How Most Annual Plans Get Built.

This article demonstrates how the best dealers don’t plan alone and how peer learning turns good plans into executable ones. Every year, I see the same scene play out… 

• A leadership team shuts the door.
• A spreadsheet comes out.
• Someone writes “2026 Goals” at the top of a whiteboard. 
• The plan gets tighter as the room gets smaller. 

And to be clear, there’s nothing wrong with that. Annual planning needs focus. It needs ownership. It needs discipline. But here’s what I’ve learned after years working with dealer 20 Groups, peer councils, and leadership networks across North America: 

The dealers who consistently outperform their peers don’t plan in isolation. They plan in community. 

They deliberately expose their thinking to other leaders who live the same realities: labor shortages, OEM pressure, margin compression, customer expectations, capital constraints. 

Not for collaboration. For calibration. That difference matters more than most leaders realize.  

Why Strategic Clarity Breaks Down Inside the Dealership 

Strategic clarity doesn’t usually fail because leaders aren’t smart or committed. It fails because clarity erodes in isolation. Inside the dealership, three forces quietly work against us: 

1. Assumptions Go Unchallenged

Every organization carries internal myths or ideas that feel true because no one has questioned them in years. I recently watched one dealer confidently present a plan during a 20 Group meeting to “increase technician headcount by 5 people in 2026.” A dealer principal peer asked a simple question: “What’s your current load per tech?” 

• Silence…
• Scrambling…
• Pulling up the business intelligence report…

Their R12 technician productivity was 65%. The peer then responded: “Why the heck are you hiring new techs if the ones you have aren’t working at their full potential?”  

The goal wasn’t wrong; it was incomplete. For this dealer, no internal meeting would have surfaced that blind spot. A peer did it in 10 seconds. 

2. Problems Feel Unique (When They’re Not)

Inside your four walls, every issue feels custom. In peer settings, patterns emerge fast. I’ve seen rooms light up when one dealer says, “Our sales follow-up is inconsistent,” and three others immediately say, “Same.” 

One dealer shares a simple follow-up rhythm that worked. Two others test it. All three improve. What felt isolating becomes solvable. 

3. Plans Don’t Get Pressure-Tested 

Inside the dealership, people tend to nod. In peer groups, they don’t. I once saw a dealer describe a new organizational design they’d contemplated to centralize all sales deals. Before the slide was done, peers asked/commented: 

• “What customer problem does this solve?” 
• “What will you stop doing to make room for this?” 
• “We tried something similar. Here’s what surprised us.” 

The idea survived. But it came back sharper, smaller, and executable. That dealer later told me, “That conversation saved us six months of wasted effort.” Peers don’t criticize. They clarify. 

A Best-Practice Model for Peer Learning and Strategic Clarity 

The best dealers I work with follow a surprisingly simple peer-learning rhythm. Here are three best practices I’d encourage any leadership team to adopt. 

Step 1: Share the Draft, Not the Deck 

The biggest mistake leaders make with peer groups is waiting until the plan is “done.” 

Polished plans invite politeness. Drafts invite honesty. 

I recently watched a dealer bring a rough, unfinished plan to a peer session. Half-formed priorities. Question marks everywhere. Instead of applause, they got real questions: 

• “Why this priority now?” 
• “What customer pain does this solve?” 
• “What breaks if this slips by 90 days?” 

Later they told me: “I walked in with a plan. I walked out with a strategy.” If you want clarity, bring the messy version. 

Step 2: Treat Peer Groups as Intelligence Exchanges 

High-performing peer groups don’t brainstorm. They exchange intelligence. The most valuable sessions are built around sharing: 

• Benchmarks that actually matte (more leading indicators than lagging).  
• Capacity constraints (not wishful thinking) 
• Hiring realities 
• Customer behavior shifts 
• What failed and why 

One dealer shared an onboarding problem. Another shared their 90-day onboarding map. 
A third shared technician mentorship data. A fourth showed retention numbers before and after. 

Within weeks, the first dealer rebuilt their onboarding system and retention improved. 

That’s not inspiration. That’s borrowed intelligence. 

Step 3: Rebuild the Plan With Accountability in Mind 

Peer learning only works if it tightens execution. After strong peer sessions, the best dealers come back with: 

• Fewer priorities 
• Clearer sequencing 
• More realistic capacity assumptions 
• Stronger metrics 
• Explicit ownership 

One dealer said it perfectly: “My plan used to be a list. Now it’s a blueprint.” 

The clarity didn’t come from working harder. It came from contrast—seeing their thinking next to others. 

When working with dealers, at Sheppard & Company we use our Top 5/Top 3 system to set priories and drive action (Top 5 priorities, Top 3 actions). Ensure you have some type of system to do the same.  

And just as important: Peers remember what you said you were going to do. That quiet accountability changes behavior. 

Annual Planning is a System

Annual planning isn’t about producing a document. It’s about building a system of shared intelligence that guides decisions all year. 

The dealers who plan in community—who benchmark openly, pressure-test early, and learn from each other’s scars—build strategies that are: 

• Clearer 
• More grounded 
• More customer-centric 
• More executable 
• More resilient 

Strategic clarity grows fastest when leaders stop planning alone.