuses on intentional living.

9. “You’re doing great for your age.”
   This can undervalue someone’s accomplishments by emphasizing age. Comparatively, say, “Your performance today set a high bar for the team.” This feels more empowering.

These compliments often come from good intentions but reflect different cultural backgrounds. The goal isn’t to silence kind words but to adjust them. Focus on effort over assumptions and invite conversation. This approach can strengthen connections across generations, leading to more rewarding interactions for everyone involved.

Taking a moment to refine your compliments can make a significant change in how they are received. In this way, genuine kindness can truly shine through.

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