As fractional agency managers, we’re often tasked with leading annual planning and strategy sessions. It can be incredibly hard for an agency with a small number of employees wearing many different hats to take the time out of the everyday management of the business to do this, so we want the time to be well-spent and effective; structuring the discussions and decision-making process effectively is almost as important as the outcomes themselves. 

Often this is the first time our agency clients have had a structured, formal planning session, so it’s important that we help them create a framework for planning that will be valuable to them both in how they approach day-to-day decisions and in how they build toward future company value.

Each session in our agenda builds on the last, helping agency leadership create a clear, realistic vision of the year ahead while keeping an eye on longer-term goals.

We draw inspiration from Traction by Gino Wickman and the entire EOS system, but we’ve adapted the process to better suit the needs of smaller agencies, especially those going through annual planning for the first time.

Here’s how we typically structure these sessions, why we do it this way, and how this approach helps agencies align leadership and operations for the year ahead.

(Just want the exact agenda we use? You can download it here.)

Why Structure Matters

• Aligning leadership around core values and vision.
• Prioritizing strategic initiatives that will drive growth.
• Ensuring financial discipline and operational efficiency.
• Clarifying roles, responsibilities, and accountability.

To accomplish all that in a day or two, we use a clear structure and get buy-in on that structure beforehand. This keeps conversations focused and prevents operational minutiae from derailing strategic work.

Setting the Foundation

Why?

Before diving into strategy, we align on identity and direction. Without clarity on the agency’s core values and ideal client/employee experience, execution tends to be scattered.

How?

We start with two foundational discussions:

• Core Values – Defining the non-negotiables that guide decision-making, hiring, and client relationships.
• Ideal Client & Team Experience – Mapping what “good” looks like in our best client relationships and internal culture.

These conversations ground the rest of the planning. If an idea doesn’t align with these values or experiences, it doesn’t belong in the strategy.

Defining the Long-Term Vision

Why?

Without a defined destination, prioritization becomes guesswork. For agencies in the $1M–$3M revenue range, we typically focus on a 3–5 year vision. This is far enough away to inspire but not so far that it feels abstract.

How?

We ask the owner:

• What does success look like for you?
• What would let you walk away from this business and say “I did something amazing."?
• What is your ideal exit scenario?
• What are your primary motivators for being a business owner and running this agency? 

Even if an exit isn’t in the cards, thinking in terms of enterprise value and long-term outcomes helps make smarter near-term decisions, like deciding how to invest funds or knowing which work to take and which work to turn down. We also include a session on enterprise value. What are the capabilities and services unique to this agency and how can we double down on those unique things to create more sellable assets and value for the agency?

Structuring for Scale

Why?

Agencies with good demand and pipeline will fail if they can’t scale operationally at the same pace they can grow revenue, so ensuring that each and every function of the agency is covered and someone is accountable for it is very important.

How?

We define every core function in the business and assigned:

• An Owner - One person accountable (even if others help execute).
• A KPI - A single number that measures success.
• Key Responsibilities - The function’s day-to-day focus.

This helped us identify gaps, overloaded roles, and where we needed to hire or shift responsibilities. It also made it easier to create clear job descriptions as we scale and gave us concrete measurables to bring to everyday management and weekly team syncs. You can read more about functional charts and charters here.

The Next 12 Months

Why?

Big visions fail when they aren’t broken down. Annual planning must connect medium- and long-term goals to immediate actions.

How?

We deep dive into the current financials of the agency, present forecast targets, and align on a topline annual goal taking into consideration what work had already been booked. We also align this goal with the 3-5 year vision and exit strategy wish list, ensuring annual revenue and profit goals are aggressive but attainable.

After analyzing the agency’s current financials, finalizing topline targets, and aligning annual goals with the broader 3–5 year vision. From there, we define:

• Leadership Initiatives - The most critical things we had to accomplish in the next 6 months.
• Investment Plan - How much can be allocated to team growth and tools
• Gap Analysis - What must happen in the next 12 months to support the longer-term vision, even if not addressed immediately

Execution and Accountability

Why?

Even the best plans fall apart without follow-through. In small agencies, leaders are often stretched thin, so accountability systems are essential.

How?

• Meeting Cadence  - Restructure meetings to drive clarity and momentum
• OKRs & Metrics - Define success indicators for each function and break goals down to manageable timelines
• Accountability Framework - Ensure every leader owns their area’s results

This ensures the planning doesn’t just live on whiteboards and in slide decks, it actually gets executed.

Annual planning isn’t just about setting goals; it’s about aligning leadership, defining accountability, and ensuring execution happens. By using principles from Traction and EOS and leaning on our client and employee experience frameworks, we were able to turn big ideas and long term vision into a structured, actionable plan that will guide our client’s next phase of growth.

It’s never too late to put together a plan for the next 12 months. Want our exact agenda for a small agency leadership planning session? Download it here.