Two Components of Being Strategic

Being strategic requires both articulating the why AND championing change

Anneka Gupta
Becoming more strategic, navigating difficult colleagues, founder mode, more

Two Components of Being Strategic

"When people say 'I want someone that's strategic,' what they're really saying is 'I want someone that can come up with and articulate a compelling and simple why behind the decisions and the direction of the company and product.' So that's number one. And the second piece is, 'I want someone that's going to champion and be a change agent to do things that may be hard but actually best for the long-term interest of the product or company, even though those things are not going to be easy to execute on.' And I think if you have one without the other, ultimately people are not going to see you as strategic." - Anneka Gupta

What It Is

Being "strategic" is feedback many product leaders receive but struggle to act on because it's often vague. Anneka Gupta decoded this feedback after receiving it multiple times in her career and identified two essential components that must work together.

The first component is the ability to articulate a compelling and simple "why" behind decisions and direction. This isn't just about having reasons—it's about making those reasons resonate and be easily understood by others.

The second component is championing change that serves the long-term interest of the product or company, even when that change is difficult to execute. This is about being a change agent who pushes for important work that others might avoid because it's hard.

The key insight: having only one component isn't enough. Great articulation of small ideas isn't strategic. Big ideas without clear communication aren't strategic either.

How It Works

Component 1: Articulate the "Why"

  • Develop clear, compelling reasoning for decisions
  • Simplify complex rationale into understandable narratives
  • Connect tactical work to strategic objectives
  • Make the logic accessible to diverse stakeholders

Component 2: Champion Change

  • Identify opportunities that could transform the business
  • Advocate for hard-but-important initiatives
  • Be willing to push against resistance
  • Focus on long-term benefit over short-term ease

The Multiplier Effect:

  • Strong why + small ideas = not strategic (you're just a good communicator)
  • Weak why + big ideas = not strategic (you're seen as unfocused or impractical)
  • Strong why + big ideas = strategic (you're seen as a leader who moves the needle)

How to Apply It

  1. Audit your current work - Look at your recent initiatives. Are they big enough to matter? Can you articulate why they matter in a simple, compelling way?

  2. Practice summarization - In meetings, practice summarizing what's been discussed and why it matters. This builds your "articulating the why" muscle.

  3. Identify transformation opportunities - Look for the 2-3 things that could fundamentally improve the business but are being avoided because they're hard.

  4. Connect small to big - When working on incremental improvements, explicitly connect them to larger strategic narratives.

  5. Make it one click better - Don't try to reinvent everything. Take existing ideas and ask: "How do I make this one click better from an outside-in perspective?"

When to Use It

  • When you receive feedback that you're "not strategic enough"
  • When preparing for performance reviews or interviews
  • When deciding which projects to champion
  • When communicating product direction to stakeholders
  • When evaluating whether your work is creating real impact

Source

  • Guest: Anneka Gupta
  • Episode: "Becoming more strategic, navigating difficult colleagues, founder mode, more"
  • Key Discussion: (00:18:57) - Anneka decodes the feedback "you're not strategic enough"
  • YouTube: Watch on YouTube

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