The Best Time to Plan for Next Year Is Right Now

Most mid-market firms wait until Q4 to begin strategic planning, and that timing is precisely why most strategic plans do not produce results. By the time partners gather in November, the calendar is already compressed, the year has been half-decided by default, and what gets called a strategic plan is usually a budget conversation dressed up in better language. Good intentions get documented. Meaningful decisions rarely get made.

The window that most firms overlook is the one that is open right now. Tax season is behind you, partners have room in their calendars to think past next week's deliverables, and there is enough runway remaining in the year to actually move on to whatever the conversation surfaces. That combination is rare, and firms that recognize it and use it deliberately tend to enter the following year with clarity and momentum that their competitors do not have.

Why Timing Changes Everything

Strategic planning done in November tends to produce incremental thinking. The year is nearly over, the pressure is to close strong, and the instinct is to plan cautiously because there is no time left to course-correct if something goes sideways. The result is a plan that looks a lot like last year's plan with modest adjustments to the numbers.

Planning done with a real runway ahead of you produces different conversations. When there is time to actually execute, leaders are more willing to take an honest look at what is working and what is not, to ask the harder questions about service line profitability, partner capacity, and firm positioning, and to make decisions rather than defer them. The quality of the thinking changes when the calendar is not already working against you.

The Strategic Planning Process

The firms that get the most out of strategic planning are the ones that go into it prepared to have uncomfortable conversations rather than productive sounding ones. That means getting clear on where the firm actually stands, not where leadership says it stands, on questions that tend to get avoided when time is short.

A few of those questions are worth naming directly. Which service lines are genuinely profitable, and which ones are being subsidized by the work the firm is better known for? Where are partners stretched thin enough that growth is creating risk rather than opportunity? How is the firm positioned in a market that is consolidating quickly, and does that positioning reflect what the firm is actually building toward? What is the growth path: organic, inorganic, private equity-backed, or deliberately independent? Each of those paths requires different decisions, and the worst outcome is drifting toward one without having chosen it.

Good strategic planning does not generate a long list of initiatives. It generates a short list of decisions with clear owners and a realistic timeline, because firms with too many priorities are really just firms without any.

Planning Session vs. Planning Exercise

Most partners have sat through planning sessions that produced a well-organized summary of conversations everyone was already having, followed by an action list that was quietly abandoned within 90 days. The reason is usually not a lack of good ideas. It is a lack of honest alignment on the decisions that actually matter, and a process that prioritizes comfort over clarity.

The planning sessions that produce real results tend to share a few common traits. Leadership comes in with a genuine willingness to evaluate what is not working, not just celebrate what is. The conversation is facilitated by someone who is not managing political relationships inside the room and can push back when the discussion drifts toward the comfortable. The session ends with commitments that have names and dates attached to them, not themes and intentions. The difference between a planning session and a planning exercise is whether the firm makes decisions it will actually keep.

Final Word

The firms that lead their markets do not get there by planning at the last possible moment and executing on whatever is left. They choose their direction when they have the time and bandwidth to choose it well, and they build the year ahead around that direction rather than trying to retrofit a plan onto a year that has already started shaping itself without one. The window to do that work is shorter than it feels, and it is open right now.

Hollinden facilitates strategic planning sessions for mid-market accounting, advisory, and M&A firms. If your leadership team is ready to move from deferred conversations to committed decisions, we can help. Learn more about our strategic planning services at hollinden.com/strategic-planning.