Not every idea deserves a test. The trick isn’t learning to say “yes” to everything — it’s learning to say “yes” to the right things.
If Experimenting with Strategy: Small Bets, Big Gains was about creating space for curiosity, this is about where to point that energy. Tolerance without direction is just chaos with good intentions.
The three filters for a good strategic bet
1. Does it protect or create value?
A good bet either keeps something valuable from breaking or unlocks something new. If you can’t explain what it preserves or creates, it’s not ready.
2. Can you test it cheaply and quickly?
If the test requires months of work, a new hire, or a big budget, it’s not a small bet — it’s a gamble. A good strategic bet has a short feedback loop. You try something small, see what happens, and decide what’s next.
3. Does the outcome tell you something clear?
Vague experiments produce vague answers. A good test has a clear signal: either it worked, it didn’t, or it taught you something specific. If you won’t know whether you succeeded, you’re not testing — you’re guessing.
What this looks like in practice
A small business owner I worked with knew work was getting stuck somewhere. Orders were delayed. Frustration was building. Instead of buying project management software or hiring a consultant to build a massive process map, they did one thing: they documented how work was actually moving through the team.
No fancy tools. No complicated frameworks. Just a simple, real-world look at the flow.
Within a week, they found the bottleneck — a single handoff point where information sat for two days before anyone touched it. They fixed that one thing. Orders started moving again. Then they looked for the next bottleneck.
Small bet. Clear result. Move on.
The pattern beneath all of this
Real change doesn’t come from one big move. It happens incrementally — a series of small, smart bets that compound over time. The businesses that pull ahead aren’t the ones that swing for the fences once. They’re the ones that keep making small, informed moves, learning from each one, and never stopping.
Next up: Embedding Experimentation into Your Plan.
Let’s rework how you work!
Read the full article on Substack →
From the SmartWork Bulletin