Sales coaching isn’t just an optional skill for managers—it’s a game-changer. Reps who rate their coaching as “Excellent” are 50% more likely to hit or exceed quota, according to insights from the State of Sales Coaching 2025 Report. Yet, the same report revealed a troubling disconnect: while 90% of sales leaders believe they’re coaching regularly, nearly 40% of reps say they rarely or never receive coaching.

What’s clear is that coaching done right has the power to transform deal execution. Effective coaching helps reps uncover deeper buyer insights, maintain deal momentum, build trust with stakeholders, and differentiate from competitors. But to deliver coaching that drives these results, managers must go beyond deal reviews and pipeline check-ins—they need to dig deeper into root causes, ask the right questions, and leverage tools like Digital Sales Rooms (DSRs) to guide reps based on data-driven insights.

In this article, we’ll outline actionable strategies for coaching your reps to improve their deal execution while incorporating a couple of statistics to drive the importance of great coaching home.

1. Improve discovery: Coaching reps to dig deeper

Discovery is the bedrock of any successful deal. Without it, reps risk building a sales process on assumptions rather than understanding. Unfortunately, many reps rush through this stage, sticking to surface-level questions about budget, authority, needs, and timeline (BANT). This approach results in weak opportunities and prospects who feel misunderstood.

Coaching your reps to excel in discovery requires teaching them to dig deeper into the buyer’s challenges, uncover motivations, and build a strong foundation for the sales process. And here’s where coaching matters most: the State of Sales Coaching 2025 Report shows that low-performing reps are twice as likely to receive no coaching at all. That lack of guidance could be why so many deals falter at the first step.

How Digital Sales Rooms support better discovery

Digital sales rooms provide managers with insights that can help tailor their coaching. For example:

• Gauge interest: If a buyer has engaged heavily with a case study in the DSR, coach your rep to dig deeper into what resonated. Ask questions like, “How do you see this applying to your situation?”
• Spot gaps in discovery: If DSR activity reveals a focus on implementation resources, yet your rep hasn’t discussed this during discovery, coach them to revisit the buyer’s technical needs and timelines.

Action point:

During your next coaching session, role-play a discovery call with your rep. Use data from a recent deal—including DSR engagement insights—to identify areas where they can ask deeper questions. Focus on active listening, follow-ups, and diagnosing the buyer’s true challenges.

2. Coaching reps to keep deals moving

One of the most common frustrations for sales reps is stalled deals. They’ve had the initial meetings, they’ve sent the proposal, but then… nothing. Deals lose momentum when reps fail to create clear next steps or don’t secure buy-in along the way.

Momentum doesn’t happen by accident—it’s created intentionally. Coaching your reps to drive progress at every stage of the deal is critical. The State of Sales Coaching 2025 Report underscores this, revealing that reps who receive consistent coaching are far more likely to hit their targets, while those who don’t often struggle to navigate challenging or stalled deals.

How Digital Sales Rooms support momentum

Digital sales rooms provide a unique window into buyer engagement, helping managers identify where deals may be stalling:

• Track proposal engagement: If a prospect hasn’t opened the proposal after several days, coach your rep to follow up with urgency. For example: “I noticed the proposal hasn’t been reviewed yet. Should we set up a quick call to walk through it together?”
• Uncover missing stakeholders: If DSR activity shows limited engagement from key decision-makers, guide your rep to loop in additional stakeholders. Suggest questions like, “Is there anyone else we should involve to ensure alignment?”

Action point:

Select a deal that has stalled in your rep’s pipeline. Use DSR data to analyse prospect engagement and identify the next step. Work with your rep to craft a re-engagement strategy, focusing on securing a specific micro-commitment (e.g. scheduling a follow-up call or involving a key decision-maker).

3. Building better relationships: Coaching reps to earn trust

Buyers today aren’t looking for transactional relationships—they want trusted partners who can help them solve their most pressing challenges. But building trust isn’t about being likable—it’s about showing empathy, delivering value, and following through on commitments.

Coaching plays a critical role in helping reps develop these skills. The State of Sales Coaching 2025 Report revealed that 99% of reps believe coaching impacts their performance, with 57% saying it’s had a significant impact. Managers who focus their coaching on relationship-building can help reps stand out in an increasingly competitive marketplace.

How Digital Sales Rooms support relationship building

Digital sales rooms offer visibility into how buyers engage, helping managers guide reps to build stronger connections:

• Identify buyer priorities: If a prospect spends significant time on content like ROI calculators, coach your rep to prioritise financial outcomes in their conversations. For example: “I noticed they’ve been reviewing ROI data—how can you tie this into their broader business goals?”
• Spot stakeholder involvement: If multiple stakeholders are engaging with different types of content, coach your rep to personalise their approach for each role. For instance, the IT lead may care about integrations, while the CFO focuses on cost savings.

Action point:

During your next one-on-one coaching session, review a deal where your rep needs to deepen their relationship with the buyer. Use DSR data to identify what the buyer is engaging with most and role-play a follow-up conversation that emphasises empathy and value.

4. Differentiating from the competition: Coaching reps to win the value game

In crowded markets, it’s not enough to have a great product—your reps need to position your solution as the obvious choice. Buyers are bombarded with options, and the easiest way to stand out is by tying your unique capabilities to the buyer’s specific challenges.

The State of Sales Coaching 2025 Report emphasises the importance of coaching here. Reps who receive coaching on competitive positioning are better equipped to overcome objections and demonstrate unique value.

How Digital Sales Rooms support differentiation

DSRs can highlight where prospects are most focused, enabling managers to coach reps on areas that resonate most:

• Identify key differentiators: If DSR data shows buyers revisiting a particular feature document, coach your rep to frame that feature as a unique differentiator tied to the buyer’s needs.
• Address competitive comparisons: If DSR activity reveals interest in comparison sheets, help your rep prepare to handle competitive objections with confidence.

Action Point:

Ask your rep to craft a differentiation statement tailored to a top competitor. Use insights from the Digital Sales Room to refine their message, focusing on specific buyer pain points and your solution’s unique strengths. Role-play common objections they may face.

How to deliver sales coaching that sticks

Even with tools like digital sales rooms, the impact of coaching depends on how it’s delivered. Here are some proven strategies to make your coaching sessions more effective:

• Start with their goals: Begin coaching sessions by aligning with your rep’s personal and professional goals. This connects their motivations to their behaviours. For example: “What would success look like for you this quarter?”
• Diagnose before prescribing: Treat coaching like a doctor’s visit—don’t jump to solutions before understanding the root cause of a rep’s challenges. Use questions and data to guide your analysis.
• Integrate coaching into the workflow: Coaching doesn’t need to be a standalone event. Tie it into deal reviews, pipeline meetings, or quick post-call debriefs. Focus on one area at a time to avoid overwhelming your reps.

Final thoughts

Sales coaching is one of the most powerful ways to drive performance, yet it’s often underutilised or poorly executed. By focusing on better discovery, creating momentum, building trust, and differentiating effectively, you can help your reps execute deals like top performers.

Utilise insights from tools like Digital Sales Rooms to guide your sales coaching sessions with data. Combine these insights with thoughtful, goal-driven conversations that focus on diagnosing challenges and empowering reps to grow.

Remember: great coaching isn’t just about deals—it’s about transformation. By investing in your team’s development, you create a culture of excellence that leads to consistent, repeatable success.

This blog was written by Richard Smith – Head of Growth at MySalesCoach. MySalesCoach is the leading Sales Coaching Marketplace, expertly matching sales teams and individuals to their perfect sales coach. Whether it be providing organisations with ongoing and regular ‘in the moment’ access to top class coaching, or tackling the root cause of missed quota, we arm revenue teams with the essential skills, tactics and behaviours, through highly curated experts.

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