Sales Pipeline

Learn how to discover and correct behavioral problems to drive predictable growth with this guide to sales pipeline inspection.

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 Table of Contents

  1. Executive summary

  2. Red flags on open sales pipeline:

    • Age

    • Activity

    • Close dates

    • Size

    • Contacts

  3. Closed opportunity analysis:

    • Conversion rates

    • Stage usage

    • Sales cycle length

  4. Creating actions and coaching moments

  5. Conclusion



FunnelCake has evaluated common process issues in opportunity management across hundreds of Salesforce implementations in B2B organizations.

This guide highlights common data points that can be used for coaching. By identifying and acting on red flags early, organizations have seen as much as a 2x improvement in lead-to-revenue conversion rates, with more reps consistently hitting quota.


Executive Summary

Sales managers need to drive predictable growth with visibility into sales pipeline and change rep behavior with coaching.

This guide highlights how you can use common process issues and red flags in CRM data to create coaching moments with your team.

The goal of any revenue organization is to help sales reps go from lead to revenue in the shortest path possible. To help them get there, sales managers need to enable reps with:

  • Visibility

  • Accountability

  • Change in behavior

A key way to achieve this is through sales pipeline inspection and coaching.


The need for better coaching

Many sales management teams are solely focused on managing specific deals in the short-term forecast. While this can be effective, it creates a top-down, siloed approach that doesn’t develop your sales team.


Forecast-centric coaching can lead to large gaps in your sales teams skill-set – by optimizing resources for the needs of management over the needs of the sales reps. This top-down approach can be effective, but leads to large gaps in reporting, disconnected processes, and a lack of development of the sales reps core skillset leading to dirty data and confusing processes.

Holistic sales management

After analyzing hundreds of sales funnels, we’ve designed a holistic sales management model that supplements existing coaching methods with actions that enable reps to change rep behavior.

This holistic model connects your CRM, processes, and targets directly to risk analysis and actions – enabling your sales reps to take direct action on your processes without the need for sales management intervention.



This guide focuses on how processes and risk analysis in the opportunity funnel can drive coaching moments that reduce risk and increase the consistent performance of your sales team.


Red flags on open pipeline 

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Managing risk in open sales pipeline can be complicated for both reps and managers. It’s easy to stay focused on the marquee deals, while other deals to fall through the cracks. 

Red flag pipeline inspection is a fast, effective way to stay on top of every deal by mitigating risks every day. The following section highlights red flags you can use to identify risk, coach reps, and enforce best practices.



Opportunity age is a highly predictive indicator of whether a deal will be won or lost.


The red flags:


The amount of time an opportunity has spent in the current stage of the funnel. This can be compared to recent wins and historical trends for that stage.


The total age of an opportunity since it was created. This should be compared to your historical sales cycle length.

Why it happens:

Opportunities at risk for age typically happen because:

  • The deal is alive, but stuck and the rep needs help moving it forward

  • The deal is alive, but delayed

  • The account has long-term potential so the rep is holding onto the opportunity to keep visibility on it

  • The deal is dead, but it has not be marked as lost


Why you should care:

If more than 10% of your opportunities are presenting risk from age it indicates a serious problem, such as:

  • A gap between the type of prospects in sales pipeline vs. the type of prospects you typically win

  • A large amount of dead, open opportunities – inflating coverage and forecast numbers

  • Reps are using the opportunity as a holding pen to manage and nurture long term accounts

There are fairly large consequences of this:

  • Inflated sales pipeline coverage and forecast numbers when planning

  • Marketing automation may be set up to ignore open opportunities, preventing communications from going out to prospects who are a better fit for nurture programs

  • If the opportunities are truly dead, lead recycling programs will not re-assign these accounts to SDRs for redevelopment

  • Conversion rates will be impacted, artificially inflating the coverage you need to hit targets while also making close rates look better than they are

Age and activity metrics (covered next) work very well together to identify risks in your funnel.

Questions to ask:

  • Is the opportunity still active?

  • Why is this opportunity stuck?

  • What can we do to move the prospect forward in the funnel?


  • Do our sales reps use the stages of our funnel in the same way?

  • Do we have clear criteria for when opportunities should enter and exit a stage, or be marked as lost?

  • Should we implement automation rules to close-out stagnant opportunities?



Activities, touchpoints, and tasks: logging these gives full transparency into what’s happened with an opportunity and what’s happening next. 


Emails, calls, meetings, notes, and files

Logging interactions with an account are critical for documenting what’s happened and when – both for reporting, but also for hand-offs between teams and postmortem analysis.

The red flags:

  • No activity has ever been logged by the rep in Salesforce

  • There is no recent activity logged by the rep in Salesforce – i.e. in the past 30 days

Why you should care:

By the time an opportunity has made it to sales pipeline you’ve spent substantial resources generating and qualifying a lead – to have it die on the vine is a huge waste.

There are a few reasons activities aren’t logged:

  • The opportunity was re-assigned to the rep and they haven’t seen it – such as a handoff with an SDR or territory re-assignment

  • The opportunity is moving along but the rep is failing to log any of the activities in Salesforce – which prevents sales managers from coaching or sharing best practices (this creates additional risk if the rep leaves the organization)

  • The rep has forgotten about the opportunity and it has gone cold

  • The deal is dead but has not been marked as closed/lost

If the opportunity is actually dead, but the rep hasn’t closed it yet, it’s falsely inflating your sales pipeline and impacting the ability for you and the team to have an accurate forecast. This also kills your ability to nurture these opportunities since most marketing automation platforms are set up to ignore contacts involved in open sales pipeline.

If the opportunity isn’t forgotten about and the rep is just neglecting to update Salesforce with progress, you’re losing out on insights about which activities, or how many activities it takes to move accounts through each stage of your funnel. You also lose the ability to have historical context if a rep leaves the organization or opportunities are handed off to a different rep.

Questions to ask:

  • Is this opportunity still moving forward?

    • If yes: why is there no touch points on the account?

    • If no: why isn’t it marked as closed/lost?

  • Have you been in contact with this account?

    • If yes: why aren’t you logging the information in Salesforce?

    • If no: why has there been no contact in 30+ days?


  • Do our reps have a consistent understanding of how they are supposed to log notes?



Most reps give up on accounts too soon – touchpoints over time ensures reps work deals to their full potential.

The red flags:

  • The opportunity has too few touchpoints within the account based on the current age and/or stage of the opportunity – either based on a service level agreement or historical performance for won deals

Why it happens:

  • The rep has too many open opportunities in sales pipeline and is selectively prioritizing which opportunities should receive a full cadence

  • The rep gave up on non-responsive prospects after a small number of touches

  • The prospect goes silent and the rep doesn’t attempt to re-engage them

  • The rep has forgotten about the opportunity or doesn’t have adequate views in Salesforce for managing sales pipeline

Why you should care:

The main concern is letting qualified opportunities die on the vine – these leads were likely time consuming and expensive to generate through Marketing and Sales Development efforts.

This can lead to long-term negative impressions about your business, such as prospects inferring a sales rep’s poor response times and lack of follow-up are how the business operates in all areas.

Questions to ask:

  • Is this opportunity still active?

  • Why haven’t you been engaging with them?

  • What steps can you take to re-engage them?


Tasks and next steps

Effectively managing tasks in Salesforce helps reps to stay on top of their follow-ups, particularly for long-term engagements.

The red flags:

  • The rep hasn’t set any follow-up tasks or next steps in Salesforce

  • There are follow-up tasks, but they are overdue (the due date is in the past)

  • Next steps are listed, but not specific, i.e. “Follow-up on Monday”

Why it happens:

Overdue tasks usually happen when:

  • The task was forgotten about, but the rep engaged in a different way

  • The task was completed, but the rep forgot to update Salesforce

  • The rep has too many tasks or inadequate task views – so the task was forgotten about and the opportunity is sitting idle

  • Automation systems are automatically creating tasks for reps to manage their funnel, which are being ignored

Missing tasks usually happen when:

  • The rep is not sure of next steps

  • The rep is not actively working the opportunity

  • The rep is managing their funnel outside of Salesforce

Why you should care:

If there is a more recent activity than the overdue task, the rep either did not see the task, ignored the task, or did not mark the task as completed in Salesforce. This can be fixed with coaching.

If the rep hasn’t logged activity since before the tasks due date this indicates an opportunity management issue. For smaller tasks like a follow-up phone call this may not have a big impact, but for bigger tasks like sending over a proposal, it can have major consequences on open sales pipeline.

Questions to ask:

• Was the task completed?
• If no: why not?
• If yes: why was it not logged in Salesforce?

• By not completing the task, is the opportunity now at risk?


  • Do our reps need additional training on how to use tasks effectively in Salesforce?

  • Do we have too many automated tasks in Salesforce that are making tasks difficult for our reps to effectively use?


Close dates

Close dates are required for an accurate forecast. Mis-managing close dates can be a symptom of larger problems.  


The red flags:

  • Close dates are overdue

  • Close dates are consistently pushed out

  • Close dates are optimistic for the current stage of the funnel compared to your historical sales cycle

Why it happens:

  • The opportunity moves slower than expected and doesn’t get updated accordingly

  • The opportunity is dead and the rep hasn’t marked it as closed/lost

Depending on how you track performance, reps may have incentives to keep dead opportunities open–such as trying to maintain a specific amount of sales pipeline coverage or win rate.


Why you should care:

Opportunities moving slower than expected and exceed the close date indicate that the sales rep is too optimistic about the deal closing, also known as “happy ears”.

If the opportunity is actually dead but is still sitting in open sales pipeline, it’s falsely inflating your open sales pipeline and impacting the ability for you and the team to have an accurate forecast. It also kills your ability to nurture these opportunities if your marketing automation platforms are set up to ignore contacts involved in open sales pipeline.

Questions to ask:

  • Is this opportunity still moving forward?

    • If yes: why wasn’t the close date updated?

    • If no: why isn’t it marked as closed/lost?

  • What caused this opportunity to move past the expected close date?

  • When do you believe the opportunity will close? And why do you believe that date is accurate?



Opportunity size helps identify if a rep is chasing the right opportunities or needs help closing a big deal.


The red flags:

  • The opportunity is larger than anything the rep has recently (or ever) won

  • The opportunity size keeps changing – this is mostly an issue when it happens on many different opportunities by the same rep

  • The opportunity is in sales pipeline but still doesn’t have a deal size set

Why it happens:

Large deals

  • The rep is working deals outside their segment

  • The rep is working prospects that aren’t a fit

  • The rep is overly optimistic about the deal size

Deal sizes are changing

  • The rep hasn’t qualified the opportunity correctly to determine the appropriate budget or solution fit to sell into the prospect

  • The rep hasn’t managed pricing negotiations and the price keeps changing

No deal size

Many organizations do not set deal sizes in prospecting stages of the opportunity funnel – however if an opportunity reaches sales pipeline without a deal size set, it should be flagged as a risk.

Why you should care:

It’s okay for reps to push the boundaries of deal size, but if reps have a high ratio of large deals in their sales pipeline, it could mean they are focusing on whales at the expense of catching a lot of fish. If this is the case, it’s likely the rep isn’t working their small deals to the same degree of effort, even if you’re more likely to win them as an organization. Deal size ranges are important to evaluate for the segment the rep is working in.

If a large deal is a good fit and well qualified, identifying it early helps bring sales leadership in to support the rep in bringing the deal across the finish line.

When deal sizes keep changing it creates a high level of volatility in your forecast.

Opportunities moving through the funnel with no deal size artificially decrease the size of your open sales pipeline, forecast, and coverage model.

Questions to ask:

  • What makes this deal different from our other opportunities?

  • Is it realistic that this deal will close?

  • What support from leadership do you need to keep this opportunity moving?



Having the right contacts engaged in the opportunity is core to moving deals forward – logging these in Salesforce ensures you can see who the rep has involved in a deal.

The red flags:

  • The opportunity does not have a primary contact

  • The opportunity does not have contact roles set up in Salesforce

  • The account does not have any contacts in Salesforce

Why it happens:

  • The rep hasn’t engaged additional contacts or the right contacts within the account

  • The rep isn’t using Salesforce and doesn’t know (or care) that they need to be adding contacts into Salesforce

Why you should care:

  • Identifying and working the right contacts can help drive the conversation forward

  • If contacts are consistently linked to opportunities, it enables sales management to help identify the health of an opportunity and coach reps on how to engage the rest of the buying team

  • If the rep leaves the organization, there will be no log of who they have been interacting with on the buying team – making it incredibly difficult to pick up the sales conversation

Questions to ask:

  • Who are you working with in this account?

  • Who else do we need to engage?

  • Why aren’t those contacts in Salesforce?


  • Which contacts do we need inside of an account to win a deal?

  • Do we need those contacts involved at specific stages of the opportunity?

  • Can we automate adding contact roles through workflows in Salesforce or third-party tools?


Closed deal analysis  

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Quarterly business reviews and postmortem deal analysis are critical steps to help each rep (and each team) understand their performance gaps. 

The following section focuses on how to use closed deal analysis to identify key trends and change bad behaviors in managing your sales funnel. 


Conversion rates

Conversion rates are the primary method of measuring the health of your sales process as a whole, identifying key stages where deals get stuck or lost.


The red flags:

  • Conversion drops consistently month over month

  • Loss in a specific stage is substantial

  • Reps aren’t able to convert any opportunities through the full funnel

Why you should care:

Conversion rates are foundational to funnel planning and forecasting – ensuring they are consistent is the primary method for creating a scalable sales process or identifying when new risk is emerging in your funnel.

Questions to ask:

  • If a high amount of opportunities are staying in a specific stage, why are they getting stuck there?

  • If a high amount of opportunities are getting lost in a specific stage, why there?


  • If a specific stage is a consistent roadblock in the business, what can be done to improve that stage’s performance?

  • If several stages of the funnel have nearly 100% conversion rates (typical for closing stages), do they need to be distinct stages?


Stage usage

Opportunities that skip stages of the funnel, or are created in the middle of the funnel.  


The red flags:

  • The opportunity was created in the middle of the funnel, i.e. stage 4

  • The opportunity skipped several stages, i.e. moving from Stage 3 to Closed Won

Why it happens:

  • The skipped stage was not necessary for that specific opportunity

  • The rep failed to update Salesforce as a opportunity passed through one or more stages

Example: the opportunity wasn’t added to Salesforce until a quote was sent to the prospect.

Why you should care:

If certain stages are commonly skipped only on certain opportunity types, you may want to consider using Sales Processes in Salesforce to customize stages based on different opportunity types.

If the sales rep failed to update stages in Salesforce it indicates a process issue that will skew your stage velocity metrics for a few reasons:

  1. You won’t be able to accurately forecast how long opportunities should spend in the remainder of the funnel certain stages are optional or frequently skipped

  2. You won’t be able to accurately measure your funnel if the stages aren’t being used

  3. You have too many stages or too rigorous of a process for specific opportunity types and your sales team is trying to streamline the CRM

  4. Your sales team needs additional training on your sales process and why stages are used. Salesforce Lightning’s sales paths and validation rules can be extremely helpful here

Questions to ask:

  • Was the stage skipped necessary for this opportunity?

    • If yes: why was it skipped?

    • If no: is this stage often skipped? Why?


Sales cycle length

Sales cycle length is an indicator of the stability and predictability in your funnel. It’s a great way to identify forecast accuracy, segment performance, and inform gut feelings in the sales process.  


One-off deals

There is always an exception – like the one deal that closed in a day, or in 24 months. But these could be the exception, not the rule – knowing the difference keeps your sales pipeline honest.

The red flags:

  • There are few deals that have “same day” close dates

  • There are few deals with a long sales cycle, creating a long tail to complete your sales cycle length (illustrated above)

  • There is a very wide distribution of sales durations within similar segments, which could indicate a lack of consistency in your sales process

Why it happens:

One-off deals happen in every organization – the risk is when one-off situations become expected or ingrained as folklore, such as frequently expecting very old deals to close.

Why you should care:

Folklore related to one-off deals can be very damaging to sales pipeline assessment and the ability for reps to accept help with coaching and reduces the likelihood of creating a culture of predictable revenue.


Backdated deals

Opportunities created in Salesforce after they have already been won.

The red flags:

  • A large amount of opportunities are backdated

  • For companies with financial compliance requirements, having even a small amount of backdated deals could cause significant issues

Why it happens:

  • The rep worked the deal in public, but forgot to add it to Salesforce

  • The rep worked the deal privately and sandbagged the forecast.

Why you should care:

When opportunities aren’t entered into Salesforce, it means you have zero ability to account for it in your forecasting while also missing out on information like:

  • What activities took place in each stage to move it forward

  • How long each stage took

  • Who was involved in the buying team

Questions to ask:

  • When did you start working this opportunity?

  • How were you tracking touchpoints, progress, and activity on this opportunity if not in Salesforce?

  • What circumstances led you to leaving this opportunity out of Salesforce?


Same-day close

Opportunities that are created in Salesforce and won on the same day.

The red flags:

  • A large amount of opportunities won are marked as same day deals

Why it happens:

Same day deals happen under two scenarios:

  • The opportunity was legitimately created and won on the same day – for transactional sales cycles this could be very common

  • The opportunity started weeks or months ago but didn’t get created in Salesforce until the day it was won

Why you should care:

If the opportunity was legitimately started and won in the same day then this is not an issue. If the opportunity was started, but not created in Salesforce until the day it was won, it causes your team to miss out on important information like:

  • How long the opportunity took in total (used to calculate sales cycle length)

  • How long the opportunity spent in each stage (used to calculate stage velocity)

  • What activities took place in order to close the opportunity

Questions to ask:

  • Did the opportunity really close in one day?

  • How long had you been working this opportunity for?

  • How were you tracking touchpoints, progress, and activity on this opportunity if not in Salesforce?

  • Was there any special circumstances with this account that made you decide to leave it out of Salesforce?


Actions & coaching moments

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Knowing is half the battle. Acting is how you win. 

To drive consistent sales performance your team needs frequent visibility into red flags, a method to be held accountable, and to change their behavior when they veer off track. 

This section highlights key ways to manage your team – through 1:1s, probing questions, and actionable notifications. 


Changing behavior with coaching

To drive a great team, your performance review should happen daily. Coaching on a regular cadence helps your team develop skills, focus on core objectives, and solve challenges early enough to make a difference.

Based on successful teams at scale, we’ve created the following sales coaching model.


  • Ad-hoc coaching on specific opportunity roadblocks

  • Automated alerts on process violations, task lists, and required follow-ups

  • In-person follow-up when alerts are ignored


  • 1:1s between sales managers and sales reps

  • Team-wide sales pipeline review meetings


  • Sales and Marketing postmortem win/loss analysis

  • Team-wide metrics review meetings


  • Sales, Marketing, and Success Quarterly Business Review (QBR)


  • Quota planning

  • Annual performance review

  • V2MOM (view the guide from Salesforce)


Automating alerts

It’s hard to keep track of every red flag on every opportunity your team is working. FunnelCake sends actionable alerts to reps and coaching moments to sales managers to help you and your team stay on top of your opportunities.



  • Pipeline inspection supplements deal coaching

  • Process enforcement is required to create a consistent, predictable sales organization

  • Process red flags are a standardized way to inspect process, identify risk, and coach reps

  • Pipeline inspection should happen frequently, from daily alerts to annual reviews 

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