Part 2: The Quiet Gap Between Knowing and Doing Coaching

A Sales Manager attends a coaching workshop, learns a few useful techniques and practises asking questions. During the workshop, everything seems straightforward. Then Monday comes. A salesperson calls because an important customer is unhappy. The manager has a sales meeting in 20 minutes and needs to resolve the issue quickly. What happens? The manager gives instructions.

That’s understandable. Sometimes the situation calls for an immediate decision. But when giving instructions becomes the manager’s usual response to almost every problem, there may be little opportunity for salespeople to develop their own judgement. This is one reason why managers can understand coaching and still struggle to practise it consistently.

In Part 1: Why Coaching Needs Sales to Work, we explored why coaching needs to support real business priorities. Now let’s look at what makes coaching difficult for the people expected to do it.

Knowing the Coaching Questions Is the Easy Part

Many managers have attended leadership or coaching training. They understand the importance of listening, asking questions and helping employees find solutions. Some can even explain coaching models confidently. But knowing the techniques and using them during a difficult conversation are two different things.

Imagine a salesperson approaches their manager with a problem. The salesperson says: “Boss, the customer is asking for an earlier delivery. What should I do?”. The manager has handled similar requests many times. It’s tempting to reply: “Call logistics, check the earliest available date and get back to the customer.”. That may be perfectly reasonable advice.

But suppose the salesperson has handled similar situations before and is capable of deciding what to do. The manager could ask “What have you checked so far?” or “What options do we have?”. The difference depends on what the salesperson needs at that moment.

Good management involves knowing when to give direction and when to help someone think through a problem. Managers don’t always find that balance easy.

Why Managers Often Return to Giving Instructions

There are several reasons why coaching can feel difficult in everyday work:

They Are Used to Being the Problem-Solver

Many Sales Managers were promoted because they were successful salespeople. They know their customers, understand the products and have experience handling difficult situations. When someone brings them a problem, their natural response is to offer a solution.

That experience is valuable. However, if the manager continues solving every problem personally, the team may become overly dependent on them. The challenge is learning when their experience is needed and when the salesperson would benefit from working through the situation independently.

They Feel Pressure to Have the Answer

In some workplaces, employees expect managers to know what to do. A manager who asks questions may worry that the salesperson will think: “Why is my boss asking me? Isn’t the boss supposed to know?”.

This can be uncomfortable, particularly for newly promoted managers. They may feel that giving a quick answer demonstrates confidence and authority. But managers don’t need to have every answer to be effective. They do need to know when a decision requires their authority and when someone else can take responsibility.

They Worry About Difficult Conversations

Coaching may involve discussing mistakes, poor decisions or behaviour that needs improvement. Some managers hesitate because they don’t want to upset the salesperson. Others worry about challenging someone who is older, more experienced or has been with the company longer.

As a result, they may avoid the conversation or give indirect feedback that leaves the issue unresolved. These situations require more than knowing a coaching model. Managers need confidence and practice in handling real conversations.

Time Pressure Makes the Habit Harder to Change

Sales managers have plenty of responsibilities. They monitor targets, review forecasts, handle customer issues, attend meetings and support their teams. When time is limited, giving instructions can feel more efficient.

And sometimes it is. For example, if a customer is waiting for an urgent decision that only the manager can approve, a lengthy coaching conversation would be inappropriate. The challenge is recognising situations where there is enough time and the salesperson has the ability to think through the issue.

A manager might spend two minutes helping a salesperson consider the available options instead of immediately providing the answer. That small choice can help the salesperson become more confident in handling similar situations.

What Does the Research Say?

Gallup reported in 2018 that only about one in four employees strongly agreed that their manager provided meaningful feedback or feedback that helped them do better work.

Source: Gallup — Why Your Managers Should Be Like Coaches, Not Bosses

The finding concerns employee feedback and management more broadly, rather than sales coaching specifically.

However, it highlights an important issue: managers may believe they’re supporting their employees, while employees don’t necessarily experience that support as useful. For sales leaders, this is worth examining within their own teams.

How Can Sales Leaders Help Managers Put Coaching Into Practice?

Sending managers for another coaching workshop may help, but first understand what they’re finding difficult. Here are three practical approaches:

1. Identify the Conversations Managers Avoid

During an individual discussion, ask the Sales Manager: “Which conversations with your team do you find most difficult?”. The manager might mention addressing poor preparation, challenging an experienced salesperson or discussing repeated mistakes. Explore what makes the situation uncomfortable.

You may discover that the manager needs help preparing for a difficult conversation rather than another explanation of coaching techniques.

2. Practise One Difficult Situation at a Time

Suppose a manager struggles to challenge a salesperson who repeatedly blames other departments for missed customer commitments. Ask the manager to explain how they would normally begin the conversation. Then practise a different opening.

For example:

“I understand there were delays from the other department. I’d also like to understand what you did when you realised the customer commitment might be missed.”

Discuss how the salesperson might respond and how the manager could continue. Keep the practice short and relevant. The manager should leave with something they feel comfortable trying.

3. Help Managers Recognise When Coaching Is Appropriate

Managers shouldn’t feel they must coach every situation. A useful starting point is to consider three possibilities.

These are practical distinctions, rather than rigid rules. Managers need to consider the person’s experience, the business risk and the time available.

A Question for Sales Leaders

If your managers have attended coaching training, consider asking them: “What makes coaching difficult for you during a normal working week?”

Listen to their answers before deciding what additional support they need. You may hear about time pressure, difficult employees, uncertainty about when to coach or discomfort with certain conversations. These answers tell you more than simply asking whether managers understand coaching. They also help HR and L&D design development that addresses the situations managers actually face.

Conclusion: Help Managers Become Comfortable Using Coaching

Most managers don’t need convincing that developing people is important. What they may need is help changing the way they respond to everyday situations. That involves recognising when to provide direction, when to ask questions and how to handle conversations that feel uncomfortable.

Sales leaders can help by understanding the difficulties their managers face and giving them opportunities to practise. But there’s another issue worth considering. Even a manager who is confident in coaching may struggle when the organisation hasn’t clearly defined what good selling looks like. That brings us to the missing connection between sales targets and coaching.

Read Part 3: The Missing Middle Between Sales Targets and Coaching.