Deal coaching: How on-the-job training helps reach sales quotas

Managing an effective and skilled sales team requires a lot—from onboarding to assessing to motivating your employees. Training your sales reps is an important part of supporting and retaining the employees most directly tied to your company’s revenue success.

But training salespeople is often challenging.

It’s tough to take them away from their jobs when they’re trying to close deals, follow up with prospects, and meet their quotas. However, to meet those quotas, they need guidance. On-the-job deal coaching is a great way to offer direction in a way that keeps deals moving forward.

Let’s look at what exactly deal coaching is, how it can impact your sales team’s success, and what it might look like in your organization.

What is deal coaching?

Deal coaching is a popular form of professional development geared toward helping develop and support successful sales reps in your organization.

Coaching has immense benefits for your sales team and is an integral part of learning and development. Deal coaching has its own unique advantages, though. So it’s important to understand how it differs from general skills coaching.

Deal coaching vs. skills coaching

Deal coaching is working with sales reps and coaching them through closing deals with specific customers. This method addresses the tools and skills needed to move that client through the sales pipeline. Deal coaching takes place in less structured sessions between a sales manager and a rep.

Skills coaching focuses on teaching broader concepts that are critical to sales success in general. It concentrates on developing the sales rep rather than on a client. Skills coaching is a more typical form of professional development and includes formal training in essential sales skills.

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How to use deal coaching

Deal coaching happens in formal or informal sessions between a sales rep and the sales manager. They discuss an existing deal the rep is trying to close, with the manager coaching the rep on the tools and skills they could use to help.

Rather than setting out detailed steps to execute, the manager’s job is to help the rep analyze what the client needs and reinforce specific sales skills for doing so. They can do this by asking thought-provoking, open-ended questions.

5 questions to ask during deal coaching

• What is the client’s need? Get the rep thinking about the pain points the client is experiencing or the goals they’re trying to achieve so they can talk about how your solution applies.
• Why is our solution the right one? This helps the rep articulate what makes your product or service valuable to the client.
• How does our solution compare to the competition? This goes further in exploring what makes your product unique. It can also help the rep round out their proposal with information that shows how they can outperform the competition.
• What objections has the client expressed? Analyzing why a client may be resistant can help the sales rep understand another pain point and figure out how to address it.
• Who is the key decision-maker in the organization? The rep wants to ensure they know who will make the decision and that they can build a relationship with that person.

These questions will get the salesperson thinking about their approach. They can also open up opportunities for coaching on specific or more advanced sales skills.

Let’s go through a couple of examples to see what a typical coaching session might look like.

Deal coaching examples

Example #1: You, the manager, are discussing a deal with a rep and ask about decision-makers. The rep shares that they have discovered their contact will not be making the final decision, but that someone further up the management chain will.

This is a good opportunity to create a plan for how the rep will start building a relationship with that manager. You share some tips to help them research the company’s leadership and offer coaching on communication skills they’ll need to start that conversation.

Example #2: A rep is creating a proposal for a new client that has been stalled in the pipeline. During the coaching session, you discuss the client’s objections, and the sales rep shares that they are concerned that your solution isn’t all that different from what they’re doing now.

You can help the sales rep talk through what makes your product stand out, including additional features the client may not be aware of.

The rep walks away from your session able to explicitly address how the client’s needs aren’t being met by their current solution. They’ll also be able to articulate how your product will make their work easier and more efficient.

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How deal coaching benefits your team and your organization

Coaching, in general, benefits your employees by boosting their overall abilities and making them more competent salespeople. Deal coaching, in specific, helps them gain hands-on experience with applying the skills that support great sales.

Working with your reps to move deals toward the close will show them how to use their skills in different scenarios.

Deal coaching doesn’t only serve your sales reps, though. It also builds your customer relationships by helping you, and your team, provide them with timely information and solutions to solve their pressing problems.

Finally, deal coaching has an immediate and direct impact on sales. It serves your company by addressing issues and shortening the sales cycle, so you have more revenue coming in more quickly.

Is deal coaching all you need?

Deal coaching is beneficial in tackling individual deals and driving results. However, it isn’t the only form of coaching and professional development your team needs. If you want to build a team ready to achieve long-term results, you need to create a foundation of solid skills and tools for success.

Combining deal coaching with a more comprehensive, engaging sales training program will give you the best of both worlds. You need to educate your employees on general sales skills and principles so they’ll be prepared to apply them when it comes to individual deals.

Planning for deal coaching success

Deal coaching is a great opportunity for real-life, in-the-moment skills application. But that doesn’t mean it shouldn’t be carefully planned.

While manager coaching sessions may be informal, they should be a designed part of your sales training strategy. To get results and ensure these sessions impact your sales reps’ performance, you need to set clear sales goals. You also need to have coaching tools and resources in place. And your managers need to have a good understanding of those resources so they can facilitate the process.

Finally, you need to take time to evaluate the results of these coaching sessions and redesign the process as needed. When you plan for and execute it well, deal coaching can be a powerful L&D effort that brings your team greater sales success.