0. Don't Say "Strategy"
Most teams quietly tiptoe around a simple truth...many leaders don't actually know what a good strategy looks like, let alone how to create one.
They've never read
Good Strategy Bad Strategy or
Blue Ocean Strategy.
They can't clearly articulate a path forward.
They've never heard of
SCQA.
Instead, the word “
strategic” gets slapped onto anything that feels important or urgent. A shiny feature? Strategic. A sales deal? Strategic. A board request? Definitely strategic.
But when everything's strategic, nothing is.
The moment you say “We need a strategy” people get nervous. Defensive. Like you're questioning their leadership. So don't. Use softer language. Say “Let's update our plan” or “Let's get clearer on direction”
Same outcome. Less drama.
1. Direction
1.1 Is there a clear direction?
Strategy starts with a choice. A real strategy points to a direction: what you're doing and what you're intentionally not doing. Strategy lives in your decisions, not your deck.
🎯 Pro Tip: Vague ambitions like “grow the business” aren't strategies. Clarity means prioritisation - choosing one thing over another.
Examples of strategic directions:
Retention over Acquisition. We're investing in the customers we already have – focusing on retention and long-term value, even if it means slowing down acquisition for now.
Supply over Conversion. We're focused on fixing the fundamentals – strengthening supply in the marketplace first, so when we optimise conversion, it's built on a solid base.
Foundations over Features. We're putting time into the foundations - tightening up our product analytics and improving the tech stack so we can ship faster, even if that means losing a few customers along the way.
1.2 When Strategy Lives in Someone's Head
If the strategic direction lives only in your founder or CEO's head, you've got a gift - an open loop waiting to be closed. Now's the perfect time to step up and help shape it. Most people drift not from bad plans, but from silence. People can't align around thoughts that aren't shared.
Ask. Write it down. Push for specifics. Don't wait for an all-hands deck or a polished “vision doc.” The bar isn't high.
Message Template:
Hey [Leader/CEO/Founder],
I want to make sure I'm aligned with our current strategic direction. Could you help clarify:
What are we focused on right now - and what are we intentionally not doing?
What's the rationale behind this focus?
I'd love to write it down and share it back with the team so we're all on the same page.
🎯 Pro Tip: If your leader prefers verbal conversations, no problem. After the chat, write down what you heard and send it back:
“Just writing this down to make sure I've captured it correctly - does this reflect what you meant?”
Getting confirmation builds shared clarity and accountability.
1.3 What if there are multiple competing goals?
You might hear: “We need to improve both retention and acquisition.”
Totally valid. Most companies do need to work on both. But trying to focus on everything at once usually means making progress on nothing. Strategy is about sequencing, not ignoring. It's not that the other goal isn't important. It's just not the priority right now.
🎯 Pro Tip: Ask your leader: “If we could only succeed at one this quarter - retention or acquisition - which one would we choose, and why?”
This forces a trade-off. And trade-offs reveal real strategy.
Once you've got clarity, you can still support the secondary goal. But you'll know where to invest most of your time and energy.
🎯 Pro Tip: Keep in mind: priorities can shift over time. What's secondary today might become primary next quarter. The key is to align your current work with the current direction.
1.4 What if priorities keep changing?
If the strategic direction shifts frequently, it may feel like there is no strategy.
🎯 Pro Tip: Ask your leader to explain the reason behind the change. Is it a pivot based on new data? A short-term reaction? Or a lack of clarity upstream?
Use the same two questions: What are we focused on right now and what are we intentionally not doing? Why?
Documenting each shift helps you spot patterns or flag when you're simply chasing noise.
🎯 Pro Tip: “Let's fix our tech debt and hit all our revenue targets.” Push for a primary focus. Ask: “If we could only succeed at one of these, which would you choose - and why?”
This surfaces the trade-off behind the strategy. Because strategy is always about trade-offs.
1.5 What if different leaders say different things?
Your manager says one thing. A co-founder says another. The CEO says a third.
🚩 Red Flag: If everything is a priority, nothing is. If every leader gives a different answer, you don't have strategy - you have noise.
Be the glue. Synthesise what you've heard and send it back to all parties:
Here's how I'm interpreting our strategic focus based on recent convos - let me know if I've misunderstood anything.
This invites alignment and shows initiative without stepping on toes.
1.6 What if the strategy isn't communicated to the team?
Even if there's clarity at the top, strategy often gets lost by the time it reaches delivery teams.
🎯 Pro Tip: Make it part of your rituals: Add a “Strategic focus reminder” to sprint planning or team meetings.
Refer back to it when reviewing OKRs or roadmaps. Ask: “Does this work support our current focus?”
You don't need a fancy strategy doc, just a consistent narrative.
1.7 What if we're pretending we've made a choice, but we haven't?
The roadmap fills up. Everyone's “aligned.” But no one can name the one thing that matters. Execution looks busy but feels aimless. Teams get pulled in opposite directions. Projects start strong then fizzle. Strategy becomes decoration.
Here's how you know the choice isn't real:
- No one can explain what you're not doing.
- Trade-offs are dodged, not made.
- Teams work in parallel instead of sequence.
- Effort spreads wide but delivers shallow.
Fake focus is worse than no focus. It creates false confidence. It hides drift behind good intentions. And it always shows up in the work.
So stop the theatre. Ask: “If we were actually making a trade-off here, what would we say no to?”
Push for specifics. Not values, not themes - actions. Then repeat it until the team rolls their eyes. That's when strategy starts working.