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It isn’t easy for a sales manager to run a sales team. There are always obstacles, including buyers and decision-makers who want a better B2B sales experience. Improving your sales force’s results requires training, development, and sales coaching. The benefits of sales coaching include better engagement from your salespeople while helping you ensure they succeed in reaching their goals.

What follows here are 10 real-life sales coaching scenarios that can help you improve your sales coaching techniques and help your sales reps.

Too Little Prospecting

One of your talented sales reps isn’t creating enough new opportunities to reach their goals. You ask to see their calendar and you find this salesperson has a lot of white space and no time blocked out for prospecting. To address this problem, you ask questions to identify the root cause of too little prospecting.

Is it a lack of discipline that prevents prospecting, or is it that the rep feels they shouldn’t have to do cold outreach? As a coach, you might ask, “What prevents you from prospecting?” You might also ask about how the salesperson will reach their goals without creating new opportunities. Using a non-directive approach transfers the challenge from you to the salesperson.

To solve this scenario, you must help the salesperson with a plan they can commit to that will allow them to do the work. You may also shorten the time between coaching meetings to create greater accountability. As a sales manager, you are better off establishing a non-negotiable cold outreach block each day.

Poor Conversions Stop a Second Meeting

To create a new opportunity, a salesperson needs to book a first meeting. That first meeting is an audition that should end with a second meeting. The salesperson you’re coaching has difficulty acquiring second meetings. To address this scenario, you need to understand the strategy the salesperson is using in their first meeting.

Your salesperson explains that they have their own style and that they do better using their own sales approach, even though it doesn’t result in a second meeting. You might ask, “Why do you believe your contacts don’t agree to a second meeting?” You can also ask “What do you think they are looking for that they aren’t finding in your first meeting?”

There are several ways you can address this scenario, including having the rep watch or listen to your top performers. You could also require them to go back to sales enablement to be retrained on your B2B sales methodology and to start using value-creation strategies that result in second meetings.

Every sales leader has the right and obligation to determine how their sales organization sells and what their salespeople need to accomplish in sales calls.

Losing Control of the Sales Conversation

Your sales cycle is too long and it’s getting longer as buyers struggle to make decisions. One of your sales reps has trouble controlling the sales conversation. You are not certain, but you suspect this salesperson is not leading their clients. It may be due to a lack of confidence, an ineffective strategy, or an inability to communicate why the client needs to take certain steps.

As you speak with your sales rep, they disclose that they believe that they are supposed to follow the client’s lead, as they are there to serve the client. You might ask, “How often do you think your contacts make the decision they are considering?” You can follow this question up with, “How do they know what they need to do to make this decision successfully?”

You decide to use your coaching sessions to teach the salesperson how to provide their clients with the advice and recommendations they need on the buyer’s journey. Sometimes, salespeople need the mechanics and the strategy to help clients move forward in the sales process.

Trouble Acquiring Decision Makers and Stakeholders

A salesperson comes to you with a problem. You like it when a sales professional has an agenda for a meeting, so you let them start by describing what they want from your coaching. This rep is having a tough time acquiring meetings with the buyers and decision-makers they need to speak with to sell successfully. When their sales champion refuses to bring in their peers, the salesperson believes they will lose the champion and the deal, especially if they push too hard.

Your first question is, “Do you believe this person is able to make this decision alone?” Your follow-up question might be, “Why do you believe this person isn’t granting you access to their peers?” Perhaps your smart sales rep responds that they believe their contact is vetting salespeople only because they prefer a different company. Or, maybe the champion is worried about losing control. You ask, "How could you make your contact less fearful of losing control?”

This performance coaching approach is a way to create a long-term improvement in results. Your sales rep practices their talk tracks and takes a run at gaining access while promising to work with their champion at the prospect company.

Pursuing Poor Prospects

A sales rep who has been struggling to create new opportunities is now in trouble. Before your coaching session, you go to your CRM to look at the companies the rep is pursuing. You notice that all the companies are too small to be valuable to either the sales rep or your organization. When you ask about the larger clients and enterprise-level companies in their territory, the sales rep explains that all those companies already have a provider.

You ask, “How do you know these companies get the attention and results they need from our competitor?” Your salesperson confesses they haven’t been able to get a first meeting with the larger companies. You ask about how much time they have spent on these larger accounts and learn that your rep gave up after one time through the list. You offer the salesperson a second session to work on their pitch for a first meeting and require them to pursue the clients the company needs.

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Lack of Motivation

A sales rep isn’t motivated and isn’t doing nearly enough work to reach their sales goals. Even your new sales objective is being ignored. Unlike the money-motivated people on your team, this person doesn’t seem interested in a higher income.

You realize that you haven’t spent enough time with this rep to know what they want, and you address your mistake in this session. You ask, “What’s important to you?” Followed up with, “Why is that so important to you?” and “What is that you want?" You discover that this salesperson is working to take care of her three children. This is her intrinsic motivation.

You realize you have been treating her as if she were money motivated. You ask her what she could do for her family if she made more money, and she answers she’d like them to go to college. Successful sales coaching helps you to know your people and their motivations.

Low Win Rates

You are looking at a salesperson who is creating more than enough opportunities to meet their sales targets, but success is still eluding them. You examine their pipeline and notice this salesperson has one of the lowest win rates on your team. You ask about their approach and when things go wrong during the sales conversation.

As you explore a half a dozen deals, you realize this salesperson knows too little about their clients, their challenges, and the implications of not making a change. Looking over their notes, you get the sense that the salesperson lacks discovery, asking too few open-ended questions and instead racing to pitch their solution.

You ask this salesperson to list questions they can ask to get a better understanding of their contacts and their prospect companies. You offer to review their next couple of meetings to check on their progress. A good sales coaching program will address a lot of sales challenges.

Negative Attitude

Coaching a sales rep with a bad attitude is one of the more difficult coaching scenarios, and it’s high risk. One person with a negative attitude can have a destructive impact on a sales team, especially if they infect others with their negativity. You need this behavior to change.

Before you demand change, you want to understand the source of the person’s bad attitude. They might experience something at home that causes them to be negative. Maybe they are entrenched in their negativity and can’t imagine operating any other way. After asking them about what makes them negative, you might ask, "What is going to need to change for you to be positive about your work here?”

You may need to offer help where you can, and you can always be a good and empathetic ear, but you can’t allow a salesperson to continue being negative around your team. This is how sales cultures become toxic.

Using These Coaching Scenarios

A great sales coach listens carefully and one that doesn’t believe the person is the problem. Instead, they are empathetic and coach their teams to address their problems and challenges.

Effective sales coaches use questions to cause salespeople to understand their challenges, using a mix of non-directive approaches and providing direction when it benefits their salesperson and their results. You can improve your ability to coach your team by working on addressing the common challenges that cause salespeople to struggle. If you need help, go here: solve for sales.

Post by Anthony Iannarino on May 4, 2023

Written and edited by human brains and human hands.

Anthony Iannarino
Anthony Iannarino is a writer, an international speaker, and an entrepreneur. He is the author of four books on the modern sales approach, one book on sales leadership, and his latest book called The Negativity Fast releases on 10.31.23. Anthony posts daily content here at TheSalesBlog.com.
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