
The Authentic Advisor
Is The Two-Day Strategic Planning Retreat Dead? If so, What Replaces it? With Russell Cummings, SHIFFT, Australia
If you run (or are thinking of running) strategy days, this episode's for you. Listen in to Mindshop Expert Russell Cummings, SHIFFT. He has 30 years’ experience running strategic planning retreats for clients. Russell explains why the two-day retreat isn't dead, but it has significantly evolved. Sharing how his pre-work system works, so he walks in with a ‘straw man' plan that's already 80-90% done, so the people in the room can focus on what actually matters. What else is covered in the episode? AI, done right. Russ is candid about where he thinks AI genuinely helps (diagnostics, competitor analysis, pulling interviews into a first draft) and where it backfires, eroding into 'AI slop' that erodes trust. Bespoke over cookie-cutter. How pre-interviews and surveys let him meet each client exactly where they're at, instead of forcing a one-size-fits-all process. Making it stick. Russell shares his cascading cadence model: a 3-year plan > annual > quarterly > 90-day cycles and the killer line 'Don't pay me for the plan, pay me for the implementation.' Don't miss this episode, it's a practical, field-tested playbook for sharper, more impactful strategy days.






