The sales manager's guide to data-driven one-on-ones


Ah, the one-on-one. Where managerial and sales worlds seamlessly align.

These meetings provide effortless clarity on performance, robust development plans, and follow up steps that are implemented from the moment the two parties leave the room with a spring in their step.


What about the last-minute spreadsheet compilations? Recklessly fast calculations to try to piece together some sort of conversions?

And what about that look in the salesperson’s eye? You know... that look they have when they give a spirited response to next week’s targets, but you’re not convinced they know how they’re going to crack it.

In this post I'll delve into why data is so crucial to being on the same page as your direct reports. I’ll look at how data can help review what matters and provide clear next actions for a new generation of salespeople who value autonomy and thrive on accountability. 

What data do you need for a one-on-one?

First, consider the options for the data you need. Weekly, monthly, quarterly, biannually, annual trends and – where applicable – projections for weeks, months and quarters.

Secondly, be sure to have these figures at a team-wide and company-wide level for comparison and context.

Then, you’ll need 10 metrics:

  1. Revenue: How have they been performing against target?

  2. Pipeline Generation: Have they been creating enough pipeline consistently?

  3. Pipeline Coverage: How much do they have booked in future periods to cover revenue goals?

  4. Pipeline Growth: Is their total open pipeline growing, flatlining, or shrinking?

  5. Funnel Stage Conversions: Which part of the funnel do they lose most deals in?

  6. Key Prospecting Event to Opportunity Created Conversion: This could be a demo, meeting or diagnosis. The last pivotal event prior to an opportunity being created

  7. Average Sales Cycle: Are they selling too slowly?

  8. Average Deal Value: Are they discounting too heavily?

  9. Average Stage Tenancy: How long do deals spend at each stage in the sales process?

  10. Pipeline Win Rate: This will support pipeline coverage and will offer clarity even if they don’t close their duff deals off

The above gives you every data point you’ll need to have specific conversations about your direct report’s performance, the reasons behind their performance, and where you can help support them.

Then, build a financial model or use an existing tool that predicts what’s going to happen next month, based on existing information. By tweaking how each metric might affect performance, you can paint a bigger picture of how your team could perform over the next month.

Using moving averages and viewing trends over time gives evidence that your coaching is effective and that your team are getting better. When raw figures can be small, make them noticeable with by providing more context.

Now, pick a metric, any metric. Has it been getting worse or better? What behaviour or skill could have accounted for this, and how could it be improved through coaching or enablement? If the metric does improve, how much could this affect performance next month or next quarter?

Notice how this method drives a targeted conversation which is measurable, meaningful and actionable. 

The importance of continual visibility

It shouldn’t be news to your salesperson that a certain trend is occurring. They should have access to these data points, and should know how they’re tracking before they head into the meeting. Why?

  • Give your salesperson complete accountability for the performance and health of their business. No more hiding and hopeful back slapping.

  • Ignorance is not bliss. To create truly successful salespeople, or to have chance of doing so, it’s important to understand every aspect of their performance.

  • To enable salespeople to perform, it’s important to know what to enable, and how this is likely to impact performance.

Set your salesperson up with their own “Business Health Centre”. It doesn’t matter if this is in your CRM, a spreadsheet, or another tool you may have. Give them true sight of how healthy their business is, and make it their responsibility to improve. We all know millennials love autonomy (see Daniel Pink’s Drive).

The Utopian outcome here is to have your salesperson bring their one-on-one to you. “Here are my weak spots. Here are the areas that have been getting stronger and I think it’s because… Here’s what I think I could work on to improve this metric, and this would close by gap to target by…” 

How exactly does data support actionable next steps?

Any good doctor will tell you that to offer a prescription or treatment, the diagnosis must be robustly based on the patient’s illness. Eek!

A one-on-one is no different. Watch your salesperson ride the hunch-driven merry go round and watch them land right back at their first thought. I’ve certainly scratched my head in a one-on-one and wondered why that person isn’t meeting targets.

Effort is too broad to measure, and measuring motivation isn’t always specific enough. But, when you can identify where’s best to direct behaviour, and this is supported by evidence, that’s when the magic happens. 

So, in summary…

  • Gather the correct performance data

  • Make the data continually available, visible and contextual

  • Provide a single source of truth for autonomy and accountability

  • Lay out next steps that you both believe is the right course of action

  • Celebrate small improvements and project how they move the bigger picture

 Rory Brown is Co-Founder and CCO of Kluster, a smarter sales analytics and forecasting platform. Read more of Rory’s sales insights on the Kluster blog.

Blog postsAlan Wanders