6 Steps to Train Sellers’ Writing Skills

By: Yuliia Suryaninova
October 22, 2025

Here's a reality check: buyers spend only 5-6% of their decision-making time actually talking to sellers.

Let that sink in for a moment. That means 94-95% of deal influence happens when you're not in the room: through follow-up emails, executive summaries, business cases, mutual action plans, and other written documents.

Yet most sales training focuses almost entirely on call skills and verbal communication. We invest countless hours teaching sales reps how to handle objections, deliver pitches, and navigate discovery calls. But what about the other 95% of the buyer's journey?

Lawrence Wayne O'Connor, founder at Storytechr and enablement expert who's built three global sales enablement programs supporting over 80 sellers, discovered this gap the hard way. In this article, we'll break down his proven framework for building scalable systems that turn every sales rep into a strategic writer who can influence decisions even when they're not in the room.

The Hidden Problem in Sales Enablement

Traditional sales training operates on a flawed assumption: that success is determined primarily by what happens during live conversations. But Lawrence's research and experience paint a very different picture.

The bulk of a buyer's decision-making process happens asynchronously. They're reading your follow-up emails at 11 PM. They're sharing your business case with stakeholders in meetings you'll never attend. They're reviewing your executive summary while comparing it to three other vendors.

This disconnect between where we focus our training efforts and where deals are actually won creates a massive gap in sales performance. Even your best sellers—those who crush it on calls—can lose deals because their written communication doesn't match their verbal skills.

The solution is to build scalable systems that develop strategic writing capabilities across your entire sales team.

Step 1: Create Clear Standards with Scoring Rubrics

The foundation of Lawrence's framework starts with creating objective standards for every document type your team produces. Without clear criteria, "good writing" becomes subjective, making it impossible to scale training or measure improvement.

Lawrence recommends building a scoring rubric for each critical document type. Let's look at his business case rubric as an example:

  • Problem Statement (1-5 scale)
  • Solution Approach (1-5 scale)
  • Expected Outcomes (1-5 scale)
  • Implementation Plan (1-5 scale)
  • ROI Metrics (1-5 scale)

The key is defining what each score level actually looks like with concrete examples. This removes ambiguity and gives every rep, regardless of experience level, a clear target to aim for.

Step 2: Define What Good Looks Like

Creating a rubric is just the start. The real power comes from defining specific criteria for each score level with examples that anyone can understand.

Lawrence shares a perfect example using problem statements in business cases:

Score 3/5: Frames a problem that will get worse over time, but hasn't been validated by the champion and doesn't include specific metrics. It's okay, but it won't drive urgency or create strong buying conviction.

Score 5/5: Champion-validated, includes specific metrics showing business impact, and has a clear timeline for when the problem gets worse. This level of detail creates urgency and makes the cost of inaction crystal clear.

The difference between these two is measurable:

  • Did you validate with the champion? Yes or no
  • Do you have specific metrics? Yes or no
  • Is there a timeline? Yes or no

Step 3: Enable Rapid Iterations Through Feedback Loops

Traditional training approaches typically involve a 30-minute session where a manager reviews a document, provides feedback, and sends the rep back to revise. This creates a slow, cumbersome process that limits improvement.

Lawrence's approach flips this model entirely. Instead of optimizing for comprehensive feedback in one sitting, optimize for the number of feedback loops you can create in the same timeframe.

How to implement rapid iterations:

  • Share drafts in Slack channels or Microsoft Teams where the whole team can see them
  • Team members provide asynchronous input using the scoring rubric
  • Feedback is objective and actionable, not subjective opinions
  • Multiple iterations happen in real-time as reps quickly revise and resubmit

The results: Lawrence found this approach delivers 5x the improvement compared to traditional one-on-one review sessions.

Step 4: Start with AI, Refine with Your Standards

One of the biggest barriers to better writing is the blank page problem. Sellers stare at empty documents, unsure how to start. They procrastinate. They copy old examples that may not be relevant. They waste time structuring rather than thinking strategically about content.

Lawrence's framework leverages AI to eliminate this friction while using your company rubric to ensure quality remains high.

The process:

  1. Generate a first draft with AI based on your discovery notes and deal information
  2. Score that draft against your company rubric to identify where it falls short
  3. Identify specific gaps like missing metrics, weak validation, or unclear timelines
  4. Refine those sections and get team feedback on the revised version

What you get:

  • The speed of AI with the quality control of your proven standards
  • AI handles structure and initial content generation
  • Your rubric ensures the output meets your specific requirements
  • Team feedback adds the human judgment that AI can't replicate

Step 5: Track Buyer Engagement Signals

Lawrence emphasizes a critical point: "The ultimate judge is the buyer." Your internal scoring rubric matters, but buyer engagement is the real metric of success.

High engagement signals:

  • Buyers request specific edits or additions to your documents—they're invested in making your business case work
  • They use your language in follow-up conversations, showing your framing has resonated
  • They reference specific sections in meetings, indicating they've actually read and absorbed your content
  • Multiple stakeholders comment on the document, proving it's being shared internally

Low engagement signals:

  • Generic responses like "thanks, I'll review this" without follow-up questions
  • No discussions or clarifying questions after you share something

These engagement signals should inform how you refine your rubric over time. If documents that score 5/5 internally aren't generating buyer engagement, your standards need adjustment. The rubric serves your goal of influencing buyers, not the other way around.

Step 6: Scale Across Your Organization

Once you've tested your framework with a small group, it's time to scale it across the entire sales organization. Lawrence recommends a phased implementation strategy:

Phase 1: Train all sales managers on rubric scoring

  • They need to become experts in evaluating documents objectively
  • Feedback should reference specific rubric criteria

Phase 2: Include document quality in deal reviews

  • Assess the quality of key documents using the rubric
  • Don't just focus on deal size and close date

Phase 3: Share best examples in team meetings

  • Highlight documents that score 4-5/5
  • Break down why they're effective
  • Create social proof and give everyone models to learn from

Phase 4: Track improvement metrics month-over-month

  • Are average scores increasing?
  • Are more documents hitting 4-5/5 consistently?
  • Is buyer engagement improving?

Phase 5: Reward reps who consistently score 4-5/5

  • Use formal incentives or public acknowledgment
  • Celebrate the reps who master strategic writing

This phased approach prevents overwhelm and allows you to refine the process as you scale. Start with one document type—Lawrence recommends executive summaries and expand from there.

Getting Started Today

You don't need to implement this entire framework overnight. Lawrence recommends starting small and building momentum.

Pick one document type to focus on first. Executive summaries work well because they're used frequently and have clear success criteria. Build a scoring rubric with specific examples for each level from 1-5. Train your team on the rubric and the scoring process so everyone understands the standards. Start async feedback loops in Slack or Microsoft Teams to enable rapid iterations. Track engagement metrics from buyers to validate that your improvements are working.

Remember Lawrence's guiding principle: the ultimate judge is the buyer. Your rubric and scoring process are tools to help you influence their decision-making when you're not in the room. If your documents aren't driving buyer engagement and moving deals forward, adjust your standards.

Conclusion

The uncomfortable truth is that most sales training misses where deals are actually won or lost. While we obsess over call skills and pitch delivery, buyers are making decisions based on documents we've written, often without ever telling us.

Lawrence Wayne O'Connor's framework solves this problem by creating scalable systems that turn every sales rep into a strategic writer. Through clear standards, objective scoring, rapid feedback loops, AI assistance, buyer engagement tracking, and phased implementation, you can transform your team's ability to influence decisions when they're not in the room.

The difference between winning and losing deals often comes down to those written touchpoints that happen in the 94-95% of time buyers aren't talking to you. By implementing this framework, you ensure your team influences those critical moments just as effectively as they handle live conversations.

Full episode on the topic ⬇️

In this episode of SellMeThisPen Podcast, Michael and Lawrence dive into why traditional sales training misses the mark by focusing on call skills when buyers spend 95% of their decision time reading documents. They break down Lawrence's proven framework for turning every sales rep into a strategic writer through clear rubrics, rapid feedback loops, and AI-enhanced processes.

Lawrence Wayne O'Connor is the founder of Storytechr and has built and led three global enablement programs supporting over 80 sellers. He's passionate about bridging the gap between sales behavior and buyer decisions, with particular expertise in helping sales teams master the written communication that drives deals forward.

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