Vision is the spark. Planning is the flame.
^ Me, Annual Strategic Planning 2026
It's the most wonderful time of the [agency] year!
Call me a nerd all you want, but tying numbers to decision making and mapping vision to an actionable plan is my FAVORITE agency activity.
When I look back at how we scaled from a messy startup to nearly $10M and 60+ people, there were a handful of decisions and practices that consistently moved us forward. Big growth is often connected to a big break, and while we had a couple of those as well, what really made the difference was the consistency we had in planning. That's what allowed us to capitalize on the big breaks and continue to grow even when things were tough. Year after year, it created the clarity that made everything else possible.
Why you should never skip planning season
Planning turns fog into clarity. Without a plan, we just react quarter by quarter. Planning gives you a beacon that connects today’s decisions to year-end outcomes. It’s the difference between feeling busy and knowing you’re moving the agency toward something specific.
Planning prevents expensive mistakes. Hiring missteps, margin crunches, and “oh no, we’re overspent” moments are usually the result of not running the numbers through different scenarios. Annual planning forces you to test those moves on paper before you commit in real life.
Planning creates alignment across leadership. When you don’t do this work, people feel scattered and struggle to work towards a common goal. Planning season makes sure finance, ops, delivery, and people leaders are moving forward with the same roadmap.
Planning builds team confidence. Teams get anxious when leadership feels uncertain. When they know there’s a clear path and understand why things are changing, they rally instead of resist. Planning gives you that narrative.
Planning reveals hidden risks and opportunities. It’s not just about numbers and headcount. SWOT conversations surface things you’d otherwise miss: an under-utilized service line, a potential leader ready to step up, or a looming client dependency that could derail everything.
Planning sets the rhythm for the year. It’s not a one-and-done deliverable. The plan becomes the compass for quarterly check-ins, monthly decisions, and weekly priorities. Skip planning, and you spend the rest of the year improvising.
Planning fuels leadership growth. This is an essential skill for founders, but teaching ops, finance, and people leaders how to think this way builds capacity across the agency. You stop being the only one holding the strategy, and your leaders learn how to build it with you.
Why you probably don't do it (or at least, all of it)
Based on the conversations I’ve had with founders and leaders this year, strategic planning is massively needed… and missing.
And after working with founders who struggle to sit down and translate their vision into an actionable plan, I think I know why.
Maybe you can relate:
Attention span is short. You finally sit down to plan… and ten minutes later you’re back on Slack.
To-do list is long. There’s always something that needs you today screaming louder than what you'll be doing 6 months from now.
Granular thinking feels boring. Spreadsheets and headcount forecasts don’t exactly light you up.
Finances feel overwhelming. There are numbers everywhere, but no clear story connecting them.
Decision-making feels scary. You start weighing the options and suddenly nothing feels like the right move.
And the kicker: “Where do I even start?” Vision, numbers, roles, priorities... pulling it all into one plan feels impossible.
This is why strategic planning doesn’t happen and why agencies end up running on reaction instead of intention.
Ok, so it doesn't feel sexy...but turning vision into decisions sure is
This is a process that can seem complex, but it's not complicated. Here's how I go about it:
Start with the numbers. First I outline expected revenue and profit based on realistic sales targets, broken out by service. Then, map out the team we’ll need to hit those numbers, including new hires, raises, and the roles that would evolve as people grew.
Pressure test the budget. Then I account for known expenses and future investments, then compare scenarios: what if sales land higher, or lag? What does that mean for hiring, margins, or capacity? What if we adjust our ratios for Cost of Service, Operations, Growth, or Profit? How does that affect actual spending, what we can invest in or need to pull back on?
Bring the team to the table. Next, I facilitate an off-site workshop for our leadership team where we look at the agency and their roles through a SWOT lens: what was working? What wasn’t? What do they want more of, and what are they ready to hand off? Where do we want to double down, pull back, or shift altogether? The outcome is clear initiatives and priorities for role evolution, hiring, service development, and internal innovation.
Translate into execution. We then apply the plan to our quarterly planning reviews and make sure every initiative has clear next steps, so we actually make progress toward those goals.
Close the loop with the team. Finally, we put together an Annual Recap presentation for the team that walks through the developments we made internally over the past year, how the numbers had landed for the agency and each department, what we expect to accomplish over the next year, and why that's important.
Granted - it's a lot of moving pieces. And while planning doesn't stop the chaos, it does give us clarity inside of it.
That’s what makes scaling feel inevitable, not accidental. The leadership team knows what decisions need to be made, when to make them, and how they'll ripple through the business. The team knows why changes were happening, why we're investing in certain areas, and how their roles connect to the bigger picture.
Why this shouldn't rely solely on you
In my opinion (and, ya know, experience), strategic planning isn’t optional if you want to build a thriving agency. It’s a requirement. And it’s one of the most valuable skills you can pass down to your leadership team.
If the plan is rooted only in a founder’s head, the agency is limited by that one person’s capacity to carry it. But when leaders at every level know how to think through sales, profit, roles, and initiatives, decisions become more aligned and the agency becomes more resilient.
Join us for SHIFT: 2026
This fall, we’re opening up the exact process we used year after year and guiding a group of leaders through it.
SHIFT: 2026 is a 12 week cohort for agency leaders who want to walk into the new year with clarity and foresight.
October-December 2025 (plenty of time to plan without pulling focus from current priorities)
Biweekly calls, Tuesdays at 11am CST (guided coaching so you don’t have to figure it out alone)
Slack support (so you can check in as you work through your pieces)
Thought exercises & resources (to shape your decisions between sessions)
Call recordings & notes (but don’t miss - the conversations are the gold)
$1,500/mo per person (our beta price, before we raise for future rounds)
This is great for founders & CEOs, but don’t forget operations, finance, and people leaders responsible for translating vision into a plan need this skill set as well.
2026 is right around the corner. We all know even the best plans will be affected by surprises.
Will your agency be stuck reacting, or will you be equipped to lead through the unexpected?