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Mentoring Honestly

Delivering constructive criticism can be uncomfortable, but in your role as a coach, mentor, or consultant, it’s a critical skill.

September 03, 2025

By Rachel Smith

If you were to ask me to edit a document for you, the comments you see when it’s returned might be:

  • This statement does not make sense. Please clarify the point you’re making.
  • This sentence has 48 words—break it up.
  • When you refer to “this” in the first line of the second paragraph, I’m not sure what the “this” is that you’re referring to.

If I were to hop on a Zoom with you to discuss the piece, the comments you might hear would sound more like this. “This is a great piece! Super interesting. You do need to work on clarity and readability a bit. But thanks for getting it to me right away—I appreciate it.” I can edit, coach, and mentor honestly on paper much better than I can face-to-face. So, I sat down with Maestro Founder and Managing Partner, Will Fuentes, to get some advice.

WHO ARE WE REALLY PROTECTING?

When we sugarcoat our feedback or buffer the criticism with positives before and after, Will says we’re being nice but not kind. Nice means sparing people’s feelings; kind means you’re being honest so that others can improve and get better. After all, if you’re serving as someone’s coach or mentor, you’re there to help them get better.

“What is it you’re trying to accomplish by not hurting their feelings?” Will asks. “Because you care about them and want what’s best for them? The reality is that, when you’re not direct in your feedback and criticism, it’s often about soothing yourself and getting yourself to a comfortable place as opposed to getting them the outcome they’re seeking with you.”

And what about balancing a good thing for every piece of criticism we give? “As mentors, we often think about sparing people’s feelings, but if you give good feedback followed by bad feedback, it’s a rollercoaster of emotion,” says Will. “What you’ve done is dramatically zagged on someone, so now something about the conversation feels inauthentic to them. They can’t trust it, and they can’t trust me. Forget about trusting what I’m saying—they can’t trust that I had good intentions or was looking out for them.” Plus, we know that biases exist. If every criticism is enveloped in positives, we know the middle will be forgotten. Which brings us to…

THE SHIT SANDWICH

At some point, we were told that, when delivering bad news, we should sandwich it in between two pieces of good news. Who thought of that first? We don’t know. Who popularized and ran with it? Mary Kay Ash, the founder of Mary Kay Cosmetics. According to Mary Kay, you should “sandwich every bit of criticism between two heavy layers of praise.” She may have called it a “feedback sandwich,” but we know what it really is.

The shit sandwich is a bad idea for more reasons than that you end up sounding inauthentic and losing trust. Getting back to biases, the parts of the sandwich that will be remembered are the beginning and the end. The recency effect describes our human tendency to remember information from the end of a sequence better than what directly preceded it. The primacy effect is our tendency to better remember the first piece of information we hear. What gets forgotten? Any constructive criticism you’ve stuffed in the middle.

Studies at the University of Chicago dating back to 2012 tell us that the shit sandwich isn’t effective. The people who receive criticism this way end up thinking they’re doing a great job. So, we should ditch the shit sandwich, but what should we be serving instead?

SANDWICH-FREE TIPS FOR HONEST MENTORING

One practice Will shared was to explain to someone why he cuts right to the chase. “I say something like, ‘I’m a creature of efficiency, and I don’t want to spend a lot of time thinking about how to soothe you with the right words. I would rather just give you direct feedback that’s going to allow you to move forward.’” A 2014 study found that students who received feedback along with the phrase, “I’m giving you these comments because I have very high expectations and I know you can reach them,” were 37% more likely to rewrite and improve their work than the students who were given the phrase, “I’m giving you these comments so that you’ll have feedback on your paper.” Letting people know your criticism comes from wanting them to succeed makes a difference.

Will gives aspiring coaches the same advice he gives to sales professionals—always prepare for the conversation. “What are the things you want to get out of the conversation? You should practice how you’re going to say those things,” he says. “You should question-tree it out—when I say this, what are the likely scenarios here?”

Part of saying what needs to be said, according to Will, also requires a prioritization of what needs to be said. What are the things that matter the most? Part of being a good coach or mentor is being able to gauge what’s a big deal and what isn’t. What has the most potential to move someone forward?

So, who’s going to let the folks at Mary Kay know that there’s a better way to deliver criticism? How’s this?

Hey, Mary Kay! I love your pink car! You might want to stop putting every piece of criticism between two layers of praise, though. Oh, but great job on the new fall eyeshadow palette!

Wait, that’s not right. We need to be direct. We need to prioritize what’s most important. Let’s try again.

 Hi, Mary Kay. You say you’re empowering women, but then you only allow them to wear skirts and dresses when they sell products in your multi-level marketing business model, in which very few of them make money. It’s disingenuous.

Too much? I don’t think so. But in all fairness, I’m safely behind my keyboard and not delivering my criticism face-to-face.

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