Enable Sales Coaching in the Field: Build Rhythm That Sticks

You’ve introduced the Sales Call Performance Checklist, agreed on coaching priorities and asked your sales managers to spend more time observing their teams in the field. That’s a good start.

But what happens when a manager spots a salesperson struggling with a customer conversation and isn’t sure how to help? Or when managers complete their field coaching visits but the quality of their feedback varies from one team to another?

These are the challenges we need to address in Enable, the second stage of the Sales Coaching Ecosystem™. In How to Build a Sales Coaching Ecosystem That Works, I introduced three connected stages: Activate, Enable and Sustain.

Activate establishes what managers should observe and how field coaching gets started. Enable makes sure managers have the skills, tools and support to coach their salespeople effectively. Let’s look at what sales leaders can do to make that happen.

1. Find Out Where Your Managers Need Help with Coaching

Before arranging another coaching training workshop, take a closer look at how your managers actually coach.

Some managers are comfortable giving feedback but struggle to ask questions that help salespeople think. Others know how to discuss sales results but find it difficult to identify which selling behaviours need improvement. A few of them may be good coaches but lack the confidence to handle sensitive conversations with experienced salespeople. These managers don’t necessarily need the same development support.

Observe a Manager’s Coaching Conversation

Join a manager during a field coaching visit. Your purpose is to observe how the manager coaches, rather than to assess the salesperson. Pay attention to a few things:

• Does the manager explain what the coaching discussion will focus on?
• Does the manager refer to what actually happened during the customer interaction?
• Does the salesperson have a chance to share their views?
• Does the discussion end with a clear action the salesperson understands?

After the field visit, speak privately with the manager. You might ask:

• “Which part of that coaching discussion did you feel went well?”
• “Was there anything you found difficult to discuss?”
• “What would you like to handle differently next time?”

These conversations help you understand where the manager needs support. They also give you a better basis for deciding what coaching training or practice to provide.

2. Use Real Sales Situations to Develop Coaching Skills

Managers learn more effectively when they can practise coaching situations they recognise from their own work. A general coaching workshop may introduce useful questioning and listening techniques. However, managers also need to know how to apply those techniques when dealing with everyday sales challenges.

For example, consider a salesperson who repeatedly offers additional discounts whenever a customer complains about price. A manager’s immediate reaction might be: “You shouldn’t give discounts so easily.”. That may be commercially correct, but it doesn’t help the manager understand why the salesperson keeps doing it.

During coaching practice, ask the manager to explore the situation differently. The conversation might begin:

Manager: “When the customer asked for a discount, what made you decide to offer one?”

Salesperson: “I was worried we’d lose the order.”

Manager: “What did you know about the customer’s main concern?”

Salesperson: “Actually, I didn’t ask. I assumed the price was too high.”

Manager: “What could you find out before deciding whether a discount is necessary?”

This gives the manager an opportunity to practise helping the salesperson examine a decision rather than simply correcting it.

Make Coaching Practice Part of Manager Development

You don’t need to organise a full-day workshop every time managers need to improve a coaching skill. During an existing managers’ meeting, allocate some time to practise one common situation. One manager plays the coach, another plays the salesperson and a third observes. After the practice, discuss what helped the conversation and what could be improved.

Choose situations that reflect your business, such as handling customer objections, discussing poor outlet execution or helping a salesperson prepare for a difficult account review. The aim is to give managers opportunities to practise before they face similar situations with their teams.

3. Give Managers a Simple Field Coaching Form

In the Activate stage, the Sales Call Performance Checklist helps managers observe what salespeople do during customer interactions.

The Field Coaching Form serves a different purpose. It helps managers turn those observations into a useful coaching discussion and keep track of what happens after the field coaching. The form doesn’t need to be complicated. I recommend starting with five sections:

An Example of How to Use It

Suppose a salesperson is responsible for developing sales through an existing distributor. During a Business Review Meeting, the salesperson presents the monthly sales figures but doesn’t explore why sales of one product category have declined. After the meeting, the manager uses the Field Coaching Form to guide the discussion.

What went well: The salesperson prepared accurate sales information and explained the overall account performance clearly.

What needs improvement: The salesperson did not explore the underlying reasons behind the decline in one product category.

Agreed action: During the next distributor review, ask about outlet demand, stock availability and competitor activity before recommending corrective action.

Follow-up: Review the salesperson’s preparation and the outcome of the next distributor meeting.

The form gives both manager and salesperson a clear record of what they discussed. It also helps the manager continue the coaching conversation at the next opportunity. Keep the form short enough to complete without taking excessive time away from customer-facing work.

4. Help Managers Handle Difficult Coaching Conversations

Not every salesperson responds positively to feedback. Some may disagree with the manager’s observation. Others may explain why a situation was beyond their control. Experienced salespeople may also feel uncomfortable receiving coaching from a manager who has less experience in their particular customer segment.

These situations can be challenging, especially for newly appointed Sales Managers. Rather than expecting managers to handle every conversation confidently from the beginning, give them opportunities to practise.

When a Salesperson Disagrees

Suppose a manager raises concerns about how a salesperson handled a customer objection. The salesperson replies: “I’ve been handling this customer for years. I know what works with them.”. A manager who feels challenged may become defensive or insist on being right.

A more constructive response could be: “I understand you’ve worked with this customer for a long time. Can you help me understand why you chose that approach?”

The manager can listen to the explanation before discussing the specific observation. This doesn’t mean avoiding difficult feedback. It means making sure the discussion is based on what happened, rather than becoming an argument about experience or authority.

When a Salesperson Keeps Giving Excuses

A salesperson may say: “The customer wasn’t interested. There’s nothing much I could do.”

Instead of arguing, the manager could ask: “What did the customer say that made you feel they weren’t interested?”. Followed by: “Was there anything else you could have asked before ending the discussion?”

These questions help bring the conversation back to what the salesperson could influence. For sales leaders, the practical lesson is to prepare managers for the situations that make coaching uncomfortable, not only the conversations where salespeople readily accept feedback.

5. Build a One-to-One Coaching Habit That Managers Can Maintain

Field coaching is valuable, but managers may not always be able to accompany every salesperson as frequently as they would like. A regular one-to-one coaching discussion helps maintain continuity between field visits.

This should be different from a routine sales performance review. A sales performance review may focus on targets, pipeline, customer coverage and outstanding business issues. A coaching discussion should focus on how the salesperson is developing the skills needed to handle those responsibilities.

Keep the Discussion Simple

A manager can structure a short one-to-one discussion around three questions:

1. What have you been working on?

“Last time, we discussed how you handle price objections. Have you had a chance to try a different approach?”

2. What happened?

“How did the customer respond?”

3. What will you do next?

“What would you like to improve before we meet again?”

The manager can refer to previous field observations and agreed actions. This helps the salesperson see that coaching is connected to their actual work.

Make Time Without Adding Unnecessary Meetings

Where possible, use an existing individual catch-up rather than creating another lengthy meeting. A short, focused coaching discussion can be useful if the manager comes prepared and follows up in the coaching conversation. The key is to make coaching a regular responsibility rather than something that happens only when a salesperson is struggling.

6. Give Your Managers Coaching Support, Not Just Coaching Targets

If you’re a regional sales leader or Sales Director, your responsibility doesn’t end after telling managers to coach their teams. Managers also need someone to help them improve their own coaching. During your regular discussions with managers, ask about the situations they find difficult.

For example:

• “Which salesperson are you finding difficult to coach at the moment?”
• “What have you tried so far?”
• “What kind of support would help you handle the next conversation?”

Sometimes, the manager may need help preparing for a sensitive discussion. At other times, you may need to demonstrate a coaching technique or observe the manager again. You can also encourage managers to share useful approaches with one another.

For example, during a regional meeting, invite a manager to explain how they helped a salesperson improve a particular skill. Ask the group what they could adapt for their own teams. This makes manager development more relevant to the challenges they face.

A Practical Enable Checklist for Sales Leaders

Before moving towards the Sustain stage, review whether your managers have the support they need.

If several managers are struggling with the same area, that may indicate a need for additional training or a better tool. If only one manager is struggling, individual support may be more appropriate. Use what you observe to decide what help is needed.

Conclusion: Enable Your Managers to Coach with Confidence

The Enable stage is where sales leaders strengthen the coaching ability of their managers. It starts by understanding where managers need help, providing practical training, introducing simple coaching tools and supporting them as they work with their salespeople.

The Field Coaching Form and regular one-to-one discussions help managers connect observations with development actions. But tools alone are not enough. Managers also need opportunities to practise, receive feedback and improve their coaching skills.

When these elements are in place, your sales organisation is better prepared for Sustain, the third stage of the Sales Coaching Ecosystem™, where coaching becomes part of leadership accountability and regular business management.

For the complete framework, read How to Build a Sales Coaching Ecosystem That Works.