It’s Strategic Planning Season: How Executive Teams Can Prepare Now to Set the Stage for a Breakthrough Year
Fall marks the beginning of strategic planning season. Here’s how executive teams can prepare - and why bringing in a third-party facilitator can unlock alignment, clarity, and bold action.
Every fall, leadership teams across industries block out calendar time, dust off their planning decks, and gear up for “strategic planning season.” But let’s be honest - too often, these sessions fall short of their potential.
Instead of aligning around a bold future, teams get lost in PowerPoints, last year’s metrics, and debates over wordsmithing the mission statement.
It doesn’t have to be that way.
Whether you’re a founder-led startup or an established business in growth mode, now is the time to prepare for a strategic planning session that actually moves the needle.
Here’s how.
1. Align on the Purpose of the Strategy Session
Before booking the venue or building the slide deck, get clear on what this session is really for:
Are you resetting priorities after a big year of growth or change?
Are you building a 3-year roadmap tied to a new vision?
Are you re-establishing trust and clarity after a period of misalignment?
Aligning on the "why" will guide everything else: the agenda, facilitation style, and outcomes.
2. Do the Work Before the Work
One of the biggest mistakes teams make is showing up cold. High-impact strategy sessions begin with thoughtful pre-work.
Encourage your team to come prepared with:
A short written reflection on what’s working / not working
A review of current performance vs. plan
Ideas for strategic bets or directional shifts
Questions that will challenge assumptions
Distribute a prep packet or “Strategy Session Guide” 2–3 weeks in advance to make the most of your time together.
3. Design the Right Experience
Don’t default to what you’ve always done.
Instead, ask: What environment will help us think clearly and collaboratively?
Do you need a fresh offsite location?
Is one day enough - or do you need more white space?
Would breakout groups improve participation?
Should customers or employees be interviewed beforehand?
A well-designed agenda and environment can foster creativity, reflection, and decision-making.
4. Consider Hiring a Third-Party Facilitator
The most common barrier to productive strategy work?
Being too close to the business.
A seasoned external facilitator can help you:
Ask the hard questions
Challenge groupthink
Keep you focused on outcomes, not just conversation
Design a flow that balances vision, data, and execution
Bringing in a third party also allows your CEO or founder to fully participate - as a team member, not the meeting lead.
5. Start Now—Not Later
Great strategy sessions aren’t thrown together the week before. They’re crafted intentionally - with the right stakeholders, inputs, and structure.
Start now by:
Scheduling your session for late September or October
Clarifying the outcomes you want
Assembling key data and trends
Engaging a facilitator or strategic partner early
Make This Your Most Impactful Planning Season Yet
When done well, a fall strategy session sets the tone for the entire next year. It’s your chance to:
Align your team
Focus your energy
And build momentum heading into Q1
If you’re looking for a fresh approach or a proven guide to help your team scale with clarity and cohesion - we’d love to support you.
