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Pro Tips for Field Sales Coaching

Field teams are some of the most expensive employees on the payroll and some of the most difficult to manage. For field sales reps including wholesalers, distributors, and manufacturing reps, sales coaching can be a challenge.

While challenging, it must be done. Think of the often-quoted conversation between a CFO & CEO;

CFO: Think of how much coaching will cost us if they leave and we have to train new reps. 

CEO: Think of how much it will cost us if they stay.

Working with many multinational companies, we asked some sales leaders who have hundreds of reps and rep agencies working for them, how they effectively coach their field teams.

Here are some of the methods that they found helpful.

Ride alongs

The simplest and easiest way to coach a field rep is to be right on top of them while they are doing their job.

Nothing beats a ride along. Nothing.

Ride alongs are when a leader or experienced rep goes with a sales rep to their meetings and reviews follow-ups. Ride alongs are immensely invaluable for both the leader and the rep. 

For the leader, it gives them an opportunity to see how their people are performing out in the wild. They can determine what, if any, of the onboarding coaching took hold, in addition to what the rep’s strengths and weaknesses are.

For the rep, they get exposure to the wealth of knowledge that the leader can bring to bear. They get to hear an outsider’s opinion of their selling style, and can be provided tips on where to lean in and where to brush up. 

During a ride along, 100% of the time isn’t spent with the prospect. The downtime traveling to and from the meetings, lunch, and coffee breaks is when the real coaching happens.


If ride alongs aren’t feasible you might consider recording your sales reps’ calls or meetings. While it sounds big brother-esque, it isn’t. Every single one of us is recorded more often than we realize.

Reps and sales organizations shouldn’t fear recordings; they should embrace it.

For instance, in the last two years my team and I had over 300 discovery calls, both in person and over the phone. Every time we asked if we could record the call. Only two people did not allow it.

Most inside sales departments record calls all the time using software such as Voicera,, and Gong.Io. If you are in person, you can use your mobile device to record conversations. The value of a recording is immense.

Like ride alongs, recordings allow sales leaders to listen to calls, for both the content and tone, something that often lost in post meeting notes and recaps. Recordings allow for metrics including how long did each person spoke, the amount of questions that were posed by the buyer or by the seller, and much more.

Some organizations use recordings for A/B testing. Different teams get different scripts to follow, swap, and see which script performed better.

Testing & Certifications

As lifelong learning is something that all organizations strive to have their reps follow, a popular way that organizations coach is through testing and certification. Testing is always tricky when it comes to your sales organization because you are taking time away from your reps doing their most desired activity; selling. To maximize rep testing, the best practices adopted by different organizations are outlined below.

  • First, make the material compelling, valuable, and directly related to their selling activities.
  • Second, make the material available wherever the reps are and whenever they have the time to review it. Remember, a field rep will likely be spending time on a plane, subway, or at a tradeshow where online connectivity can be a challenge.
  • Third, provide reps with bite-size bits of information with ample review so when they have fifteen minutes between meetings, they can do some meaningful learning and achieve a certification milestone.
  • Lastly, it is important to reward sales reps for following through the material and succeeding in testing. This gives them a sense of validation for their effort, while motivating the laggards in the organization to push forward with their coaching program.

Coaching field teams can be challenging, of that there can be no doubt. Field agents are rarely in the office. They are traveling, they are bouncing between commitments, and tying together thirty consecutive minutes of their time is a task. To effectively coach field reps, you need to be creative and cognizant of their constraints. Being able to coach them on their schedule will increase the likelihood that the coaching will be useful and long-lasting.

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