Offsite Horror Story

Imagine bringing 15 of your company’s most important leaders together for an offsite

And then being told it was a waste of time.

This happened to me. Here’s the story:


Before starting my own companies, I worked for multiple CEOs as their 2nd in command - Chief of Staff, CFO, Head of Strategy & Operations, etc.

One of these companies was experiencing enormous growth, but was facing serious issues around an increasingly toxic culture.

I was given budget by the CEO to address the issue via a company offsite with leadership.

So what did I do?

I hired a professional: A facilitator and coach tasked with helping us make progress on these issues.

Here’s what she did:

  • Spoke with me for 30 minutes about my team’s needs

  • Pulled activities from her facilitator/coach training books to create an agenda

  • Facilitated an offsite where she ran through her activities with us

  • ✌️

These were the results:

  • We never dug into the difficult conversation of the root issue, so nothing got better

  • Leadership was pissed at me for wasting their time with silly activities

  • Victims of the toxic culture lost faith in me because nothing changed.

The whole idea of a company-development-focused offsite was counted as a failure.

We never tried another facilitated conversation like this again,

And this mistake could have cost me my job.

I think about this moment often as I build Pearl & Elmore with my cofounder, Dr. Josh Elmore.

It’s the horror story that drives us to be different.

For the teams we work with, this might be the only time they get to meet in-person to:

  • Set their winning strategy

  • Clear company-ending issues

  • Align disagreeing or miscommunicating teammates

  • Address an elephant in the room that's preventing everyone from moving forward

And we take the responsibility of facilitating this conversation VERY seriously.

  • It’s why we take a science-driven approach

  • It’s why we spend hours before the offsite, getting to know the whole team

  • It’s why we custom-build every agenda from scratch, based on the company’s unique issues and goals

  • It’s why we put a psychologist from Columbia and a Stern/Deloitte-trained executive in the room, while other facilitators come with backgrounds like "Trainer", "Life Coach", and "Yoga Teacher"

For someone helping a CEO run a company, offsites are such an incredible tool for clearing issues and getting everyone back to working well.

But get one wrong

And that tool could get wiped from your budget forever.

I've been there, and I know the stakes.

I've seen the 10X ROI transformations that happen when an offsite is taken seriously and executed excellently.

And I've seen the damage done

When that opportunity is missed.

Do you know a Chief of Staff, EA, or HR peer who's been asked to plan an offsite this year?

Please share this note with them!

It's the note I wish someone had sent to me.

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