The best strategic thinking stays locked in boardrooms. Which is exactly why it shouldn't. atpractice.substack.com/p/inviting-strangers-int...

What happens to strategy when you stop thinking in private and start thinking out loud with strangers? atpractice.substack.com/p/inviting-strangers-int...

What if the stuff we're measuring isn't actually moving the needle, and we just don't want to admit it? atpractice.substack.com/p/the-line-that-didnt-mo...

Day 2 in Portugal and so far I’ve learned:
- Portuguese drivers are more pedestrian friendly than Canadian drivers
- If you purchase a building with a tiled exterior, you can’t change it. Heritage restrictions
- The tarts are WAY better with a cinnamon dusting. Never going back

Strategy lives in small rooms. Nobody outside ever really sees how you think - not because it's secret, but because there's never been a reason to expose it.

I've been thinking about why we keep strategy locked in conference rooms. There's something powerful about letting strangers poke holes in your thinking. atpractice.substack.com/p/inviting-strangers-int...

I've been thinking about how easy it is to commit to something without ever defining what done actually looks like. atpractice.substack.com/p/the-line-that-didnt-mo...

Been thinking about how much courage it takes to show your actual thinking, not just the answer. The messy process, the tools, the doubt. That's where real feedback lives.

atpractice.substack.com/p/inviting-strangers-int...

Really appreciating that saying no to things isn't that's laziness. The people who move the needle aren't the ones saying yes to everything. They're the ones protecting their focus.

New essay: "Inviting Strangers Into the Strategy Room"

Why we should share the thinking, not just the outcomes. atpractice.substack.com/p/inviting-strangers-int...

I've been thinking about how the higher you climb, the more feedback you get about everything except yourself. At some point people stop telling you the truth.

open.substack.com/pub/atpractice/p/the-fee...

Most strategy stays abstract when it should be concrete. That gap? That's where the real work lives.

Yeah, at least the Raptors have that scrappy DNA. Leafs and Jays both feel like they're playing not to lose lately. Toronto sports is a trip.

LOL these agent-first systems are a rabbit hole of endless edge cases.

Yes adding communication channel makes sense. Yes it was more than I expected. And yes I do want to to flip a table now.

(╯°□°)╯︵ ┻━┻

Saw a job posting yesterday that asked for "10+ years experience" and "proven track record at scale." They were hiring for a role that needed someone scrappy and willing to learn. They filtered out every person who could actually do it well.

When your team stops bringing you bad news, you've already lost them. They're just waiting for the exit.

The best teams tell you what's broken. Early. Often. Even when it hurts.

Ask yourself: would you use this if no one was watching? If the answer's no, you're probably building theater.

In theory! But I’ve seen too many sales & marketing team fight over the SQL definition. And criteria always change more frequently than CRM contract renewals. Also Support teams who incentivize “resolving” tickets, only to get pissed off customers when reps jump the gun. I don’t see this ending well

Easter weekend...the perfect time for our 14 year-old to launch their merch store, and start shilling it to extended family 🙄

Entrepreneurial little blighter. Suppose I've only myself to blame.

Caught up with someone who's mind is like a trap. I'm always impressed.

Someone who remembers what you said six months ago and brings it back up, unprompted, is rare. Not taking notes, just listening.



If you have someone like that, they're worth keeping close.

Outcome-based pricing is interesting. But how do you even measure 'outcome' in enterprise AI without it becoming a negotiation nightmare? "resolved issues" and "qualified leads" is going to become an annoying definition come renewal time.

As you climb, you lose the feedback that matters most. People tell you about the org. Nobody tells you about you anymore.

open.substack.com/pub/atpractice/p/the-fee...

Been staring at a metric that's been flat for months. Not because we're stuck - because we've been okay with stuck. That's the harder conversation. atpractice.substack.com/p/the-line-that-didnt-mo...

This week I chatted with someone who turned down a job offer because the team was "too much." Smart, driven, working long hours. Said it felt like proving yourself every single day. Never thought about it that way before.

Watched a founder hire for "culture fit" and accidentally hire for "thinks like me." Two years later, best ideas in the room came from the one person who didn't. Culture fit is a trap. Cognitive diversity is the actual moat.

Hired someone who'd worked at one of the "Big 3" consulting firms. First week they said: "How do you want me to think about this?"

🤦 TLDR: they'd learned to optimize for what leadership wanted, not what was actually true. That's the real cost of big company time.

Totally agree on execution speed. But I'd push back slightly - first-time founder conviction matters more than you'd think. Chance plays such a role, and "naiive optimism" lets them take chances more easily.

This is it. The people who learn fastest are the ones willing to look dumb in public. Your future self will thank you for posting imperfectly today.

Pricing is where founders accidentally reveal what they actually believe about their product. Too low? You think it's commodity. Too high? You're betting on scarcity or status. Most just copy competitors and call it strategy.

Most accountability fails because we never actually define what done looks like. Vague commitments feel safe until they don't.

atpractice.substack.com/p/the-line-that-didnt-mo...