After 20 years in sales and sales leadership, and having spoken with close to 1,000 sales leaders, I believe coaching is one of the most important jobs of a frontline sales manager. And 74% of U.S.-based executives at leading companies agree with me, according to Forbes Insights.

So why is the average sales manager spending so little time on this critical activity that will help them succeed and progress their own career? A common explanation from the manager is that they talk with reps all day every day about deals and meetings, so they’re coaching all the time. That is one important element, but it's just not enough.

If you probe more deeply, what you’ll discover is that many managers don’t really grasp what coaching really means. Those who want to be a great coach and understand conceptually why it's important struggle with how exactly to do it. I know I sure didn't know the first time I became a manager.

Just about every sales manager is a former successful salesperson, which doesn’t necessarily mean they’ll be a successful manager. On the flip side, those who do understand how to coach realize it’s probably the most important thing they do. The reason they were promoted is likely because the VP of Sales saw them as someone who can teach and make other salespeople better.

At LevelEleven, our goal is to transform the world of sales from reactive, top-down sales management to proactive, transparent sales leadership -- to get sales leaders to stop managing salespeople only around what’s closing and start motivating around the behaviors that will lead to closing. Research has found that the most effective sales coaching is consistent and data-driven, which is why we built a coaching add-on to our sales management solution that snapshots sales activity data and documents one-on-one sessions, all within Salesforce.

What we learned during this process is that everyone has a different idea of what sales coaching is. Some managers think that every interaction they have with a sales rep counts as coaching. Others know they need to have 30-minute one-on-one sessions with each of their reps every week, but aren’t sure what framework they should follow during that meeting.

The majority of sales coaching can be broken down into three categories.

Deal Coaching

Sales managers are typically former sellers who experienced a lot of success. They understand the many nuances to win business and beat quota and were promoted so they could bring that knowledge their sales team and make other people successful, too.

As a result, they’re typically very comfortable with deal coaching, which typically occurs on an ad hoc basis when a rep needs help. When a manager sees or hears about their rep struggling with a deal, they jump in. The manager asks questions about the opportunity like …  

  • Who’s involved?

  • What’s the timeline?

  • What are the external and internal obstacles to winning this customer?

  • Do we have any references we can introduce?

  • Do we have any relevant case studies?

The manager then provides her input and helps remove any obstacles, whether they be internal or external.

Meeting Coaching

This is focused on the nuances of messaging, how to command a room and people dynamics (mostly communication and soft skills). Managers provide their reps with very specific, candid feedback about a meeting to help them improve. Most frontline managers, especially new ones, don’t do this as they’re afraid they’ll hurt the rep’s feelings. But when done right, the opposite happens: Your reps will thank you and beg for more.

For a pre-meeting coaching (planning) session, a manager should sit down with reps and ask questions like …

  • What’s the goal of this meeting?

  • What do you hope to leave here with?

  • Who’s going to be in the meeting?

  • How long do we have?

  • How are you going to kick off the meeting?

  • What questions are you going to ask?

  • What do you think the customer is expecting from this meeting?

  • Who do you want talking the most?

  • What could make the meeting go sideways and how do we prevent that from happening?

Managers can also host a post-meeting coaching session. The manager attends (or listens in on) a meeting hosted by the rep and takes very detailed notes. I like to keep my notebook open and jot down what the rep did really well and where they could have improved. I usually put a simple plus (+) or minus (-) next to my notes so I can remember afterwards. It’s important to have very specific examples, which is why you should write it all down. Some examples...

  • “Great job opening the meeting to set the tone on the topic.”

  • “I would have asked each person to explain what they want to get out of the meeting.”

  • “You sounded a little hesitant when we started talking about deal terms. I know it’s a big topic, but you need to be confident here.”

  • “Great job stating your goal for the meeting at the beginning.”  

  • “You should have probed a bit when they said…”

  • “Nice job on having clear next steps.”

This feedback helps reps understand what specifically they need to work on to make their future meetings better. Also, before giving my feedback, I like to ask the rep to tell me how they thought the meeting went and why. You’ll hear great insights and self realizations around what needs to improve.

Salesperson Coaching

This is more about overall salesperson performance and is what a weekly one-on-one should be focused on. It’s a chance for both the salesperson and the manager to step back and discuss how things are going. Host these meetings on a regular schedule, either once a week for 30 minutes or once every other week for 60 minutes.

It’s best to have the agenda set ahead of time and that the salesperson comes to the meeting prepared to discuss those specific topics. You don’t want them walking in wondering what you’re going to talk about. Sure you’ll likely have some unique topics of your own, but you don’t want to start with both of you staring at each other waiting for who goes first.

The simple and common agenda would have a combination of subjective and objective topics. For example:

  • What’s going well?

  • Where do you need help?

  • Review key sales metrics and progress to goals, e.g., calls, meetings, new pipeline, pipeline to quota ratio.

  • Which specific deals will get you to quota this month or quarter?

When you hear the salesperson’s comments on all of this, it will be more clear where coaching and help is needed. The objective part is so often missed, which is a big mistake. Salespeople get easily distracted and lost in deals and administrative work, and don’t realize they’re missing on basic fundamentals like prospecting, having enough VP-level conversations or building pipeline. Reviewing this weekly keeps the fundamentals top of mind.

No other sales productivity investment improves rep performance better than coaching, and each of your reps needs these three types of sessions. If you want to learn more about sales coaching, we just hosted a webinar with some more best practices. Click here to watch the replay.

Being a great sales manager is so much more than working deals. It’s really about how to make other people better. If you do that consistently, there will be many more career growth opportunities in store for you.


Bob Marsh is Founder and CEO of LevelEleven, a sales engagement platform used by VP's of Sales to drive their transformation into a modern sales organization. High growth companies including HubSpot, Symantec, and Rocket Fuel use LevelEleven to keep salespeople focused on the behaviors that drive revenue, and help sales managers be modern, metrics driven coaches. Bob has more than 20-years of sales and sales management experience, and prior to founding LevelEleven in 2012, Bob spent more than a decade at ePrize which went from startup to more than 400 employees during his time there. Bob lives in metro-Detroit with his wife and three children.