The Strety leadership team just got back from our annual off-site in Las Vegas with Lisa Gonzalez as our EOS Implementer — my first time ever using an Implementer for a company I’m actively operating. I have previously sat in on EOS sessions for another company I was helping, so I’m not a total newbie to the way of the Implementer. But there was something different and special about our first Implementer-led session for Strety.
I have a bunch of thoughts to share, but first, here are the two most impactful takeaways for me…
- For strategic planning sessions: no technology in the room is the only way! (For a software guy, this is literally mind-blowing)
- Having an Implementer as a facilitator was a game changer vs. self facilitating
Context on the Where & Why & How
This off-site was actually planned before we decided to start working with Lisa. The original plan was two full days, self-run, similar to how we’ve done our annuals in the past. Which means it would have been very informal — half days of work in a room, and the other half covering the agenda while having some fun outdoors. In fact, our last quarterly in person was done all day in Saratoga Springs, NY before a Dave Matthews Band concert.
After we signed up with Lisa González (and with her blessing) we decided not to overthink the setup and keep the trip as planned. Since we had such a long history of self-implementation, she suggested we let our first day be our normal style and she would facilitate a full second day for a kind of “easing into” professional implementation. So off we went to this hybrid annual planning meeting.
Day one was all about some tactical product work we wanted to do and to level set on the previous year and the plan for day two. Plus general team bonding which I think is so important. In our style, our first day ended up being a few hours meeting in the room and the rest of the afternoon/evening walking around Vegas, checking out different casinos and settling at a lounge at the Wynn. The agenda was loose and fluid and I think it was a great way to start the retreat. Because day two was really the main focus.
On day two, Lisa was ready to get to work and to be honest, we really didn’t know what to expect.
Thankfully, with her experience and her knowledge of us, she didn’t force a perfect EOS Annual agenda or try to do everything “by the book.” Instead she split the morning between refreshers of all the core tools and EOS and Team Health. And in the afternoon we really got work … creating our yearly plan, refreshing our three-year picture, and setting quarterly Rocks for Q1. However simple that sounds, the experience felt so different than past meetings, and led to plenty of learning.
A-ha moment #1: No tech in annual planning sessions
The biggest a-ha for me was simple, but powerful: nothing substitutes being in the room WITHOUT technology.
We’re a small remote team. We move fast. Everyone is busy. And I’m a software person at heart — building tools is literally my job. Not being in front of my laptop for an entire day seemed insane. But I was wrong. There is something that just doesn’t translate when you’re on screens, even with the best intentions. Add to that, getting out of our normal environment (in a different city) and sitting together in the same room all day , and the quality of the conversation changed in a meaningfully positive way.
In classic EOS Implementer fashion, Lisa used markers and giant post-it notes that filled up the walls. We hammered the agenda she laid out in about 8 hours of focused work. Not once did I feel like tech was missing either. It was refreshing not to worry about it at all — everything critical was captured in the post-it notes.
We obviously know software is incredibly useful for capturing decisions, documenting plans, and turning ideas into execution afterward. But at the moment, software had no place in the room. That was mind-blowing.
A-ha moment #2: Professional facilitation made my life MUCH easier
The other big shift for me personally was what a difference it made to have a facilitator who wasn’t one of us. When you self-implement EOS, you’re constantly splitting your attention — running the agenda, watching the clock, thinking about what’s next, and trying to participate at the same time. You don’t notice how much mental load that creates until someone takes it off your plate.
Having Lisa worry about the process and the flow meant I could just be present. I could listen, think, participate, and engage — without also managing the day. I think the rest of the team felt that as well. There was more engagement, more focus, and a completely different energy in the room than we’ve had in past annuals.
EOS Implementers always say they are teachers, facilitators, and coaches. Not consultants. I never fully appreciated how much value that hands-on approach brings until this experience.
Proving how much we enjoyed our session, we quickly decided our next quarterly will be in-person instead of the planned remote one. We’re headed to Lisa’s turf in Denver, CO in April.
What next?
First, you better believe the fact that the quality of in-person, no tech strategic planning has my product mind spinning. How can we best support a seamless transition from critical in-person planning to remote, software-driven execution? This is something we’re all thinking deeply about.
And in the weeks to come, I’ll share more tactical things I picked up within the EOS tools that Lisa re-taught us. But for now, I hope you enjoyed my first couple of nuggets from our first Implementer-led session. Many more to come!