When Context Keeps You Stuck in the Past: with Olivia Leigh

Strengths On Fire

What happens when Context is your #1 strength—or your dead-last #34? In this episode, Sarah and Bill sit down with Olivia Leigh, data analyst, coach, and co-founder of Tradewinds Leadership, to explore how Context shows up in work, relationships, and decision-making.

From constipation jokes to car shows, from systems trauma to six-hour road trips filled with ideation, this conversation proves that Context is so much more than “being stuck in the past.” Olivia shares how Context fuels her curiosity, relationships, and innovation—while Bill confesses to having Context envy (and zero memory for names).

You’ll hear how Olivia balances her top Context with Input, Ideation, and Activator, why she loathes making the same mistake twice, and how she and her husband (aka her favorite storytelling partner) use their opposite strengths to fuel purpose-driven work in high-stakes industries like construction and mining.

Main Takeaways

• Context isn’t about clinging to the past—it’s about informing the present through the past.
• People with high Context often crave understanding the “why” before they can move forward.
• Context paired with Individualization creates powerful curiosity about people’s stories.
• Input + Context fuels research and recall—but can spiral into 1,500 open browser tabs.
• Activator + Context can mean “storming the hill without the troops” if you don’t slow down to communicate.
• Partnerships thrive when one person brings historical depth and the other brings in-the-moment adaptability.
• Comfort with what’s familiar is often why people resist change, even when the new way is easier.
• Context envy is real—those without it often feel shame about poor recall or memory gaps.

Sound Bites

• “I loathe making the same mistake twice. If there’s a hole in the sidewalk, I want to see it once—not five times.”
• “Context is the iceberg. People only see the tip—but I know everything underneath that got us here.”
• “Storming the hill without the troops—that’s my Activator hijacking Context.”
• “Systems trauma is real. Don’t tell me the new CRM will be better. I know my 50 clicks.”
• “Sometimes Context gets mislabeled as being stuck in the past. For me, it’s fuel for innovation.”
• “When I’m in flow, it’s Ideation + Significance: finding the nugget that inspires people to act.”
• “My husband used to resist me—now he knows if I say, ‘trust me on this,’ he listens.”
• “Input says: park the Ferrari. You can’t drive every good idea today.”
• “You’re not paying for the tip of the iceberg—you’re paying for everything the coach has gathered underneath.”
• “Context envy is real—some of us just don’t remember names, even if we remember faces.”

Bill's Top 10 CliftonStrengths

1) Individualization

2) Developer

3) Activator

4) Woo

5) Restorative

6) Empathy

7) Harmony

8) Connectedness

9) Relator

10) Learner

Sarah's Top 10 CliftonStrengths

1) Positivity

2) Woo

3) Communication

4) Harmony

5) Activator

6) Developer

7) Input

8) Individualization

9) Responsibility

10) Arranger

Official Strengths On Fire Website: https://strengthsonfire.transistor.fm

GET MORE FROM BILL AND SARAH:
Bill's info:
https://billdippel.com/
https://www.linkedin.com/in/williamdippel/
https://www.instagram.com/billdippelcoach/

Sarah's info:
https://www.wearecollinsco.com/
https://www.linkedin.com/in/sarahcoachcollins/
https://www.instagram.com/sarahcoachcollins/