Story Time: Executive Retreat

Leadership retreats, preparations, and observations from someone who probably shouldn't have been invited. An interesting take, but ultimately, it didn't lead to career growth

Story Time: Executive Retreat
Photo by Christina @ on Unsplash

Back in winter of 2007/2008 I was invited to participate in an “Executive Retreat”. We had a new CEO, and this was one of his go-to practices to get a gauge for his “teams” of leaders. I am unsure of why I was included. I was just a senior product manager, and all the others on the invite list were directors or senior directors. Engineering, Operations, Finance, Sales, and our VP/GM, across two of the 4 business units1.

The pre-work

The process was a bit weird. It began with a session with an “Industrial Psychologist” at his family compound in Wisconsin. At this session, there was a detailed profile of me, my life, my work experience, and then some directed work around the current business and organizational structure/operations.

I was there for two nights (the others had longer because they did it about 8 weeks earlier) and it was rather intense. A big part of it was putting in writing my early childhood, family information, and other background administrivia.

But, then it got interesting. At that point, I had been working in that role, in that business unit for a little over 5 years, and I had notes. Lots of notes. I wrote about the structure, the personalities, the interplay between the personalities, the good, the bad, and the ugly.

image - movie still from the good the bad and the ugly
A scene from the classic Eastwood movie, The Good, the Bad and the Ugly

I will admit that it was cathartic. I wrote all the dirt that I had. The petty squabbling. The horseflesh trading when it was time to lay off people, the friction between software and hardware teams, the insanity of the support leaders who liked to stand on the sidelines and pour gasoline on smoldering issues to turn them into conflagrations. Frankly, it felt good. Really good. This was solely to be read by the CEO, and I pulled no punches.

The last phase of the pre-work was for me to list out all my recommendations. Anything was on the table. Org changes, personnel changes, people who deserved more responsibilities, groups that could be better structured and motivated? It was all open to discussion.

I put a LOT of effort into this. I wrote pages and pages. I was specific. I put reasoning and logic into the rationalizations. Since this was going to be shared with the others in the retreat, I was a bit less brutal in my wording about some of my peers, but the recommendations were sound, and – if I do say so myself – the recommendations were far better than what a later (different company) evaluation by McKinsey2 review recommended.

As to the family compound in Wisconsin, it was in the hills, it was wooded, it was quiet, I spent time in the afternoon of the second day strolling the grounds. The Industrial Psychologist was a bit of an eccentric, but he collected classic cars, and he showed me his garage and collections. He told stories about every year going to Barrett’s auctions in Phoenix every year to buy some, and he showed me his latest pride and joy, a 1940’s Mercury with a blown (supercharged) motor.

The main event

The retreat itself was a 3 day off-site at a resort in Santa Barbara. I will say that the venue was spectacular. The room was one of the nicest rooms I ever stayed in3.

The sessions were long, and while we all had our differences, we built a lot of camaraderie amongst ourselves. The only person less prepared than me was our new Executive Vice President, who had joined literally two weeks prior to the off-site. He had the abbreviated pre-work, and since he didn’t have history with the organization, he had no recommendations.

I have done several off-sites before and after, but mostly they were lower key, less luxe, and less impactful.

The sessions were intense. We were respectful, but the facilitator really kept pulling good stuff out of us. I will say there were some confrontations, some shitty comments, but a lot of honesty, and we all bonded as well as sharing the experience.

But, what really resonated with me was that I got to participate with the big boys (it was a sausage fest, and that makes me sad), and I got some face time with our new EVP. I had been close to his predecessor (she was amazing, and I kept in touch with her for several years) so I wanted to make sure that I got some connection to the big man. And I was successful at that4.

The best part was that we all took our last part of the pre-work – the recommended actions – and create a presentation outlining it. Some interesting things that I no longer remember, but I do remember that mine was pretty well received. I made rational, realistic recommendations.

We all shared our early background, and one thing stood out. Of all 11 people in the session, I was the only one who came from a broken household. All of their parents stayed married, they had stable households, largely upper middle class upbringing, and all the advantages that offered. I was the only one who had to deal with adversity. That was an eye opener.

Then we went our own way. I left about a year later, but I did take note that the new EVP had heeded some of my recommendations, and I was nodding at some of the changes.

That felt good.

Coda and Follow up

I left, moved into a different industry, and pretty much forgot all about this. When I left, I created a repository on our file server and left a package for those who would replace me so they wouldn’t have to reinvent the wheel.

In 2016, I had moved to a different state, and out of the blue I get a ping on LinkedIn from one of my successors. He was in town and wanted to grab coffee. I said sure, why not.

We met and he bought me coffee (he had the expense account) and we chatted for about 90 minutes. Turns out he found the documents from the executive retreat, and he mentioned that virtually all of the recommendations (organizational structure, business recommendations, personal adjustments) were actually put into practice.

I gotta admit that I was floored. I left on good terms (that went sour later) but apparently the EVP took my thoughts to heart and made good on them.

  1. The company had two halves, a process equipment half, and a metrology half. I was in the latter, and there were two such Executive Retreats for each half.

  2. That cost somewhat more than $200K to get done - yeah, not an apples to apples comparison, but you get the idea.

  3. One day, I will recount my last minute trip to Korea and because of a huge conference in Seoul, I got to spend three nights at the Park Hyatt, at a cool $1,200 a night with cut granite to make the shower stall. That was exquisite.

  4. This will be fleshed out in a future story…