“Come on, what are you trying to prove?!”
This was Mr. Kaye’s favorite line to scrawl across my essays for English class my sophomore year in high school.
I hated seeing that line for two reasons:
- Because I thought my point was perfectly clear (though in hindsight, I’m sure it wasn’t nearly as clear on paper as it was in my 15-year-old brain at the time).
- Because it gave me no indication of what wasn’t clear, or guidance on how to fix it.
As far as I was concerned, he might as well have just written “this is stupid – and so are you” on the page, as it would have had the same effect.
That being said, I am grateful for that experience, in hindsight, because it has served me as a perfect example of what NOT to do.
Why Feedback Skills Are Essential for Leaders
Giving constructive feedback is a regular and frequent requirement in life, whether in teaching, managing, parenting, or leading in any other capacity. And the ability to deliver it well, so the other person understands both the content and your intent behind giving it, is one of the most under-rated skills on the leadership profile.
It’s also one of the most frequent issues that comes up organically in discussions with my executive clients, when pressures for quality and results are extremely high, tolerance for mistakes is all-but-nonexistent, and emotions can both cloud judgment and derail communication. (If that’s a common source of stress for you and/or your organization, feel free to reach out to me here.)
The LinkedIn Post That Got It Right
That’s why I was so impressed by this great post a colleague of mine recently shared on LinkedIn.
For context, he is judging tech founders' investor pitches – and mostly complaining about the kind of mistakes they make… specifically the ones that drive him crazy. So yes, his tone is frustrated and no, he doesn't mask his frustration at all – which is perfectly acceptable for a LinkedIn post.
But notably, the frustration never crosses the line into disrespectful or humiliating; it’s authentic and professional.
One way or another, the principles he addresses are extremely relevant and how he addresses them is illustrative for anyone who has to give constructive feedback, whether during annual reviews at work or even behavioral correction for your kids at home.
5 Simple Rules for Giving Feedback That Actually Helps
In my assessment, he follows five very simple, applicable rules that make feedback mercifully clear and actionable, so the recipient knows exactly what to do to improve:
- Headlines — For each point, he identifies the topic up front. He doesn't “bury the lead,” or subtly hint at the issue. It's a headline, clear and unambiguous. (Just like I'm doing in this list.)
- Conciseness — Sentences are short; no rambling. Each point is crystal clear. He makes each point, then moves on. As the saying goes, “be brilliant, be brief, and be done.”
- Directness and objectivity — There is no sugar-coating, but there is also no personal attack. (Just a little self-acknowledged grumpiness at the beginning, which does not infuse the feedback itself.) There are only facts – statements about what works, what does not, and why. That's it. In that objectivity is diplomacy.
- Evidence — There are multiple points of reference to patterns he has seen time and again, not just over-generalized one-off moments.
- Motivation — He shares WHY he was inspired to take the time out to write the post and share with his audience of med-tech (and other) founders: because if you DON'T follow his expert advice, “you’ll have exactly negative cred with any actual decision makers in the space.”
In other words, it’s because he wants more people to succeed. So he's giving them a road map to success.
Does It Still Sting a Bit? Sure.
Might one or two of the founders who pitched that day feel a little embarrassed for demonstrating some of the pitfalls that inspired the post, even if he didn’t call them out by name?
Probably.
But if they're smart, and have the constitution and resilience for the otherwise-very-harsh reality of being a tech founder (especially med-tech), they'll realize this feedback was the equivalent of a pat on the back and an “I know you are capable of better” pep talk.
Where can you apply this?
The simple truth is that this applies whether you’re managing a team, mentoring a rising star, collaborating with peers—or parenting teenagers.
Yes, I Actually Use This Stuff Too
Coincidentally, pitch coaching has been a theme lately.
For example, I’ve been doing some pitch coaching for finalists in an upcoming “shark-tank” style event I’ll be emceeing, which is always fun. (If you know anyone who is looking for someone to moderate panels, facilitate or emcee a future event, feel free to reach out to me here.)
It was also one of many topics I spoke about with Allison Summers on the Disruptive CEO Nation podcast.

Allison and I dig into the leadership moments that matter most, including:
- The “authenticity myth”
- How to tap into your voice’s “digital mixing board” for fine-tuning your delivery to meet the needs of the audience without changing who you are
- Why even the quietest voice can command a room
- How to craft a TED-worthy talk, and
- How to make networking feel natural.
Final Thoughts
Whether you’re climbing to the C-suite, raising a round, or leading a mission-driven team, it’s essential to align what you say with how you say it so your credibility, clarity, and confidence are undeniable and leave the desired impact.
