When deciding how to train a head of sales, start by delegating specific decisions and arranging a weekly review with an experienced leader. In the first few months, the head of sales must choose an action for the team, explain the reasons for it and review the consequences; the mentor helps identify the mistake, and the owner sets acceptable limits. Give the head of sales more independence when they can handle a new situation without a ready-made answer from someone more senior.
You have appointed a head of sales. They read materials, ask sensible questions and bring you suggestions. But each suggestion ends with a request for approval: who to help with negotiations, what task to give a salesperson, whether to meet a buyer again. You reply quickly: the team needs to work. By evening, the head of sales has a list of completed instructions, and you have spent another day managing sales.
Buying them training seems sensible. But what exactly should they learn? Are they unable to choose a course of action, or have they already chosen one that your company will overturn unless it has been approved?
I believe preparing a head of sales starts with the owner deciding for themselves which work they are willing to stop correcting in advance. Otherwise, the person will learn to guess your answer. There will still be no decisions of their own to review.
Training a head of sales
Before choosing a programme, ask the head of sales to prepare examples of several recent situations in which they needed your help, ready by the fifth working day. For each one, you need their initial suggestion, their reason for coming to you and your final decision. The head of sales gathers the material. You decide what they need to learn by comparing what was proposed with what was done.
- The head of sales did not suggest an option: they did not know what information to ask the salesperson for. They need to review the task with a mentor and make an independent attempt using another example.
- The suggestion was well founded, but the head of sales asked permission for a routine action. Here, you must first confirm their authority openly in front of the team.
- A decision was made, but the salesperson did not carry it out, and the head of sales did not follow up on the task. They need to learn how to get instructions followed: set a deadline, spot when things go off track and require corrections.
- The head of sales is ready to do the work themselves but cannot explain it to a salesperson. They need to learn how to train an employee: demonstrate an action, let them repeat it and review their independent attempt.
These gaps call for different kinds of preparation. A lecture on motivation will not teach someone to understand the terms of a deal. A sales funnel review will not give them the authority to require former colleagues to follow instructions. A general course is useful for getting to know the tools, but the owner's task is to name the specific action that will change in the department after training.
Who will review decisions
Appoint one person to work with the head of sales every week: a commercial director, another experienced leader or an external mentor. They need experience of managing salespeople and access to the facts of the situation being reviewed. Being good at running a training session is not enough.
Agree on the process: the head of sales comes with their own decision and evidence of how it was carried out. The mentor finds out what information they considered, where they made an assumption and why they rejected another option. After the conversation, the head of sales gives the salespeople their instructions. If the mentor starts managing the team themselves, the person being trained once again becomes someone who passes on other people's answers.
The owner can also be the mentor. If so, put this work in your calendar and recognise it as part of your workload during the training period. Hoping to teach someone between messages leaves them with a random collection of tips. I have described the boundary between reviewing the head of sales' actions and taking over their role in a separate article, “No one is monitoring this right now. So what is the head of sales doing?”.
Head of sales training
It helps to build the programme for the first few months around one area of sales. For example, the head of sales learns to choose the next step after the first meeting with a buyer: send a proposal, clarify requirements or bring the right person into the conversation. Below is a suggested training sequence; the timings mark points when the owner makes a decision, without promising to train anyone in three months.
First month: independent choices on a familiar task
First, approve the boundaries of the area. The head of sales assigns work to a salesperson, chooses how to help and sets a deadline for replying to the client. Price changes, new company commitments and additional spending still require approval. The head of sales needs access to agreements with the buyer and information about what the company can deliver.
The first time, the mentor reviews the task with them and explains how to make the choice. The head of sales handles the next similar task independently. Before acting, they write down the reasons for their decision and the immediate result they expect. Making this record beforehand protects the review from a convenient explanation after the event: the buyer agreed, so we did everything right; the buyer refused, so the salesperson was to blame.
Start with actions the department can correct before the client suffers harm: preparing for negotiations, choosing questions, helping an employee. A costly concession or a promise to meet an unconfirmed deadline is unsuitable for this kind of practice. If the mentor sees a risk of failing to meet commitments, they intervene immediately and explain why.
Here is a completed sample record for a weekly review. This is a training example, not a RENTROP case study.
- What happened. After the first meeting, the salesperson plans to send a proposal. Their contact is comparing suppliers, while the finance director approves spending. The requirements for the calculations have not yet been received.
- What the head of sales decided. By Friday, the salesperson will ask their contact what information the finance director needs and agree who will pass the proposal on to them. They decided not to arrange another full presentation.
- Why they chose this. The buyer already understands the offer. It is unclear whether they can present it to the person who approves spending. Going over the product again will not fill this gap.
- What we expect. We will get the requirements for the calculations and an agreement on passing the proposal on. Sending an email does not, in itself, count as the result of this task.
- What the outcome was. The contact sent the requirements but refused to introduce the salesperson to the finance director. They agreed to pass on the materials themselves and say when to expect a response.
- What to review with the mentor. Is this way of passing on the proposal sufficient for this deal? What signs will show that the materials have actually reached the approval stage?
There is something to learn from here: the head of sales chose an action to establish a missing fact and obtained new information. The lack of a direct introduction to the finance director does not automatically mean the attempt should be declared a failure. The next decision depends on how the buyer approves spending and which agreements they are ready to confirm.
Second month: the same skill under different conditions
Now the mentor chooses a situation where the usual action is unnecessary. In our training example, another buyer has already sent the finance director's written requirements and agreed a date for reviewing the proposal. The head of sales still insists on another meeting: meetings were exactly what the recent training covered.
This is where you can see what they have learnt. If the head of sales repeats the meeting because that is what they did before, they have memorised an action. If they see that the necessary information has already been obtained and ask for the calculations to be prepared by the agreed date, they know how to choose.
The weekly review now has a new purpose: to show which change in conditions led the head of sales to change their approach. Ask the mentor to bring the owner a pair of examples like this by the end of the second month. You do not need to manage both deals all over again. You need the starting conditions, the head of sales' different decisions and an explanation of the difference.
The training topic is chosen to match the gap identified. If they confuse the approval stages, they examine how the buyer reaches a decision. If they give a salesperson vague tasks, they practise stating the expected action and deadline. If they assign training to everyone indiscriminately, they learn to choose a specific employee and mistake. This gives the material they read a place in their current work.
Developing a head of sales
By the third month, the owner needs to decide whether the head of sales can take on the next area. One successful decision is not enough: it was made with the mentor's help or on a familiar task. The basis for expanding their responsibilities is independent work in different conditions, including a case where the first action did not help.
Ask the mentor and the head of sales to prepare a brief assessment by the end of the month:
- Which decisions the head of sales now makes independently, with examples where no guidance was given before the action.
- Which mistake they noticed and corrected without a reminder.
- Which decision they passed to the owner and why it was beyond their authority.
- Where they still need help and which exercise has been assigned to address that gap.
Look at the help itself too. At first, the mentor explains almost the entire choice. Later, they ask a clarifying question. Then they discuss a decision that has already been made. As the nature of the help changes, you can see exactly what the head of sales has become able to do. Simply reducing the number of meetings is a poor goal: the head of sales can stop asking questions and also stop reporting problems.
Which mistakes are acceptable during training
An idea that does not work out within the agreed limits is material for review. The head of sales chose a method, noticed that they were not getting the response they needed and changed their action. In this situation, you should assess them on the reasons behind their choice and how quickly they corrected it.
It is a different situation when the head of sales hides a breach or repeats a mistake already reviewed, even though they knew the rule and had the information they needed. You cannot simply explain this away by saying “they are learning”. The owner restricts a specific part of their authority, sets a condition for restoring it and a deadline for deciding on the person's future role.
For example, the head of sales promised a buyer delivery without confirmation from production. Until they demonstrate that they can get deadlines properly agreed, such promises go through someone more senior. Meanwhile, helping salespeople prepare for negotiations remains the head of sales' responsibility. Returning every matter to the owner will erase the independence already gained along with the dangerous mistake.
Do not expand their authority just because the ninetieth day has arrived. If the reviews show one persistent gap, keep their area of responsibility the same and assign work on that gap. If the person avoids decisions even with a clear task, support and time to try, reconsider the appointment. Another course on its own does not remove the need for that decision.
How to develop a salesperson into a head of sales
Before promoting a salesperson, offer them a chance to try work where another employee achieves the result. Let them help a colleague prepare for negotiations: find out what the difficulty is, assign a task, observe an independent attempt and review it. The owner tells the team in advance what task they have given the candidate and what they expect colleagues to do.
The most revealing moment is when the colleague makes a mistake. Does the candidate take over the conversation and close the deal themselves? Or can they explain what needs to change and be patient while someone else tries? With an urgent deal, direct help is appropriate. But to decide on a promotion, you also need an example where, after their involvement, the salesperson was able to act independently.
Make sure the person also wants to manage people. The authority to manage former colleagues brings difficult conversations: requiring instructions to be followed, giving feedback, refusing a strong salesperson an exception they are used to. Offer a limited trial with a date to discuss the result. Returning to sales afterwards should not look like punishment for honestly discovering that the role is not a good fit.
Before the trial, agree which part of their own workload you will remove and who will take it on. The question of time has already been covered separately: “We need to sell better. The head of sales is busy with their own clients”. The key point here is different: the candidate needs experience of achieving a result through a colleague who can work without their constant presence.
To start the training, the owner can give the head of sales and mentor this ready-made assignment:
By the fifth working day, prepare a programme for the first month on decisions about the next step after a meeting with a client. Bring examples of difficulties, a list of decisions to make independently and the limits beyond which approval is needed. The head of sales records their choice before acting, and the mentor reviews it once a week. By the end of the month, show an independent attempt, a corrected mistake and an area where help is still needed. I approve the scope of authority, the time freed up and the decision on expanding the work.
If there is no one to provide training and review decisions
Developing your own head of sales is a company task in its own right: it needs the candidate's time, the mentor's experience and permission to try. If the owner is not ready to review decisions regularly and has no one within the company to assign this to, training the head of sales remains another of their responsibilities. This demand on their attention must be recognised before the appointment.
For an owner who wants to hand over the daily management of the sales team, RENTROP offers turnkey sales management: a team takes on the work, and the owner stops acting as the overall head of sales. We do not sell courses or training.
At the start, the head of sales brought every suggestion to you for approval, and you decided for them. Training changes the content of this conversation: the head of sales explains a choice already made and comes to you for a decision only where your authority begins. Then their learning gradually frees up your time instead of taking it up indefinitely.