"Automate or Fall Behind" sounds dramatic, but it points to a quieter question leaders are facing in 2026: are our systems designed for how we want to lead? In this episode of Reflect Forward, I sit down with Nadav Wilf, founder and CEO of Align Coach, to explore how AI and automation can either amplify leadership clarity or reveal where teams still rely on outdated structures. This is not a conversation about chasing the latest tools. It is about building a strategic AI vision, addressing resistance to change, and creating the training cadence required for new ways of working to actually stick.

Most leaders are already experimenting with AI in some form. They have a ChatGPT subscription. They use AI to draft emails or summarize notes. Nadav draws a critical distinction between manual AI and automated AI. Manual AI creates speed in isolated moments. Automated AI creates leverage across the organization. Without that shift, companies remain stuck in fragmented experimentation rather than building scalable systems.

A central theme of this conversation is that AI adoption fails more often due to leadership behavior than to technical complexity. Leaders underestimate the importance of vision, overestimate how quickly habits change, and stop training too soon. Nadav breaks down why consistency is the determining factor. When training stops, people revert to old workflows, and leaders walk away with false proof that AI does not work.

I grounded the conversation with a real-world example from StoneAge. Instead of purchasing expensive accounts payable automation software, we built a custom GPT layered on top of our existing ERP system. In a matter of weeks, we automated manual work, accelerated internal learning, improved job satisfaction, and avoided a six-figure software spend. The win was not just technical. It was cultural. The team experienced firsthand how AI could remove low-value work and free them to focus on higher-impact responsibilities.

The episode also explores the human dynamics that quietly shape change efforts. Nadav introduces the concept of elevators, resistors, and supporters. Elevators lean in and move change forward. Supporters follow the dominant energy. Resistors, often unintentionally, can stall progress by clinging to familiar systems. Leaders who fail to name these dynamics allow resistance to run the strategy by default.

Throughout the conversation, one message becomes clear. You do not need to understand every detail of AI to lead effectively in this era. You need to take responsibility for the direction, cadence, and mindset your organization brings to it. AI is not a side project. It is an operating decision.

Automate or Fall Behind is an invitation to reflect on what you have been carrying that technology can now handle, and to move forward with intention rather than urgency. Leaders who do this well will not just be more efficient. They will create calmer teams, better work, and organizations designed for how people actually want to lead and contribute in 2026.

Connect with Nadav

Leading AI Enhanced Teams: Download our step by step guide for leaders ready to embed AI into their core operations.

Complimentary AI Strategy Session: For those with a desire for efficiency through AI implementation book your 30-minute Align AI Strategy Session to assess ROI for becoming an AI Intelligent Company.

For AI and Automation latest news and implementation, connect with Nadav on LinkedIn

Connect with Kerry

Visit my website, kerrysiggins.com, to explore my book, The Ownership Mindset, and get more leadership resources. Let’s connect on LinkedIn, Instagram, or TikTok!

Find Reflect Forward on YouTube: https://www.youtube.com/@kerrysiggins-reflectforward

Find out more about my book here: https://kerrysiggins.com/the-ownership-mindset/

Connect with me on LinkedIn: https://www.linkedin.com/in/kerry-siggins/