Ride the Wave Already Moving with Sarah Olivieri

Strategic planning gets treated like a decision you make in a quiet room, then hand down to the team. So leaders sit down to "set direction," invent something new from scratch, and spend the next year trying to force it into existence. The resource burn is real. The traction usually isn't.

In this solo episode, Sarah breaks down why strategy is mostly discovered rather than decided, and how to tell the difference before you commit the year to it.

In This Episode, You'll Learn

  • The two sides of strategy — fixing what's already running and growing what's new — and why they need different thinking

  • Why deciding a brand-new direction is one of the most resource-intensive moves a leader can make, and when it's actually worth it

  • What "sprouts" look like inside your organization and out in the wider world, and how to spot them early

  • Two strategic questions Sarah keeps coming back to (including the Dan Sullivan three-year question)

  • Why listening — to words, data, body language, and energy — is a core strategic skill, not a soft one

Who This Episode Is For

• Executive directors staring at a blank strategic plan template wondering where to start

• CEOs who feel like every new direction is being pushed uphill

• Leadership teams heading into a planning retreat and wanting to walk in with better questions

• Anyone who has ever committed to a bold new strategy and watched it stall out by Q2

More on the subject

• Before you decide a new direction, list what's already emerging inside your team, your programs, and your data

• Run the Dan Sullivan question with your leadership team: if we were meeting in three years and everything had gone really well, what would need to have happened?

• Ask the One Thing question: what's the one thing that, if solved, would make everything else easier or unnecessary?

• Treat listening as a strategic activity, not a management courtesy — put time on the calendar for it

About Your Host, Sarah Olivieri

Bold, strategic, and refreshingly human…

Sarah Olivieri is the go-to expert for conversations on aligned leadership, outcome delegation, and sustainable growth.
She brings wit, warmth, and real-world wisdom to mission-driven founders, visionary CEOs, and change-makers who want more clarity, more joy, and more results.

Most leaders hit a wall when success depends on them holding it all together.

Sarah helps them change that by redefining leadership around outcomes instead of activity, empowering teams to own results that scale and freeing leaders to focus on the vision that drives them.

A former director of three nonprofits and founder of five businesses, she has a rare ability to spot opportunity where others see chaos, shift stuck patterns, and build organizations that support both legacy and life.

Sarah leads with the same mindset that made her an award-winning sailor: iterate on what works, stay focused in the storm, and never forget the joy of the journey.

Links

Website: saraholivieri.com
LinkedIn: linkedin.com/in/sarah-olivieri

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