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Good morning,
2026 will belong to sellers and sales leaders who adapt faster than the tools they use. The world of sales is shifting: AI, automation, hybrid work, and buyer self-education are rewriting the rules. But the fundamentals remain the same: influence, clarity, and connection.
The best sellers are the ones who can combine timeless skills with tomorrow’s technology.
For sellers, mastering these topics means becoming indispensable, the person buyers call first because you understand both the product and the problem. For managers, it means leading teams that perform with precision and resilience. For business owners, it means scaling systems and people who can outperform in any market.
This workshop is a roadmap for your next leap forward, a guide to mastering the habits, tools, and mindset that will make 2026 your best year yet.
TEST YOUR KNOWLEDGE
Question | Format | Answer Key |
1. What’s the biggest advantage of combining human selling skills with AI tools? | A) Saves time B) Creates more data C) Increases personalization and speed D) Reduces meetings | C |
2. True or False: Buyers now complete over 60% of their decision-making process before ever speaking to a seller. | True/False | True |
3. Name one way you can improve your “pipeline velocity” this quarter. | Short Answer | Example: “By focusing on qualified deals and removing stalled opportunities earlier.” |
DO’S AND DON’TS
Do’s | Don’ts |
Do evolve your skills every quarter, the tools are changing, and so should you. | Don’t assume what worked in 2020 will work in 2026. |
Do use AI and automation to gain leverage, not replace human empathy. | Don’t over-automate, sales is still personal. |
Do focus on learning across sales, leadership, and business ownership. | Don’t separate “seller skills” from “leader skills.” They’re connected. |
THE WORKSHOP > 3 MODULES
MODULE 1: THE SELLER OF 2026: SKILLS THAT SET YOU APART
OBJECTIVE: Identify the key sales and communication skills you’ll need to excel in the new era of selling.
EXERCISE: MAP YOUR 2026 CORE SKILLS
Category | Skill Example | Real-World Use | Impact |
AI-Enabled Prospecting | Research | Use AI to build and score lead lists | Saves hours per week |
Consultative Selling | Discovery | Ask questions that align to revenue outcomes | Builds trust |
Financial Fluency | Business Acumen | Understand P&L, ROI, and margin dynamics | Improves credibility |
TIPS
Start each week by focusing on one micro-skill to improve.
Rehearse AI-assisted calls to blend efficiency with empathy.
Treat financial understanding as your new sales edge.
CASE STUDY: A digital media rep learned to use AI for lead scoring, financial literacy to interpret client balance sheets, and consultative questioning to close complex deals. Within 90 days, her close rate doubled and her average deal size increased by 40%.
DISCUSSION QUESTIONS
Question | Answer |
1. Why is financial literacy now a core selling skill? | Because clients buy outcomes, not activities. |
2. What can AI not replace in the sales process? | Empathy, insight, and relationship-building. |
3. What’s the difference between activity and performance? | Activity is motion; performance is measurable impact. |
MODULE 2: THE MODERN SALES LEADER: LEADING TEAMS FOR GROWTH AND CLARITY
OBJECTIVE: Learn how to lead sellers in a high-change environment using structure, data, and emotional intelligence.
EXERCISE: BUILD YOUR LEADERSHIP FRAMEWORK
Focus Area | Action | Result |
Coaching | Weekly 1:1s with structured feedback | Improves accountability |
Metrics | Track leading indicators (calls, connects, demos) | Predicts outcomes early |
Culture | Recognize micro-wins publicly | Builds momentum |
TIPS
Lead with transparency, show how metrics connect to mission.
Mix human coaching with AI insights for precision.
Turn every team meeting into a learning session.
CASE STUDY: A regional VP implemented a “Data + Dialogue” framework: AI provided insights, while managers coached behavior. The result, 25% improvement in pipeline conversion and 18% reduction in turnover.
DISCUSSION QUESTIONS
Question | Answer |
1. Why do high-performing sales teams crave structure? | It gives freedom through clarity. |
2. What’s the modern manager’s real job? | To remove friction and coach for consistency. |
3. How can AI make coaching more effective? | By surfacing insights and saving time for real conversation. |
MODULE 3: THE SELLER-OWNER MINDSET: BUILDING SYSTEMS THAT SCALE
OBJECTIVE: Think and operate like a business owner, using systems, data, and strategy to grow sustainable revenue.
EXERCISE: WAYS SELLERS CAN THINK LIKE BUSINESS OWNERS
Focus Area | Tactic | Outcome |
Revenue Forecasting | Use data to predict 30/60/90-day performance | Improves accuracy |
Personal Brand | Build LinkedIn thought leadership | Expands pipeline |
Efficiency | Automate admin tasks via AI tools | Saves time and increases selling hours |
TIPS
Treat your pipeline like a business portfolio.
Build repeatable processes for prospecting and follow-up.
Use data dashboards to run your territory like a P&L.
CASE STUDY: A seller adopted an “owner’s mindset” by managing her territory with CRM dashboards and automated workflows. Within one quarter, she grew her booked revenue by 35% and reduced admin time by half.
DISCUSSION QUESTIONS
Question | Answer |
1. What changes when you think like an owner? | You shift from reactive selling to proactive planning. |
2. Why does personal branding matter in 2026? | It builds inbound trust and shortens the sales cycle. |
3. What’s the #1 productivity killer for sellers? | Administrative overload. fix it with automation. |
PATH TO FLUENCY
Timeframe | Focus Area | Fluency Indicators | Manager KPI / ROI Signals |
30 Days | Awareness | Can name top 10 skills needed to succeed in 2026 (And have at least 1 experience texting out 10 new tools) | Increased engagement and confidence |
60 Days | Application | Applies AI and consultative methods to live deals (Even if only in the testing phase, but you HAVE to try) | Improved pipeline velocity and accuracy |
90 Days | Mastery | Operates like an owner, strategic, data-driven, and consistent | Stronger close rate, higher deal quality |
RECOMMENDED READING
Title | Author | Year | Publisher |
John McMahon | 2021 | HQ Publishing | |
Stephanie Woerner, Peter Weill & Ina Sebastian | 2023 | Harvard Business Review Press | |
Mort Greenberg | 2025 | digitalCORE Publishing |
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The Revenue Workshop isn’t theory. It’s a field-tested system used by real leaders, in real markets, under real pressure.
Each newsletter is based on one of over 300 workshops and worksheets found in the eight books of the RevenueVsSales.com and TheFocusedSeller.com book series.
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