In our highly digital, AI-powered world, I wonder if workshops and strategy sessions are becoming a thing of the past. Has technology removed the need for people to come together to work through big questions and big ideas? Asking for a friend…
I've led strategy and planning workshops, and I've been in the sessions where design thinking and brainstorming was the exercise at hand. You clear the calendar, get everyone in a room, and work through what the future needs to look like.
And there's always at least one person who rolls their eyes, checks their phone, and thinks this is a waste of a day they don't have. They want to get back to their work. What they typically don't consider is that the work they want to get back to is probably already headed in the wrong direction. That's usually why we're there in the first place.
Almost without fail, that same person leaves having learned something, contributed something, and said the thing nobody else was willing to say. They walk out with more clarity and more energy than they walked in with — not because the coffee breaks had those awesome jumbo-sized cookies, but because the work actually produced alignment, a plan of action, and real results.
That's the part worth remembering today. Everyone's leaning hard on platforms like Asana, Notion, Slack, Confluence... now with AI! All built to help compile information, guide thinking, and move faster. Most of it genuinely works. A person, a prompt, a fast answer.
What it can't do is get a room full of people to disagree and then work it out. Uncover blind spots, identify unseen opportunities, and leave the room aligned and moving in the same direction. That happens face-to-face. And the more uncertainty defines our world — the business, the industry, people's own sense of where they stand while the ground beneath is constantly shifting — the more that kind of alignment matters.
I led a cross-functional team in a two-day strategy and planning workshop. They had a patchwork of systems, no long-term strategy, and no goals directing efforts. This was the first time many of them had been brought together for something like this, and when I walked through the agenda and intention for the two days, they looked at me like I was from another planet (or maybe another time and place).
As we started our work, they saw that there was no connection between company goals and what they were doing day-to-day. They were using tools like Slack and Asana to track projects, map progress, and share updates, but had no clear view of where they were heading. The strategy discussions and OKR work that followed surfaced a key insight that aligned their product strategy directly with the company's core growth target. They walked out of the room with a clear strategy, a new action plan for product launch, and a business model to match. Six months later, they had accelerated their launch-to-scale and became part of the company's growth narrative.
Workshops and in-person sessions aren't the thing you do instead of the work. Done right, they are the real work — the place where everything afterward is clear, has direction, and holds together.
I love leading these workshops. Watching the eye-rollers become believers, witnessing leaders leave genuinely aligned, seeing the moment when one idea in a room changes the direction a company is heading. And we leave Slack outside with the jumbo cookies.