by Art Waskey | Feb 4, 2026 | Art of Sales Weekly, Featured
This article on Monthly Sales Assessment is the last in my series on the AI-Enabled Sales Process. The Monthly Sales Assessment is a joint manager-salesperson meeting that reviews 10 key metrics across Outcomes and Territory Management. I consider it to be the foundation of sales success.
This critical monthly discipline ensures that everyone has a clear understanding of sales expectations. It ensures accountability, uncovers real issues beneath surface problems, and integrates all AI-enabled sales tools into one cohesive system. Consistent execution of monthly assessments directly correlates to sustained revenue and margin growth.
The Purpose
The purpose of the Monthly Assessment is to uncover root problems. As Gino Wickman writes in Traction: Get a Grip on Your Business, the goal of an assessment is to “clearly identify the real issue, because the stated problem is rarely the real one.” An assessment cuts through surface-level reporting to uncover the real drivers—or obstacles—to sales success. By reviewing specific metrics monthly, patterns emerge that reveal whether problems stem from activity levels, conversion rates, or strategic focus.
Two Critical Components
As shown in the illustration of a typical industrial gas distributor above, the Monthly Assessment has two critical components — Outcomes and Territory Management.
- Outcomes measure results that directly impact revenue (these values are only illustrations, not observed implications). New Business ($4,000/month target) and Penetration ($1,000/month) track your ability to grow the business. Cylinders placed (20/month), Contracts (2/month), and Customer 360 Files (1/month) measure execution of key sales activities that protect and expand your customer base.
- Territory Management tracks the activities that feed your pipeline. Prospective calls (20/month), Funnel Prospects ($340,000 total value), Top 5 Calls (6/month), and Key Accounts (50/month) ensure consistent prospecting and relationship maintenance. Sales (8% growth) and Margin (10% improvement) provide the ultimate scorecard.
Integration of AI-enabled tools
Notice how this assessment integrates all the AI-enabled tools covered in this series. These tools include call reporting, calendar planning, Customer 360 meetings, dashboards, and the Reflect & Direct framework. Also, making an assessment by integrating all these elements creates a system of analysis where each component reinforces the others.
The Cost of Inconsistency
I have found that clients who get distracted and fail to demonstrate consistent monthly meetings are less successful. Moreover, these companies often find that until they get back on track with assessments, their revenue and margin growth are inconsistent. The Monthly Sales Assessment is the discipline that separates high-performing sales organizations from those that plateau.
Build your Foundation
To build a strong foundation for sales success, schedule Monthly Assessments at the same time each month. Be sure that management and the sales team complete the form together, and that both parties sign off on it. Lastly, this simple discipline, maintained consistently, creates the traction your sales organization needs to achieve predictable, sustainable growth.
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by Art Waskey | Jan 28, 2026 | Art of Sales Weekly, Featured
Throughout this AI-Enabled Sales Management series, we’ve examined AI tools that help maintain analytical focus on key performance indicators (KPIs). These tools help ensure alignment between representatives and management. Additionally, a critical component of this alignment is the monthly Travel Day—a non-negotiable requirement for effective sales leadership. Outside sales representatives (OSRs) must know exactly what their sales managers expect from travel days.
The requirement
Every sales manager should spend at least one day a month in the field with each OSR. When a manager cannot devote one day a month to an OSR, I have found that success becomes unlikely. Moreover, a manager’s time spent with a rep is essential for building trust, providing coaching, and understanding the real-world challenges each rep faces.
The Four Essential Components
There are four essential components to the Travel Day requirement.
- Monthly Review (30 Minutes) – Begin each Travel Day with a focused review of AI-enabled KPIs, including In-the-Funnel prospects, Dashboard metrics, and Sales Results. This review is an efficient and valuable way to set the tone for the day’s activities.
- Calls by Appointment – The OSR schedules appointments with both key accounts and prospects. Key account calls should address issue resolution, penetration opportunities, or significant account changes. For prospect appointments, the OSR must demonstrate knowledge of decision-makers, including their DISC profile type. Dominance (D), Influence (I), Steadiness (S), and Conscientiousness (C). This demonstrates preparation and strategic thinking.
- Call Reviews – Following each appointment, review the OSR’s performance using the AI agentic call report framework. The representative should provide evidence of their position in the sales cycle. Is it in building trust, establishing need, interacting with decision-makers, addressing investment concerns, or proving product value? Immediate feedback like this accelerates skill development.
- Set Next Appointment – Before concluding each meeting, schedule the next Travel Day. This commitment ensures continuity and accountability, preventing the all-too-common excuse that field time “just didn’t happen this month.”
Travel Days Matter
Travel Days transform the manager-representative relationship from one of supervision to one of collaboration. Also, managers gain firsthand understanding of market conditions, customer challenges, and competitive pressures. Representatives receive real-time coaching, validation of their approach, and support in navigating complex sales situations.
In my 50+ years of sales management experience, I’ve consistently observed that organizations with disciplined Travel Day practices outperform those that treat field time as optional. Also, AI tools make preparation for Travel Days more efficient, but do not replace the human connection, observation, and coaching that only face-to-face interaction provides.
Lastly, make monthly Travel Days non-negotiable in your sales organization—your team’s success depends on it.
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by Art Waskey | Jan 22, 2026 | Art of Sales Weekly, Featured
In my career in sales management, I witnessed too many outside sales reps (OSR) get distracted and lose some top account opportunities. Today, AI can help with the challenge of defining your Top 5 Prospects. AI-Enabled Management can identify the best and most probable prospective closures.
Understanding the customer
A firm understanding of the customer is essential to focused sales momentum. After reading Stephen Covey’s The 7 Habits of Highly Effective People in the mid-90s, his principle of “First things first” had an impact on how I viewed prospecting. To enhance the closure rate of my team, I developed a list of 5 factors that should be part of the monthly sales manager’s OSR reviews.
Elements of the Top 5 Review
For each Top 5 prospect, consider these factors:
- Type: Identify the opportunity. Firstly, not all prospective opportunities are new accounts. Overall sales and margin growth may come from expanding wallet share in an existing account or closing a new account entirely. Clearly identifying the opportunity type ensures you apply the right strategy to each account from the start.
- Goal: What is the specific, measurable goal you would like to achieve? Whether pursuing a new account or deeper penetration in an existing one, it is paramount to stay focused on the single most important directive to secure success. Moreover, developing a singular goal with your customer helps avoid confusion and diluted effort.
- Value: Quantify the opportunity. AI tools can determine the potential sales and gross margin for new prospective opportunities. For existing accounts, AI can analyze your current wallet share and identify the highest-value product or service expansion opportunities. Also, without understanding the financial impact of your actions, you cannot properly prioritize your efforts.
- Competitor: To build an effective strategy, you must know which competitor currently has the business. In addition, if there is a significant weakness or gap in your competitor’s offering, there is no urgent incentive for the customer to change. Intelligence drives strategy.
- Current Next Step: Every strategic plan must be broken down into small, achievable next steps with clear ownership. Too often, the OSR and customer become discouraged by trying to accomplish too much too soon. Define one concrete action that moves the opportunity forward.
- Date: Each next step requires a completion date to maintain momentum. When initiating a prospective project, avoid listing a closure date unless only one action item remains. Realistic timelines build credibility and prevent pipeline fantasy.
The Top 5
The Top 5 Prospect list framework succeeds because it imposes disciplined prioritization on the chaotic reality of sales pipelines. In conclusion, require your OSRs to define opportunity type, singular goals, quantified value, competitive landscape, actionable next steps, and accountability dates. Lastly, this methodology separates real opportunities from wishful thinking and keeps you focused on what matters most.
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by Tera Jewell | Jan 15, 2026 | Art of Sales Weekly, Featured
Throughout our AI-Enabled Sales Management series, we’ve explored AI directives for call reporting, calendar planning, prospecting, dashboarding, sales reviews, and Customer 360 meetings. In this article, we examine another essential component of AI Sales Management — the Reflect and Direct Report. This is a concise snapshot of last month’s results and next month’s goals, which keep your sales team aligned on priorities and progress.
Reflect
Reflect on your activity in these four areas to understand your current sales position.
- New Business Closures – List new businesses, including products sold, estimated annual sales, business type, and relationships formed. This review celebrates wins and helps managers understand market penetration.
- Existing Business Penetration – AI identifies products that existing customers could buy from you but purchase elsewhere. Document new wallet share opportunities by product category with annual sales estimates. Demonstrate your ability to grow existing relationships.
- Significant Account Changes – Report major changes management should know about, such as accounts lost, closed, or experiencing rapid growth. Your AI agent can identify these shifts before they become problematic.
- Monthly Notables – Report concerns with suppliers, customers, or internal issues. This communication prevents small problems from becoming major obstacles.
Direct
In order to direct your sales team in a meaningful way, develop a plan for the next 30 days. Include the following:
- Top 5 In-the-Funnel Prospects – List current next steps for your top five prospects with specific dates, contacts, and actions. This ensures accountability and momentum.
- Customer 360 Meetings – Review scheduled dates and materials for strategic meetings with top accounts. These conversations protect your most valuable relationships.
- Significant Projects – Discuss training sessions, joint calls with suppliers, industry events, and other important endeavors. This enables managers to provide support and remove obstacles proactively.
Implement
Implement actions with best practices using your Reflect and Direct Report results.
- Keep it Concise – Have 15-20 minute discussions with team members that focus on highlights, concerns, and action items.
- Be Consistent – Schedule reviews at the same time monthly, preferably within the first week after month-end results are available and data is fresh.
- Use AI Insights – Leverage AI tools to pre-populate data so conversations focus on interpretation and strategy rather than data gathering.
- Document and Follow Up – Use standard templates for consistency and review last month’s commitments.
Reflect and Direct
Reflect and Direct Reports transform monthly sales reviews from administrative requirements into strategic conversations that drive results. By examining past performance and planning future actions, managers and representatives build stronger partnerships, avoid surprises, and maintain momentum.
In my 50+ years of sales management experience, I found that the most successful teams create regular reflection and planning rhythms. AI tools make this easier than ever to execute effectively. The clarity, alignment, and accountability provided by these reports yield improved performance and stronger relationships.
Lastly, start your first Reflect and Direct review this week and make it a non-negotiable part of your monthly sales management routine.
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by Art Waskey | Dec 17, 2025 | Art of Sales Weekly, Featured
We’ve all experienced the disappointment in learning that one of our Top Ten Accounts is switching to a competitor. There is a practical way to avoid key customer churn. First, you must understand that you need to show your customers what you do to support them. Meet with your client’s decision-makers annually for a comprehensive review of ongoing activities that you execute on their behalf. I call this a Customer 360 Meeting.
Three key meeting components
A 360 Meeting should be held annually and include these three key components:
- Account Support Activity. This gives the customer details on the time and effort you have invested to keep their business running smoothly.
- Sales History. Be transparent with your sales history. Openly review the last two years of sales.
- New Action Plan. Developing a new action plan is your opportunity to collaborate with the customer on growing their business using your consultative abilities.
A strategic investment
Customer 360 Meetings help retain customers and represent a strategic investment in your most valuable relationships. In today’s competitive marketplace, retaining key accounts is just as important as acquiring new ones—and often more profitable.
Use AI to compile comprehensive account activity data. Then be transparent in its presentation so that you can collaborate with your customers on future growth strategies. This way, you can transform routine account management into strategic partnership building. Your customers will see and appreciate the extraordinary effort you invest in their success.
Show the full picture
The question isn’t whether you can afford to implement Customer 360 Meetings—it’s whether you can afford not to. In my 50+ years of sales management experience, I’ve watched too many “secure” relationships disappear to competitors simply because we failed to show customers the value we were consistently delivering.
Lastly, don’t let your best customers become someone else’s success story. Show them the full picture, and they’ll never want to look elsewhere.
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by Art Waskey | Dec 10, 2025 | Art of Sales Weekly, Featured
Throughout our AI-Enabled Sales Management series, we’ve explored AI directives for call reporting, calendar planning, prospecting, dashboarding, sales reviews, and Customer 360 meetings. In this article, we examine another essential component of AI Sales Management — the Reflect and Direct Report. This is a concise snapshot of last month’s results and next month’s goals, which keep your sales team aligned on priorities and progress.
Reflect
Reflect on activity in these four areas to understand your sales position today.
- New Business Closures – List new businesses, including products sold, estimated annual sales, business type, and relationships formed. This review celebrates wins and helps managers understand market penetration.
- Existing Business Penetration – AI identifies products that existing customers could buy from you but purchase elsewhere. Document new wallet share opportunities by product category with annual sales estimates. Demonstrate your ability to grow existing relationships.
- Significant Account Changes – Report major changes management should know about, such as accounts lost, closed, or experiencing rapid growth. Your AI agent can identify these shifts before they become problematic.
Monthly Notables – Report concerns with suppliers, customers, or internal issues. This communication prevents small problems from becoming major obstacles.
Direct
In order to direct your sales team in a meaningful way, develop a plan for the next 30 days. Include the following:
- Top 5 In-the-Funnel Prospects – List current next steps for your top five prospects with specific dates, contacts, and actions. This ensures accountability and momentum.
- Customer 360 Meetings – Review scheduled dates and materials for strategic meetings with top accounts. These conversations protect your most valuable relationships.
- Significant Projects – Discuss training sessions, joint supplier calls, industry events, and other key initiatives. This enables managers to proactively provide support and remove obstacles.
Implement
Implement actions with best practices using your Reflect and Direct Report results.
- Keep it Concise – Have 15-20 minute discussions with team members that focus on highlights, concerns, and action items.
- Be Consistent – Schedule reviews at the same time monthly, preferably within the first week after month-end results are available and data is fresh.
- Use AI Insights – Leverage AI tools to pre-populate data so conversations focus on interpretation and strategy rather than data gathering.
- Document and Follow Up – Use standard templates for consistency and review last month’s commitments.
Reflect and Direct
In conclusion, Reflect and Direct Reports transform monthly sales reviews from administrative requirements into strategic conversations that drive results. By examining past performance and planning future actions, managers and representatives build stronger partnerships, avoid surprises, and maintain momentum.
In my 50+ years of sales management experience, I found that the most successful teams create regular reflection and planning rhythms. AI tools make this easier than ever to execute effectively. The clarity, alignment, and accountability provided by these reports yield improved performance and stronger relationships.
Start your first Reflect and Direct review this week and make it a non-negotiable part of your monthly sales management routine.
Get tips and tricks like the above in The Art of Sales books. Or subscribe to the FREE monthly articles here.
