Planning Season: Don’t Just Plan the Work. Plan the System.

Actual Lucid board output from one of our annual team planning sessions

Guess what time it is? If you’re like most teams, you’re knee-deep in annual planning. You’re defining next year’s goals, clarifying priorities, and mapping out initiatives. It’s a familiar rhythm: we plan what we’ll be doing and how we’ll measure success. In doing so, however, many teams miss the why, the how, and the who. Why does this work matter? How will it actually get done? Who will make it happen?

Those questions help determine whether a plan turns into meaningful progress... or just another spreadsheet of good intentions.

That’s where the classic People, Process, and Technology framework comes in. It’s a tried-and-true way to evaluate how effectively your team is operating. Personally, I’d argue it’s not quite enough. When I guide teams through planning, I like to assess across six key dimensions:

1. Strategy

Where are we going and why? Is there a clear vision and roadmap, or just a list of projects? It’s easy to focus on tactics and deliverables, but make sure your strategy connects back to the “why.” People need to understand how their work ladders up to something meaningful.

2. People

Who’s doing the work? Do they have the right skills, experience, and support? Are there new capabilities you’ll need to hire for next year? Think beyond individual development goals. What collective coaching or training could lift the whole team?

3. Process

How is the work getting done? Are there bottlenecks, quality issues, or decision-making delays? All of these signals point to process problems. Ensure you're proactively identifying and addressing these issues. When processes are intentional and inclusive, work flows better and outcomes improve.

4. Technology

Are your tools helping or hindering? Look at your team’s tech stack with fresh eyes. Are there redundant systems, outdated tools, or opportunities to modernize? Sometimes, streamlining tools is the simplest way to reclaim lost time and energy. New tools can also re-energize employees, especially if they're perceived as vital new tech to master.

5. Structure

How is the team organized? Are roles and reporting lines clear? Structure shapes how work and communication flow. If you’re shifting priorities or scaling new areas, it might be time to adjust your org chart or clarify ownership.

6. Communication

This one’s huge and often invisible until it breaks. Does information flow freely and effectively? Do people feel safe speaking up? Which teams feel continually "left out of the loop?" One way to asess: map out your team’s communication channels. Where are the gaps, overlaps, or black holes? Then simplify. The best communication systems are the ones people actually use.

When I’ve led teams through this annual planning exercise, we’ve used a big digital whiteboard. Each of the six dimensions gets its own section and everyone adds notes for what’s working well and what needs improvement. The conversations that emerge are gold. They surface blind spots, reveal strengths, and lead to simple but powerful changes.

So please, carry on and keep planning. Set goals and define initiatives for 2026. But while you’re doing that, take a step back and assess the system that will make those goals achievable. Your future self (and your team) will thank you.

What frameworks or rituals help you approach annual planning with more intention?