How to Coach a B2B Sales Team to Win Bigger and Better Deals

January 18, 2018

Every sales manager wants their team to close bigger deals. How much would revenue go up if your entire team was closing deals like your best sales rep? What if every rep was prospecting as well as the rep generating the most leads? Your team’s success starts with you. Let’s talk about how to become the manager of a sales team where every rep performs at their absolute best.

A great sales team starts with a manager who’s also a great coach. How is a good soccer coach different than a bad soccer coach? A bad soccer coach just tells you what they want and what to do. For example, they might yell at their team for not playing ‘good defense’ or ‘not scoring enough.’ A good soccer coach identifies the specific skills team members should improve to enhance their performance, provides their players with insights into how they can be better, and then creates the drills to help the team achieve their goals.

For example, a good coach may notice that some people on the team are scoring on a low percentage of their penalty kicks. This coach might identify the person who’s the best at penalty kicks on the whole team, and then enable that talented team member to teach everyone else their technique. Then the whole team would drill what they learn together and all improve at their scoring percentage.

I’ve learned some powerful coaching techniques to help sales reps reach their full potential. One of the most important sales management tricks I have come across I learned from a great manager I had when I was a Field Sales Rep at Google, Mark Flessel. I saw him seek and identify when a rep on the team had a particular strength or skill. If a rep on the team did something well, he would ask for details about how exactly they went about doing it. He would watch the numbers, talk to the reps, and keep his fingers on the pulse of what people’s actual activities were so that he could figure out if someone was doing something particularly well or had developed a skill that he could replicate across the team.

Mark might find that one rep on the team was good at generating new leads, another rep was talented at running effective customer meetings, and another was the best at asking for the business and closing the deal. When he found an activity or skill in which one person was particularly talented, he would empower the rep to teach the rest of the team that best practice.

The reps that were teaching their peers appreciated the opportunity to take on a leadership role and be recognized for something they were doing well. It improved every individual on the team when best practices were shared. It was almost like Mark was cloning his top reps – he was taking the skills of the top performers and replicating those skills across the sales team.

Break your sales process down into skills

How can we break down what Mark was doing into a repeatable process that can be replicated to other sales teams? For starters, as a manager, you’ve got a deeper level of insight into your sales team’s performance than anyone else. It’s your job to improve their weaknesses. But before you can improve their weaknesses, you need to recognize their strengths.

The first step is to ask yourself: “Which skills determine whether my team succeeds or fails?” Break your sales process down into those skills. You’ll end up with a few key skills for each stage of your sales cycle.

A few examples of the types of skills that can determine how successful your reps are:

  • Prospecting
  • Building Rapport
  • Qualifying
  • Giving Persuasive Sales Presentations
  • Timely and Relevant Follow-up
  • Overcoming Objections
  • Negotiating
  • Closing
  • Managing the Ongoing Relationship

Remember, it’s easy to get distracted by the deals your reps are closing without considering all of the other skills that lead to a successful win.

Ask yourself: “Who’s the top performing sales rep at each skill?”

Once you’ve identified the key attributes and skills that make your reps succeed or fail, rate each rep on your team on how good they are on a scale from 1 to 10. Measuring this can feel a bit subjective, but the goal is to identify who is really good at a given skill so that they can be the model for the others. Remember, if no one on the team is good at a certain skill, you can always tap your network, an expert, or a consultant to fill in on a certain area.

Use your judgement and historical sales data to rank your reps from 1 to 10 in each category. A 10 is the highest a rep could potentially perform a certain skill. A 10 in ‘Timely and Relevant Follow-up’ means the rep could not do this particular skill any better than they currently are.

It can be informative to ask members of your team and get their feedback on what they think they are good at and what they perceive others on the team to be particularly good at. How do they feel about their performance? What part of the sales process do they like most? The least? Have them score themselves on each skill in your ranking system.

Collect their feedback and put the self-evaluated score next to the ranks you assigned. Self-evaluation is a powerful tool. You might notice that the Reps who are honest and aware about their performance are the most coachable and might improve the fastest.

In those same one-on-one conversations with your reps, you can also ask them to talk about who they feel is great at what on the sales team. Who do they turn to for help when there are questions about the product? Who do they think is the best negotiator? Have them talk about who they think is great at what. Reps tend to notice when their peers are particularly good at something. Leverage their eyes on each other – you only have one set of eyes, but a great leader leverages the knowledge of their team – so be sure to ask their opinions!

You don’t need to show your ranking list to the team, the point is to give you a clear view of who is good at what so that you can have the most talented people share their skills and knowledge. Compare your opinions with what the reps thought about themselves and about their peers.

Now you’ve got a list of your reps in order of ability. Pay special attention to your top performer in each skill set. They’re going to be your go-to resource for improving your sales training and getting the rest of your team up to speed. Now it’s time to put your coaching plan into action.

Dividing your coaching plan by skill set will maximize the ROI of each rep’s training. Most reps don’t need “new hire” sales training all over again, they just have one or two under-trained skills holding them back. Now you know who on the team needs help, and who on the team is in the best position to help them.

Turning your most talented reps into coaches

Now that you have recognized what is important to be successful on your team and who is good at what, its time to turn your best reps into coaches.

First, meet with your top ranking reps and discuss their strengths and weaknesses. No matter how great they are, they aren’t perfect. Coach your best reps first so they know how to train the rest of the team.

Spend a few days shadowing your top reps. You’re looking for opportunities to improve their weaknesses and learn how they utilize their strengths. Analyze their daily schedule, how do they use their time in order to operate at such a high level?

As a manager, your job here is to help your sales reps understand the subtleties in what they are doing on the skills that you have identified are their real strengths. Then you can help them understand why they are good at something, and that will help prepare them to communicate what they are doing with the rest of the team. Even the best reps aren’t naturally great coaches. A lot of their skill is ingrained and they might not be able to explain some of the subtleties of their sales performance.

Also, don’t just look at what they are doing differently, but look at how they are performing the activities that they are especially good at. For example, watch how your top reps:

  • Plan their day
  • Decide what to do first
  • Organize their information
  • Prepare for sales calls

Find the details that create champions. You want to find obvious ones, like getting to work early, and less obvious traits, like the body language they use with prospects. Look for situational sales training material too. How does your top performer approach a gatekeeper? What’s their personal qualification process?

Below are some examples and actionable strategies to help your reps become great coaches.

Prospecting and Building Rapport

You want to watch for things like how your top rep:

  • Starts a call
  • Becomes friendly with the prospect
  • Personalizes their offer
  • Asks prospects to take the next step

Finding the right opportunities is key to closing higher ROI deals. This depends on a lot of different factors, including the amount of leads the rep is contacting, but proper technique will help everything else fall into place. Tonality plays a big role in how your sales reps are perceived by buyers. If your reps sound annoyed while prospecting they’re setting themselves up for failure. Pay attention to how your rep approaches prospecting and building rapport so you can help them get ready to communicate their approach.


Qualifying prospects is an underrated part of the sales process. Qualification ensures your reps aren’t wasting time with people who don’t have the ability to make purchasing decisions.

How does your best rep:

  • Decide which leads to approach
  • Score the leads they find
  • Have a qualification conversation
  • Prioritize their prospects and opportunities

Qualifying the right opportunities makes closing them easy. A lot of sales reps ignore the qualification aspect of sales, they chase after the first deal they see so they can get to the next one. But not all deals are created equal. Help your reps who are best at qualifying figure out what is special and what they are doing to effectively qualify their opportunities and prioritize the best ones.


How important is it that your sales team brushes up on their negotiation skills? Learn about what your best negotiator is doing so that you can enable them to share their skills with the team.

Understand the details around how your best rep:

  • Prepares for a sales negotiation
  • Organizes and interpret the details of the deal
  • Draws out and overcomes last minute objections
  • Presents the contract

Help your top rep collect everything he or she is doing into a playbook that they can teach to the team. Use your top rep’s situational tips to create scripts, situational checklists, and other resources for your sales team. Negotiation is an art and a science, it’s also highly situational. Having your best reps reveal to your team the list of things to keep in mind (such as never offering discounts on certain size deals, or leading with one offer while having an upsell in mind) will help everyone on the team strengthen their negotiation style. My negotiation course covers this in detail.

Cloning your Top Reps across the team

Now that you’ve identified the skills a sales rep needs to be successful on your team, and you’ve figured out who has the deepest expertise in each of those skills, it’s time to execute and enable your best reps to teach the rest of the sales team how to also master those key skills. It’s time to prepare your top reps to “clone” themselves – it’s time for them to teach class.

Group training sessions are an easy way to get everyone on the same page. Reps can show the rest of the team how to utilize their technique in situational exercises. The rep teaching the class can demonstrate their skill live, or if your sales team is remote you can do it remotely. In general I’ve found that in person training is more engaging and people learn better in person and when they can do exercises that engage them. After your rep has taught the skill, you can try having the other members of the team practice the skill in pairs or groups.

The reps that are learning will probably pay close attention to the lesson because they likely know that their peer who is teaching them is giving them the tips and tricks that they need to be successful. Also, since they are often teachers now too, but of a different skill-set that they happened to be great at, they can better empathize with what it’s like to be a teacher.

You can host these training sessions as a part of a weekly meeting, or at your monthly, quarterly, or annual meetings. I like to have skills taught regularly, and make learning a regular part of the cadence of the job. It’s hard to teach your reps a ton at once, but they can absorb a bit at a time. You’re likely to get better results in terms of knowledge retention and skill development if you teach new skills for one hour a week than you will if you cram 10 hours a day straight for a week at the annual kickoff.

This process can also uncover who on the team needs extra help. Pay attention to the reps who haven’t improved after the group training sessions and have your expert reps mentor these reps personally. They can meet with them and discover their problem areas. Make sure to document the breakthroughs that help them improve in your training material to help anyone who has similar issues in the future. Also, this is creating training materials for the future, and you can continue to update it over time. This all takes time, but the results of improving your team will certainly show up in your sales results.

If your cloning strategy works, your entire team will start closing more deals. By turning your best reps into coaches you set a new standard for the rest of the team. This creates a healthy sales culture focused on self-improvement and performance.

Your Team Needs Regular Coaching

There are two styles of sales leadership in the world – spreadsheet managers and coaches.

Spreadsheet managers aren’t necessarily connected to their team’s activities, they are focused on the results. Coaches are right there on the sideline, ready to jump in and help when the time is right.

Most sales managers are a mixture of both, which is where you want to be. But a lot of great managers slip into a pure spreadsheet style of leadership. There’s so much to do, it can be exhausting staying on top (and connected) to your team and their performance. Don’t allow yourself to lose sight of what matters; the actual people you’re leading.

Smart coaching puts the team in a position to succeed. You’re giving your reps the skills and abilities to win bigger and better deals by focusing on the most important part of their performance: who they are as salespeople.

Managing a person isn’t the same as managing a spreadsheet. Understanding the difference is an essential part of building a high performing team. Just like a great coach names team captains, you can deputize the reps on the team who are the strongest in a particular area to lead, coach, and develop the rest of team. Not only will this spread the skills of your top performers to the rest of the team, it will also develop the next generation of leaders.

Steve Benson

Founder and CEO

Steven Benson is the Founder and CEO of Badger Maps, the #1 route planner for field salespeople. After receiving his MBA from Stanford, Steve’s career has been in field sales with companies like IBM, Autonomy, and Google – becoming Google Enterprise’s Top Performing Salesperson in the World in 2009. In 2012 Steve founded Badger Maps to help field salespeople be more successful.