September 29

What’s Keeping Your Sales Reps Up At Night?

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We’ve all heard at one time or another that we need to find out “what’s keeping our prospects and customers up at night.”  Effective salespeople engage in pre-call planning and create questions to uncover the answer. Finding out what’s keeping prospects and customers up at night shines a light on the right course of action to take with sales recommendations.

Sales managers, integrate this selling approach into your sales management coaching conversations. When meeting with members of your sales team, ask and uncover the answer to the powerful question:  

“What’s keeping you up at night?”

It’s a simple coaching question, one that’s not asked often enough during one-on-one coaching sessions. This question opens up bigger conversations and builds deeper relationships with members of your sales team.

Deal coaching is important, however, getting deals across the finish line may not be what’s keeping your salesperson up at night.

For example, you might hear a salesperson say, “There is so much information coming at me every day. I’m not sure how to keep up.” 

Overwhelm may be keeping your sales reps up at night.


Their answer doesn’t have anything to do with opening or closing business.

It has everything to do with helping you customize your coaching conversations in order to help your salesperson.  

  • Maybe this salesperson needs help in getting crystal clear on what information is critical to their sales success.
  • Perhaps the salesperson simply needs more education around priority management or time management.
  • Or, there’s a good chance that FOMO is making an appearance. Fear of missing out can create overwhelm because the salesperson is exhausted chasing shiny new objects...for fear of missing out!   

The answer from your salesperson may have nothing to do with business and everything to do with something happening in their personal life. You might hear:

  • My aging parents are in denial. They think they can stay in their home and it’s getting to a point where it’s not safe for them to be in their own home.
  • My teenager is feeling a little lost because she just moved to a new school and I am worried about her.
  • My husband’s father is ill and he’s been the rock of the family for years.

Now, you might be wondering, what can I do about any of these personal issues? I’m hired to drive sales. I’m not a retirement counselor or therapist.

You are correct.

However, knowing this information means you can do something that is in your full control and capacity as a sales leader. 

You can show you care. It’s amazing how far a little caring and support goes to helping people sleep at night.

You can connect your salesperson with resources or other people dealing with similar issues. A support group often helps people sleep better at night.

You can check in with your salesperson and ask how things are going with the issues they shared.

What’s keeping you up at night? A great question to ask during your one-on-one coaching sessions.

Good Selling!


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