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Each and every lead should fly through our funnels without a hiccup, in a perfect world that is.

The reality, though?

Many sales teams are stuck with pipelines that aren’t exactly in tip-top shape.

And hey, we totally get it. That’s why we recommend that you regularly check in with your sales reps to perform a pipeline “health-check.”

Doing so can identify bottlenecks and help your team avoid potential headaches before they spiral out of control.

But the question remains: what’s the best way to assess your pipeline and what questions should you ask your reps, anyway?

How to figure out if your pipeline is healthy?

We asked ten sales professionals about their process for a pipeline health-check.

No matter what you’re selling, the following strategies can offer some much-needed insight for teams stuck second-guessing the state of their pipelines.


Mike Kunkle

Vice President,
VP, Sales Enablement Services – SPARXiQ

Are the opportunities qualified and to what level? Do they have NASA and does the rep have the FACTs straight?

NASA: Need And Solution Alignment
FACTs: Funding, Alternatives, Committee, Timing

How effectively are the Buying Process Exit Criteria being managed, by decision maker?

Do we know what each needs to see, hear, feel, understand and believe in each stage, to move forward to the next stage, with us? How well is the rep uncovering, clarifying, meeting, and confirming acceptance of provided support, for these exit criteria?

Exit Criteria: specific requirements that determine whether a certain stage in the sales process has been completed and identify that the buyer can move on to the next stage in the sales process?

At a high level, that’s where I’d spend my energy on pipeline management. Then, the feedback or coaching that’s needed is contextual to the opportunity (based on the above stuff and your overall situation assessment).

Ask Mike on pipeline management


Trish Bertuzzi

Founder and CEO at The Bridge Group, Inc.
Author of “The Sales Development Playbook”
SDR / AE / CSM Evangelist

Let me give you my fav question for a Manager to ask a rep during a pipeline health check.

On a scale of 1 to 4 with 4 being a done deal how likely is this organization to do business with us?

If less than a 4, the follow-up question is:

– Lay out for me everything we need to do to make this deal happen.

– Then that plan is what you coach to.

Ask Trish on Sales coaching


Richard Harris

Founder – The Harris Consulting Group

I will take a completely different approach.

Pipeline meetings are the perfect place for career and skills development.

This strategy works for the most advanced and newest members of your team. Ask one simple question for each deal you discuss.

Convince me what it will take to close this deal by XX date? And if it won’t close, what would prevent it?

This teaches real accountability, by showing them how to come prepared to a pipeline meeting.

Additionally, you can still ask and use all the other suggestions mentioned, but I find starting at this 60k foot view is most helpful in long and short term.
The only “gotcha” in this scenario is that a manager will often believe the sales rep because of their own happy ears. One must keep digging to get to the truth.

If the deal falls through and you say, “But you told me!”, then that is actually on the leadership for not asking enough of the right questions.

Ask Richard about Coaching your Sales Reps


Bob Perkins

Founder & Chairman – AA-ISP,
(American Association of Inside Sales Professionals)

Try and identify “missing information”. Try to uncover what is not known to the salesperson. The more missing info tends to point to more risk.

Missing info: Any engagement data, communication activity and other essential data for each opportunity in your pipeline. Missing info is a great symptom of your sales pipeline having an un-healthy look.

Ask Bob about leveraging information to minimize risks


Jim McDonough

Strategy Consultant at OpFocus, Inc.

What’s the state of our Inflow/Outflow report?

One of my favorite things to look at in terms of a health check for sales pipeline is an Inflow/Outflow report.

Every morning I take a look at how many new opportunities were created the day before and how many closed or pushed out. I do this by record count and dollar amount.

Additionally, I ask the reps to answer questions prior to the meeting so I can review them ahead of time. This allows us to have a more strategic conversation about how to move the deals forward vs a more tactical conversation which I find tends to happen when the conversation is happening in real time during the meeting.

Inflow/Outflow report: a report that shows what goes to your pipeline and what comes out of it. In other words, Inflow is the new opportunities that enter your pipeline from a multitude of channels; while Outflow is made up of all Closed-Won and Closed-Lost opportunities.

Ask Jim on pipeline management


Alice Heiman

Co-Founder and CRO at TradeShow Makeover

I personally like to look at the shape of the pipeline which I call a sales funnel.

I like the image of a funnel better. We know there needs to be a lot in the top for the appropriate sales revenue to come out the bottom. If the shape is off, I know what to focus on. For example, if the top of the funnel is very small, I know we need to generate more leads. If the funnel is bloated in the middle, I know we need to get those opportunities moving. Then I can dig in with questions and solutions to make that happen.

Sales funnel: a visual representation of the buying process that a customer goes through from the first contact to the purchase.

Ask Alice about pipeline management


Bob Hatcher

CEO at Bettersell Solutions

A great question is simply this:

What’s your plan to close the deal?

Nine out of ten reps will know the few next steps but won’t have a plan to close the deal.

Ask them to start at the end with “We just got a signed contract, now work backwards to where we are today and tell us your plan.” Far too many reps (and people in general) think their success is in their own hands and forget to account for outside forces.

So, another interesting question is this:

Who are we competing against and based on what we know about them, what actions should we expect from them and what should we be doing?

Lastly, the “pre-mortem”. Simply ask this:

We executed our plan flawlessly and still lost. Why?

This asks the rep to look for unidentified risks and will expose many of the things above. The lesson here? Planning is the most underused sales skill out there.

Sales planning includes sales forecasting, demand management, revenue targets, strategies and tactics to achieve the set goals.

Ask Bob about Sales planning


John Barrows

Owner and CEO of JBarrows Sales Training

The questions I ask customers that dictate my forecast is

What happens if you don’t make this decision?


What happens if you don’t make this decision by the date you told me?

There is either a real answer to this question with real impact or there isn’t. If there isn’t a real answer with real impact, then you’re either not talking to the right person or I wouldn’t forecast that opp.

Ask John on Customer communication


Karthik Subramanian

Content Marketer at Paperflite

How much time prospects spend on sales content?

One way of doing it is by seeing how much time they have spent on the content that sales reps share with prospects. It is a good indicator if customers are interested in the product/service/solution.

Ask Karthik about Sales content


Nancy Nardin

Founder, SmartSelling Tools
Co-founder Vendor Neutral

I’ll add a few questions that are somewhat different like:


If something were to make the deal go south, what would it be?


What questions/issues does the prospect keep asking about?


What question should you ask the prospect or buying team, that you just haven’t asked?

Ask Nancy about Customer pain points


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