What Sales Coaching Looks Like on a Messy Monday Morning
Monday morning. The sales team has finished its weekly meeting.
Last week’s numbers have been reviewed. This week’s priorities are clear. Everyone knows which customers to visit, which opportunities to pursue and which targets need attention.
The Sales Manager also has a few coaching conversations in mind. Perhaps a salesperson needs to improve account planning. Another could be more effective at developing new business. And the third one needs help to take on larger customers. All good intentions. Then the working week begins.
And just like that, coaching starts moving down the priority list.
The Team Is Busy, but Nobody Is Helpless
In many established sales teams, salespeople know how to get things done. An experienced salesperson can handle a difficult customer, negotiate an order, follow up with a distributor and find ways around operational problems without calling the manager every hour. That’s part of what makes the business work.
Take a food service salesperson managing several hotel and restaurant accounts. One customer frequently places orders at the last minute. Another expects urgent deliveries. A distributor occasionally runs short of stock. The salesperson knows the routine. They make a few calls, rearrange deliveries, follow up with the relevant people and keep the customers satisfied.
The manager may never hear about most of these issues. From the outside, everything looks fine. But here’s something worth asking: Has the salesperson become better at managing these accounts, or simply better at coping with the same problems?
There is a difference worth exploring.
When Coping Becomes the Normal Way of Working
Think about the small inefficiencies that sales teams learn to live with.
A salesperson spends too much time servicing accounts with limited growth potential. A distributor keeps ordering the same products, even though there may be opportunities to introduce other categories. A Key Account Manager prepares a detailed monthly report, but the customer discussion rarely goes beyond reviewing sales figures.
None of these situations necessarily creates an immediate crisis. Orders still come in. Customers remain reasonably satisfied. Salespeople continue working hard. Over time, the team becomes familiar with these ways of working.
People may even take pride in being able to manage difficult situations. And why wouldn’t they? Their experience and commitment help keep the business running. The concern is that everyone can become so accustomed to managing the work that nobody questions whether there is a better way.
This is where a good coaching conversation can help. For example, instead of reviewing another month of distributor sales figures, a manager might ask: “We’ve been visiting this distributor regularly. What has actually improved in the business over the last three months?”, or “Which part of your current routine is taking a lot of time without giving us much return?”.
These questions give an experienced salesperson room to examine something they may have accepted as normal.
Why the Coaching Conversation Keeps Getting Postponed
Now consider the Sales Manager’s week. Monday starts with the sales meeting and forecast review. Tuesday may involve a joint visit with a key customer. Wednesday is taken up by distributor discussions, internal meetings or a regional business review. Thursday brings another round of follow-ups, customer negotiations and commercial decisions. By Friday, everyone is checking what has been achieved and what still needs to be closed.
The manager has been working throughout the week. So has the team. There may even have been several conversations between the manager and salespeople. But most of those conversations were about getting the work done.
- “What’s the latest update with this account?”
- “Can we close the order this month?”
- “Have you followed up with the distributor?”
These are necessary management questions. What may be missing are conversations about how the salesperson approaches the work, what could be improved and what they should try differently. The coaching conversation is postponed because the business can continue without it today. And when tomorrow arrives, the immediate work is still waiting.
Sometimes the Salesperson Doesn’t Raise the Issue Either
There’s another side to this. Not every salesperson will openly tell the manager that something isn’t working.
An experienced salesperson may prefer to handle a problem quietly rather than appear unable to manage their responsibilities. A younger salesperson may hesitate to question an established practice, particularly when more senior colleagues have been doing it that way for years. Others may feel that raising an issue will only create more discussion, reporting or follow-up work.
Of course, this varies between individuals, teams and organisations. We shouldn’t assume everyone behaves the same way. But it does mean that a manager cannot always rely on salespeople to volunteer what needs improving.
Consider a salesperson who has been servicing the same group of customers for several years. They know the customers well. They maintain good relationships and consistently achieve reasonable sales. During a business review, the manager might ask: “Which customers do you think have more potential than we’re currently getting?”.
The salesperson identifies two accounts but explains that both are comfortable with their current purchasing arrangements. Rather than immediately suggesting a promotion or a new product, the manager could explore further:
- “What have we learnt about their business recently?”
- “Who else in those accounts could help us understand their plans?”
- “What would make it worthwhile for them to consider something different?”
The salesperson may already know much of the answer. The conversation helps them look at a familiar account from a different angle.
A Busy Week Still Offers Opportunities to Coach
Sales Managers don’t need to turn every conversation into coaching. Some situations require a quick decision. Others need clear instructions or immediate action. But there are opportunities during the week when a manager can move beyond reviewing activities and results.
Here are three situations worth paying attention to:
1. During a customer or distributor review meeting
Instead of spending the entire discussion on sales figures, choose one account that has remained relatively unchanged. Ask the salesperson what they believe is limiting growth and what they have tried so far. Agree on one different approach to test during the next visit.
2. After a joint customer meeting
Rather than immediately giving feedback on everything that happened, invite the salesperson to review one important part of the discussion. For example: “We had a good discussion with the Purchasing Manager. What did we learn about their priorities for the coming quarter?”
If the salesperson missed an opportunity to explore the customer’s business, discuss how they could approach that conversation next time.
3. When reviewing a familiar sales routine
Look at an activity the team has been doing for a long time. It could be the weekly sales call plan, distributor follow-up or preparation for a monthly business review meeting. Ask:
- “Is this still helping us achieve what we want?”
- “What could we change to make it more useful?”
The purpose is to help people improve how they work, especially when existing routines have become automatic.
One Practical Change for Next Week
If you’re leading a sales team, try this. During your next weekly sales meeting, ask your team to identify one recurring issue or routine that consumes time without producing enough value. It could be repeated customer follow-ups, unnecessary reporting, low-value visits or an account that hasn’t progressed despite regular attention.
Choose one issue that the team can influence. Then have a short discussion with the salesperson or people involved. Find out why the situation continues, what they’ve already tried and what they think could work better. Agree on one change to test during the week. At the next meeting, review what happened. Did it save time? Improve the customer discussion? Create a new opportunity? Or reveal something else that needs attention?
You may not solve the entire problem in one week. But you will have started a useful conversation about improving the work, rather than simply getting through another week.
Conclusion: What Gets Done Is Not Always What Gets Better
A messy Monday morning doesn’t necessarily mean a sales team is disorganised. Quite often, the team is experienced, hardworking and capable of handling the demands of the business. Customers are served. Problems are managed. Targets remain in focus. And that can be precisely why coaching gets pushed aside. The work continues, so the need to improve how the work is done becomes less visible.
For sales leaders, the challenge is to notice what the team has become accustomed to doing and create opportunities to question whether those habits are still effective. You don’t have to coach every issue or turn every meeting into a development session. Start with one familiar situation that deserves a fresh look. Because a sales team can be very good at getting through the week, while still having plenty of room to get better.
