Deal Coaching 101: A Step-by-Step Guide For Sales Leaders

Think you’re doing deal coaching? If your sessions aren’t sparking action, surfacing blind spots, and building rep confidence, you’re not coaching — you’re just holding a fancier pipeline review. If you're not sure, find out what is deal coaching.

This step-by-step guide, built from the hard-won insights of our expert sales coaches: Hillary Wild, Aaron Margolis, Steve Myers, Volker Ballueder, Richard Bounds, Alan Duncan and Alan Clark.

Let's dive in.

Learn how to measure deal coaching, and what is the difference between deal coaching and pipeline reviews. and the differences between deal coaching vs skill coaching.

Step 1: Start with Curiosity, Not Control

Why this matters:

The biggest coaching opportunities lie in how reps think, not just what they do. Early in the conversation, reps often reveal uncertainty through vague language or emotional language — that’s your leverage point.

If you try to impose structure too soon, you miss the chance to understand how they’re currently evaluating deals and making decisions .

“Start open, then get more pointed to guide them toward the right conclusion.” — Hillary Wild

How to do it:

• Begin with open-ended, TED-style questions:

  “Tell me about…”, “Explain to me how…”, “Describe to me when…”

• Listen for “I think”, “I hope”, “I feel” — signals they’re guessing, not grounding in fact.

• Avoid leading questions that close down reflection.

Questions to ask:

• “Why did you choose this deal for coaching?”

• “How do you assess what makes a good deal?”

• “Imagine you’re in your next call — what do you want to learn most?”

Step 2: Decode Their Notes Before You Coach

Why this matters:

The way a rep captures and shares deal information is a window into how they think, how they organise, and whether they’re operating off facts or vibes. Hillary Wild uses pre-session notes to gauge a rep’s mindset — whether they lean on metrics and frameworks or rely on anecdotal hunches .

“How they structure deal info tells you how they think.” — Hillary Wild

What to look for:

• Concrete data vs. vague “good meeting” fluff

• Stakeholder maps with names, roles, influence

• Clear next steps, timelines, and risks

• Signs of qualification frameworks (MEDDIC, etc.)

Red flags:

• Meandering bullet lists

• Overuse of soft language (“Joe seems keen…”)

• No clear decision criteria

Questions to ask pre-session:

• “Can you share your notes including stakeholders, next steps, and key metrics?”

• “Where are you confident, and where are you guessing?”

Step 3: Structure the Session for Action

Why this matters:

As Hillary and Aaron both stress, deal coaching isn’t a discussion for its own sake. It’s about sharpening judgment and creating forward motion. The session must end with concrete next steps — or you’ve just had a nice chat .

“You’re not coaching a deal for coaching’s sake—you have to go do something now.” — Hillary Wild

“Come with a solution. I don’t want to speak first.” — Aaron Margolis

Timing is important in deal coaching. Don’t wait until the end of the cycle when there’s no room to act. Whether it’s during qualification, stakeholder mapping, or close strategy, coach at the stage where you can still affect the outcome .

“It’s important that you do it in enough time to take full advantage of the advice… if you’re that far down the process, sometimes the die’s already been cast.” — Alan Duncan

Session breakdown:

1. 5 minutes of free talk — spot the vague language.

2. Framework check-in — MEDDIC, mutual action plans, next meeting structure.

3. Rehearse the next step — what the rep will actually say/do.

4. End with accountability — confirm action items.

Questions to guide discussion:

• “What’s your plan for the next call?”

• “What’s the one question you’re nervous to ask?”

• “What’s the blocker from your side?”

Step 4: Identify the True Blockers

Why this matters:

Our coaches all agree that the barrier isn’t usually the buyer — it’s the rep’s hesitation. Hillary identifies fear (especially fear of being bold or direct) as the most common deal-killer. Reps often know the exact question they need to ask — they just don’t feel like they can .

“Nine times out of ten, it’s fear of asking a question.” — Hillary Wild

Richard’s advice sharpens the blocker diagnosis: focus on what you’re really solving, the impact of delay, and how you’re managing internal champions or “mobilisers.” Blockers often lie in unchallenged assumptions .

“Challenge assumptions, guide how to manage champions, clarify clear next steps that help bring the deal forward.” — Richard Bounds

Common internal blockers:

• Fear of being pushy

• Imposter syndrome with senior buyers

• Relying on hope vs. evidence

External blockers to assess:

• Multiple stakeholders

• Procurement delays

• Competitive threats

Questions to surface blockers:

• “What question are you avoiding?”

• “What’s the buyer not telling us?”

• “What would happen if you asked them directly?”

Step 5: Create Aha Moments

Why this matters:

Hillary and Aaron emphasise that mindset shifts — not tactical plays — are the true signs of effective coaching. When a rep goes from “Can I say that?” to “I should say that,” they’re beginning to sell like a pro. The goal isn’t to coach every deal — it’s to make reps more independent over time .

“You are not inferior to your buyer.” — Hillary Wild

“Eventually, they need you less. That’s the win.” — Aaron Margolis

The best coaching develops a rep’s critical thinking, not compliance. Great coaches teach sellers to question what they don’t know and avoid blindly following checklists. His lens is pragmatic but diagnostic.

“Can you articulate pain at three levels? Who are the champions? The Black Knights? What’s your hypothesis about the decision-making process?” — Steve Myers

Examples of breakthrough moments:

• “Wait… I can just ask them that?”

• “I’ve been trying to avoid that conversation — I need to lean in.”

• “I’m not here to impress the buyer. I’m here to help them succeed.”

Step 6: Don’t Mix It with Pipeline Reviews

Why this matters:

Our coaches are adamant on this. Pipeline reviews and deal coaching serve different purposes. One is about where a deal is — the other is about how to move it. Confusing the two leads to shallow insights and missed opportunities for growth .

“Ideally you want to coach outside of the pipeline review.” — Aaron Margolis

How to keep them separate:

• Block separate time for coaching deep dives

• Focus on 1–2 deals max per session

• Keep pipeline reviews factual; coaching sessions diagnostic

Step 7: Prioritise Deals (and Reps) Like a Coach

Why this matters:

Not every deal deserves coaching. Coaches like Steve Myers and Alan Clark urge sales leaders to prioritise coachable reps and stuck-but-salvageable deals — not just big-ticket opportunities. The goal is ROI on your coaching time, not a vanity scorecard .

When it comes to deal coaching, size doesn’t always matter. Steve stresses coachability and proximity to close as more important than deal value. Don’t waste time on reps who won’t act or on early-stage fluff.

“The lazy answer is to focus on bigger opportunities. Prioritise based on coachability.” — Steve Myers

“Focus on deals that are stuck but winnable.” — Alan Clark

Make deal coaching a non-negotiable habit. If a rep is stuck, they need to raise their hand early. Prioritise based on urgency and coachability — and don’t be afraid to get hands-on.

“Prioritise it like a boss. Block it in. If you need deal coaching—if you are stuck—make time for it.” — Volker Ballueder

When it comes to deal coaching, size doesn’t always matter. Steve stresses coachability and proximity to close as more important than deal value. Don’t waste time on reps who won’t act or on early-stage fluff.

What to prioritise:

• High-impact or high-risk deals

• New stakeholders or recent changes

• Coachable reps who’ll implement advice

• Patterns of stuckness you can fix at scale

Step 8: Build a Culture of Honesty

Why this matters:

Reps don’t bring you real problems unless they trust you. Aaron and others stress that psychological safety — built through vulnerability, empathy, and shared mistakes — is the foundation of effective coaching. You earn that trust by being human first, leader second .

“It comes down to trust. I’ve made the same mistakes they’re making now.” — Aaron Margolis

How to build that culture:

• Share your own war stories — especially failures

• Give honest, respectful feedback

• Celebrate bold questions, not just closed deals

Final Thought: Deal Coaching Isn’t a Meeting — It’s a Skill

Real deal coaching reshapes how reps think, not just what they do. It’s not about you having the answer. It’s about helping them discover it — and believe in it.

“Deal coaching isn’t about telling someone what to do. It’s about helping them realise how to improve — and believe they can.” — Hillary Wild

Your Reps Need Deal Coaching. You Don’t Need To Do It All Alone.

Between back-to-back meetings and pressure to hit targets, most sales leaders struggle to give every deal the attention it deserves.

The result? Stalled deals, missed learning moments, and inconsistent growth.

That’s where MySalesCoach steps in.

We pair your team with seasoned sales coaches who deliver targeted, tactical deal support—so your reps keep progressing, your pipeline stays healthy, and you stay focused on leading, not firefighting.

👉 Book a call with one of our experts to share some ideas around deal coaching—and explore how we can support you.