Podcast Summary: Leading Organizations That Matter
Episode 99: "I Want to Become More Strategic"
Host: Rey Spadoni
Date: March 10, 2026

Episode Overview

This episode focuses on the concept of becoming more strategic as a leader, particularly within mission-driven and nonprofit organizations. Host Rey Spadoni explores the frequent desire among leaders to "be more strategic," unpacking what this really means, how it differs from related skillsets, and practical steps listeners can take to build their own strategic thinking abilities.

Key Discussion Points & Insights

The Common Desire to "Become More Strategic"

• Rey opens by noting how often his clients express a wish to be more strategic, especially those who already have a record of success and are seeking growth or advancement.

  • "I can't tell you how often I hear these words from my clients..." (00:21)

• He emphasizes that people often conflate being 'strategic' with other, more specific professional skills:

  • Understanding workflow = Operational knowledge
  • Financial proficiency = Analytical skills
  • Reading the room = Emotional intelligence

• Rey advises that before working on strategy, it's important to clarify exactly what someone means when they say they want to be more strategic.

  • "The first thing that I try to do is understand what they mean by that and what they're really hoping for. Definitions are important..." (01:30)

Rey's Definition of Strategic Thinking

• Rey shares his nuanced definition, highlighting the mindset required:
  • "...the ability to see and consider that which is beyond the immediately obvious, to understand the larger context, and to anticipate how different variables could shape the future. It requires the coming together of disparate pieces of information, the identification of important and quite possibly impactful patterns, risks, opportunities, and then the consideration of the potential ways forward." (02:00)
  • He connects strategic thinking to mission, vision, and values alignment.

Practical Tips for Becoming More Strategic

Rey offers a concise four-step framework for analyzing situations strategically, whether the organization is thriving or facing challenges.

1. Multiple Angles

• "How can I look at this from multiple angles? How will all those involved or impacted in some way see this situation? What do they want? What is the win and loss scenario here for everyone?" (03:00)
  • Recognize that stakeholders may have different stakes and viewpoints.

2. Options, Risks, and Mitigations

• "What are my options here and specifically and most importantly, what could go wrong with each one of them? Then what am I going to do when those things go wrong?" (03:36)
  • Identify options, potential pitfalls, and proactive mitigation strategies.

3. 360 Degree Implications

• "What are the upstream and downstream implications? ...who and what are impacted and how? This is the 360 degree perspective thing." (03:57)
  • Consider the broader, system-wide consequences (both positive and negative).

4. Identify the Gaps

• "What are my gaps? What don't I know and is that important? And then how do I close the gaps?" (04:19)
  • Acknowledge unknowns and make plans to address them.

Framework Recap (04:40)

1. Multiple-angle points of view
2. Options, risks, and mitigations
3. 360 degree implications
4. Identify the gaps

Notable Quotes & Memorable Moments

• On Client Ambitions:
  "It's not uncommon that these are the very things that many of my clients are searching for." (00:54)
• On the Importance of Clarity:
  "Definitions are important, and so over the years, I've developed my own vocabulary, my own perspective and mindset. When it comes to this notion of strategic thinking..." (01:30)
• Practical Advice:
  "The next time you are pondering something that could benefit from a greater strategic perspective, try this exercise. I think you'll find it helpful." (04:54)

Useful Timestamps

• 00:00 – Introduction & Common leadership aspirations
• 01:30 – Defining strategic thinking
• 02:00 – Rey’s working definition and linkage to values/mission
• 03:00 – Step 1: Multiple perspectives
• 03:36 – Step 2: Options, risks, mitigations
• 03:57 – Step 3: Upstream/downstream implications
• 04:19 – Step 4: Identify and close knowledge gaps
• 04:40 – Framework recap and encouragement
• 04:54 – Closing thoughts

Tone & Language

Rey maintains a conversational, direct, and empathetic tone throughout, using examples drawn from his own coaching experience and keeping the advice practical and actionable.

Final Takeaway

Rey Spadoni encourages leaders to move beyond vague aspirations to "be more strategic" by adopting a clear, structured approach to thinking—and rethinking—organizational challenges. His four-step framework offers listeners a concrete tool to practice strategic analysis in their daily work.