In the age of remote and hybrid work, are in-person strategic planning offsites worth the investment when leadership teams are already adapted to virtual collaboration?

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Director of Innovation, Technology and Knowledge Management15 hours ago

Remote and hybrid have made us efficient at sharing information; they haven’t made us better at making decisions. I use in-person offsites with intention, for the work that benefits most from real-time collaboration and sense-making. If we’re aligning on a multi-year strategy, killing pet projects, reviewing POCs, or repairing trust across teams, being in the same room pays for itself in speed and clarity. Everything else stays virtual. My model is hybrid by design, gather input asynchronously, circulate two or three decision documents, then use the offsite as a working session with clear outcomes, three to five priorities, owners, budgets, and a 30-60-90 plan. We leave with a one-page set of commitments and a cadence to inspect what we said we’d do. Run this way, offsites aren’t retreats; they’re accelerators. And the side benefit is real: the hallway chats, dinners, and social hours build the relationships that make execution smoother.

Senior Director, Enterprise Architecture in IT Services15 hours ago

Ultimately the in-person investment depends on how far away, how many of the leadership team need to come together and for how long, but the benefits of having everyone in the same time zone, focused in the same room and being able to quickly break-out and reform with side discussions can be significant. Maximising time and continuing discussions over dinner are not easily done on-line.

I would question if leadership teams are truly adapted to _interactive_ virtual collaboration, rather than linear on-line meetings. I've seen people at all levels struggle to use related virtual tools effectively; whiteboards, breakout rooms, mood polls etc. Investment in these skills will bring virtual collaboration closer to the benefits of in-person sessions, but can't replace it.

Chief Information and Technology Officer2 days ago

I've been part of Strategic planning both internally and externally and without a doubt, these are best held in-person and not remote. There is so much value with the interactions and sharing that takes place, especially in a cross-team setting. Some key elements I've had success with;
- Transparency and confidentiality. If you don't have candor and/or people don't feel what they say stays in the room, you aren't going to get engagement.
- Make it a workshop format with an agenda that includes everyone. There's mention in this thread regarding listening to presentations all day is boring. I couldn't agree more.
- Participation, I always ensure most people have a role to play in presenting - no wallflowers
- Have a strong facilitator that's prepared to shift the agenda to meet everyone's needs. There isn't one of these that I've done that didn't require adjusting the agenda and some cases, I've changed the whole approach.
- Have some fun with it....we have a number of different 'ice breaker' sessions that I use when we need brainstorming.... Mix and Mash, This is not a rope etc. These are good at getting people to relax and you can't do these remotely

Hope this helps the conversation.
Robin

1 Reply
no titlea day ago

My short answer is 'Yes'. It is not only about the Strategic agenda itself, but the interactions and influence of the discussion that comes with it. i.e. online collaboration as good as it has come does not have a way of making up for those side conversations, relationships that are reinforced and or established. Also, the scale of influence is increased, i.e. many (most) online interactions are one conversation at a time.<br><br>Then, there is the whole concept of Strategy, it's over the horizon stuff, getting a shared view of where you want to go up front increases the chance of you all being at the same point on the other side of the journey that will get proposed.<br><br>And then finally, the old school saying 'A stitch in time saves nine'

Chief Information Officer in Manufacturing2 days ago

I think an effective off-site (on-site) that is authentic (not over-the-top, forced, off-brand, fake) nurtures a sense of belonging and community. This is an essential ingredient to energize delivery towards outcomes, not just tasks. If team members feel they are delivering for something they belong to (not for someone else), they are more likely to collaborate, be creative, expend discretionary energy and passion, take risks together etc. Organic networks are also more easily built in person and often more effective at getting things done and enabling the toughest transformations than org structures and job descriptions. If the in-person session is just sitting in a conference room listening to presentations and directives, I don't think it is worth it at all. If it is only a round-table planning and problem solving setting - maybe. But if it is set up to also nurture the more human side of us - absolutely.

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CISO in Finance (non-banking)3 days ago

To the extent that "collaboration" is focused on executing on clearly defined efforts, with clearly defined goals, in teams that have clearly defined roles; there is little need for in-person planning. However, I've never seen an organization with projects, goals, teams, and roles like that. When things are unclear or strategies are being formed, TRUST is what allows for speed in the absense of clarity. If 'trust' sounds too moralistic, then consider 'confidence' or 'preditability'. Humans are simply wired to build trust/confidence in a face-to-face setting, with all the nuance of voice-inflection, body language, physical spacing, etc.
Building trust is not just so we all feel good; but so teams and whole organizations can move quickly without all the friction which comes with mistrust.

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