October 6, 2022

What are Executive Off-Sites Good For?

The Theatre of Planning

A blessed Q4 be upon you. And you as well.

It’s that time of year when companies perform the sacred ritual of annual planning. As a strategy consultant I get pulled into quite a lot of these for clients. They’re fun (especially as an outsider!). But are they useful?


Here’s John Cutler with a great post Why Goal Cascades are Harmful (and What to Do Instead) about why the conventional top-down model of “3-5 top goals with everything else laddering up” might be misguided:

  • The cascade reinforces a directed graph-like structure with a small number of goals at the top and many goals at the bottom. It is a tree (like the org chart in most organizations). In reality, variables very rarely have such a simple relationship. Efficiency in one part of the organization could have a widespread impact and kick off virtuous loops. Moving an input “at the frontlines” could be very high leverage.
  • The cascade often leaves things out due to the forced simplicity at the top. It can be heavily biased towards new stuff and leave out ongoing activities. Some teams openly admit that the top-level goals “don’t replace all the normal stuff we do.” The lack of connection can alienate teams, diminish teams, and generally lead to incongruence.
  • With the cascade, you often find teams shoehorning anything into the roadmap because they can make a semi-plausible connection to the highest-level goals.
  • An executive offsite typically tries to simplify the roadmap into a small set of top level goals. One problem with this is that it’s incredibly fragile - when reality changes (spoiler alert, it does!) it’s hard to maintain the hierarchy.

    Instead John has some thoughts about identifying “points of leverage”. These are single points of leverage that affect multiple top level objectives. It would be refreshing in a way for an executive offsite to spend a lot of time in the weeds discussing specific points of leverage for the business..


    Adam Fishman has a great post annual planning is a waste of time with lots of quotes from various executives about perspectives on the annual planning process. He calls it a hot take, but clearly everyone agrees that the annual planning process is a bit broken!

    There’s a nice variety of perspectives and I encourage you to read the whole thing but in particular I like this concept of explicitly planning various ideas on different time horizons:

    From Ben Williams, VP Product at Snyk:

    “The best annual planning processes are aligned but not uniform across the org. There may be some functions (GTM org in B2B for example) where they weigh more heavily to thinking through that longer time horizon, and other functions (eg R&D) where thinking through and discussing priorities and goals for the year may be useful, but that you're going to need to plan and mobilize teams far more dynamically - most likely on a quarterly basis.”

    This maps well to my experience - the company wants to set a 1/3/5 year goal (which might be fine!) but there are lots of nascent initiatives that you simply can’t talk about over that time horizon yet. They’re still incubating.


    Vaughn Tan has a deep dive on his approach to strategy planning called Boris: Unpacking Boris:

    Boris is a facilitated workshop I run for organization leadership teams that fixes this problem. Boris significantly improves on conventional goal-setting processes (such as OKRs) by taking a fundamentally different approach that focuses on understanding acceptable tradeoffs among participants. The outcome of Boris is that different parts of the organization become free to operate autonomously in pursuit of the organization’s shared goals without working at cross-purposes to each other.

    There’s a lot of this that resonates with me - many executive strategy planning sessions come out with a nice-sounding strategy which just crumbles as soon as various teams start trying to shoe-horn their own agenda onto it. In fact teams can end up working against each other which is the exact opposite outcome you’re trying to get to with a strategy planning session!


    I’m still working on a formalized process and methodology for running executive off-sites. I have an approach and format that works but I think it can be more opinionated. And obviously the best approach is tailored to the specific company and situation.

    But here’s some principles I think are worth aiming for:

    1. Pre-work is essential. There’s a lot of value in holding space for the executive team to come together and review the whole parts of the business. This requires each function preparing a useful deepdive and situation report of how that function works. This pre-work needs to be carefully managed, thought through and you need to enforce that the executive team spends time with the pre-work before the offsite.
    2. Don’t stop the deep-dives. Sometimes executives get confused (or are too afraid) to step on toes and so avoid getting into the weeds. It’s seen as a waste of time or somehow not practical to spend the exec team’s time discussion “lower level” things. But where there are critical initiatives (see John’s point about points of leverage) I think you should get into as much detail as you can.
    3. Be explicit about company clocks. Brian and I wrote about company clocks and I think one of the most useful outputs from an executive team is a sense of how urgent something is. Not everything is equal and agreeing not just on what needs to be done, but how fast it should be moving is useful.
    4. Make the trade-offs clear. Cribbing this one from Vaughn - being explicit about tradeoffs helps reveal areas where projects may be unrealistic, or where teams actually have competing values.


    Of course, all of this is trying to make the strategy planning session useful. But it assumes that the strategy is the most important outcome of the session. In reality, a lot of the value for an executive strategy session lies in the communication:

    • Ensuring that senior leaders feel like they are a part of the executive team and involved in decision making
    • Giving the executives a space to practice defending their decisions and talking about the roadmap
    • Finding shared language between functions so that after the offsite the various teams and functions across the organization feel like the company has a plan and has it’s @!#% together!

    If the CEO company all-hands is a theatre performance. Then the executive offsite is the dress rehearsal.

    I use the language of theatre to suggest that performance, communication, language and feeling are important. But don’t be fooled - just because we live in the theatre of work doesn’t make it any less important or useful.


    What is the best executive offsite you’ve ever been to? What have you seen that works?

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    This post was written by Tom Critchlow - blogger and independent consultant. Subscribe to join my occassional newsletter: