Off the cuff, I put together another little survey on something I’m curious about. The overall experience people have had working with strategy freelancers.
If you have ever hired or worked with freelance strategists, I’d love your answers to a quick 4 questions:
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Our main story tonight is about teams and departments.
I have historically used the two somewhat interchangeably.
When asked about pros and cons of freelance, my first response is always about how I miss having a team. In this case, I mean department. Because every project is a new team and I genuinely enjoy getting to be a part of so many.
And I honestly think that as far as the work goes, your core team should be defined by a shared account rather than discipline.
This has been A 3 paragraph set up to say that more often than not, the “strategy team” is another way to say “strategy department.”
But philosophically they aren’t the same and there are actually some pretty interesting and radical implications to pulling the two apart.
A department is top down. You hire based on open positions And you staff based on a balance of strategy need + what rates the budget has room for. There are a set number of positions and an org chart that shows who answers to who. My hot take: A department is an authoritarian model.
A team is bottom up. You hire based on need, skill set and value add. Staffing is done based on project x experience fit and titles are indicative of experience rather than position. a team is an anarchist model of governance.
Some concessions; you likely still need a bureaucratic dept head to act as owner of pay, promotions, and contact for staffing. But even that could be an elected position.
In the team model, you might have several VP/Director level individuals, essentially replacing the Group Director position.
Ideally a system of master/apprentice would develop rather than manager and subordinate.
I can’t promise this would be a utopian way of working, but it feels worth a shot.
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This feels relevant to the world at large…
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Kinda old news at this point, but I was featured in the Recess 2025 Creative Playbook. Apparently I was the most recommended newsletter among contributors which is wild looking at the other newsletters in there.1
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Me, presenting WIP strategy slides:
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I find myself reflecting on what makes a good presentation a decent amount.
Is it “that was productive” or “that was well received”?
Sure, ideally it’s both. But design for the former and hope for the latter, not the other way around.
Well received is the wrong pursuit.
Ask instead how things were moved forward2.
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"The biggest killer of good ideas is not research or clients or budgets. It's The Big Show." - Bob Hoffman
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Doing some go to market work at the moment and came across a couple good references to save.
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I guess I decided this is going to be a long one, because there are a couple old ideas I feel like resurfacing.
“Create a space for projects with lower ambitions, to focus on simple executions of simple ideas”
→ I believe this to be true for one’s own personal hobbies and projects, but it is also worthwhile thinking about as a comms approach. There’s a whole book about the effectiveness of “little bets” (it’s called “little bets”), and creating a pillar or work-stream around it would almost certainly bare fruit?
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“Forward facing strategy”
This is the principle my entire freelance practice is built on.
Forward facing has a few implications.
Primarily, when you are with someone else and are both forward facing, you are inherently going to be shoulder to shoulder. There is no “forward direction” in a pitch meeting other than the screen which feels counter productive. You are a partner, not a vendor.
Forward facing also means working towards incremental progress with the stakeholder, not polishing slides for stakeholder approval. You are value progress over polish.
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ooof3.
WEEKLY MONSTER
I think I have a make-plaster-skulls compulsion disorder.
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Thanks to Tai Koga, Senior Brand Strategist at Wieden + Kennedy (Japan), Micaela Ortego, Social Strategy Director at Monks EMEA (Spain), Sofia Gamiz, Senior Strategist at Wieden + Kennedy (Mexico) and Juan Cistoldi, Creative Strategist at Superside (Argentina) for the shout out.
(ideally this means more than “approved”)
I meant to write about the conflict I’m having working in advertising while we actively devolve into an authoritarian oligarchy. But honestly I don’t have the energy or emotional bandwidth to take that on.
Just going to keep reiterating the importance of community building and mutual aid.
Maybe down the road we can all help develop go to market plans for molotov cocktails.
First time reading your newsletter, definitely subscribing.
Curious as to the source for the positioning chart--would like to learn more.
Thanks.