28 Jan 2026 · 3 min
Bill Gallagher on running annual strategy sessions: hire an outside facilitator, go off-site to somewhere inspiring, include everyone, review your BHAG and vivid vision, then break it into quarterly plans. Meals and walks matter.
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What makes for great annual strategy and planning work? Well, this was very self serving, but I would say get yourself an outside facilitator. Get somebody else to lead you through it so you can be fully engaged in it, not trying to lead it yourself. Doesn't have to be me. Probably can't be me. There's way too many of you listening and watching to these things than I could possibly take care of or even our whole team as as it stands today.
So but get somebody that you trust.
And if it is us, fine. We'd love to talk to you about it, but get somebody to do it. Now a couple other things.
Go off site, get away, add some.
Meals, add some experience, use the space.
Get a meeting room.
It could be an Airbnb, a VRBO could be a really cool house, living room with a great view and some outdoor space. I love that. Go to the mountains or go to the beach. Go along the shore. Go somewhere that's a little bit inspiring. That'll help you get in a big picture mindset. Take care of yourselves collectively. Like have a nice meal, have a nice environment. Don't go weird and cheap and be too hurried with the whole thing. Settle down for a minute. So get some outside help. Go somewhere great, nice view, use your clubs, use your friends club, use your friend's place. Or you know, you can go to a big resort. We do a lot of them in great resorts and that kind of thing. You don't have to do the whole corporate meeting room thing and the great expense of of doing that at a hotel resort meeting room. You could do it in lots of creative ways to still get it. Get a big suite somewhere and just use the suite for it. Or that's where the Airbnb Review. VRBO goes in.
So go off site, take a day.
Or two to do it. Use a facilitator, make a great thing. Take care of yourself. Allow a little like extra time for some walks. Allow a little extra time to meet and connect over a meal. Do something experiential together. Add some beach time or some sport or something that you like. Include everybody in it. Do it in an inclusive way so that people can experience something. But like don't just get down to business right away to do that. It'll help your thinking, the quality of your thinking, your outlook if you do your annual and strategy planning that way. And then of course like our quarterly planning, we want to do some review and then we want to look really big picture. Is the BHAG still relevant? Do we have a vivid vision that's sufficiently updated? Then from there we can reflect on how the last year's gone and what are the big things we need to focus on for the year ahead. So that's how to make for great annual strategy and planning sessions. That's the time to re look at all the things in your seven strata and the top part of your vision summary. That's the work to do for annual strategy and planning work. Go big picture, go long term. Then you can work back to each of your quarterly plans and it'll have it make a lot more sense and don't shortchange all those other like the little things around the experience of it. They'll help you do better thinking bigger things and align and work well together as a team. Those are probably the biggest things that I would say around annual strategy and planning and great execution. Until next time. Hope that's helpful. Talk to you again soon. Bye bye.
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