Future Facing Engineering Leadership with John Szeder

Future Facing Engineering Leadership with John Szeder

Engineering leaders today are navigating rapid change, rising expectations, and the accelerating impact of AI. In this Leadership Briefing, Technology Executives Club® founder Alex Jarett speaks with engineering leader and CTO John Szeder about how to lead with a future facing mindset and what the coming years will require from executives.

A Leadership Ritual Learned on a Northern Canadian Farm

John begins with an unexpected story from his childhood. At the end of every harvest season, his father would walk the fields, look at the results of the year, and reflect on what came next. Good year or bad year, the ritual was the same: assess the outcomes, consider what could improve, and mentally prepare for the next cycle.

That practice shaped how John approaches engineering leadership today.

“Growing up on a farm and leading engineering teams aren’t as different as you might think.”

When you ship a product, finish a major cycle, or close out a year, you reach the same moment:
What did we learn, and what will we do differently next year?

Why Postmortems Alone Don’t Create Progress

Many organizations run standard postmortems: three columns, a shared doc, a meeting. Then the process ends and the commitments fade.

John argues leaders need something deeper.

• Identify what you truly want to improve
  
  
• Capture the commitments in writing
  
  
• Revisit them regularly
  
  
• Hold yourself and the team accountable
  
  

He often uses a simple and effective cadence:

→ 3 months discussing the improvement
→ 3 months rolling it out
→ 6 months enforcing accountability

This keeps improvements real instead of theoretical.

How Leaders Should Begin Their Own Future Facing Process

John recommends a blend of individual and team reflection.

First, take time alone. Even a half day can reset your thinking for the year ahead.
Then involve your team. The person who becomes the “curator” of improvement for the coming year may not be who you expect. It might be the most passionate contributor, a product partner, or someone who sees a better path forward.

The outcome should be a shared commitment:

“What are we going to do to make next year better?”

Then revisit that question at the midpoint and at the end of the next cycle.

Three Priorities Every Leader Should Consider for 2026

Alex asked John for the top priorities leaders should put on their improvement list. John’s response focuses on three areas with the highest impact.

1. Hands-On Engagement with AI

John recently spoke with a product leader who spent a weekend modifying code in Cursor just to understand how modern AI-assisted workflows behave. That initiative is exactly what leaders should model.

→ If you haven’t used AI tools yourself, you can’t effectively lead AI-driven initiatives.

This doesn’t require a massive budget. It can be as small as:

• Paying for a tool personally
  
  
• Testing workflows
  
  
• Using AI as a team member for everyday tasks
  
  
• Understanding productivity gains firsthand
  
  

We are now fully in the age of AI. Leaders cannot stay on the sidelines.

2. Becoming Significantly More Efficient

John points to Salesforce’s announcement that AI-driven productivity will reduce headcount needs by thousands. The message for leaders is clear:

→ The bar for output is rising.

John predicts the strongest performers next year will be those who become ten times more productive through AI-driven leverage. That means:

• Managing larger teams
  
  
• Delivering more output
  
  
• Using AI as a performance multiplier
  
  
• Identifying who is adapting and who is resisting the shift
  
  

Efficiency isn’t optional anymore. It’s survival.

3. Leading Through Rapid and Increasing Change

John notes that the pace of change is increasing, not slowing. Leaders will face difficult staffing decisions, shifting talent needs, and organizational redesign.

At three different companies, John earned the nickname “Darth Szeder” because he had to make hard staffing calls during accelerated periods of change.

He emphasizes that leaders must learn to:

• Move quickly
  
  
• Spot the people who embrace AI
  
  
• Recognize those who are falling behind
  
  
• Make decisions that keep the organization aligned with the future
  
  

And debates around the legality of AI training data or model settlements won’t slow the momentum.

→ “The genie doesn’t go back in the bottle. Once the settlements are done, these tools will still be here.”

Refusing to use the tools puts leaders at a disadvantage.

Navigating the Coming Technology Shift

Alex adds an important context. This moment feels similar to previous industrial transitions. It’s not just disruption. It’s the start of a new era.

Leaders who embrace change, adopt the tools, and guide their teams responsibly will be the ones shaping what comes next. Those who worry about responsible AI should become the voice inside their organizations helping to drive ethical, practical adoption.

Final Thoughts

This discussion is part of John Szeder’s ongoing Executive Engineering Leadership series for Technology Executives Club®. His message is clear:

Reflect consistently.
Commit to improvement.
Engage with AI directly.
Lead through change with clarity and speed.

John welcomes conversations with executives who want to understand the implications of today’s technological shift and prepare their organizations for the future.

Learn more about John and see all of his thought leadership videos on his channel here.