When Development Depends on Individual Heroics

Every sales organisation has a few people everyone knows they can count on. They understand their customers, know the market and have built strong relationships over the years. When a difficult negotiation comes up or a major account is at risk, these are often the people who make the difference.

Some are experienced salespeople. Others are Key Account Managers, senior Sales Managers or long-serving employees who know the business inside out. Having these people in the organisation is a real advantage.

But there is something worth examining. How much of your team’s success depends on what these individuals know, rather than what the wider team is capable of doing? It is an important question, particularly for sales organisations that want to grow without becoming increasingly dependent on the same few people.

When Experience Becomes the Team’s Greatest Asset

In many businesses, experience carries considerable value.

A salesperson who has spent 15 years developing relationships with distributors, retailers or corporate customers often understands things that cannot be found in a CRM system. They know how different customers make decisions, which relationships need careful handling and what has worked in previous commercial discussions. They may also understand the informal practices, expectations and sensitivities that influence business relationships.

That experience is valuable, especially in markets where trust and long-term relationships play an important role in doing business. It is natural for sales leaders to rely on people with this depth of knowledge. The concern arises when the organisation becomes so comfortable relying on them that very little of their expertise is passed on to others.

The Knowledge That Never Gets Shared

Consider a sales team managing several major customer accounts. An experienced Key Account Manager has worked with one customer for many years. They understand the customer’s buying patterns, internal stakeholders, business priorities and commercial expectations. Their account performance is consistently strong.

When a new colleague joins the team, the experienced manager may share customer information, explain the account history and provide useful advice. But much of their actual expertise remains difficult to transfer.

For example, how do they recognise that a customer’s priorities are changing? What makes them decide to involve a different stakeholder? How do they judge when to defend a commercial position and when to consider alternatives? These decisions often come naturally after years of experience. The experienced person may not even realise how much judgement is involved.

The newer colleague receives useful information but may not understand the thinking behind the decisions. Over time, this creates a difference between people who know what to do and people who also understand why and when to do it. That difference becomes important when the business needs more people to handle complex customers independently.

Why This Dependence Often Goes Unnoticed

Most sales leaders pay close attention to revenue, customer retention, pipeline performance and other commercial results. When the numbers are healthy, there may be little reason to question how the results are being achieved.

A strong performer who consistently delivers is usually recognised and rewarded. Their contribution gives management confidence. Meanwhile, less experienced colleagues continue developing through their own customer interactions, observing others and seeking advice when necessary. This arrangement can work reasonably well for years.

However, the organisation may not have a clear picture of how widely important sales knowledge and judgement are distributed across the team. That becomes more noticeable when circumstances change. An experienced Account Manager is promoted. A senior salesperson retires. A business expands into another territory. A major customer is reassigned. The organisation then discovers that transferring customer records is much easier than transferring the experience behind those records.

The Risk Is Bigger Than Losing a Key Employee

Employee turnover is one obvious concern, but the issue goes further. When important expertise is concentrated in a small group, several things can happen.

Customer relationships become difficult to transfer. A new Account Manager may inherit the sales history but need considerable time to understand the customer’s expectations and internal decision-making.

Sales performance varies across territories. Two salespeople selling similar products to similar customers may achieve very different results because their approaches and commercial judgement differ.

Business expansion becomes harder. An organisation may have enough salespeople to cover new territories but insufficient experienced people to guide more complex opportunities.

Strong performers become overstretched. The same people may be asked to manage important customers, support major negotiations, guide colleagues and contribute to new business initiatives.

None of these situations necessarily indicates poor management or weak salespeople. They do, however, raise an important question about how well the organisation develops and shares the expertise it already possesses.

Start by Identifying What Your Best People Do Differently

Sales leaders can begin with a practical exercise. Choose one area where certain salespeople consistently perform better than others. It might be developing new accounts, managing distributors, expanding business with existing customers or handling difficult commercial negotiations.

Then look beyond the sales numbers. What do the stronger performers actually do differently? For example, a Sales Director reviewing key account growth might discover that successful Account Managers:

• Engage more than one contact within an important customer account.
• Review the customer’s business plans before proposing new opportunities.
• Identify potential business changes earlier.
• Prepare alternative commercial options before negotiations.
• Follow through on agreed actions with greater consistency.

These are examples of behaviours worth examining, rather than a universal checklist for every sales organisation. The aim is to identify the specific practices that contribute to stronger performance in your own business. Once those practices become clearer, they are easier to explain, develop and assess across the team.

Make Experience Easier for Others to Learn From

Experienced salespeople are often willing to help their colleagues, but simply asking them to share their experience may produce general advice. They might say, “Build a good relationship with the customer,” or “You need to understand the customer’s business.”. Both are sensible suggestions. However, less experienced colleagues may still struggle to translate them into specific actions. A more useful approach is to explore a real commercial decision.

Suppose an experienced Account Manager successfully expanded business with an existing customer. Instead of asking, “How did you achieve the growth?”, the sales leader could explore:

• What first made you recognise the opportunity?
• What did you find out about the customer’s situation?
• Which people were involved in the decision?
• What alternatives did you consider?
• What would you approach differently next time?

The answers help uncover the judgement behind the result. They can also reveal which practices are transferable and which depend on the particular customer or market situation. This makes experience more useful to others without pretending that every successful salesperson must work in exactly the same way.

Give More People the Opportunity to Build Judgement

Sharing knowledge is helpful, but people also need opportunities to make decisions and gain experience. In some sales organisations, major accounts and complex opportunities remain with the most experienced people because the commercial risks are high. That is understandable.

However, if other team members are never involved in these situations, their development may remain limited. Sales leaders can create gradual exposure without unnecessarily putting customer relationships at risk.

A developing Key Account Manager, for instance, might initially contribute to customer business reviews, prepare opportunity assessments or take responsibility for a defined part of an account development plan. As their confidence and judgement improve, their responsibilities can increase.

The experienced Account Manager remains accountable for the relationship while the colleague gains practical exposure. This approach is especially useful when organisations are preparing people for larger accounts, new territories or future leadership responsibilities. The intention is to develop more people who can handle greater responsibility over time.

Three Questions Sales Leaders Should Ask

A simple review can help identify where the organisation may be relying too heavily on individual expertise:

These questions are useful during sales organisation reviews, succession discussions and capability planning. They can also help HR and L&D leaders work with the sales department to identify development priorities based on actual business needs.

There is no need to turn this into a complicated assessment exercise. Start with the most important customer relationships or commercial activities, identify where the dependence is greatest and decide what expertise needs to be developed more widely.

Conclusion: Strong Performers Should Help Build a Stronger Team

Every organisation benefits from having experienced, dependable salespeople. Their customer knowledge, relationships and commercial judgement often take years to develop. These contributions deserve recognition.

But sales leaders also need to consider what happens when the business grows, responsibilities change or experienced employees move on. A team becomes stronger when more people can handle important customers, make sound commercial decisions and take on greater responsibilities.

That requires organisations to pay attention to how valuable experience is shared and developed across the team. The question for sales leaders is: If your three most experienced salespeople were reassigned tomorrow, how much of their expertise would remain within the team? The answer may tell you more about the strength of your sales organisation than its current sales results alone.