Effective Sales Coaching


There is no one size fits all formula for effective sales coaching. But with the right style of individualized coaching, it can be the most effective way to improve sales performance and make behavioral changes that optimize results.

Change doesn’t happen overnight. It takes the fundamental soft skills of resilience, self-motivation, confidence, focus, ambition, and many more qualities no matter how many hours of practice you’ve had. 

Take professional tennis player Naomi Osaka right now. She’s cruising into the third round at the Australian Open 2021. Osaka's current coach is Wim Fissette. 

He reveals if you want to be an effective coach it’s crucial that you get respect and trust. This often comes from your own professional experiences. If you have someone that wants to listen and learn from the conversations you have, they are more likely to apply them. 

For Osaka, it works to have a coach that’s calm and knowledgeable, and someone that adds something to her team. Both coach and coachee need to believe in each other and see the potential in their relationship. Both should want continuous improvement and sometimes agree on working in certain areas to develop. 

Watch this video to find out more.

Sales Managers, like sports coaches, can use analytical data to reflect on their “student”. With this, they can see what actions need to be made to get to the next step. 

Understanding your coachee is really important and can be discovered in analytical data. Reflecting on how they think; or knowing how they will perform at certain points in their journey will give you an insight into how you can help them. 

See how Jiminny can help you capture and analyze your reps conversations here

Goals for Sales Coaching

Is your goal a number? 

Is your goal to improve sales revenue by 5% per quarter or more?

For Osaka and Fissette, their agreed goal is to win Grand Slams and for her to be the Number 1 Women’s Tennis Player in the world. But in order to do this, they must plan on how they will produce this goal into a strategy. Perhaps Fissette will implement a coaching focus on maximizing her motivation. This can help all aspects of her game like preparation and a desire to work hard and improve. In turn, this strategy can lead to their goal and help her win.

Coaches can’t manage the result but they can manage behaviors that lead to winning results. 

You can train your reps to work on new skills, coach them on soft skills / behaviors and share knowledge on how to change things that will make their sales process more effective. 

Focus on the character to help achieve a results-orientated mindset

An effective coach can support the rep to develop good habits that will allow them to reach their own and company goals. This is the most conducive way to spend their time. They should be reinforcing positive behavior and reflecting on how to do things differently from negative behavior. 

Read more about setting character goals for your team here

How much time are managers spending per week on Sales Coaching?

In a recent sales coaching workshop for sales leaders by Shelley Lavery, she asked the audience a question:

How often is coaching happening in your business today?

They were asked to pick one of the following options;

  1. Daily
  1. Weekly
  1. Monthly
  1. Sporadically

In a virtual room of approx. 80 people the overwhelming majority of sales people answered “sporadically.”

If sporadically is the answer for most then why aren’t Sale Managers investing more time to this? 

Do managers realize effective coaching is imperative to the development of their team? Or could it be that they are facing challenges to coaching?

Challenges to the manager in Sales Coaching?

Shelley asked the group why they didn’t prioritize coaching as an important part of their week. Here are some of the responses;

  • Have no time

  • Don’t have resources or tools to coach

  • Not sure what to coach

  • Unsure how to introduce coaching to get the team onboard

  • Don’t know how to start a coaching conversation

  • Not sure when to coach or when to train

In order to tackle the challenges I think it's good to explain why Sales Coaching is important first. This will help your coach to understand why they should be doing this and later introduce coaching to the team.  We need both parties to fully embrace coaching and make it the best part of their week.

What are the benefits of Sales Coaching? 

Ultimately we coach to improve the bottom line. 

Effective coaching can increase win rates, improve rep career development, and can enhance any previous sales training. 

When reps become more successful and have someone investing time in them they are more likely to stay with the company. 

When managers have a good retention of staff, they are happy as they spend less time onboarding and more time getting their team to produce revenue.


Happy reps are also encouraged to share their success with other members of the team to learn from to. 

Read more about the benefits of Sales Coaching here

Are you encouraged to put coaching nearer the top of your priority list yet?

How to overcome obstacles in Sales Coaching?

The time factor - Stress less. If you are a manager, coaching will help you understand your team and then delegate tasks better. This will save you time! When we learn  each person's strengths, personalities, behaviors and skills we can connect our team to support each other. Then the onus isn’t just on you. If one rep is strong in an area another rep is struggling with you can match them together. Delegating and connecting your reps can be an impactful way to help them grow. Read more about connector style leadership in this blog here.

Tools and resources for coaching - getting data from all your conversations so you can highlight key areas, identify trends and analyze factors impacting deals so you and your rep can understand where, why and how things went  right or wrong is a great place to start what you should be coaching. With accurate and full transparency on all interactions it's easier for the coach to give feedback and for the rep to realize what they need to coach. See what Co-Founders of Jiminny, Tom and Shelley Lavery love, try and avoid in coaching sales calls in this video.

Sometimes the sales data and analysis can identify that the rep will need more training in a certain aspect of the sales process. For example, closing skills. You could provide them with a call recording from someone in the team who has recently nailed their closing. Plus provide training on all the key elements to include. This is an example of when to train rather than coach

However, if the data and analytics reveals that it's perhaps some of the “soft skills” like needing to be more confident in their presentation that need to be improved to close better, then role play is often used in conjunction with providing coaching.

Find out more about how Sales Intelligence and Analytics can help you train and coach your team here.

How to start a coaching conversation 

Having good instincts and knowing how to connect best with individuals so you get the best from them is important. We often see in sport that coaches are hired and fired with the drop of a hat. Maybe because the coach doesn’t seem to connect with the person. It can take time to build trust and rapport. 

You can experiment with various coaching methods to see what works best. Remember you will need to need time to prepare your coaching sessions and also time to reflect on how your coaching is going and if you are seeing the desired outcomes. 

Checking you both feel in a comfortable environment during the coaching session so you are relaxed and being open with each other is a good start. You don’t even have to sit on a video call or in the same room. You could do this whilst on your mobile going for a walk, although often it's nice to watch body language to see how they are responding. 

You can share a  call recording a couple of days prior to the coaching session. Perhaps a call that shows some gaps in their performance; or one that they did really well and should repeat more often. Don’t give them an explanation or any agenda. Just simply ask them to take a look and then start by asking them what they thought

Ask your rep if there is anything they want to accomplish in their coaching. This can be either in their personal or professional life as often the two are connected. . Find out more here.

Remember to stay positive, this is in your feedback and general tone. The sessions should be constructive, helpful and build on good behavior so always giving more good examples of what they did well rather than what didn’t work well is important.  At the end of your session or after a short course you can ask each rep for their feedback on your coaching style so you can learn from the experience too.

When you have software that provides unbiased analytics with historical trends and activities it makes deciding what and where to coach that much easier to make the best use of your time.

Top 3 takeaways on effective sales coaching

  1. To be effective your coaching should be individualized to suit the coachee
  2. Use Sales Intelligence tools and analytics to help you decide where your coaching should be focused
  3. Reflect, measure results, revise, and ask for feedback on your coaching style - it's a learning process for both parties