Interrogate Your Pipeline; Coach Your People

Pipelines

During pipeline reviews, it’s not enough to perform a brief circuit around the room and ask each seller about their current deals. Instead, the best sales leaders truly interrogate their pipeline to ensure they effectively coach their people. Here’s how:

The Power of Interrogating Your Pipeline

Sales give your company oxygen. If you know precisely how much oxygen you’ll have, you can tailor the rest of your company’s activity around that knowledge. 

Interrogation of my pipeline was surprisingly a solitary activity – analyzing our data, reviewing seller and sales manager’s insights plus personal experience/instinct – to determine with confidence how much revenue was going to close. Overestimate and the company can experience excessive cash burn possibly leading to layoffs and capital crunch.  Underestimate and the company can underinvest, forgoing growth, opportunity and ceding share to a competitor. Every revenue leader is expected to deliver the number but, even more so, is expected to accurately forecast what number they will deliver.

Often, after interrogating my pipeline, I would call the CEO or tell the board “We will make this much money this quarter.” Properly interrogating my pipeline has placed me within $50k of my incoming revenue on millions of dollars of sales. Even if the CEO didn’t like the number, with a nine-month sales cycle there was little we could do to change the forecast in the quarter and an inaccurate number would have led to far worse decisions.

How to Interrogate Your Pipeline

Data – not emotion or optimism, enables accurate predictions. When getting a sales interrogation practice up and running, I recommend truly diving deep into your pipeline every month – well beyond the stages and the numbers in your CRM and the instinct of your sellers and sales managers. Here’s how to get that revops practice up to speed:

1. Gather Good Data

Data powers your knowledge. On the customer side, all your engagement points should feed into one data warehouse. (This process requires cookies or pixels on your website, integration with your marketing automation system, advertising analytics, webinar analytics and any other touchpoints – video, SMS – through which your buyer is engaging with your business). Then, combine that customer-side data with data from your team.

You can gather this data by hand or use software to help. If your GTM function uses a customer data platform like Segment, you’ll already have everything in one place. Some enterprises integrate the data into dashboards where you can see each channel’s performance but that requires extensive custom integrations into your CRM to align the channel data with individual contacts, accounts and opportunities. Historically I’ve combined a spreadsheet from Salesforce with my marketing data and legal documents. While this compiling process can be done manually, it can feel tedious. I’m excited to be using Segment to expedite this part of pipeline interrogation.

Not all the data is quantitative. Listening objectively in a buying conversation will unveil other insights – what is the seller worried about in the deal? Is the buyer an actual champion or a coach? Does the buyer have an urgency driver that is propelling momentum for the deal? Can the buyer articulate the value the buyer will realize from the deal? Using Gong or Chorus, sales managers, CROs and CEOs can quickly assess the texture of an opportunity and add that to the interrogation and ensuring coaching. These sales coaching platforms will often provide recommendations for the coaching action to help improve the pipeline’s potential. If you don’t have a system, sales team meetings where sales managers ask open ended questions to unlock those insights makes the pipeline development and coaching process more productive.

You’ve completed the data-gathering when your process has radically reduced its blind spots. This means you have data on most every point of customer engagement, even information on SMS conversations.

Ramping up this habit can take a while, but it’s invaluable once it’s complete. Many of my pipeline interrogations have forecasted better than AI prediction systems like Clari, largely because I incorporated more information and I could adjust for the swings of large deals on a forecast. Clari is still a favorite of mine as it captures the development of the pipeline and forecast over time and can be configured to make Deal Desk a breeze.

2. Analysis

You shouldn’t have to ask the prospect if they’re interested. You can see it through their activities. 

Activities prove interest

Is the prospect:

  • Taking calls?
  • Sending emails?
  • Replying to SMS?
  • Coming to your website?
  • Reading your information?
  • Watching your videos?
  • Sharing your information inside their team?

If you have a single hub capturing every client conversation, you should easily be able to note every action that the customer is taking toward your deal. Ideally, you should expect to see multiple contacts within an account engaging with your business digitally with increasing frequency as the opportunity matures.  This pattern lessens once the opportunity is in the final stages of contract negotiations.

In addition to those more-narrative pieces, there also exist a few key data points that imply interest:

  • Proof from multiple people at the customer. No high-priced software is bought by a soloist, so you should be on the lookout for multiple stakeholders demonstrating tangible interest. That’s your buying team.
  • Negotiation. Very few customers buy without requesting a discount. Big companies have procurement officers incentivized to get the best deal from you. In smaller companies, a controller or CFO will play that role. If they haven’t queried you about a discount, implementation services, support packages, they’re less likely to be serious.
  • Deal necessities, specifically around legal and security. Are their lawyers reading your contract? Have they asked for your SOC 2 report? No major company buys software without reading your contract and reviewing your security and privacy. If they aren’t doing their due diligence, they aren’t really moving the deal forward. Sellers need to proactively coach their buyers through the conversations and gates that are likely to be required to advance their opportunity.

3. Feed-Forward Into Action through Coaching

Not only does this analysis inform you about your current state; it enables you to accelerate your deals. If the customer has expressed interest, for example, but isn’t reviewing your contract or SOC 2 report, prompt them to! They will need to run these legal and security reviews before signing. Inexperienced buyers may not prioritize these activities, but realizing they cannot execute without them will slow or torpedo your deal.

If a prospect hasn’t started legal or security review, nudge them as soon as possible. These sorts of tactics help avoid later delays, especially with large companies, where reviews can take a while.


If an account shows only a single contact engaging with your business, that’s a red flag. Coach your seller to map the account, identify the likely other stakeholders and be unafraid to reach out to those senior stakeholders directly or through an executive at your own company.

When engagement accelerates or decelerates for an account (not just a contact), the sales team should adjust their strategy and tone for how to support their champion.  This is often an opportunity to determine if your champion is actually a coach and ensure that the economic buyer is getting the information needed to support your opportunity.

Get to know what engagement opportunities (particularly content, tools, videos, webinars, events) correlate to opportunities that you win, faster sales cycles and higher prices. While precise attribution is impossible for a complex sale where there are 11-13 touch points per opportunity for each of 5-11 contacts, over time patterns emerge for what content correlates with won opportunities. That information can lead to higher return on investment for sales and marketing resources.

More Accurate Predictions → More Deals

Many revenue operations teams fail to recognize and realize the massive value of comprehensive and accurate pipeline knowledge. They simply perform a perfunctory review that notes which deals are moving from state to stage. They waste time on poor prospects and mis-state their upcoming earnings.

When you truly interrogate your pipeline and use it to coach your people, the precise understanding more than pays for itself, providing accurate information you can use to reorganize your resources and power your company’s growth.

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