Development in 2026: You Can’t Give What You Don’t Have

Start the Year by Investing in What Matters Most

As we kick off 2026, there’s a lot of noise about New Year’s resolutions, goal-setting, and fresh starts. But here’s the truth that most business owners need to hear: you can’t develop your team if you’re not developing yourself first. This is about development in 2026.

In our first podcast episode of the year, Episode 257,  I sat down with Brian Nolan to talk about personal and professional development and why the quiet months of early winter are the perfect time to focus on your “want-tos” instead of just your “have-tos.” Brian shared his personal development goal for 2026 (spoiler: it involves a Half Ironman), and we dove deep into how to develop one of the most critical roles in your field operations: the Field Supervisor.

[Watch the full episode here on Youtube]

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Your Window of Opportunity

Brian reminds us of something important: “discipline is remembering what you want”. When you’re in the thick of May, June, July, and August, you’re too busy to think about development. But right now? This is quiet time. This is when you can step back and ask yourself: What do I want my world to look like this time next year?

Your people are asking themselves the same question. They’re thinking about what the next year holds for them. If you’re not intentional about their development now, you might lose them to another opportunity…or worse, watch them plateau right when your business needs them to step up.

Picking your Personal Challenge & Leading by Example

Before we talked about developing anyone else, I asked Brian what he’s personally working on in 2026. His answer? He’s training for a Half Ironman in June with a goal to finish under 7 hours. But it’s not really about the race. It’s about what he said next: “Pick one big thing that scares you, that makes you work, that pushes you outside of who you are—so that after you do it, you’re different.” – a quote from Ryan Holiday. Brian is a big Daily Stoic fan!

That’s the mindset every business owner needs when approaching leadership development. It’s not about checking boxes. It’s about transformation, for yourself and for your team.

The Field Supervisor Role: Why It’s Make-or-Break for Your Business

We used the Field Supervisor role as our example throughout this conversation, but these principles apply to any key leadership position in your company.

Here’s what makes the Field Supervisor so critical: this person sits between your crew leaders and your operations manager. They’re responsible for making sure jobs come in “happy and under, “meaning customers are satisfied and the work is profitable. They supervise crew leaders, ensure training is happening, manage customer relationships, and drive financial performance.

Too many companies promote their best crew leader into this role and then wonder why things fall apart. Being great with a paint brush or a shovel doesn’t automatically make someone great at developing people, managing financials, and implementing systems.

So how do you develop someone into a true field leader? Brian broke it down into three essential areas.

The Three Pillars of Field Leadership Development

Pillar One: Emotional Intelligence

We start here because you can’t skip this foundation. A Field Supervisor who doesn’t understand their own communication style, who can’t self-regulate under pressure, or who doesn’t know how to give effective feedback will struggle no matter how many systems you put in place. This means understanding your DISC profile and Working Genius. It means knowing how you show up to your crew leaders and being intentional about protecting culture at the ground level. And most importantly, it means mastering the art of developing people, not just managing tasks.

The difference between a Field Supervisor who develops crew leaders versus one who just assigns jobs? That difference shows up in your retention rates, your productivity scores, and your Net Promoter Score.

Pillar Two: Financial Management

Here’s where a lot of field leaders get stuck. They know how to run jobs, but they don’t understand the revenue cookbook, job costing, or crew leader benchmarking. Brian explained how their benchmarking template allows you to look at every crew leader’s productivity, gross profit, and revenue over the last month or quarter. Suddenly, you’re not just reacting to one bad job, you’re seeing patterns. You’re having objective conversations backed by data.

When a Field Supervisor understands these numbers, morning huddles change. Conversations with crew leaders become about strategy, not just tasks. You start making surgical decisions about what types of work you should be pursuing and what you should walk away from.

Pillar Three: Systems and Processes

This is where most people want to start; building checklists, creating operations manuals, implementing new technology. But here’s what Brian said: “The biggest issue I see is not that people don’t have systems. It’s that the systems aren’t consistently followed.” You can have a pre-job walkthrough checklist. You can have daily huddle protocols. You can have all the SOPs in the world. But if your Field Supervisor doesn’t have the emotional intelligence to hold people accountable and the financial literacy to explain why these systems matter, nothing will stick.

That’s why you can’t skip straight to systems. You need the foundation first.

What Becomes Possible When You Get This Right

I asked Brian what becomes possible in a business when field leadership is truly developed and functioning at a high level. His answer was simple but powerful: The owner can finally do strategic thinking instead of tactical thinking. You’re not running around setting up jobs or dealing with customer problems, your Field Supervisor handles that first. You’re not stuck in the day-to-day operations. Instead, you get to coach the critical roles that drive your business forward.

And isn’t that what most of us want? The time and space to work on the business instead of in it. The ability to focus on growth, not just survival.

Taking Action in 2026

If you’re listening to this and thinking, “I need to develop my Field Supervisor” or “I need to step into this development work myself,” here’s where to start:

First, get honest about where you are. Are you developing yourself? What’s your “one big thing” for 2026? Second, identify the critical role in your business that needs development, whether that’s a Field Supervisor, Operations Manager, or another key position. Third, understand that this is a 90-day minimum commitment. Development takes time.

We’ve built the Field Leader Accelerator program specifically for this purpose, to help Advanced Crew Leaders, Project Managers, and Field Managers develop the critical skills they need to lead effectively. Our Coaches & Summit Members, Mike Freeman and Sheldon Stewart,  are leading this one-on-one coaching program, and we’re kicking off our first cohort this month.

The Bottom Line

You can’t give what you don’t have. If you want your field leaders to be self-aware, financially literate, and systems-focused, you need to model that yourself. The new year gives us permission to reset, refocus, and remember what we want, but only if we’re willing to put in the work.

Here’s to developing yourself and your key leaders in 2026. Here’s to picking that one big thing that scares you. And here’s to a year where your business grows because your people grow.

[Watch the full episode on YouTube]