Your Annual Strategy Meeting: A Playbook for Leaders with Dan Clifford

Dec 10, 2025

Dan Clifford, a strategic advisor and former CEO, shares insights on planning impactful annual strategy offsites. He emphasizes the importance of pre-planning and choosing inspiring locations to foster creativity. Dan also discusses leveraging data and AI to inform discussions while ensuring the right attendees are present. They explore strategies for maintaining focus during sessions, the significance of agenda flow, and how to effectively follow up to ensure accountability and continuous improvement for the year ahead.

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ADVICE

Schedule And Block Time Early

Get your annual planning on the calendar well in advance and block the team's time.
Clear calendars and set a prep schedule a month ahead to ensure focus and commitment.

ADVICE

Choose An Inspiring Location

Hold your offsite somewhere that inspires and offers indoor-outdoor space.
Avoid windowless hotel rooms and choose locations that boost optimism and movement.

ADVICE

Budget Hacks For Venues

If budget is tight, swap rooms with peers or use law firm/bank/museum spaces for free.
Use creative local venues to get quality space without hotel premiums.

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How do you run a year-end strategy offsite that’s focused, fun, and actually gets results

In this episode, Bill is joined by strategic advisor Dan Clifford to walk you through how to plan and execute a high-impact annual strategy session offsite. From pre-planning to post-event execution, Dan shares his years of business knowledge with the audience today. Whether you’re a founder, CEO, or senior leader, this conversation will help you rethink your next big planning meeting and make sure it drives real outcomes for the new year to come. You’ll learn how to choose the right environment for deep thinking, gather and synthesize the right data before you meet, build an agenda that creates clarity and momentum, and ensure your team actually follows through long after the offsite ends.

Topics explored in this episode:

(03:25) The Pre-Planning Stage

*If it’s not on the calendar, it doesn’t exist.

*Find a good off-site location that has both indoor and outdoor options..

*Don’t just go through ‘the motions’ of an agenda; schedule downtime, walks, and thinking time.

*Think about what success would look like at the end of the event.

(19:05) The Pre-Meeting Stage

*If you have more than 8 people in the room for year-end planning, you need to hire a facilitator.

*Get your data and numbers together, as well as a company-wide survey on what’s working and what’s not.

*Bill likes to use AI to summarize the data collected and offers some tips on how to leverage this fully.

*With a critical meeting like this, set the expectation with senior leadership that there will be no laptops and no cellphones.

(41:40) The Agenda

*Start with big-picture thinking, then narrow into what the action plan looks like.

*What resources do you currently have vs. what you need to achieve your BHAG?

*Walk out with 3–5 big priorities.

*Bill likes to start with good news, human connection, and a bit of play before the big-picture strategy conversations begin.

(31:35) The After

*Don’t just set it and forget it. Schedule weekly follow-up meetings to keep momentum.

*Focus on Q1 for now; don’t try to forecast Q2-Q4 yet. A lot can change in 90 days.

*Don’t be afraid to use AI to help you along this process!

Thanks to Dan Clifford for being on the show!

Connect with Dan: https://www.linkedin.com/in/danclifford/

Bill Gallagher, Scaling Coach and host of the Scaling Up Business podcast, is an international business coach who works with C-Suite leaders to achieve breakthrough growth.

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