To become a better leader, we are told that we need to think more strategically. But what does that mean, and how do we know we are thinking strategically? The examples we are typically given are obvious and do not really help us to become more strategic. Thank goodness for LLMs. I asked this same question, and below is what it gave me. Hopefully, this can help you too.
1. Start with the end game (not the task)
Most people operate at the task level:
“What do I need to get done this week?”
Strategic people start with:
“What outcome actually matters 6–12 months from now?”
Practical shift:
Before you start work, ask:
- What does success look like for the business (not just my team)?
- If we win big this year, what had to go right?
👉 In your role (managing engineers), this might look like:
- Not “deliver projects on time”
- But “increase throughput of high-value work by 25%”
That changes everything about how you prioritize.
2. Connect your work to company priorities
If your work isn’t tied to company goals, it’s just activity.
Strategic thinkers constantly map:
My work → Team goals → Department goals → Company strategy
Action:
Take your top 5 current efforts and force yourself to answer:
- Which company priority does this support?
- If I stopped this, would leadership care?
If the answer is “not really,” you’ve found noise.
3. Think in trade-offs (this is the big one)
Strategy is mostly deciding what not to do.
Average thinking:
- “We should do A, B, and C”
Strategic thinking:
- “If we do A, we probably can’t do B well—so which matters more?”
Practice this:
When making decisions, always ask:
- What are we choosing NOT to do?
- What are we risking by this choice?
If you’re not making trade-offs, you’re not being strategic—you’re just adding work.
4. Look for leverage, not effort
Non-strategic:
- “How do we work harder/faster?”
Strategic:
- “What’s the 1 change that makes everything easier?”
Examples in your world:
- Fixing a broken process in Jira → improves 15 engineers’ output
- Coaching 1 weak team lead → multiplies impact across a whole group
- Killing low-value meetings → frees hundreds of hours
👉 Strategic thinking = highest return per unit of effort
5. Extend your time horizon
Most people think:
- Day-to-day or sprint-to-sprint
Strategic thinkers think in layers:
- Short term: this week
- Mid term: this quarter
- Long term: this year+
Habit:
Once a week, ask:
- What problems are coming that no one is addressing yet?
- Where are we going to break in 6 months?
If you can solve problems before they show up, you’ll stand out fast.
6. See patterns, not just problems
Anyone can solve a problem once.
Strategic thinkers ask:
- Why does this keep happening?
- Is this a one-off or a system issue?
Example:
Instead of:
“This project slipped”
Think:
“Why do 40% of our projects slip?”
That’s where real value is.
7. Get closer to how leaders think
If you want to be seen as strategic, align with how senior leaders evaluate decisions:
- Risk
- Cost
- ROI
- Talent impact
- Long-term positioning
Simple upgrade:
When you present ideas, don’t just say:
“Here’s what we should do”
Say:
- Here are 2–3 options
- Here are trade-offs
- Here’s my recommendation and why
That alone will separate you.
8. Create space to think (this is underrated)
You won’t become strategic if your day is packed with reactive work.
You need:
- 30–60 minutes weekly to think, not execute
Use it to:
- Review priorities
- Look for patterns
- Anticipate problems
If you don’t protect this time, strategy won’t happen.
What this looks like in practice for you
Given your role managing engineers:
A non-strategic manager:
- Tracks tasks
- Runs meetings
- Reacts to issues
A strategic manager:
- Improves system throughput
- Eliminates bottlenecks
- Develops leaders under them
- Aligns work to business impact
- Anticipates problems before leadership sees them
Bottom line
Strategic thinking is a set of habits:
- Start with outcomes
- Prioritize ruthlessly
- Make trade-offs
- Look for leverage
- Think ahead
- Fix systems, not symptoms
Do this consistently, and people will stop telling you to “be more strategic”—they’ll start asking for your input earlier.