👋 Hi Reader!
This week, we'll explore:
- What overthinking looks like
- What underthinking looks like
- What Properthinking looks like — and how to help teams do it
Let's Properthink
A cornerstone of the work I do with both teams and individuals is to help them Properthink valuable challenges. This helps them sprint forward fast, but with an appropriate amount of rigor.
What Overthinking Looks Like
Corporate environments (and lots of other environments for that matter) lead to overthinking. Overthinking looks responsible. It disguises itself as diligence, thoroughness, and intelligence. It’s none of that.
It mistakes motion for progress.
More discussion feels like forward momentum… but decisions never actually arrive.
It’s fear wearing a suit.
Most overthinking is CYA behavior. If we never commit, we can never be blamed.
It’s additive by default.
It tries to listen to everybody. Every new voice gets to add a new concern, a new angle, a new “but what about…” and there’s no mechanism to stop it.
It erodes confidence, rather than building it.
The longer we discuss something, the more doubt accumulates — even when the original instinct was right.
It treats all decisions as if irreversible.
Overthinking applies the same weight to a logo choice as to a company merger. Almost nothing actually deserves that level of scrutiny.
It kills momentum for everyone watching.
Teams who witness endless deliberation at the top stop bringing ideas forward. Why bother if nothing ever gets decided?
It produces the illusion of alignment.
Long discussions feel like they’ve built consensus. Often, people have just stopped arguing because they’re exhausted.
What Underthinking Looks Like
I love workshops, but many of them lead to underthinking. Underthinking masquerades as efficient. It feels like a bias towards action, but is often rushed and mistake-prone.
It confuses speed with clarity.
Making a fast decision and making a good decision are not the same thing. And sure, any decision is better than no decision. But a good decision is best.
It skips key voices.
Decisions get made by whoever’s in the room, without asking whose perspective is missing.
It forces decisions between lukewarm options.
They might have floated to the top of early thinking, but nobody bothered trying to push past them.
It produces shallow solutions to deep problems.
Without pressure-testing, ideas look solid until reality applies pressure — and then they crack.
It creates false confidence.
“We made a decision” feels like progress. But decisions made without proper diligence simply delay the real reckoning.
It can cost more to fix than it saved.
The time “saved” by “deciding fast” can be dwarfed by what’s needed to correct it. An extra few hours in this stage can help save months later on.
What Properthinking Looks Like
Properthinking is structured, bounded, and intentional. Acting with speed, as well as rigor.
It uses constraints to both sharpen thinking and speed things up.
None of this “let’s discuss this until we feel done” (which is never) nonsense. More like, “we’re dedicating [this amount of time], and then we’ll decide.”
It asks the right questions before it looks for answers.
What are we actually deciding? What would change our minds? What would have to be true for this to work? What will doing this mean?
It deliberately brings in absent perspectives.
Not just the people in the room — but customers, frontline staff, competitors, cynics, people who tried this before and failed (or succeeded).
It separates the idea from the execution.
First: is this the right direction? Then: can we actually do it? Conflating these two conversations is where most teams get stuck.
It pressure-tests without destroying.
The goal isn’t to poke holes until the idea collapses — it’s to find the weak spots before reality does, and either fix them, compensate for them, or accept them.
It accepts that uncertainty will always remain.
The process ensures that things have been thoroughly explored. But it also knows that universal agreement and alignment are a fantasy. Due diligence, then decisions.
It builds genuine confidence — not just consensus.
The team doesn’t leave because they’re tired of talking. They leave because the process has done the work.
5 Ways to Help Teams Apply Properthinking
This is not at all exhaustive, but here are five things you can start applying with teams right away.
Name decisions before discussion
Too often, discussion simply kicks off around a topic, instead of around a clear goal. Write this on the biggest board you can find in the room: We are deciding: ___. If the group can’t complete the sentence, nothing else happens until they get clarity.
The Reversibility Check
Before diving deep, ask: is this reversible or irreversible? Reversible decisions deserve less time. Irreversible ones deserve more. Most teams unconsciously approach everything as if irreversible — and that’s the root cause of most overthinking spirals.
What Would Have to Be True?
Instead of pointing out flaws and giving up, ask the group: what would have to be true for this to succeed? Approach with an everything-is-figureoutable mindset instead of a let’s-look-smart-by-pointing-out-problems mindset.
Consider The Absent Voices
Whose perspective isn’t in the room? You don’t necessarily have to go get them. More isn't better. But those perspectives have to be considered, or an absent voice might become a very present scream later on.
Take a Confidence Snapshot
After the top ideas are narrowed down (but before any discussion), have everyone anonymously rate their confidence in the ideas from 1–10 and reveal the results simultaneously. (Online polling tools are helpful for this.) This will surface a LOT about where extra rigor needs to go.
Know any teams that could use help properthinking? Kindly send them my way, and I’d love to chat.
If you’re an independent facilitator or consultant and want to experience a facilitated Properthinking approach yourself, please consider signing up for next week’s “Create Your High-ROI Facilitation Offer” Sprint. It’s completely free, as long as you actually do the work. And I'm really excited for people to experience it.
CLICK HERE TO LEARN MORE ABOUT THE SPRINT
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Smiles,
-Tim-
