Coaching Happens Weekly, But Deals Should Move Daily

Sales is all about momentum. Every day, your Account Executives (AEs) are working to align with buyers, tackle new objections, and move deals closer to the finish line. Yet surprisingly, many sales teams only dedicate one hour a week to coaching and strategizing on those critical deals.

For most sales leaders, the typical cadence looks like this:

• AEs meet with their sales director or VP every week (or two) for one-on-one coaching.

• Each AE picks two deals to discuss.

• The sales leader uses a structured, Socratic method to dig into risks, blockers, or next steps for those deals.

Sound familiar? While weekly coaching sessions can be effective, here's the big question you should be asking yourself:

Why are we doing this just once a week, and why are we focusing on only two deals?

If you want your team to maximize pipeline velocity and hit revenue targets, coaching cannot be a one-hour-per-week task. Your deals should be moving forward daily, with insights and actions that keep momentum alive.

The Secret to Closing Deals Faster Is Momentum

Buying processes are complex. That's the reality. Stakeholders shuffle priorities, budgets shift, and timelines get extended. Without proper oversight and action, promising deals can quickly stall without anyone noticing until it's too late.

Sales leaders often focus on the big picture metrics like deal velocity, win rates, and pipeline forecast accuracy. But these all hinge on one crucial factor in the trenches: deal momentum.

Momentum in sales is created by:

• Consistent Engagement: Frequent touchpoints with decision-makers across the buying committee.

• Proactive Risk Management: Identifying potential blockers before they fully surface.

• Clear Next Steps: Knowing what each stakeholder needs to move forward.

Think about it this way. If deals aren't progressing DAILY, how will your team have enough pipeline coverage to hit monthly or quarterly goals? Unfortunately, a single weekly coaching session isn't nearly enough to tackle the rapid shifts happening in your pipeline every day.

Coaching One Hour per Week Isn't Enough

The problem with relying solely on weekly coaching is simple:

• It's Reactive: By the time you address risks, the deal may already be in jeopardy.

• It's Limited in Scope: Discussing two deals leaves the rest of the pipeline largely untouched.

• It's Resource-Intensive: A manual approach to deal inspection takes up valuable time for both sales leaders and AEs.

This isn't to dismiss the importance of coaching. Weekly one-on-one sessions are still necessary to strengthen your team's skills, align on goals, and refine strategies. However, the core issue is that they're being treated like the only opportunity to strategize.

The solution? An always-on system that ensures deals progress daily—with or without the weekly check-in.

Introducing the Always-On Sales Assistant

Imagine having a 24/7 AI sales assistant working alongside your AEs to maintain deal momentum, identify risks, and recommend next actions. Instead of relying on weekly coaching to uncover important details, this assistant consistently works in the background to keep your pipeline healthy.

Here's how it can transform deal management for your team:

1. Daily Deal Progress

AI-powered systems analyze deal activity every day, flagging stalled opportunities or gaps in stakeholder engagement. This ensures that no deal goes "cold" simply because it wasn't discussed during weekly coaching.

2. Automated Risk Analysis

Risk factors like insufficient buying committee coverage or lack of recent activity are automatically surfaced by AI. You'll know immediately when a deal needs attention, rather than waiting until it becomes a problem during a coaching session.

3. Actionable Next Steps

The AI assistant provides your AEs with specific, actionable recommendations to move their deals forward. For example:

• "Send a follow-up email to [Stakeholder Name] regarding timeline alignment."

• "Schedule a meeting with the financial decision-maker to confirm budget approval."

4. Streamlined Coaching

When it's time for your weekly coaching session, you'll focus exclusively on the deals that require strategic intervention. The repetitive, low-value tasks will already be handled, allowing your team to focus on high-impact actions.

5. Scalable Best Practices

AI can analyze patterns from your top-performing AEs and automatically apply those insights across the team. Reps at every level benefit from proven methods without requiring constant hands-on coaching.

Simplifying Weekly Coaching with Data-Driven Insights

An always-on system not only boosts daily productivity but also enhances the value of your weekly one-on-one sessions. When your coaching is fueled by live deal data, you can:

• Prioritize the most critical deals for discussion.

• Use AI-driven insights to fill knowledge gaps before the call even starts.

• Shift the focus from deal inspection to strategic planning.

For example, imagine starting every coaching session with a dashboard that shows:

• Which deals are at risk and why.

• Real-time buying committee engagement levels.

• Suggested next steps for each high-priority opportunity.

Instead of focusing on low-impact conversations like, "What happened in this deal last week?", your coaching sessions shift to tackling high-level challenges and seizing new opportunities.

Why Sales Leaders Need to Act Now

For VPs, Directors of Sales, and Account Executives alike, the pressure to hit ambitious revenue targets is unrelenting. And with buying committees growing larger and sales cycles getting longer, improving pipeline management is no longer optional.

By investing in an AI-powered assistant now, you position your team for sustained success in three key ways:

• Smarter Time Management: Redirect time from manual deal reviews to strategic planning.

• Improved Forecast Accuracy: Eliminate surprises with consistent, real-time visibility into deal progress.

• Enhanced AE Productivity: Provide every rep with tailored guidance that mirrors the playbooks of your top performers.

Closing Thoughts

Momentum wins deals, not weekly one-hour coaching discussions. If you want to move your team from sticking points to closed-won opportunities, you need a system that works as fast as the pace of modern business.

Take the first step to revolutionize your sales coaching today. Equip your team with the tools they need to make daily progress and consistently crush their quotas.

Want to see how it works in action? Sign up for a free trial of our sales assistant platform now and start moving deals forward every single day.

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