How to Nail Your Forecast in Week 1: Part 3 (Video)

Headshot photograph of Anthony Cessario, VP of Industries and Market Expansion at Clari

Anthony Cessario
VP of Sales, Enterprise



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Photograph of two sales leaders sitting  in front of a laptop at a conference table discussing the sales forecast
Photograph of two sales leaders sitting  in front of a laptop at a conference table discussing the sales forecast

Anthony Cessario leads Clari's Enterprise West sales team.

Hey everyone, welcome to step 3 of How to Nail Your Forecast in Week 1. In steps 1 and 2, I shared you how to triangulate a reality check and then, using those insights, how to inspect you current and out-quarter pipeline to identify risk and opportunity.

Those two steps are the first pieces to the puzzle and they've helped me come within 2% of my sales forecast in week 1 every quarter since joining Clari. Today, I'll be sharing the next step in that process. For reference, here are the previous and future steps:

Without further ado, let's dive into step 3.

Step 3: Conduct data-driven one-on-one sales coaching sessions

Your one-on-one sales meetings should be 90% coaching around risk mitigation, pipeline acceleration, and deal execution, and 10% reporting the news. Unfortunately, almost all one-on-one sales meetings are on the exact opposite side of that metric.

Frontline sales managers are to blame, not the reps.

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When we as leaders don’t come to these one-on-one sales meetings with a data-driven POV on open opportunities, we are forcing reps to report the news and we will inherently spend less time coaching while our reps spend more time reporting — going deal by deal and giving updates on activities and engagement.

A sales leader at one of our customers told me that his reps say their favorite thing about Clari is how they spend 50% less time reporting the news to their bosses. At the same time, his managers tell him that they’re having much more meaningful conversations with the reps. Win-win.

As I go into these first one-on-one sales meetings with the team, here’s my process:

  1. Come with a point of view. We start with them sharing their POV on the quarter and how they think their business will perform.
  2. Have specific questions prepared. I then pivot to asking very pointed questions based on my pipeline inspection (part 2) research to pressure test weaknesses in the risky deals that Clari’s AI surfaced.
  3. Spend time strategizing. We then spend the majority of our time strategizing how to de-risk the risky deals and accelerate the strong ones.

Last quarter, two of those deals that Clari’s data science identified as risky ended up being pushed out to the next quarter to better align with the natural sales cycle.

For one of them we were able to leverage our current customer community for an intro to the economic buyer which helped us de-risk the deal and accelerate the close.

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However, the reality is some deals just need to be pushed. In order to backfill those deals that fell out of quarter, we took a look at out-quarter for deals where Clari showed promise based on:

  • CRM Score: An AI and machine learning analysis of historic win and loss data to predict which deals are most likely to close)
  • Sales activity data: Meetings, emails, file attachments Marketo engagement, account-based marketing engagement, etc... that are automatically tracked and attached to the proper opportunity so reps don't have to.

Then we pressure tested them for opportunities to pull them in quarter and cover any deals that we identified as at risk.

With our deals set for the quarter, we're ready to share with the entire revenue operations team with confidence. We'll be covering how all of the pieces of the puzzle come together in Part 4.

While you wait for the last section in our 4-part series, be sure to watch the videos from Part 1 and 2 below.

Step 1: Triangulate a reality check.

Step 2: Inspect current and out-quarter pipeline.

Step 3: Conduct data-driven one-on-one sales coaching sessions.

Step 4: Bring your revenue teams together. One of the benefits of pressure testing out-quarter deals and forecasting out-quarter pipeline is that this forward-looking visibility gives the entire revenue team much more confidence in the pipeline going into the quarter. I'll walk through what this looks like. (Available September 25)

Interested in hearing more? I’m happy to share my learnings. Email me at a or request a demo from one of our Clari experts.