What’s the Difference? And Why It Matters
Picture this: a sales leader steps into their weekly one-on-one and immediately jumps into dissecting pipeline deals. After 45 minutes of CRM spelunking, the meeting ends. The rep leaves with a task list—but no new capabilities, no clarity on career goals, and certainly no uptick in confidence.
Sound familiar?
If you’re coaching only deals, you’re missing two-thirds of the picture. The best sales coaches know how to blend deal coaching, skill coaching, and sales coaching to drive both immediate results and long-term performance. But what’s the difference between them—and when should you use which?
This article is part of Deal Coaching, and find out more about why we launched deal coaching from our Founder & CEO Kevin Beales here.
Let’s break it down with some wisdom from the MySalesCoach bench of coaching pros.
Deal Coaching: Move This Deal Forward
- The problem: Many leaders mistake pipeline reviews for coaching. But without strategic direction, it’s just… commentary.
- The alternative: Effective deal coaching is about rolling up your sleeves and helping a seller think through one specific opportunity. You’re digging into the risks, spotting the gaps, and co-creating a plan to get that deal unstuck.
As Kaitlen Kelly puts it:
“Deal coaching is really getting into the weeds. You’re taking it one deal at a time… what can we do to move it one step forward and strategically drive that progression?”
Alan Clark echoes the point:
“Deal coaching is about this deal right now that we’re talking about.”
As highlighted in our article, “Deal Coaching vs Pipeline Reviews: Stop Mixing Them Up”, it’s crucial to distinguish between pipeline reviews and deal coaching. While pipeline reviews focus on the health of your sales funnel, deal coaching dives deep into individual opportunities to strategise and overcome specific challenges.
Things to Do:
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Analyse stakeholder mapping and decision process.
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Stress-test next steps and timeline.
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Identify gaps in discovery or proof points.
Questions to Ask:
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What’s the real reason this deal is stuck?
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Who else needs to be engaged?
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What’s our mutual plan with the buyer?
Skill Coaching: Upgrade Their Capabilities
- The problem: Reps plateau when they’re not building new capabilities. Deal-by-deal reviews don’t teach better objection handling, discovery, or storytelling.
- The alternative: Skill coaching targets how someone sells. It’s about developing repeatable techniques, not just winning a deal.
Alan Duncan explains,
“All sellers have strengths and weaknesses. As coaches, we can help develop a range of skills and help progress sellers’ capabilities to make them better.”
Whether it’s cold calling, writing better emails, or running a smoother demo—this is where skill coaching shines.
In our blog, “Deal Coaching 101: A Step-by-Step Guide To Winning More Deals For Sales Leaders”, we emphasise the importance of understanding a rep’s mindset and approach. Skill coaching involves dissecting these aspects to build stronger, more effective sales techniques that can be applied across various deals.
Things to Do:
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Roleplay common call scenarios.
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Give specific feedback on objection handling.
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Build mini-practice sessions into weekly 1:1s.
Questions to Ask:
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What part of the sales process do you feel least confident in?
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What skill, if improved, would unlock the most deals?
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What feedback have you received from buyers?
Sales Coaching: Build Long-Term Growth
- The problem: Without broader coaching, reps may hit target but stall in career growth—or worse, burn out.
- The alternative: Sales coaching blends deal and skill coaching, then goes deeper. It’s about mindset, motivation, and momentum. This is where you install habits and build future leaders.
As Alan Clark puts it:
“Sales coaching is the broader journey… you’re trying to install habits, mindsets, where their career is going, what’s motivating—all that kind of stuff.”
Volker Ballueder adds,
“Sales coaching can be a little bit of mentoring… helping someone from a leadership perspective, or to get unstuck.”
Our article, “The Power of In-the-Moment Deal Coaching: Why Timing Can Save Deals”, discusses how timely interventions can significantly impact a rep’s performance and mindset. Incorporating real-time coaching moments into your sales coaching strategy can help reinforce positive behaviours and address challenges as they arise, fostering long-term growth.
Things to Do:
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Set career growth milestones.
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Explore personal motivators and blockers.
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Coach mental fitness: resilience, confidence, self-awareness.
Questions to Ask:
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Where do you want to be in 12 months?
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What’s holding you back right now?
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What would success feel like—not just look like—for you?
You Need All Three
Volker Ballueder nails it:
“One-to-ones are more personal growth, performance, career. But deal coaching is a lot more tactical, a lot more focused.”
All three forms of coaching—deal, skill, and sales—play a crucial role. If you want reps who close more, grow faster, and stick around longer, you need to flex across all of them.
Takeaways:
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Deal coaching = Tactics for this opportunity.
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Skill coaching = Techniques for repeatable success.
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Sales coaching = Trajectory for the whole career.
Make sure your coaching calendar reflects all three. Your reps—and your pipeline—will thank you.
Want coaching that covers it all?
MySalesCoach offers deal coaching, skill coaching, and sales coaching for both individuals and teams—so you don’t have to choose between immediate pipeline impact and long-term growth.
Book a call with our team to see how we can support your sales goals.
