How Sales Coaching Work

What makes sales coaching effective? Is it the coaching skills of the manager? The willingness of the salesperson to learn? Or the support provided by the organisation? These are useful questions for anyone responsible for developing a sales team.

I recently joined Michelle Achuthan from Coaching Culture International for a conversation on Conversations with Coaches, where we explored what makes sales coaching work in a real business environment.

Our discussion covered several important areas, from developing selling skills and confidence to the role of sales leaders in supporting long-term performance. I’d like to share five takeaways from that conversation, along with some questions sales leaders can consider when looking at their own teams.

1. Sales Coaching Needs to Address More Than Selling Skills

When we discuss sales development, the conversation often centres on selling techniques. How well can salespeople prospect, ask questions, present solutions, negotiate and close? These skills are important. Salespeople need to know how to handle different customer situations. But knowing a technique doesn’t always mean someone can use it confidently.

Say a salesperson who understands how to approach senior decision-makers but hesitates whenever an opportunity to meet one arises. The difficulty may have little to do with knowing what to say. Perhaps the salesperson worries about being rejected, feels intimidated by senior executives or doubts whether they can contribute anything useful to the conversation. Additional selling techniques alone may not address those concerns. This is where coaching can help salespeople understand what influences their decisions and behaviour.

For sales leaders: When someone struggles with a selling task, don’t assume the problem is always a lack of knowledge. Find out whether they need better skills, more confidence, clearer expectations or support in dealing with a particular situation. The type of support you provide should depend on what is actually holding them back.

2. Effective Coaching Brings Together Skills and Mindset

Sales performance involves both the practical and personal sides of selling. The practical side includes product knowledge, sales processes, customer management and commercial skills. The personal side includes confidence, motivation, adaptability and the ability to handle setbacks. Both influence how salespeople perform.

For example, two salespeople may have similar product knowledge and selling experience, yet respond very differently when they lose an important account. One may review what happened and look for another opportunity. The other may become discouraged and avoid approaching similar customers. The difference may be in how they interpret and respond to the experience.

As a sales leader, you need to recognise when someone requires technical guidance and when they need help working through their thinking. A salesperson who doesn’t understand a pricing calculation needs an explanation. Someone who understands the calculation but feels uncomfortable discussing price with customers may need a different conversation.

For sales leaders: Before deciding how to help, ask yourself: “Does this person need to learn something, practise something or work through something?”. It’s a simple question, but it can help you choose a more suitable approach.

3. Think About Immediate Improvement and Long-Term Development

Sales leaders naturally face pressure to deliver results. There are monthly targets to achieve, customers to retain and opportunities to close. When a salesperson struggles, the immediate priority is often to help them overcome the problem. That makes sense. However, there’s another question worth asking: Will the salesperson be better prepared to handle a similar situation independently next time?

Let’s say a Key Account salesperson is preparing for an important annual business negotiation. The Sales Manager may need to provide guidance on pricing limits, commercial terms and the company’s negotiating position. That’s part of the manager’s responsibility.

But the discussion can also help the salesperson develop their commercial judgement. For example, the manager might explore how the salesperson evaluates different negotiation options and considers their possible consequences. The immediate goal is to prepare for the upcoming negotiation. The longer-term goal is to develop someone who can make better commercial decisions in future situations. Both matter.

For sales leaders: When helping a salesperson solve a pressing problem, consider what capability you also want them to develop. That way, your support contributes to the current business need and the person’s longer-term growth.

4. Sales Leaders Have a Strong Influence on Whether Coaching Works

A salesperson’s experience of coaching is influenced by the way their manager leads. Some managers create an environment where people feel comfortable discussing difficulties and asking for help. Others may unintentionally discourage openness because every conversation quickly turns into criticism or a demand for immediate results.

Think about how your team responds when something goes wrong. Do salespeople raise concerns early, or do they wait until the problem becomes difficult to hide? Are they comfortable admitting that they don’t know how to handle a customer situation? Their responses may tell you something about the working relationship they have with their manager.

Trust matters because coaching often involves discussing areas where someone is uncertain, inexperienced or struggling. That doesn’t mean managers should avoid holding people accountable. Salespeople still need clear expectations and responsibility for their performance. But they should also know they can discuss difficulties without every conversation becoming a judgement of their ability.

For sales leaders: Consider what your team members are comfortable telling you. If they only share good news, you may be missing important opportunities to help them develop.

5. Coaching Needs a Clear Purpose Beyond the Conversation

A coaching conversation can feel productive. The salesperson may leave feeling encouraged, motivated or clearer about a problem. That’s positive, but it doesn’t tell us everything about whether the coaching has helped. What matters is whether the person can use what they’ve learned.

For example, a salesperson may gain confidence in approaching a difficult stakeholder. The next question is whether that confidence helps them prepare more effectively, initiate the conversation or handle the relationship differently. The value of coaching becomes clearer when there is a connection between the conversation and the person’s actions. This also helps sales leaders avoid treating every encouraging discussion as evidence of performance improvement.

For sales leaders: Be clear about what you hope the coaching will help the salesperson do. It may involve making a better decision, handling a difficult conversation, taking responsibility for a customer issue or becoming more independent in their role. Look for progress in those areas rather than relying only on how positive the coaching conversation felt.

Watch Our Conversation: How Sales Coaching Works

These five takeaways offer a starting point, but there is more to explore about the relationship between selling skills, mindset, leadership and coaching.

In my conversation with Michelle Achuthan on Conversations with Coaches, we discuss some of these areas and why they matter when developing salespeople. If you’re a Sales Director, Sales Manager or HR/L&D leader looking to strengthen sales coaching in your organisation, I encourage you to watch the discussion.

Watch the full conversation: How Sales Coaching Works

As you watch, consider which areas deserves more attention in your own sales team.

Three Questions Worth Discussing With Your Sales Managers

If you’re responsible for several Sales Managers, you can use the video as a starting point for a management discussion. Ask your managers:

1. What tends to hold our salespeople back most? Is it selling skills, confidence or something else?

This helps identify whether everyone is making the same assumptions about performance problems.

2. When we help someone overcome a sales challenge, what do we want them to be able to handle independently next time?

This encourages managers to think beyond resolving the immediate issue.

3. What could we do differently as leaders to make our salespeople more comfortable discussing their difficulties?

This opens a useful conversation about the working environment managers create.

You don’t need to cover all three questions in one meeting. Choose the one most relevant to your team’s current situation and give managers time to share their experiences.

Conclusion

Sales coaching involves more than knowing how to ask good questions or conduct a coaching session. Salespeople bring different levels of experience, confidence, motivation and personal challenges to their work. Their managers also influence how willing they are to learn, seek support and take responsibility.

Effective coaching requires us to understand these differences and respond appropriately. For me, one of the most important considerations is whether coaching helps salespeople become more capable of handling their responsibilities and making decisions. That’s a useful question for any sales leader to keep in mind.

If you haven’t watched the conversation, you can find it here: How Sales Coaching Works: Conversations with Coaches.