Leadership decisions are never purely about authority. Every choice has tradeoffs — team dynamics, organizational alignment, timing, and trust.
The human side of engineering at scale — navigating resistance, quantifying hidden costs, and building the conditions where teams make good decisions on their own.
Series · 3 parts
Scaling engineering leadership isn't a technical problem—it's about distributing real authority while keeping the organization coherent. You do this by making decision-making transparent and collaborative, structuring teams to force ownership down instead of hoarding it at the top, and recognizing that your biggest obstacles are often your most capable people, who need strategy ownership and clear guardrails, not workarounds. Get the people architecture right and the technical decisions almost make themselves.
View full series →The best decisions in engineering aren’t made by the loudest voice or the highest title — they’re made through genuine collaboration with clear final authority. Here’s how to build a culture where people are heard, trade-offs are understood, and decisions actually stick.
I had the opportunity to work closely with John during some of the most challenging and fast-moving initiatives at Metrc, including the Retail ID program. He consistently brought a strong combination of technical depth, ownership, and steady leadership to the table. …
Chief Product Officer - Retired, Metrc, LLC
Worked with John at Metrc · May 2026
I had the opportunity to work with John and always appreciated his willingness to engage, learn, and push through challenges. He brings a strong work ethic and a thoughtful approach to his responsibilities, consistently showing up ready to contribute and improve. …
Chief Technology Officer, MedSuite
John Reported to James at Ministry Brands · April 2026
I’ve known John Tolar professionally for about 30 years. He’s just a solid guy one who’ll step into a tough situation and stay with it until it’s handled right. He’s smart and easy to work with, and people trust him. I’ve always respected how he handles being in charge. …
How you structure your engineering org isn't just an operational decision — it's a cultural one. The right structure pushes ownership down to the people closest to the work, builds future leaders, and scales without losing accountability.
The hardest part of a major platform migration wasn't the architecture — it was the person who'd built what we were replacing. Rather than working around the lead developer's resistance, we made them the owner of the migration: formal title, a 90-day challenge, guardrails that protected quality without threatening autonomy, and recognition tied to the outcome. The technical migration succeeded because the people strategy came first.
Lead Software Engineer, Metrc, LLC
Reported directly to John at Metrc · April 2026