As a sales manager, I have pipeline meetings often. But along the way, I’ve learned that pipeline review meetings can be an incredible coaching opportunity — you just have to approach it right.
Let’s start with an analogy: You wouldn’t expect a rookie with no training to pick up a bat in a major league baseball game and knock it out of the park on his first try. Similarly, if a sales manager is only spending 30 minutes a month coaching each of their reps, it’s unreasonable to think that the manager is going to improve rep performance.
But these pipeline reviews should be true coaching sessions — not data-scrubbing meetings. I’ve found salespeople become more capable of closing deals only when managers actively coach them, not when they’re badgered about getting the forecast right. Unfortunately, many pipeline conversations resemble the latter more than the former.
Today, I’ll review the best pipeline coaching strategies and share some tips from my experience along the way.
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Table of Contents
- What is pipeline coaching?
- How to Conduct a Pipeline Review That Actually Moves Deals Forward
- Pipeline Coaching Strategy Tips
- Turn Strategy Into Action With Pipeline Coaching
What is pipeline coaching?
Pipeline coaching is when a sales manager mentors a rep during a pipeline review, focusing on deal strategy rather than just forecasting. Instead of only tracking numbers, the conversation should center around:
- How to improve deal conversion rates.
- Addressing common roadblocks in the sales process.
- Coaching reps on outreach, follow-ups, and closing techniques.
Numbers alone don’t help reps improve. They need guidance on how to move deals forward. Effective pipeline coaching ensures that every conversation adds value, helping reps navigate objections, refine their approach, and close more deals.
Importance of Pipeline Coaching
Pipeline coaching is one of the most powerful tools a sales manager has. Why? Because it directly impacts:
- Forecast accuracy. Reduces pipeline bloat by helping reps focus on real opportunities.
- Deal velocity. Helps move deals through the pipeline faster by eliminating roadblocks.
- Win rates. Ensures reps are properly qualifying leads and closing the right deals.
Without effective coaching, reps waste time on bad opportunities, miss key buying signals, and struggle to close.
But here’s the problem: Most pipeline meetings aren’t coaching sessions. They’re status updates. Reps list off deals, managers listen, and nothing changes.
Leslie Venetz, Founder of The Sales-Led GTM Agency, sees this all the time. She puts it bluntly, “Instead, use pipeline meetings as a way to dig into where deals are not converting. Uncover trends and use it as an opportunity to provide reps specific coaching on nuanced elements of the sales cycle.”
So, what does good pipeline coaching look like? I’ll get into it in the next section.
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How to Conduct a Pipeline Review That Actually Moves Deals Forward
The last thing salespeople need is another meeting that doesn’t add value. A poorly run pipeline review can feel like just another calendar block filled with status updates that no one actually benefits from. That’s why I focus on making every pipeline review a high-impact working session — something that actually helps reps close deals.
For reps, this means getting real support in the areas they need most — whether that’s overcoming objections, multi-threading effectively, or re-engaging stalled prospects.
For managers, it’s an opportunity to coach with intention, identify deal patterns, and help the team make real progress.
Here’s how to make sure every pipeline review delivers value.
1. Start with preparation.
A great pipeline review starts before the meeting even begins.
I fully agree with Venetz’s advice here: Reps should come in prepared with 2-3 areas where they need support. This flips the conversation from a passive update to an active coaching session.
For example, instead of a rep saying, “I have a deal at 50% likelihood of closing,” she should be saying, “I’m struggling to get buy-in from the CFO. I’ve built a strong case with the VP of Sales, but I need help navigating the financial objections.”
Now, instead of just reviewing raw numbers and CRM updates, you’re strategizing together on how to win the deal.
2. Focus on conversions instead of updates.
If your pipeline meeting is just a rundown of open deals, you’re doing it wrong.
Look for patterns. Are deals stalling at the same stage? Are certain accounts ghosting reps after a proposal? Is there a common objection that keeps surfacing?
Instead of asking, “How many deals are in your pipeline?” I recommend asking:
- Which deals have stalled, and why?
- Where are you losing the most opportunities?
- What’s keeping this deal from moving forward?
By shifting the focus from what’s in the pipeline to why it’s not converting, you uncover real coaching opportunities that actually improve performance.
3. Give your reps ownership.
A pipeline review shouldn’t feel like an interrogation. If reps are just responding to your questions, they’re not thinking critically about their deals.
Flip the script — let them lead. Instead of managers running the meeting, I like to give reps some ownership in the discussion, asking questions about:
- Deals that are at risk (“I think I’m about to lose this one — here’s why”).
- Areas they need help with (“I struggle with urgency — what’s the best way to create it?”).
- Their strategy for moving deals forward (“I’ve had success multi-threading — here’s how I did it”).
I’ve learned that these tactics help shift meetings from status updates to real problem-solving. And more importantly, reps walk away with clear next steps instead of just passive feedback.
4. Focus on next steps — not just strategy.
A deal with no momentum is a deal that’s going nowhere. If a rep says they’re “waiting to hear back,” that’s a red flag.
Challenge them to be more proactive:
- “Just checking in…” → “I know this is a key priority for Q2 — would you be open to a quick call to align on next steps?”
- “They’re thinking it over.” → “Who else needs to be involved in the decision-making process?”
If a deal is sitting stagnant, push for clarity:
- What’s the plan to re-engage?
- Who else can we bring into the conversation?
- What’s stopping them from deciding today?
Now you’ve got the basics on how to run a pipeline review meeting — next I’ll share some expert tips to help you improve your strategy.
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Pipeline Coaching Strategy Tips
Once you’ve structured your pipeline meetings to be more than just a forecast review, the next step is optimizing your coaching approach. I’ll share three key strategies to make your pipeline coaching more effective and results-driven.
1. Talk about early-stage and late-stage deals.
Even though it’s tempting to only address the deals about to close, I think it’s important to spend time on deals early in the selling process as well. Why? It’s an opportunity to get bad deals out of the pipeline early so reps don’t waste their time and to offer reps some valuable insight.
Obviously, closing is the final (or second-to-last, if you count retention) step of a sales process, and a sales pipeline represents the sum of a rep’s opportunities — along with where they stand in each stage of that progression.
If a rep is going to learn, grow, and ultimately become as well-rounded a salesperson as possible, they need to have perspective on their opportunities at every stage — even if they don’t all end in closed-won deals.
That doesn’t mean you have to dig into a thorough investigation of every last qualified lead in a rep’s pipeline during these kinds of meetings — but you shouldn’t focus exclusively on late-stage deals either.
I think it’s a tough balance to strike — as you don’t want to exhaust too much of your and your rep’s time — but a rep’s pipeline isn’t limited to the home stretch. Make sure you cover those additional, earlier bases as well.
What I like: Sales managers can have a greater impact on a deal in its early days, increasing the likelihood of earning the business.
2. Spend more time on fewer deals.
The natural inclination of sales managers is to get through the entire pipeline during each meeting, but in my opinion, this isn’t the best use of time. I recommend focusing intensely on a handful of deals, and doing a deep dive into each — the competition, the buyers in the organization, the rep’s approach, and so on.
As I touched on in the previous section, you don’t want to spend too much time on pipeline coaching — especially if you have a larger team of reps to account for. You’ll stretch yourself too thin, and in many cases, too much pipeline coaching can have diminishing returns.
When it comes down to it, discerning which deals in a rep’s pipeline deserve extra attention is a judgment call. If possible, I would try to strike a balance between highlighting some wins and constructively touching on some deals that show room for improvement.
Example: Rather than skimming over 20 deals in one meeting, spend 15-20 minutes breaking down two or three critical opportunities. If a rep is struggling with an enterprise deal, walk through a step-by-step strategy to navigate the complex buying process.
There’s something to be learned from both opportunities that go well and ones that don’t pan out — so try to offer a mix if possible. That said, don’t indiscriminately cover every last opportunity in depth each time you have one of these meetings. You’ll likely wind up being redundant and wasting time if you go that road.
What I like: A manager can change the trajectory of a deal if it’s at risk of going awry or address emerging problems.
3. Coach more, inspect data less.
Managers who have been promoted from reps earned their management role by selling well, not inspecting data well. And yet, data-scrubbing is often the focus of pipeline management meetings. While accurate data is important, more time should be allotted to coaching reps through deals than cleaning up the numbers.
If you can, use data to inform the coaching session as opposed to dominating it — let the numbers guide where the conversation goes, but don’t just sit there rattling off figures and then sending reps on their way when you’re done.
Pro tip: “Coaching requires a leader who comes prepared to offer insights, ask questions, make space for role-playing or brainstorming, and lead the rep to better outcomes because they understand WHY they need to change their habits to get better outcomes,” says Venetz.
Corny as this might sound, sales is — at its core — a fundamentally human practice. Any data your sales org gathers is ultimately people-driven. If a rep’s numbers aren’t where they should be, use that as a starting point in a pipeline coaching session.
From there, you can dig into the elements of their efforts that might be skewing those figures away from their goals. There’s a difference between simply relaying information to a rep and helping them make sense of it. Be constructive — and teach more than you dictate.
What I like: By spending less time inspecting data, your sales managers can mentor reps on their process and give advice about live deals.
Turn Strategy Into Action With Pipeline Coaching
Overall, a good pipeline review session is more forward- than backward-looking. I like to influence live deals today rather than merely documenting their outcomes later. Hopefully some of these tips inspire you in your next pipeline review session.
By focusing on early-stage deals, prioritizing deeper coaching, and shifting away from pure data inspection, you turn pipeline coaching into a powerful tool that drives results for your team.
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- People to Meet
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