Let Them Go Well with Sarah Olivieri

The thought shows up quietly and then keeps coming back. Maybe this person is not right for us. Then it sits there for months while you look for more evidence and rehearse a conversation you never have. Meanwhile the person you are worried about is stuck in a job that is grinding on them too.

In this solo episode, Sarah walks through how to know when it is time to let someone go, and how to do it in a way that leaves everyone intact.

In This Episode, You'll Learn

  • Why Sarah has never seen the instinct "I think I need to let this person go" turn out to be wrong, and what to do with that

  • The two categories to check before you act, fit with the team and fit with the role, and why only one of them is fixable

  • Why a bad hiring process is usually the thing that produced the conversation you are dreading

  • How to turn a firing conversation into a quitting conversation, and when that serves both of you

  • What nonprofit staff in particular need to hear before they can let themselves leave

Who This Episode Is For

• Leaders who have been carrying the same thought about the same person since spring

• CEOs who keep reshuffling a role hoping it will fix a fit problem

• Anyone who has avoided a hard conversation because they were afraid of how the person would react

Practical takeaways

• Run the two-category check. Is this about the team and your guiding principles, or is this about the role

• Check your state's employment laws before you plan anything else

• Have the clear conversation first. To be clear is to be kind, and simple, explicit, unjudgmental language is the whole skill

• Decide your boundaries before you walk in. Last day, terms, severance, what is flexible and what is not

• Do not surprise people with money. Be as generous as the timeline allows

• Leave room to ask them what would make this transition feel best

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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