Happy Labor Day weekend to my North American readers, and everyone who works for an NA company. My wife and I are in Bar Harbor, Maine this weekend. Taking a break from the day-to-day, hiking, letting nature do whatever nature does to clear the brain. But let’s be honest, it takes more than a quick weekend to reset.

No big story to tell you this week. Just wanted you to know where I'm writing from.

So here’s what’s on the Bar Harbor, ME docket:

We're starting with the next round of Don't Get Fired (last week was Own a Number). Executive Comms, including the most important lesson I’ve learned over the last 10 years of running teams… how to red team a board deck (or any presentation) before your board ever sees it (Andrew Lau taught me this one the hard way, and I still use it). From there we move into ten forms of positivity, pulled from a book that's giving a lot of good vibes and changing the way I think about culture at work.

And if you missed it last week... I’m launching a new podcast this month called Head Trash. Fifteen to twenty minutes with one guest at a time, talking about how they wrestle with the voices in their own head.

A bunch of you already replied wanting to come on. I see you. I'll be following up this week.

♥️ kyle

20 Lessons from 15 Years of Marketing Leadership

If you missed last week... I turned a 90-minute talk I gave to Pavilion's CMO School into a newsletter series, because fifteen years of running marketing teams produces a LOT of stories.

Quick recap of the full list since why not, right? Twenty lessons broken down into five buckets.

• Revenue & Pipeline (own a number, report it weekly, run a pipeline council, build a handbook, BFF your CRO... that was last week).

• Executive Comms, which is today

• Team & Culture

• Budget & Brand

• Leadership & Career

We've got sixteen lessons left after this one group, so buckle up, it's a fun journey.

Today we're doing Executive Comms. And here is the main lesson: the skills that got you a VP, SVP, or CMO role aren't the skills that keep you in it. You can be the best campaign builder and still get eaten alive in a board meeting because you never learned how to translate what you do into language the room actually understands.

Translate Marketing Into Exec and Board Language

I've sat through hundreds of marketing updates in my career and there is nothing that ends credibility faster than comments like: "I scheduled 10 social posts this week."

There's ZERO chance a member of the board has EVER cared about super tactical commentary. Instead of 10 social posts, say this instead:

"We're reinforcing our latest campaign with organic posts, and three are already driving high engagement," with the metric attached.

I mean, even that line sounds a little contrived, but we will go with it. :) 

And that's the more junior/IC challenge, it gets so much worse at the CMO level, because I made this exact mistake for years. Don't tell the board you drove MQL growth by 30%. Nobody cares. They still don't have any idea what MQL actually stands for. What do they care about?

• How much pipeline did you create?

• Do we have enough coverage for the sales reps?

• Did that pipeline actually close into revenue that hits the number they promised the market?

How much translation you actually need depends entirely on the room. At Jellyfish, I had a boardroom full of finance people, and I got torn apart in those meetings more than once before I figured this out. At Lessonly, it was a mix of operators, marketers, and VCs, which was a much easier room to read. Same content, completely different translation required. You have to know who's sitting across from you before you know what language to speak. More to come on how to do that a little later. 

Own Performance and Don’t Surprise Your Boss

Own your underperformance before someone else raises it for you. I'd rather know something's off track from you than get surprised by someone above you. Control the narrative on the bad stuff, not just the good stuff.

A lot of really talented people have a hard time being visible about what their team is doing because it feels like bragging.

It's not.

It’s impossible to overshare unless someone has explicitly told you that you're oversharing, and even then it's rare. Market yourself internally with the same intention you market the brand externally. Doesn't matter if your team is 50 people or 10,000. Salesforce's marketing team is genuinely one of the best I've ever seen at this, and they're a massive company.

And close it out with something simple. Call your boss with a five minute check-in. This is working, this isn't, here's what I'm watching. It costs you almost nothing and it means you're never the person explaining a miss after the fact instead of during it.

Translation and visibility both come down to the same discipline, really. Say the right thing, at the right time, before anyone has to ask. Which brings us to the moment where all of that gets tested at once.

Red Team Everything

My first Jellyfish board meeting is where I learned this the hard way. It was a disaster. First, I was feeling under the weather and we were only a handful of months outside of that weird "need a facemask" era.

Secondly, I wasn't prepared. My last two companies had very different approaches to their meetings and I knew most people on both boards. Not this one. Someone asked a question I didn't prep for, and my brain did that thing where it tried to answer anyway. "Well, yeah, maybe... I don't know, it could be this channel, but I'll need to check." Fail.

Now, they are just watching me flounder and try to find an answer.

And here's the most important lesson I learned: Build a deck 48-72 hours before the board meeting. That deck's only job is to get destroyed multiple times over. We've lovingly called it: red teaming.

Andrew Lau, the CEO at Jellyfish, was brilliant at it. You build the deck, you get in a room with the exec team, and they act like they're the board, and they just rip you apart. Not to be mean. To find the hole before the board members find it.

The questions that come up in that red team session are ALWAYS the questions you get in the board meeting. Every single damn time. I've never once been surprised by a board question after a good red team.

Want to try it tomorrow? Oh, I know you do. :)

Build the deck 48-72 hours out. I'm not sure what to tell you if you don't have your board deck built out before the board meeting. Lots to work on if that is the case. Remember, you need real runway to revise and adjust.

Assign someone to play a board member. Maybe multiple people if you feel spicy. Not a yes-man. You want someone who is skeptical and can dig into the numbers, and ask the question you're hoping nobody asks. If you don't have a full exec team to pull from, one sharp peer works fine.

Have Claude build the questions if you're short on people. Feed it the deck and ask what a skeptical board member or CFO would grill you on. Hand those questions to whoever's playing the room. It's not quite the same as a live gauntlet, but it gets you most of the way there, and it's available at 11pm when nobody else is.

I liked this step enough that I turned it into an actual skill instead of just describing it. Steal it. Download the file or paste the whole thing into a new Claude chat, attach your deck, answer the six questions when it asks, and it'll generate the exact questions the board would throw at you, sorted by category, with a suggested answer to rehearse for each one.

[Get the Red Team My Deck skill]

Moving on…

Actually let them destroy it. You are going to feel uncomfortable here, and that's okay. It's important that you don't feel like you need to defend every slide. Let the holes surface.

Revise based on what broke. Pretty straightforward, right? Take the feedback and improve it.

BONUS TIP: If you still get blindsided in the actual meeting, don't guess. "That's a great question. I don't know that offhand; I'll get back to you tomorrow." Half the time they forget they even asked by the next meeting.

If your deck can't survive your own team, it won't survive the board.

That's Executive Comms. Three lessons, one theme underneath all of it... the room you're in doesn't owe you the benefit of the doubt. You have to build it, deck by deck, sentence by sentence, update by update.

Next week, Team & Culture. Leading with clarity, why asking permission to do your job isn't humility, and why good taste is the one thing your competitors genuinely can't copy from you.

Now, let’s get some POSITIVITY IN HERE.

On What We Actually Mean When We Say "Good Culture"

I've been reading Barbara Fredrickson's Positivity this week, which has been a welcome reprieve from some of the "fighting trauma" books I've been reading recently. She does an amazing job breaking down "positivity" and what it means for us, humans.

It's an interesting book because everyone walks around with their own definition of "being positive" or "feeling positivity," and most have no idea what it actually means. Barbara breaks it down into ten distinct feelings instead. And as I was reading through her definitions of each one, I couldn't help but think back to all the different times I'd felt "positive" around culture at work, and how those moments actually connect to something real.

I liked the list enough that I turned it into my Friday note to the Docebo marketing team this week. I’ve included it below: 

I don’t ever expect anyone to hit all ten on a given workday, because that’s damn impossible. However, I do think it’s worth thinking about what we’re actually striving for when we say we want people to like working here and on this team.

Barbara writes about them in a specific order, so let’s jump in.

Joy. Bright, light, a little playful. The feeling when something good just happens to you, not because you engineered it. Lisa Kaspari got recognized by one of our vendors this week for the work she's been putting in. 

Gratitude. Real gratitude opens you up. It makes you want to do something for someone else. Its evil twin is indebtedness, which just makes you feel like you owe someone something. If you've ever thanked a teammate and felt a weird flicker of tension underneath it, that's the evil twin talking. I know because I've felt it plenty. When's the last time you felt actual gratitude at work, not the Slack-emoji kind?

Serenity. Underrated as hell. A day where the calendar isn't a wall of color blocks and you actually get to think. We don't talk about this one enough because it never feels productive in the moment. It never looks like "getting something done." But serenity is what's made some of my hardest stretches survivable.

Interest. You're safe, but something new pulls at you anyway. A weird customer problem. A gap in the pipeline that could go either way. When's the last time something at work actually hooked you, and where's it showing up right now?

Hope. Not naive optimism, that stuff isn't worth much. Hope is what you feel when you're not sure but you're still leaning in anyway. I felt it at Inspire, standing backstage not totally sure the keynote was going to land. Leaned in anyway. Worked out. That's the feeling.

Pride. Comes with a healthy side of guilt and shame, always has for me. What have you built or shipped or fixed lately that you're actually proud of, even if not one other person noticed?

Amusement. The stuff that makes you laugh out loud at your desk. Megan K's gif game in Slack is genuinely elite, best I've seen on any team I've been part of. I don't think that's an accident. Teams that laugh together tend to trust each other faster.

Inspiration. You watch someone operate a level above ordinary and it resets your own bar. Manny and the team on the Inspire creative. Amanda wrangling my chaotic website ideas into something real. Laura P pushing through more adversity than anyone should have to handle in a single stretch and still showing up. The MLT team just... leaning in, over and over. I notice it. You should too, out loud, to the person's face.

Awe. Goodness on a scale that makes you feel small in a good way. Rare at work, but it happens. Learning what our customers, places like Special Olympics and CAMH, are actually doing with what we build. That's awe. That's not a case study, that's a gut punch in the best way.

Love. A little much for a company note, I know. But it's in the book, so here we are. Fredrickson's take is that love isn't its own separate feeling at all. It's all the others (joy, gratitude, serenity, hope, pride, amusement, inspiration, awe) showing up inside a relationship you trust.

I'm not walking away from this thinking everyone needs to hit all ten, every day. That's impossible, and chasing it would be its own kind of miserable. Most days I'm lucky to land two or three.

When we talk about "good culture" as leaders, we usually talk about the absence of bad stuff. That's necessary, but it's not the same thing as good. Good has its own identity, and a few different parts of positivity help. 

So maybe the question isn't "does my team like working here." Maybe it's which of these ten shows up on your team, and which ones you've never once tried to create on purpose.