Winning Moves | 102026

Stress-test what's working and brainstorm what's next — before you walk into annual planning.

October 13th, 2026, from 1:00–1:30 pm ET

Winning Moves brainstorm season shouldn't start from a blank whiteboard.

Every fall, teams sit down to evaluate their Winning Moves and dream up new ones for the year ahead. Most of the time, that conversation starts from gut feel and whatever's top of mind in the room, not from a real read on what's actually worked. The new Ask Patrick changes that. It can run scenarios against your actual plan data and walk your team through scripted prompts, so you go into that session already knowing what's holding up and where the real openings are.

This session is for you if:

You're heading into annual planning and need to know whether your current Winning Moves still make sense
You've ever sat in a Winning Moves brainstorm that stalled out because nobody knew where to start
You want a faster way to stress-test an idea before it becomes a bet for the year
You're looking for a repeatable way to run this exercise instead of reinventing it each planning cycle

What you'll walk away with

This isn't a product tour, it's a look at how AI can turn Winning Moves work into a guided, repeatable exercise. Here's what we'll cover:

1. Evaluate your existing Winning Moves

Are these still the right bets? See how to prompt Ask Patrick with scenario questions that test each current Winning Move against what's actually happened in the market and in your plan data this year, so you know which ones earn a spot on next year's plan.

2. Brainstorm new Winning Moves, faster

Where's the next real opportunity? Learn how to use Ask Patrick to run structured brainstorm prompts, turning a blank-page exercise into a guided conversation that surfaces real candidates fast.

3. Walk into annual planning ready

Are we planning from evidence or guesswork? See how combining scenario-testing and scripted brainstorming means your team shows up to annual planning with a shortlist of tested moves and vetted new ideas, not something built live in the room.

Meet Ryan Walcott

Head of Product

Ryan Walcott is Head of Product for Rhythm Systems, specializing in helping firms with over $10M in revenue focus and align their teams to accelerate their growth by establishing a healthy rhythm of strategic thinking, execution planning, and doing the work.

He leads the design, development, and implementation effort of the Rhythm software which enables clients to work on and record strategy, build effective execution plans, collaborate with their teams, and see the status of plan execution using dashboards. This is what allows clients to achieve success and grow their business.

Meet Jessica Wishart

Rhythm Product Manager

As Sr. Product Manager at Rhythm Systems, Jessica gets to collaborate with our amazing customers and internal teams to understand problems, brainstorm possibilities, and launch product solutions. Our tools help people achieve their goals through better execution habits.

Jessica's educational background in counseling helps her deeply listen and empathize with the needs of our customers and the market, and our strong execution culture helps us deliver great products with the same focus, alignment, and accountability our methodology provides for our customers.