Picture this: A rep is deep into a high-stakes deal. Things were moving, momentum felt good, but suddenly—it stalls.
A key decision-maker goes dark. Objections pop up like weeds. The rep’s confidence wavers. They have questions they need answering, quickly.
It’s at this point, if action isn't taken quickly, most deals end in no decision.
This is the critical moment a deal coach needs to jump in, ask the right questions, support their rep and rescue the deal.
A post-mortem is no good. Real-time, targeted support that unblocks, refocuses, and accelerates towards wins is key.
Our Sales Coaches Steve Myers, Richard Bounds, Aaron Margolis, Alan Duncan, Volker Ballueder, Kaitlen Kelly and Alan Clark share their expert views in this article, and help you to ask the right questions at the right time to rescue your own deals.
Let's dive in.
This article is part of Deal Coaching, and find out more about why we launched deal coaching from our Founder & CEO Kevin Beales here.
When the Clock is Ticking, Coaching Needs to Be Immediate
Too many sales orgs operate with a lag. They review deals after the quarter ends, after the loss, after the lesson has already cost them.
While pipeline reviews focus on forecasting and deal hygiene, they often miss the nuances of real-time deal dynamics. In contrast, deal coaching zeroes in on the tactical moves needed to advance specific opportunities.
As Steve Myers puts it:
“In-the-moment deal coaching is often the difference between a deal that drifts into ‘no decision’ and one that actually closes.”
Richard Bounds echoes this:
“It helps win rates by getting a new perspective, digging deeper into your deals, giving analysis, addressing challenges as they happen, and giving suggestions to move and progress the opportunity forward.”
Alan Clark doesn’t mince his words:
“When a deal goes quiet, gets a bit messy, stuck—you know, quick, targeted coaching at that moment can help unblock before it actually dies.”
For a clearer distinction between these two critical processes, explore our detailed comparison in Deal Coaching vs Pipeline Reviews.
Things to Do
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Embed deal coaching into your sales process as a just-in-time intervention
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Create Slack channels or hotlines where reps can request live deal help
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Schedule weekly “deal sprints” where stuck opportunities get coached in real time
Questions to Ask
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Where are reps consistently getting stuck in the cycle?
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Are managers jumping in too late to make a difference?
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How often are we catching deals before they stall, rather than after?
Coaching in Context: Supporting the Rep Without Taking Over
One of the biggest challenges? Coaching without hijacking. As Aaron Margolis describes:
“I always wanted to make sure that the salesperson was seen as the director of the deal, and I would only insert myself at times when it made sense to do so.”
Alan Duncan builds on his point:
“You get the passion from the seller, the passion from the client, and they can understand where some of the opportunities might be. And an impartial view to really helping a seller progress and close deals in the moment is really vital.”
In-the-moment coaching isn’t just about rescuing a deal. It’s about equipping the rep just enough to course-correct while staying in the driver’s seat. Think second brain, not co-pilot.
Implementing effective deal coaching requires more than just good intentions; it demands a structured approach.
Our comprehensive guide walks sales leaders through the process of embedding deal coaching into their teams, from setting clear objectives to measuring outcomes. Discover actionable strategies in Coaching a Sales Team on Deals.
Things to Do
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Role play tough conversations with your rep before big calls
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Review emails or proposals before they go out
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Debrief live interactions immediately, while the context is still fresh
Questions to Ask
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Am I empowering or overshadowing the seller?
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What signal does my presence send to the buyer?
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How can I stay supportive without taking the wheel?
The Org-Level Impact: Confidence, Forecasting, and Faster Closes
The benefits don’t stop at the rep. In-the-moment deal coaching levels up entire teams. Volker Ballueder summed it up:
“It unblocks deals, sharpens thinking, brings confidence—so they’re asking better questions, and they win faster.”
And the ripple effects run deep:
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Teams learn from shared challenges
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Enablement spots gaps in real time
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Forecasting becomes grounded in reality, not hope
Kaitlen Kelly adds:
“It gives visibility into where deals get stuck or lost… and helps ops with forecasting.”
Alan Clark shared this gem from a sales leader:
“He now gets fewer late-stage surprises from the team, which is a nice thing to have.”
And Richard Bounds drives this home:
“It builds best practice, repeatable questions and approaches that help you beyond the individual deal. Critically, it helps with deal velocity, win rates, and building seller confidence.”
Understanding the impact of your coaching efforts is crucial for continuous improvement. Our experts share key metrics and evaluation techniques to assess the effectiveness of deal coaching, ensuring it drives the desired results. Learn how to quantify success in How to Measure Deal Coaching Effectiveness.
Things to Do
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Capture insights from live deal coaching sessions for team learning
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Use those insights to refine enablement content
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Analyse which coaching moments correlate most with win rates
Questions to Ask
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Are we spotting repeat patterns across deals?
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What tools are we giving reps to self-diagnose stuck deals?
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How do we scale this approach across regions or teams?
Conclusion: Make Coaching a Reflex, Not a Recap
In-the-moment deal coaching isn’t a nice-to-have—it’s a muscle. One that turns reactive reviews into proactive moves. It speeds up sales cycles, builds seller independence, and improves team-wide performance.
Most importantly? It helps close deals that would otherwise slip away.
🚨 Do Your Reps Need Deal Support Right Now?
Not Sure Where To Find The Time To Do This All By Yourself?
As Sales Leader, you're spinning many plates and are already spread thinly.
You may not always be able to provide that critical, time sensitive support that could be the difference between winning and losing a deal.But what if a deal coach could jump in right then?
MySalesCoach compliments your internal coaching, and offers same-day (often same-hour) deal coaching delivered by sales experts who’ve been in your rep’s shoes—and won.
Whether your seller is stuck on a stalled deal, facing last-minute objections, or trying to re-engage a ghosted buyer, our coaches have seen it before and know how to win.
👉 Book a call to find out more about how we can support your team.
