What if annual planning no longer fits the world we live in? In this episode of Pure Signal, the team explores why traditional playbooks fall short in an AI-driven era and how leaders must rethink priorities, timelines, and team structures to stay competitive.
With 2026 around the corner, Kevin Erickson, Jake Carter, and Ryan Medellin explore the tension between bold innovation and responsible execution, questioning whether traditional planning models can keep pace with the speed of change. Pulling insights from real client conversations and the recent All-In Summit, the episode explores what AI-first planning actually looks like: budgeting for compute and data readiness, rethinking project structures, balancing near-term experimentation with long-term transformation, and most importantly, investing in your people. This is the year leaders can’t afford to default to copy-paste plans.
Whether you're in strategy, innovation, or delivery, this conversation offers a clear-eyed framework for how to think, plan, and lead in a future that’s already here.
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Quotes
"Getting your employees upskilled when it comes to AI and how to be effective is really important right now. And then you pair that with some selective hiring. You don’t have to go replace your entire workforce. But you do need the injection of fresh thinking." – Jake Carter
"I would encourage our listeners to really focus more on the strategy. Put a ton of thinking about the strategy of where you want to go, the outcomes that you want to have, and let that start to dictate where you're at versus the mechanics of the buildup of classical elements of that. That will come. In fact, I think you should be using AI driven tools to be able to accelerate that." – Kevin Erickson
"We all want to be part of something big. We want to be part of something that gets us excited to go into the office. I want leaders that dream big, but I also want to be able to see that vision and how I can help support getting there." – Ryan Medellin
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Time Stamps
00:00 Intro
00:30 Waymo rides and the All-In Summit
08:40 How AI-first companies are built different
11:00 The future of annual planning
17:00 Supporting the entire organization
21:00 Upskilling your teams for 2026
24:00 The power of curiosity
28:00 Let people own outcomes, not just projects
34:00 What leaders need to be focusing on
37:00 Boldness doesn’t mean recklessness
42:00 Final takeaways
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Links
Connect with the hosts on LinkedIn!
