Transform Tough Conversations at Work Into Precious GEMS

Updated: Aug 25, 2020

It’s 9:15 AM. Your daily standup meeting is just wrapping up when Josh, your Social Media Manager, walks in late. As usual.

Now, Josh is a good guy. He’s full of great ideas, and he’s enjoyable to work with. Once he shows up.

But the point of the daily stand-up is for the entire team to be in the same place at the same time, and the fallout from Josh’s repeated tardiness is spreading. Yesterday the marketing director had a question only Josh could answer. And this morning Xiao Lin was five minutes late as well, and gave you that “I dare you to say something” look when she took her place in the circle.

Clearly, you’re going to need to sit Josh down for a tough-love one-on-one very soon.

When there’s a difficult conversation to be had, it can be hard to focus on anything else. It can affect our mood, our productivity, and even our health.

Happily, there’s a simple trick that can transform even the most potentially contentious conversation into a productive strategic collaboration.

If you’re thinking it’s the old “compliment sandwich,” in which a critique is sandwiched in-between compliments, think again.

See, the problem with padding hard-to-hear feedback with flattery is that people can tell when you’re being insincere. And as soon as they hear a compliment that doesn’t feel genuine, they are silently building up their defenses, just waiting for that other shoe to drop...

To truly disarm a person’s knee-jerk defenses, you need to offer them your true GEMS:

Give Genuine Admiration

Step one is to find something, anything, that you genuinely admire about this person. Not too tricky in the case of Josh, but sometimes it can be a real challenge to feel authentic admiration when your anger and frustration are drowning out all other emotions.

A good rule of thumb is that you aren’t in the right headspace to have that tough conversation until you can get in touch with your sincere admiration for that person.

Dig deep. Maybe you admire the way they are challenging your authority or standing by their principles. Maybe you appreciate their work ethic, or their infectious positivity, or their dedication to family.

Whatever it is, make sure it’s authentic, and specific. People can smell B.S. from a mile away.

Bottom line: if you can’t find anything admirable about this person, they should NOT be on your team!

Here’s how you might open up that conversation with Josh:

“Hey, Josh. It’s a real pleasure to have you on the team. I love your innovative ideas, like that clever social media quiz that brought in so much web traffic. And your positive attitude brings up the mood of the entire team. So when you’re not here, we notice.”

The idea is to put Josh in the right frame of mind to be able to take in the difficult feedback you’re about to deliver by making sure he doesn’t feel personally attacked. Otherwise his defenses will go up immediately and he won’t be open to hearing what you have to say.


Put yourself in their shoes. Why are they behaving this way? What problem are they trying to solve?

Do your best to understand where they’re coming from and offer empathy for whatever they’re dealing with.

Sometimes this is obvious enough. If Josh were a new parent, for example, his tardiness would be easily explained, and you could empathize with him around the challenges of getting enough sleep and getting to work on time with a baby in the house.

If you happen to know that he’s a night owl, you can empathize with the difficulty of trying to force yourself into a 9-5 schedule when your body prefers to stay up late working and then sleep in.

But sometimes you simply don’t have all the information, and you end up empathizing with an abstract.

For example:

“I’m not sure what’s going on in your life right now, but I want you to know that I understand how challenging it can be to stick to a schedule in the midst of chaos. We’re all doing our best under whatever circumstances life throws at us, and we never really know the full extent of what anybody else is dealing with.”

The important thing is to make sure your interlocutor feels seen and understood to the best of your ability. This will put them at ease and let them know they don’t need to waste their time and energy trying to make themselves understood: You already get where they’re coming from.

Make Objective Observations

The key here is to offer only factual observations, NOT your personal evaluation of their behavior.

An observation is a piece of objectively observable data, something indisputable that anyone who observed it would agree upon.

OBSERVATION: Josh has been late for stand-up every day this week, and four out of five days last week.

An evaluation, on the other hand, is your interpretation of those events.

EVALUATION: Josh doesn’t care about stand-ups.

Any hint of assumption, inference, or accusation can make an otherwise productive conversation go sideways, fast.

So, stick to the facts:

“I’ve noticed that you’ve been late for the 9 AM stand-up meeting nearly every day for the last two weeks. Sometimes, like today, you miss it altogether. That means anyone who’s waiting on you to unblock them will have to keep waiting, and that if you’re blocked on something you’ll need to interrupt someone else’s workflow to get the info you need. It also gives other folks the idea that it’s okay to show up late for stand-up, which erodes my authority and affects morale.”

Simply lay out the problematic behavior you’ve observed, why it’s problematic, and any consequences that have resulted or are likely to result should the behavior persist.

Strategize an Alternative

Research has shown that the best way to break an old habit is to create a new one. So instead of simply chastising Josh’s behavior, why not help him come up with a viable alternative?

But before you go offering a bunch of vague, unsolicited advice, let’s clarify our terms.

Advice is a personal recommendation that may or may not resonate with the person at whom it’s directed.

ADVICE: Try setting your alarm five minutes earlier every day. Pretty soon you’ll be getting up half an hour earlier!

There’s nothing wrong with that advice, per se. But the chances of Josh following it are low because he has no investment in it. That’s the problem with advice: it’s someone else’s idea, so we have to get past our pride in order to adopt it.

Strategizing an alternative means helping someone come up with a specific course of action designed to create a more positive outcome. It requires information from, and collaboration with, the person you’re helping.

Strategizing starts with asking questions, and ends with a viable solution to their problem.


YOU: What is it that’s keeping you from getting to work on time?

JOSH: Well, it seems like no matter how early I set my alarm for, I just can’t get myself out of bed in enough time to get ready.

YOU: Why do you think that is?

JOSH: Well, probably because I have a hard time getting to sleep before midnight. So then in the morning, my alarm goes off, and I’m still exhausted, so I push snooze over and over until all of a sudden it’s a panic to get ready and get to work.

YOU: What have you already tried?

JOSH: I tried going to bed earlier, but I still couldn’t get to sleep before midnight so I figured, what’s the point? I just end up lying there messing around on social media for hours.

YOU: Social media is pretty stimulating, especially for you! Could you try doing something a little more calming for your brain when you’re winding down?

JOSH: You mean like… listening to an audiobook or something?

YOU: Does that help you relax?

JOSH: Yeah. It does.

YOU: Great. So tonight, can you try getting to bed a little earlier than usual, silencing your phone, and listening to an audiobook, and see if that helps you get a little more sleep?

JOSH: Sure. But I’ll be honest with you, I’m probably still gonna hit snooze in the morning. LOL.

YOU: Have you tried using a sunlight alarm? It mimics the rising of the sun, helping you burn off melatonin and wake up more naturally. It really works!

JOSH: Cool, can you send me a link?

YOU: Sure thing. So, can you sum up your new strategy for getting to work on time?

JOSH: Well, I’m going to start going to bed earlier, NOT doing social media, and using a sunlight alarm. WITHOUT a snooze button.

YOU: Awesome. I’m really looking forward to having your energy back at the stand-ups. It makes such a difference to have everyone there.

Conversations are only tough when we don’t feel like we’re on the same page, working toward the same goal. Nobody wants to be made wrong or to feel like someone is just waiting for them to fail. It’s your job as a leader to make sure those potentially tricky talks go smoothly by making it clear that you want to help them succeed.

Next time you see a need for some radical candor in the workplace, save the sandwich for your lunch break, and offer them GEMS instead!

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