Scaling Up Podcast

10/12/2025

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 ex*****on, 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.

Join Bill in the Growth Navigator Coaching Program: https://ScalingCoach.com/workshop

Bill on LinkedIn: https://www.LinkedIn.com/in/BillGall

Bill on YouTube: https://www.YouTube.com/

03/12/2025

What if chasing “having it all” is exactly what’s making you miserable?

In this episode, Bill challenges what “having it all” means and explores what actually creates sustainable happiness for high-performing leaders. He shares moments from when he had money, success, and recognition, but still felt empty, and explains why joy often comes from subtraction of things.

Topics explored in this episode:

(03:40) Success Without Joy Is Emptiness
*Bill reflects on hitting financial and professional milestones; yet still feeling a strange emptiness.
*Challenge the belief that: achievement = happiness.
*External wins don’t always translate to internal satisfaction.

(07:15) Why the Gratitude Advice Doesn’t Always Work
*Break “Thanksgiving” into two core practices: Thanks (appreciation) and Giving (generosity).
*Start with gratitude for team members, family, and yourself.
*Let go of expectations, and express that through generous action.

(10:50) The Secret Might Be: Wanting Less
*True happiness often comes from removing things, not adding more.
*Reconsider the idea of “having it all.”
*Creating fewer goals for yourself actually might be the real key to fulfillment.

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.

Join Bill in the Growth Navigator Coaching Program: https://ScalingCoach.com/workshop
Bill on LinkedIn: https://www.LinkedIn.com/in/BillGall
Bill on YouTube: https://www.YouTube.com/

Visit https://ScalingUp.com to learn more about Verne Harnish, our team of Scaling Up Coaches, and the Scaling Up Performance Platform, which includes coaching, learning, software, and summit. We share how the fastest-growing companies succeed where so many others fail. We help leadership teams with the biggest decisions around people, strategy, ex*****on, and cash so that they can scale up successfully and beat the odds of business growth.

Did you enjoy today’s episode? If so, then please leave a review! Help other business leaders discover Scaling Up Business with Bill Gallagher so they, too, can benefit from the ideas shared in these podcasts.

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Scaling Up is the best selling book and world renowned growth platform from Verne Harnish and the team at Gazelles. Working with over 70,000 leaders, our programs and coaching have helped:

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