You’re a Sales Manager in charge of a team. Your job is to make sure they are hitting goals and outputting their best effort, and a large part of that is coaching and having check-ins with each member of your team. But do you know if your weekly one-on-one’s are constructive, data-driven conversations; or do they always turn into sales pipeline interrogations, trying to figure out what went wrong last week?

One of the most powerful tools in developing your sales team is the weekly one-on-one, but a lot of Sales Managers don’t do it right. The employee is left scrambling to justify his or her numbers while the manager is thinking “I wish I had a way to get my reps to be honest with themselves about deals and their likelihood to close.” Sound familiar? Well here are three ways to help your employees be better equipped for your one-on-one’s.

1. Have them keep an eye on stalled opportunities

A sales rep needs to actively work an opportunity for it to progress down the pipeline. So if an opportunity hasn’t had an activity logged against it in a couple weeks, there’s a good chance that it is not being worked efficiently, and these are the ones in danger of slipping through the cracks. Have your sales reps pull a report of open opportunities and highlight the ones that haven’t had an activity in 10 business days. If they can come into the one-on-one without a single opportunity that’s stalled, that’s a great start.

State of Pipeline

(We created a bubble chart to show the current pipeline. Bubbles in red are stalled)

2. Have them know their sales cycles in terms of deals won or lost

The longer a deal isn’t closed, the more likely you’ll lose that deal. When looking at open opportunities in your employee’s pipeline, it is critical to understand their sales cycle and more specifically their sales cycle by stage. Take a look at the chart below:

Stage Won vs. Loss

This shows how long won or lost deals stayed in each phase of the sales cycle. In this example, we see that for the deals that were won, they spent about 4 days longer in the trial phase than the deals that were lost. So why does a longer trial lead to more closed won deals? Are some dropping out early from the trial so the ones that stay actually close? Does that mean your trial needs to be tweaked to show more immediate value at the start? These are the questions your sales rep should have answers to, or at least be prepared to discuss during your one-on-one. Insights like these can lead to a shift in your sales process that could lead to big wins.

3. Have them explain any close date changes

Since we are on the subject of being honest about deals, have you ever had a rep push the close date of an opportunity out several times? Understandably some deals just take longer and may not close when they are projected to, but what if the deal is just continually getting pushed out? Is this a real deal?

Change in Opp

Have them bring a list of opportunities that have had their close dates pushed off. This will keep them accountable not only in keeping accurate close dates, but they won’t be pushing them out unless they have a good reason.

As you can see, having your sales reps come prepared with analytics to your one-on-ones will prompt them to be more data-driven. Arming themselves with data will make your meetings much more productive, and most of the heavy lifting will already be taken care of. Your reps knowing how you’ll be looking at their data is a great way to keep them motivated and goal oriented.

There you go let’s start having data-driven conversations in our one-on-ones!


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