Trust Enablement

Improving Sales Performance with Enablement Recruiting, Consulting, Outsourcing, Coaching, and Insights on Strategies, Tactics, and Tools

Sales Coaching

Sales Coaching is the best way to raise the overall performance of your sales organization.

Enablement teams should seek to integrate coaching into their organization but recognize that they may or may not have the skills themselves depending on their backgrounds. If you have never sold, and have not been formally trained to coach, don’t try to do it yourself.

What is sales coaching?

Sales Coaching results from personalizing sales training to the individual seller to improve specific skills or a specific situation.

Sales Coaching vs. Sales Training

In sales training, new skills are taught in a general manner to the entire sales team and all sales managers.

While efficient, this broad brush, generalized approach is not an effective way to teach information that is expected to drive your sellers’ behavior change.

To have the most significant impact possible, successful sales coaches personalize sales training and apply it to each seller’s needs at the time of need.

Are individual sales development reps struggling to make enough calls? A great coach will partner with the seller and their leader to identify and fix the personal barriers to success?

Perhaps a handful of sellers cannot get their deals across the finish line; their close rates are abysmal. Again, to have the most significant impact, effective coaches will seek to understand the challenges across the individual reps and develop a unique approach to supporting each in their journey of improvement.

Struggling to teach leaders how to teach sales skills?

Why is coaching so important

Industry research is clear; structured coaching is one of the most powerful tools for increasing sales teams’ effectiveness.

Here are a few coaching statistics

Research from CSO Insights has previously demonstrated that your sales management’s ad hoc coaching leads to poorer outcomes — you must have a formal, structured approach.

  • According to Vantage Point Performance, effective coaching can improve win rates by as much as 29%.
  • According to Aberdeen Research, companies that provide real-time, deal-specific coaching increased revenue by 8.4% year-over-year – a 95% improvement over companies that don’t offer that coaching level.


Note these facts:

  • Harvard Business Review notes, “The real payoff from good coaching lies among the middle 60% — your core performers. For this group, the best-quality coaching can improve performance up to 19%.”
  • Dave Kurlan observed that sales managers who devote at least 50% of their time to coaching have salespeople who score 13% better in Qualifying and 24% better in closing than the salespeople whose sales managers rarely coach.

Done well, this pays off.

However, done poorly, it can lead to poorer performance (as noted by CSO Insights when they still existed).


What does a sales coach do?

A great coach can be a difference-maker for your business.

How do these professionals determine their coaching goals and what they should focus on each day?

Let’s read on and see.

How to be a good coach 

Want better results? The good news, if you are willing to plan first, and execute second, you can leverage coaching to improve overall sales performance.

Here are a few best practices for you to use as part of your coaching program.

  • Form an executive council to ensure you have buy-in, support, and active participation across sales leadership and other leaders
  • Us a seller advisory board, this is a great way to identify how to improve and develop champions to support the effort
  • Identify individual areas of improvement across all team members
  • Identify personal skills to allow them to make full use of their natural strengths
  • Based on what they learn about personal weaknesses, and the individual reps’ skills, they will create unique action plans for each seller
  • Customize each coaching session based upon the in-the-moment, real-time needs of individual sales reps
  • Put ownership of the coaching in the hands of the individual salespeople and front-line managers
  • Recognize that the best coaches treat coaching as an ongoing process, never simply a one, and made conversation

Coaching Models

It is helpful to have a coaching model, more on this to be added soon.

What Capabilities do Effective Sales Coaching Solutions Need?

And this is the critical question.

  • Your business must define the behaviors expected of your sellers and teach all sales managers what good looks like.
    • Your coaching software must take in these rules and behaviors. We have not found any sales coaching tools capable of doing this.
  • Your coaches must deliver training regularly and in microburst just in time.
    • Sales platforms can, to some degree, analyze conversations and spotlight key phrases and topics but do not have the richness of functionality to quickly identify the top 1 or 2 things to practice following any meeting. Humans must review the game tapes and provide that feedback.
  • Coaches identify the areas to work on, but they also help sellers create an improvement plan, check on progress against that plan, and performance improvements in real-time if possible.
    • Sales coaching tools will not help reps create a plan, check in on them, and confirm that the seller made the improvements.

Today, sales coaching tools only cover small slices of the coaching universe and generally fall into two major categories.

  • Sales practice tools. These platforms provide sales reps with a task to perform, such as delivering the elevator pitch and asking them to record themselves doing the job.
  • Sales meeting analysis tools that analyze conversations for keywords, tonality, topics, etc., and alert “coaches” to review those sections.
Sales Practices Tools

Many of the Enablement platforms we cover in our certified tech stack come with practice capabilities.

The essential features of these tools are to identify something for the rep to record themselves doing, and upload it for review by the sales coaches, managers, or Enablement teams.

None of these tools can perform a useful analysis and identify meaningful changes, co-creating an improvement plan, and validate in-the-field performance improvement.

These solutions create a lot of work for reviewers, so often, videos are never reviewed.


Sales Meeting Analysis tools

Sales Meeting Analysis tools, like Gong,, and many others, identify audio/video playback locations to help reviewers pinpoint key moments (based upon keywords or similar approaches).

Like practicing tools, the solutions do not create improvement plans or validate live improvement based upon them.

However, unlike practice solutions, these operate against live conversations versus practice recordings.


How do you determine the right sales coaching software for your needs?

Ideally, your teams will make use of both types of tools. Unfortunately, given that many of these solutions are expensive, you may need to make decisions around this.


Sales Coaching Software – Practicing Tools

We recommend Sales Hood as the Trusted Vendor to work with for Sales Practice tools, but also feel good recommending Allego as a Participating vendor to consider.

Keep an eye out for, as well as this team is innovating the depth of real-life role-playing for those looking to create a more robust practice environment.

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Coaching Books

Disclosure: The recommended coaching books are affiliate links. If you decide to purchase any of these resources, I earn a small commission at no additional cost to you. I recommend these books only because I have read them and feel they will provide you with value. For more info, read my disclosure policy here.

General Coaching Tips and Insights

Coffee, Collaboration, and Enablement in AfricaRegional Host for Africa, Dave Nel, loves coaching. He loves it so much that he has been interviewing coaches across the globe via his Movement Life Coaching Business. These video interviews are all available on LinkedIn, and we are simply providing you with an easy-to-access index of interesting conversations.

The idea is to learn from expert coaches around the world. Not all conversations are focused on sales coaching, more around the concept of coaching. These short videos give an introduction to a concept that if you are interested in you can explore further by either contacting the coach directly or doing your own research.

Coaching the full funnel

We speak with expert coach Roland Cox. Coaching is about exploring the full picture. In order to help your clients shift you need to understand what is happening in the body, emotion, and language of your client. Take a listen to Roland and feel free to reach out to him if you would like to explore further.

Trust your instincts

We speak with Sales Enablement expert Pooja Kumar. Coaching has many tools, structures, and methodologies. These tools can be really helpful. What they can also do is distract from that coaching relationship and process. Love the question: “What can you tell me that I don’t know right now?”

Find the balance of using tools and being present with your clients. Give a listen and then feel free to reach out to Pooja if you would like to explore further.

Bias in coaching

We spoke with Master Coach (MCC) Soni Bhattacharya about the impact of our own personal bias in our heads. Checking in with what assumptions or biases you may be bringing into a coaching conversation is key. A bias can limit the areas of the client’s world you explore. Supervision is a great way to get feedback on your coaching and the bias you may be bringing in.

Give a listen and feel free to reach out to Soni should you wish to explore further.

Coaching women in leadership

We spoke with a coach who works with women in business to help them find their voice. The imposter syndrome and inner critic is in all of us. Colleen Swarts gives us insight into the fear and flight responses we often resort to. Colleen speaks about the self-talk of NOT TODAY!

Give a listen and feel free to reach out to Colleen.

Importance of setting a goal

In order to create a real shift in coaching, you need to have a goal or destination for the coaching process. In this conversation, Dave Nel speaks about how to set a goal in the coaching relationship. Set the end destination and be clear in how you will know when you are there. Coaching is all about facilitating a shift for your clients.

Give a listen and feel free to reach out to Dave at Movement Life Coaching.

Advice from Around The Globe

“Sales Coaching is a powerful tool to further develop each sales rep’s full potential and which allows unfolding areas for improvements through questioning techniques; advanced through data and insights sales coaching can unlock even greater potential: it allows coachees and coaches to run more meaningful and evidence-based coaching conversations focusing on the right areas for performance improvements and development. This is also described as data-driven sales coaching.”

Stefan Funk, Global Program Lead, Data-Driven Sales Coaching, SAP SE


✅ Create a call framework that has well-defined phases — e.g., permission to proceed, then pitch, then close.

✅ Then create call dispositions that map to those phases. This tells you which part of the call each SDR is struggling with.

You effectively have a funnel with conversion rates from phase to phase, and you can coach against the conversion rates.

, Sr. Director of Global Enablement at Redis Labs

Regional Host for Africa, Dave Nel, shares some great insights on the Miller Heiman Group “I Know, I Care, I Can” framework.

Dave Nel, National Head of Sales Enablement at Investec

Gayle Charach shared her insights on how to overcome imposter syndrome when sales coaching.

Tip – There is no “I FEEL” in sales coaching. As a coach or manager what I feel about my rep or the team is irrelevant.

It is all about Data, Discipline & Dedication coaches have to give in to their reps & teams through rigourous call shadowing and observing every customer engagement activities.

Biswarup Bhattacharjee (BB) Sales Coach & Onboarding Lead Autodesk

Our second coaching tip comes from Regional Host for ASEAN and India, Pooja Kumar. Pooja shares her thoughts on “what is sales coaching” in this six-minute video.

“To enable sales, you need to think like a salesperson and understand your company’s sales stages. Create content based on how your salespeople will use and map select marketing content in a way that sales can understand.”

Pam Didner, B2B Marketing Consultant and Author of Effective Sales Enablement.

[This only works if you record sales calls]

? Create a discovery call guide that includes expectations on what should happen, along with 4 to 7 criteria against which the calls will be evaluated.
? Set an expectation that every month AEs have to evaluate 1-2 of their own calls and 1-2 of another AE’s calls, using those criteria.
? Then have frontline managers schedule recurring call coaching sessions with each of their AEs. During that call, they’re listening to one of the AE’s recorded calls, with the manager providing feedback as they listen — then at the end of the coaching session the manager evaluates that call using the same criteria.

, Sr. Director of Global Enablement at Redis Labs

Its essential that you develop insight on how a client values a particular element of an offer, and to what extent.

Mike Macioci
Sales Coach helping sales teams accelerate sales and improve customer experience

“Remember that every person you coach is a unique human being. To help them, first take the time to understand them. Be curious, ask meaningful questions, actively listen and then ask some more. This deeper understanding will help you tailor your sales coaching to speak to their real motivators for lasting impact, avoiding “vanilla” coaching that will do little to change behaviours or improve their results.”

Ben Gaston, UK Sales Director, Toshiba


It’s so simple…and valuable!

All AE’s who come through onboarding will listen to multiple discovery and demo calls.

They will then use the same scorecard and grading system the sales managers use.

I ask for their insights and expertise on what they might have done differently and what they thought was effective.

Some may stop here but in the spirit of coaching for a well-rounded seller, I will ask them to schedule a feedback session with the AE they reviewed and provide feedback.

Peer-to-peer coaching is incredibly effective!

It helps me to understand the new hire in how they think about the sales approach, how they approach delivering feedback, and how they themselves would coach.

This can be done even with your tenured reps.

? Win-Win?”

Crystal Nikosey, Sales Enablement Manager, Cloud Academy

Trust Enablement Contributor, Peter Hawkins, shares her insights on how to become a multiplier coach. This video is only five minutes long and well worth your time.

ASEAN and India Regional Host, Pooja Kumar and rock star enablement leader, Lipika Subbiah (she/her) had a great on the show around Sales Coaching, from Concept to Practice. Check it out.

Crystal Nikosey shared her insights on peer-level coaching.

Anita Nielsen shared some wonderful thoughts:

Trust in the context of coaching goes a step beyond what you’d expect.

Sure, those being coached have to trust their coach’s experience and expertise and know they are capable of supporting them.

Table stakes.

The major impact happens, though, when someone being coached completely trusts that their coach has their best interest at heart and is committed to helping them succeed beyond their own expectations.

There are so many reasons this level of trust is powerful and there’s one you may not realize, at first: People have to trust that their coach is in their corner and will help them address the issues that are inhibiting them from achieving their goals…. Even if that means pushing them out of their own way.

That’s the key.

In my experience, “tough love” goes a long, long way in helping people grow. In order for it to work, however, the person being coached must believe that the difficult to hear feedback comes from a place of LOVE.

Often times, people who struggle with holding themselves accountable are easily able to achieve so much more when they feel accountable to someone who they know is invested in them – that deeper level of trust.

That’s the difference between an average coach who checks all the boxes and follows a rigid methodology or framework and the best coaches. The coaches that TRULY create a lasting impact on their clients know how to put their head AND heart into their coaching conversations and relationships.

Coaching can be such a pure, positive human to human interaction – the heart and humanity in these interactions is rocket fuel for achieving desired growth and positive change.

Trust Enablement Contributor, Peter Hawkins, shares her insights on the dos and don’ts when it comes to effective 30/60/90 day coaching plans.