online sales coaching

The Complete Guide to Online Sales Coaching

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Online Sales Coaching - Top Questions from Google


Online Sales Coaching is a process for developing individual salespeople to improve their performance. Coaching follows a methodology using a question-based model to improve the skills strategies and tactics of the sales rep. Studies show reps who receive coaching are more likely to increase their effectiveness and be successful.

Why is sales coaching Important?

Online Sales Coaching is important quite simply because it drives performance which in turn drives results. Professional Selling can be difficult and it can be a lonely job when results aren’t going your way. Coaching provides time out to talk through problems and change the perspective.

What do sales coaches do?

Sales Coaches support Sales Reps to grow and develop their sales activities, sales skills and Sales Mindset. Effective Coaching is primarily question based, which encourages the coachee to develop their own answers, thoughts and feelings. Sales Coaches help embed new knowledge & skills learned in training by demonstrating their practical application in real life scenarios.

In this article we will cover...

“The most useful and best days training I’ve ever had.  Love your style.”

Gary – CEO

1. Introduction to Coaching

Coaching for Salespeople which was once only the preserve of large organisations is rapidly becoming the Sales Leaders tool of choice for developing sales teams. More often than not the coaching is combined with Sales Training to provide a holistic approach. Even Coaching for Entrepreneurs has become popular as studies show that Coaching provides a great return on investment, with Harvard University claiming an 88% increase in productivity when combined with training, and Fortune Magazine claiming a conservative return of six times the cost of coaching.

Furthermore, Sales Coaching can be delivered remotely which removes the need for expensive travel and reduces time away from the office, allowing Sales Reps & Sales Leaders more time to focus on learning and their regular work duties.

New and updated to include the latest remote selling techniques we have a full range of coaching programmes for CEO’s, Sales Leaders, Sales Managers and Salespeople.

2. Why Hire a Sales Coach?

According to research by Harvard Business Review the top 3 reasons to hire a Coach are:

1. Develop high potentials or facilitate transition – 48%

This very much resonates with our own experiences and some real-life examples would be coaching a Pre-Sales Technical in the transition to a very successful full-time Account Director at Microsoft.

We also coached a fantastic Business Development Rep in his transition into a full-time Key Account Manager.

2. Act as a sounding board – 26%

A common reason sales professionals looking to hire a coach is for a sounding board. We have coached Sales People, Sales VP’s, Business Owners & Entrepreneurs and in many cases they like to talk to someone to ensure they are doing the right things or following the right path. The coaching helps build their confidence.

3. Address derailing behaviour – 12%

The word derailing conveys someone trying to block or obstruct and this can happen when change is introduced into a Sales organization.

This could be a new VP of Sales, a new CRM system, or a change in territories. Human Beings are hard-wired to resist change but as long as the individual has the right values this can be overcome.

Sales Management KPIs

3. Creating an Effective Sales Coaching Strategy

In the Sales Maturity Model, best in Class Sales Organisations consistently provide effective sales coaching for all their sales team members, however, we appreciate this is a journey and not every organisation is in that position. The most common barriers to effective sales coaching are:

  1. Sales Managers are time poor and simply don’t have the bandwidth to coach their Reps. This is common as most Sales Managers still carry a sales target and they are forced to choose between coaching or selling. In most cases, the Sales Managers were originally Sales Reps so they will always choose selling before coaching.
  2. Sales Managers may not have been taught how to coach and are therefore uncomfortable in the coaching role. They will claim they coach while on the job, however this is not the same thing and is much less effective.
  3. No sales budget to hire external coaches to take the pressure off sales managers, which is akin to the chicken and the egg scenario. The reason most companies say they can’t afford coaching is that their reps are under-performing and need a coach.

So what is the best Sales Coaching Strategy you can adopt? Well in our experience here are some ideas you should explore:

  1. Are your Sales Managers comfortable coaching – if not coaching is a proven way to support sales teams.
  2. Dedicate coaching time with sales team members to improve your sales process. Often times salespeople understand the process but they find it difficult to take prospects through the sales process.
  3. Techniques coaching is a common way to help improve specific techniques such as onjection handling, or controlling thee sales conversation.
  4. You should also consider using video to record some of your coaching, so the coachee can see for themselves the improvements they are making.
  5. Telesales coaching is a great way to develop outbound team members with the coaches making live calls to demonstrate techniques and tips in action.
  6. Marketing and sales are no longer the silos they used to be, Great sales people can market and great marketers can sell so help your salespeople improve their marketing skills.
  7. Make coaching one of the KPI’s for the Sales Managers and sales team members. This way you are sending a signal that this is important. 1 x 40-minute session every 2 weeks.
  8. Separate Coaching sessions from training, sales meetings and pipeline reviews. Coaching needs it’s own space if it’s to deliver an ROI. 
  9. Create a transparent Sales Coaching Process with templates and logs so everyone becomes comfortable with the new system. Transparent as in what the process is not what the conversations are.
  10. Consider having the sales coaching delivered by someone other than the Sales Manager. Often times the Sales Manager will have to hold sales reps accountable and have difficult conversations with them. This makes the Sales Reps much less likely to “open up” in a coaching session if it’s being facilitated by the Sales Manager, who just told them off about their expenses being late an hour ago.
  11. The overall goal should be to develop a Coaching Culture within the organisation, this will take time to achieve. In turn, this will deliver increases in efficiencies and win rates across the board.

4. Who Benefits from Sales Coaching?

Online Sales coaching works for busy Salespeople and sales managers who have little spare time and need a flexible solution that is not dependent on their location. Coaching should be targeted and relevant to everyday work challenges in order to build confidence.

Some people are not coachable, as they may not be interested in learning or improving. Even with unlimited resources, you have to choose where to focus your energies because:

a) Does the biggest opportunity for improvement lie in coaching and training the top performing 20% of your sales team? Probably not. If these people are already hitting their sales targets, then you might want to leave them for now.

b) Does the biggest opportunity lie in coaching the bottom 20% of your sales team? Probably not, as often Sales Managers retain under-performers longer than is necessary. There are valid exceptions to this rule, for example if the company hired these under-performing Sales Reps, then the company needs to take responsibility and help them. This means giving them every form of support necessary however, if they still don’t respond it’s usually not the best place to spend your Learning and Development budget, because they may be simply a square peg in a round hole.

c) The biggest opportunity for improvement that you have is usually moving the 60% average Salespeople towards the top 20%. A mere 1% increase in sales performance, multiplied by 60% of your sales team, can be huge in terms of revenue. Typically these people are more interested, more motivated and willing to learn than any of the other groups.

5. Online Sales Coaching Plans

Online Sales Coaching can be very difficult depending on the person being coached, and the circumstances. Our Sales Coaching Plan uses a proven framework based on the highly successful OKR business goal setting methodology.  Whilst we predominantly use this online we also have delivered coaching in person and a combination of the two. 

The OKR model helps align the companies overall sales strategy and objectives with the coaching at every level of the organisation.

Sales Coaching is the process of supporting Salespeople to achieve improved results. By its nature it can then only be successful when you are working on live opportunities, in real-life scenarios – which is one of the benefits of online delivery.

As Sales Coaching should always be supportive this is not a meeting to criticise, discipline or embarrass, but instead an opportunity to build confidence and guide the Sales Person.

The Sales Coach is there to show the practical application of what has been taught in Sales Training. This means that the coach should be able to actually do the sales activities, not just talk about them.

Online Sales Coaching for Teams
Sales OKR examples

6. GROW Sales Coaching Model

As an Online Sales Coaching company, we use the GROW coaching model which is probably the most common coaching model and it’s well-proven over the years in many different applications. The GROW coaching model is:

G – stands for Goals. What are your goals for the session?
R – stands for Reality. What is the current reality of the situation?
O – stands for Obstacles. What obstacles are preventing you from reaching your goals and what options do you have open to you?
W – stands for Way & Will. What actions do you commit to undertaking to move forward?

As you see from the questions the onus is very much on the Coachee in terms of what they want to get out of the session. It’s also important to require the Sales Reps to complete the first part of the Sales Coaching form before the coaching session.

It ruins every session when the sales rep turns up and then spends 10 minutes trying to decide what they want to get from the session. Sales Leaders can help here by suggesting topics to discuss with their coach in between the coaching sessions.

“Klozers are the Sat Nav for sales success.”

Alan – Business Manager

7. Coaching Questions

It’s widely accepted in business and personal coaching that the Coach is not there to provide answers. This, however, is not always true for Online Sales Coaching. Professional Selling can be a very high-pressure environment and many salespeople who are desperate to hit their sales targets simply want a straight answer to their questions and not spend 40 minutes trying to work out the answer.

This, of course, depends completely on the style of the sales rep, but you should be prepared to answer their questions if required, hence for us, experience in sales is a must-have prerequisite for Sales Coaching.

That said here are some questions you can use at each stage of the GROW coaching model:

 G – stands for Goals. What are your goals for the session?

  • Do you have any specific skills you want/need to improve?
  • Do these goals fit with your teams’ objectives?
  • Do you have the skills but need to be held accountable?
  • How will you know when you have achieved those goals?
  • Why do want to be coached now?

R – stands for Reality. What is the current reality of the situation?

  • What is happening now?
  • What is the effect if this continues?
  • What have you done to try and fix this yourself?
  • How do you feel about this?

O – stands for Obstacles. What obstacles are preventing you from reaching your goals and what options do you have open to you?

  • What constraints are on you?
  • What obstacles are in your way?
  • What do you need to stop doing to achieve your goal?
  • What are the disadvantages or advantages of your options?

W – stands for Way & Will. What actions do you commit to undertaking to move forward?

  • What will you do now?
  • Is there anything that might stop or hinder you?
  • How will you measure progress and success?
  • How will you keep motivated?

These are generic questions, however they are a great starting point and combined with real sales experience and knowledge can provide transformative coaching. The questions serve as prompts and get the salesperson talking about real-life scenarios they are facing. 

To wrap up every session it’s good to include a final question as follows:

What is your Biggest Takeaway from the session today?

Lastly, the coach must take accurate notes so that they can refer back to them. It’s also good practice to get the sales reps to sign a coaching log or a worksheet that summarises what they have agreed to do before the next session. 

In certain circumstances, if the Sales Coach is not the Sales Manager it might make sense to share this with the Sales Manager so that he or she can ensure whatever the agreed actions are happening. This additional accountability can be important because the Sales Coach cannot make the Sales Rep do anything but the reps line manager can.

Grow Sales Coaching Model
Sales OKR examples

8. The Coaching Mindset

Check the Sales Rep’s mindset – if they have given up, aren’t engaged, don’t care or think they know everything; stop. You cannot make anyone want to improve and you simply may be too late.

You can deliver a motivating talk that peps them up, but the minute you leave the room it’s like pulling a plug from the socket in the wall, and the energy starts to drain from them and they will quickly revert to type.

Motivation has to come from within, so if the Sales Person’s mindset is not right before you start coaching, work on a personal Goal Setting session that ties their sales performance into their personal goals.

As a Sales Manager, you have a very limited amount of time and coaching C players in most cases is not the best use of your time or theirs. Investing your time on Salespeople who want to get better will always deliver a higher return.

9. Sales Data

For your Sales Coaching Plan to drive improvement and be successful, it must be supported by data, as without real data you only have one person’s opinion versus another, and it’s important that the coaching is objective.

Gather data from the best performing Sales Person so you have an example of “best practice” to compare with.
If you have no hard facts and data to prove that something can be done, try doing it yourself and if you can’t do it then it could be that you are asking for the impossible.

Asking Salespeople to do something that you either cannot do or cannot prove that someone else in the organisation can do, will lose you respect and encourage the good salespeople to look for another position.

Sales Analysis
Sales Management Performance Review Template

10. Personal Sales Coach

We appreciate that many coaches will tell you they don’t need to have done something or be an expert in a particular field for them to be able to coach someone, and maybe you don’t however, in our experience in Sales, it definitely does make a difference.

Coaching a Salesperson on how to make a Sales Call is much more believable for the Sales Person if the coach can pick up the phone, and demonstrate by doing it themselves.

The coaches role is to help with the practical application of the theory and knowledge learned in training and this isn’t possible unless you have done it before and can still do it.

11. Online Sales Training

Most good sales coaching programmes will provide access to online sales training material. This may be a bespoke sales training programme which is self paced but also can be provided ad hoc to the coaching if specific needs arise out with the general training programme.

Klozers provide SaaS Sales Training, Telesales Training, Key Account Management Training, Consultative Sales Training, Sales Foundations and LinkedIn Training online.  

When done correctly the sales training will compliment and support the sales coaching process. 

12. Individual vs Group Coaching

The majority of our coaching is Individual Sales Coaching which provides targeted support based on the Individuals needs.

This is vital for our Executive Sales Coaching programmes, however, in addition to Individual sales Coaching we have experienced equally good results when facilitating Group Sales Coaching of sales teams.

This has the added benefit of Sales People learning from their peers and it’s a great way to share best practice, share customer stories and build teamwork.

Although the danger is that in some cases salespeople will be reluctant to participate and open up as they lack confidence.

With this in mind, our most successful projects have involved a combination of both group and 1-2-1 sales coaching.

To combine Group and 1-2-1 coaching simply set up a three hour or afternoon Coaching session every two weeks and dedicate the first hour to the group, followed by 2 x 40 minutes 1-2-1 sessions.

This can be run weekly with Sales Reps rotating the 1-2-1 slots so they each are receiving a 1 x 1-2-1 session every two weeks.

13. Sales Coaching Checklist

Before starting any sales coaching it’s vital to obtain and provide certain information to your Sales Reps. This is the best time to set any “rules” and manage expectations in terms of the sales coaching process, and how the coach can best help them.

We do this via a Sales Coaching Intake List which includes questions on:

What are the Sales Reps aims from Sales Coaching?

  • Ask “What do you want to achieve from Sales Coaching?”
  • Do you have any specific Sales or Personal Goals or issues to resolve/meet?
  • How will you know when you have achieved those goals?
  • Review Sales & Personal Goals Sheet. If not completed, ask for by next session
  • Why did they seek coaching now? This ‘treasure’ is key for their motivation

What Sales Coaching Is and Is not

  • Coaching is a relationship between your coach and you
  • You are the expert in your life. Coaching helps you connect to you, your wisdom and take action to create the life you want
  • Coaching is 100% Confidential & Non-Judgemental
  • Ask for two-way confidentiality (covers what you share too)
  • Coaching is NOT counselling or therapy

What Sales Coaching involves – what they should expect

  • How sessions will go/session structure
  • That their goals and focus may change
  • That Ups & Downs are normal in coaching as is reaching a plateau. The down cycle is where we do most growth
  • Gain permission to:  Interrupt them, get tough with them, challenge them, ask difficult questions, repeat back what they have just said, give them forms, exercises, research, homework between sessions
  • The client decides what to cover, how/when to end coaching

The role of the Sales Coach – what they should expect from you

  • Set your boundaries here, e.g. returning email and phone calls within one working day
  • I will help you set, clarify and maintain focus on your goals
  • I will hold you accountable – for what you say you’re going to do
  • I will help you establish your solutions & strategies
  • I will encourage, support & believe in you even when you may not!
  • I will challenge you and help you recognize where you may be holding yourself back.
  • Together we raise your self-awareness

The role of the Sales Rep – what the Sales Coach expects from them.

  • YOU are responsible for YOUR results. Success is directly related to your commitment and the effort you make
  • To be honest and open (and to tell me when you can’t be)
  • Willing to adopt a more positive outlook on self and life
  • Ready to be fully accountable for your life/decisions/actions

How do you want to be coached

  • Ask, “How best can I coach you – what tips can you give me?”
  • What can you tell me about your learning style?
Sales Management KPIs

14. Is Sales Coaching Confidential

This is a really important question that you must address during your on-boarding session.

Confidentiality is important for many reasons such as the Sales Rep could feel embarrassed, ashamed or anxious if the coaching conversations were revealed to their work colleagues.

Additionally, they may reveal details around clients or pricing that could be damaging if it reaches the wider public which could result in a lawsuit for the sales coach and at best their business would be destroyed.

So with that said confidentiality is extremely important, especially if you are using an external Sales Coach.

In our opinion, Best Practice would mean that the Coach and the Coachee sign a NDA (Non-Disclosure Agreement) before starting.

Confidentiality between the Coach and the Sales Manager can also be an issue as the Sales Manager wants to know how the sessions are progressing.

In most cases this is simply because they want the Sales Rep to be successful, however, in some cases, the Sales Manager might be part of the problem so the Sales Coach needs a way of feeding this back without breaking the confidentiality of the Sales Rep.

Again these issues are rarely a problem if you agree in advance what the ground rules are between all three parties.

An example could be that the Coaching notes and any feedback is open to the Sales Manager unless the Sales Rep specifically requests otherwise.

This compromise allows the Sales Manager and the Sales Rep confidentiality where they specifically want it, rather than just blanket coverage.

Confidentiality is also important from the Sales Managers perspective as he may specifically want the Sales Coach to address issues that the Sales Rep is avoiding and the Sales Coach who is being paid by the Sales Manager has to somehow introduce this.

15. What Makes a Great Sales Coach?

In our experience the single biggest issue that Sales Managers experience with sales coaching is frustration.

They are frustrated that the Sales Reps just don’t get it. 

They are frustrated because the Rep isn’t as good as they were.

They are frustrated because they are emotionally involved in the outcome. 

This means more often than not the Sales Manager wants success more than the salesperson. Whilst this might seem odd the minute the Sales Manager becomes emotionally involved and wants the success more than the rep, it’s over. The Rep can sense it, they can feel it and any Rapport and Trust that has been built up disappears. At this point the sales person will close down and worst-case scenario blame the Sales Manager for their lack of success.

Coaching is an art and a skill, very different to training, selling and managing salespeople. It’s a specialism but it can be learned if you have the time and energy to do so.

The success of your Sales Coaching is as much down to the Sales Leaders Emotional Intelligence as it is their Sales skills, experience, and knowledge. Treat Sales People like adults, respect them and never judge them.

16. Sales Coaching Tools

These are the tools and the processes that we use for sales coaching.

  1. Sales Coaching Worksheet – this provides a structure and consistency to the coaching process.
  2. Sales Coaching Check list – this helps set the ground rules, manage expectations and obtain vital information at the start.
  3. Sales Performance Review – this ensures the activities of each sales rep are aligned with the companies sales strategy and they are consistently reaching or exceeding their sales goals.
  4. Sales Content – it’s unreasonable to expect Sales Reps to learn and understand everything either face to face or over a call.  It’s important to have good quality, relevant content in different formats that suit the Sales Reps learning style.
  5. Microsoft OneNote – we use Microsoft OneNote to build and store our Sales Playbooks.
  6. Communications – we use Microsoft Teams for all coms with Zoom and a telephone as a back up.
Sales Performance Review Template
Sales Management Performance Review Template

“A fantastic learning experience”

Amanda – Account Manager

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Author Bio

Iain Swanston has spent over 30 years in B2B sales selling, training and leading teams both domestically and internationally.  In addition he serves as an Associate at Strathclyde University Business School where he has delivered the sales content for the Masters in Entrepreneurship since 2015.

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