My 2026 Sales Playbook, Lessons, and Levers

What Got You Here Won’t Get You There

Less than two weeks ago, I was handing out Halloween candy on my street in Roscoe Village in Chicago… so you can imagine my surprise when I was walking my dog this morning and saw a house already decked out in full Christmas decorations. I love the holidays as much as anyone, but they completely skipped Thanksgiving. That jump felt like a fast-forward button on the calendar—and a reminder that the rest of the year will fly by whether we’re ready or not. With only five full workweeks remaining and the holidays upon us, it’s time to pause, reflect on this year, and start planning for next year. Statistician W. Edwards Deming once said,

“The systems you have in place are perfectly designed to get the results you got.”

When it comes to Butler Street and the staffing industry, I take this quote quite literally. Whatever process, system, or strategy I employed in 2025 was perfectly designed to get the results that I got. These could be good or bad results. Regardless of whether your year went up, down, or sideways, using Q4 to reflect on what happened allows you to make the necessary adjustments. We don’t learn from experience; we learn from reflecting on experience. Here are the steps I’m taking to reflect and plan intentionally.

Finally, as a salesperson, it’s important to never stop selling. My first CEO always told me,

“Your top customer this year will not be your top customer next year.”

Thirteen years later, that sentiment has never been truer.

What Went Wrong: As I write this, I have this year’s forecast document open and let’s just say the customers I thought I was going to have in 2025 do not match the customers I actually have in 2025.

So, what did I learn?

I started the year banking on certain customers spending a certain amount of money. So, when they didn’t, I put myself in a tough spot in Q1. Being overly reliant on a handful of customers automatically puts you at risk as a salesperson. That’s why it’s so important to continuously prospect, a lesson I was reminded of quickly early this year.

If you’re doing sales the right way, you’ll have more L’s than W’s. But it’s the W’s that count. While looking back, I can pinpoint a few missteps: time spent in the wrong places and calls I could’ve prepped for better (one meeting still haunts me). But those moments were necessary. Each mistake revealed a blind spot that eventually led to a win.

How I’m Using This Information to Direct My Efforts

As I approach my two-year anniversary with Butler Street, I’m taking everything I learned this year (the good, the bad, and the ugly) to guide how I’ll operate in coming year.

Here’s my approach:

1. Start with the System, Not the Outcome

Deming’s quote isn’t just a clever line; it’s a tool. Instead of asking, “Why didn’t I close that deal?” I’m asking, “What part of my system led to that outcome?” Was it my pipeline diversification, my pre-call planning, or my touch? Once you identify which part of your process caused the result, you can fix the system instead of just the symptoms.

2. Double Down on Pipeline Health

This year taught me that “hope forecasting”, counting on certain clients to renew or expand, is a silent killer of momentum. In the coming year, I’m setting a target for new meeting every week, regardless of how full my pipeline looks. The best salespeople I know treat prospecting like brushing their teeth, a non-negotiable habit, not a task that depends on how they feel that day.

3. Prioritize the Right Metrics

It’s easy to track what’s easy- revenue, meetings booked, calls made. But the more valuable metrics are those that measure quality over quantity: meeting-to-close ratio, client engagement scores, and renewal percentage. By aligning activity metrics to outcome metrics, I can better understand what truly drives results.

4. Make Reflection a Habit, not a Season

Most people wait until December to reflect. I’m committing to structured reflection every quarter, short debriefs after wins and losses, using a simple framework:

• What happened?

• Why did it happen?

• What will I do differently next time?
  

This cadence prevents surprises at year-end and builds a culture of continuous improvement.

5. Lead Myself Before I Lead Others

At Butler Street, we coach others to “become the coach they wish they had.” That starts with self-leadership. Before I can help clients or my team grow, I need to hold myself accountable to the same behaviors I expect of them - preparation, follow-through, and curiosity.

If any of this resonates and you’re ready to upgrade your sales system for 2026, let’s talk. Butler Street helps teams build repeatable growth with proven training, consulting, and AI coaching. Contact us to schedule a call and we’ll align on where your process needs the biggest lift.