Happy February! Already one month of the year in the books. Things are off to the races for my clients.
Now that we’re fully wrapped up with annual planning and roadmapping, I wanted to circle back and share a little more detail on how that process actually works in practice. If you recall, before Christmas I shared the planning document I use with clients to help them dream big about the year ahead (message me if you didn’t get it and would still like a copy). After all those dreams get poured onto paper… what happens next?
This is where the rubber meets the road—and, in my opinion, one of the primary functions of a CFO. The CEO answers the questions “what” and “why.” The CFO helps answer “how” and “when.”
After a client completes their goal-planning reflection, they send it over and I start my initial analysis. I go through their responses, make notes, highlight areas that need clarification, and which goals we may need to tease out more on. I start to identify priorities and “weights” across the different components of what will make up their ideal year—so I know exactly where we need to drill in. From there, I send over a scheduling link and we get time on the calendar together.
That session is what I like to call a
collaborative dreaming session. The goal is to define what truly makes up an ideal year. There are a few guiding principles: we’re not solving yet, we stay focused on the what and why, nothing is off limits, and we don’t say no to ideas. This is where the peer-leadership side of the CFO role really comes into play—“I’m in this with you, and I want to help make this an awesome year.” A lot of this session is coaching and mindset-driven, making sure what we’re putting on paper is truly aligned with what the owner wants. If goals are artificial or half-hearted, the plan will eventually veer off track—and that never ends well. So we really take the time to suss everything out in what ends up being an intensive, but highly fun, session.
Coming out of that meeting, I usually have copious notes and a strong sense of how to frame the year. Then I head into the
CFO lab. This is where the financial planning and modeling kicks in. I take the client’s vision and start mapping it into a detailed financial roadmap—layering in their business reality, market conditions, feasibility, team capacity, and timing. It’s mentally taxing but incredibly fun—like working a real-life, dynamic puzzle, or painting a work of art piece-by-piece. We start placing initiatives into specific months, projecting business performance, layering in constraints (time, people, market forces, customer dynamics), mapping required resources and expected outcomes, and making sure there’s still room for distributions, tax payments, debt obligations, and—most importantly—a healthy bank balance throughout the year.
Beyond the numbers, a critical part of this process is driving
action. We do this in two ways. First, we maintain an overarching goals sheet that we revisit in every monthly CFO session. Second, we translate those goals into clear, actionable next steps. After each session, we define the handful of actions that need to happen before the next meeting to keep the plan moving forward and the year-long outcomes on track.
From there, it’s back to monthly business-as-usual: running the business, taking action, adjusting as needed, and staying focused on what matters—so that by year-end, all those puzzle pieces come together into a clear, cohesive masterpiece.
I wanted to share a bit more detail on what this process actually looks like behind the scenes, in case there are a few nuggets you can apply in your own planning. If you ever want to chat through the nuts and bolts, I’m always happy to.
All the best until next time—and here’s to turning 2026 into a Mona Lisa of a year. 🎨

