About this episode
"You have to be willing to be the worst in the world at the thing your customer values least."
Trainual just came out of two days of planning in Flagstaff, so Chris Ronzio, Jonathan Ronzio, and Sasha Robinson open the whole process up — including the parts that took eight years to get right. The through line is a correction most companies need: strategic positioning has to come before strategic planning. If you can't say what game you're playing and where you sit against the field, you're not planning, you're generating a to-do list. Chris walks through the buying criteria exercise that produces that clarity, using IKEA against Restoration Hardware to make it concrete, and Sasha names the reason it's so hard — deciding what to be genuinely bad at feels awful, and most teams flinch.
There's also the tactical stuff nobody writes down: why you can either participate or facilitate but not both, the step teams always skip where you flip every danger into an opportunity, why post-it colors matter, and how the crowdsourcing from department managers happens weeks before anyone gets in the room. Plus what a strategic goal becomes once it stops being strategic, why Trainual's over-engineered goal framework had to be torn down, the priority star, and an honest case that ghost tours and blind water tastings are load-bearing infrastructure rather than filler.
Key Takeaways:
- Positioning comes before planning, and skipping it is why planning produces task lists. The exercise: name the five things your customers actually buy on, rank them from most to least important, then score yourself one to five on each and plot the line. The ideal is a clean diagonal — strongest where they care most. What you usually get is spaghetti, and that shape is what should drive the plan. Map two or three competitors on the same grid and your real positioning becomes visible. Chris's framing is that this work fuels a decade, not a quarter, which is why it belongs upstream of any goal-setting.
- Being the best at one thing requires being genuinely bad at another. IKEA has decided its buyer doesn't value assembly time; Restoration Hardware has decided theirs won't touch a screwdriver. Trainual doesn't build VR scenario training with proctored exams, because that path leads to seven-figure enterprise contracts — a different company entirely. Sasha's honest caveat is that this is the hardest part to actually execute: the thing you're choosing to be worst at is still something customers value somewhat, and high performers hate being bad at things. Most teams say they'll make the tradeoff and then quietly don't.
- Strategic goals are supposed to expire. Jonathan's test: a strategic goal requires you to change something, add something, or operate differently — by definition, what you're doing today isn't producing that outcome. Once the systems are stood up, the owners are in place, and the trend is moving the right way, it stops being strategic and becomes a health metric you monitor like any other. If it isn't working, it stays strategic and you course-correct. The failure mode is a goal list that only grows because nothing is ever allowed to graduate.
- Over-architecting the framework is a real and common failure. Sasha's advice is blunt: simplify, simplify, simplify. A goal and a metric to measure it is enough to start. Trainual's own arc went from a list of a hundred projects — where the team asked, reasonably, what the actual strategy was — through a period of trying to build too much structure, which got confusing and frustrating, to OKRs. Jonathan's line on the early days: doubling website traffic was a goal, but it was never a strategy.
- The room isn't where planning starts, and the social programming isn't filler. Weeks ahead, Jonathan meets separately with every people leader in sales and marketing: what's going well, where the bottlenecks are, and what they'd change with a magic wand. That raw material gets clustered and reverse-cascaded up into agenda topics. Then every department head opens the offsite with their good, bad, and ugly, alongside standing people and financial snapshots. And the mini golf, the axe throwing, the Salem ghost tour that ended at their own Airbnb — Jonathan argues those are what let a hard conversation stay about the problem instead of becoming personal.
Chapter Markers:
[0:03] Cold open: Quiet Week, marathon training, and a 48-hour fast
[3:09] Trainual's first planning session, in a rented conference room
[4:13] Why you shouldn't plan anywhere you can drive home from
[5:50] The DOS exercise: dangers, opportunities, strengths
[9:14] The mechanics: post-its, music, and colored markers
[10:29] You can either participate or facilitate, not both
[11:04] The step everyone skips: turning dangers into opportunities
[13:20] When a strategic goal becomes just another health metric
[17:07] Frameworks, and why you shouldn't over-architect
[21:07] Positioning before planning: the buying criteria exercise
[25:09] Best in the world at one thing, worst at another
[31:55] Crowdsourcing from managers before the offsite
[36:03] Standing agenda: people, financials, and the good, bad, ugly
[40:11] Ghost tours, water tastings, and why the fun is load-bearing
[47:03] The priority star, and leaving with commitments
[49:52] What Quiet Week is
Resources:
Want more resources from this episode? We've got an episode recap, replay, and every template, process, and resource we covered right here: Organize Chaos
Trainual
Organize Chaos is where founders and leaders learn how to build businesses that scale. Hosted by Chris Ronzio, Jonathan Ronzio, and Sasha Robinson, each episode explores the systems, leadership, operations, performance, and AI strategies behind high-performing organizations. Through candid conversations, practical frameworks, and real-world experience, they help you replace chaos with clarity — so your business can grow with confidence.
This is one of a few podcasts from Trainual, a software platform that helps businesses build playbooks to train and grow their team. You can check out the rest of our shows here: Podcasts
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