Chapter 1: Introduction

Coaching is one of the most crucial components of being an effective sales leader.

According to a report by Forbes Insight and Brainshark, 74% of leading companies cite coaching and mentoring of sales reps as the most important role for sales managers.

By creating and committing to a solid sales coaching program and leveraging latest advancements in AI, you can set up your sales team for success and growth without sacrificing your weekends.

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What does a good sales coach look like?

Sales coaching motivates, guides, and strengthens the skills of sales reps, which in turn leads to a more profitable team.

Research by the Sales Executive Council showed that high-quality coaching can improve the performance of your core sellers by up to 19%.

Sales coaches act as teachers for their reps. Educating them on how their role within the sales cycle impacts the team and sales organization. Coaching also reinforces open communication & teamwork across all departments.

It's important to remember that sales coaching is not the same as sales training or managing.

While all of these are necessary in order to develop and lead a successful sales team, coaching focuses specifically on helping reps with their long-term improvement and growth.

“Coaching is way more important than we give it credit for. It's not enough to just look at the reports and check how your team is performing. Coaching is a commitment. Make sure that the 1:1 sessions are scheduled and you invest your time to listen to calls so that you can provide ongoing guidance to your team.” - David Dulany, Founder & CEO of Tenbound

Why do leading companies invest in sales coaching?

Simply put, effective sales coaching can increase productivity, revenue, and retention.

In fact, companies with effective sales coaching programs see 28% higher win rates.

Unfortunately, 73% of managers spend less than 5% of their time coaching their sales teams.

With only 50% of sales organizations investing in the continual training and development of their sales managers.

Here are a few more reasons why coaching can have a profound impact on business:

• Improves productivity and performance
  Coaching sales teams means encouraging successful habits and increasing resiliency among sales reps. These factors not only lead to higher levels of productivity but also stronger long-term performance and accountability.
• Boosts revenue
  Organizations that provide dynamic and effective sales coaching can reach 7% greater annual revenue growth.
• Increases job satisfaction
  Great sales coaching helps you retain your top talent. Studies have shown that 60% of sales reps are more likely to leave their job if they feel like their manager is an inadequate sales coach.

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Chapter 2: Tips for world-class coaching

Establishing a solid sales coaching program is essential to leading a successful team. With a comprehensive structure in place, you lay the foundation for a more prepared and effective team that is more likely to reap the benefits of sales coaching.

Here are some essential coaching tips that you can integrate into your organization:

Tip 1: Create a sales coaching structure

Oftentimes, a coaching program involves integrating a specific coaching model or goal-setting method.

The three most popular coaching models are GROW, OSKAR, and CLEAR.

• GROW (Goal. Reality. Options and Obstacles. Way Forward) The main focus of GROW is to form a clearly defined goal, and acknowledge the current situation. Then create a strategy or roadmap to reach that goal.
• OSKAR (Outcome/Objective. Scale. Know-How, Affirm and Action. Review) OSKAR is a solutions-based, behavioral approach that encourages progress and incremental achievements with positive affirmations. It also spurs self-reflection, which improves self-awareness and intentionality.
• CLEAR (Contracting. Listening. Exploring. Action. Review) CLEAR's main focus is on creating lasting change and instilling new habits. Active and focused listening, consideration, and empathy from sales coaches are paramount for this model to be successful.

When creating a sales coaching programs, review your data and consider feedback from your team. This will help you create a program customized for your reps' specific needs and increase the likelihood of successful sales coaching.

Tip 2: Be flexible

Once you've settled on a formal sales coaching program, it's important to stay flexible. As industries and markets change, the way you coach your reps will need to change as well.

Every sales manager has their own style of coaching. And every sales rep has their own way of learning. So, it's important to create an adaptable program.

Tip 3: Set up team touchpoints

Sales managers need to own their sales coaching structures and make implementing them a priority — effective coaching takes time and patience.

On average, 70% of new sales training implementations fail to achieve their goals. So it's imperative that you remain focused on helping your reps succeed and grow.

Implement both weekly 1:1 check-in meetings as well as recurring structured coaching calls with your reps.

With individual check-ins, try to meet as soon as possible after shadowing a rep's call.

If you can't shadow the meeting, review the recording and then connect to understand how they perceive their performance and discuss ways to help them improve.

For remote reps specifically, disconnection, lack of communication, and unclear goals can be some of their top challenges. Designate a set time each week for sales coaching to ensure that it is a priority for both you and your reps.

Tip 4: Trust your reps

Trusting your reps is crucial throughout the sales coaching process. Give them the resources and support they need. Then trust that they can move forward with confidence.

A BambooHR survey of over 1,000 employees found that having a boss who doesn't trust them is the number one cause of frustration.

“One of the more important things to do when developing a coaching plan is to determine an objective baseline to measure from for each rep. Depending on the sales role (SDR, BDR, AE) you need to break down the major components of the role (cold call, conversation, qualification call, qualified call, demo/presentation, proposal, close) and the conversion rates between them for each individual rep. From there you can identify the weakest link and coach on strategies to address them. Too many sales managers are way too subjective when it comes to coaching and they tend to only coach on things they know and are good at. Objectivity is the key.” - John Barrows, CEO of JBarrows Sales Training

Tip 5: Coach to one aspect

You can't fix everything at once, though you might want to!

“Focus on the individual and the most pressing issue. Observe their development and then move on to the next issue. It may be a slower process, but it will have greater lasting effects for the rep and your team overall.”- Veronika Wax, CEO at Demodesk

Coaching doesn't necessarily mean you're going to solve all the problems within your sales team at once. Instead of focusing on speed, take the time to target each rep's specific skills, goals, and obstacles. Coaching with intent will set your reps up for long-term success.

Tip 6: Provide extra support

• Establish a personal development budget
• Facilitate team-building off-sites
• Organize informational panel discussions & conferences
• Provide additional training sessions
• Encourage networking within the sales community & other departments
• Share useful online courses

According to research by Gallup, 87% of millennials — currently the largest segment in the workforce —say that professional development or career growth opportunities are very important to them in a job.

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Chapter 3: Tailoring your coaching to different reps

When you coach different types of reps, it's critical to first understand the role that each one plays in your company's ecosystem.

For every type of rep, you need to determine which specific metrics to track for measuring their performance. Then compile the necessary materials to adequately coach them.

Sales Development Representatives (SDRs)

The sales process generally starts with SDRs — they are the ones who build out the future pipeline and are usually the first point of contact for a prospect.

• Onboard efficiently
  Create a streamlined onboarding process providing them with standardized sales playbooks and mentorship programs.Help them understand the company goals and show how the SDR department fits into these goals.
• Encourage an open SDR-AE relationship
  SDRs tend to work very closely with Account Executives. When you are coaching your reps, it's important to encourage strong relationships between these teams.
• Pinpoint the right metrics
  An SDR's quotas and goals are typically measured by the number of calls and emails they make, as well as the number of meetings they schedule.However, it's important to help them distinguish the difference between the quantity of meetings booked versus their quality.

Account Executives

AEs are responsible for closing deals and bringing revenue into the company. So the main focus for you as a sales coach is to work with them to improve their metrics and processes.

• Pick a sales coaching model
  Select a sales coaching model that takes both the AE's personality and your management style into account. ‍
• Review your compensation plan
  The right compensation plan can motivate your AEs to increase their productivity and boost their overall sales performance.
• Focus on the customer meeting experience
  AEs interact with prospective clients more than anyone else. So working with them to improve their sales skills should be the main focus during sales coaching sessions.

Sales Enablement Specialists

Sales enablement specialists focus on optimizing sales resources for higher win rates and greater revenue. They also identify and assist with closing any noticeable gaps in the sales cycle.

• Set up transparent communication across teams
  A frequent challenge for enablement specialists is transparent communication across all sales teams — create a cross-communication system or feedback loop to gain more insight into the common challenges that reps are facing.
• Centralize your content library
  Create a centralized library where your enablement specialists can own all the available sales content. This will encourage more collaboration between the enablement, sales, and marketing teams.
• Understand the differences in their metrics
  Sales enablement's success is typically measured by a combination of indirect and direct metrics. A direct metric would be sales content usage and an indirect metric would be conversion rates when the seller uses the sales content. The focus should be on the effectiveness of the content.

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Chapter 4: Coaching your reps to reach quota

Coaching your team to reach quota is essential to creating a successful and productive sales organization.

In CSO Insight's 2019 Sales Enablement Report, actively coaching a sales team showed a 21.3% increase in quota attainment and a 19% increase in win rates over the study's average.

Set attainable and realistic quotas

Document and communicate the quotas with your team on a regular basis and be sure they understand the expectations. Consistently refer to these numbers in your 1:1 meetings. Use a centralized dashboard or reporting system so reps can have real-time access to their quota expectations.

Be open to feedback in your coaching sessions — acknowledge and understand that quotas will likely need to be reassessed and adjusted over time.

What if your reps aren't reaching quota?

Despite consistent coaching, there is always a chance that sales reps still won't hit their quotas. If that's the case, it's necessary to reassess the internal structure and systems that you have in place.

Review the quality of your leads

A study by ValueSelling Associates and Selling Power found that 69% of B2B salespeople do not have enough leads in their pipeline to meet their sales quotas.

Review your pipeline and compare the number of opportunities to the conversion ratio. Are there significant gaps? If so, work with your reps to see why these leads may be falling short.

Reassess your onboarding process

Review your internal onboarding and training structure and ask yourself the following:

• Are your reps getting proper sales training?
• Are they fully prepared for selling your product?
• Do your reps thoroughly comprehend the specifics of your sales process?

If any of these areas are lacking, then pinpoint the issue and adjust your process accordingly.

Review your sales collateral

It's possible that your sales reps are either not utilizing all of the sales content at their disposal, or there is not enough quality material for them to use.

Take a look at your customer engagement metrics — are your customers interacting with your content? If not, loop in your sales enablement reps and marketing team to create more engaging or interactive material that can help your team achieve greater results.

By analyzing how the content is used, you can see where they may need more support or clarity.

With Demodesk playbooks & battlecards you can ensure that reps have access to standardized content from one central location. Explore it for yourself!

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Chapter 5: Analyzing the effectiveness of your sales coaching

Analyzing your team's performance using metrics like KPIs, activity data, and both quantitative and qualitative feedback is a great way to determine whether or not your coaching methods are working for your team.

You'll also want to measure both short and long-term goals — this way you can coach your reps through their daily challenges, but also work on their development and growth at the same time.

Automation and other reporting tools can also help you organize sales metrics on both macro and micro levels. This will allow you to measure both the overall success of your team and individual reps' performances.

Sales rep performance metrics

Here are some examples of team KPIs and individual KPIs:

Individual KPIs

• Quota Attainment
• Sales Pipeline
• Win Rate
• Average Sales Cycle Length
• Number of Opportunities
• Individual Conversion Rates
• YOY Comparison
• Conversational Metrics

Team KPIs

• Revenue
• Monthly Sales Growth
• Productivity
• Opportunity Win Rate
• Average Deal Size
• Outreach Metrics (SDR Team-Specific)
• Forecasting Metrics (AE Team-Specific)

Measuring sales metrics

To analyze the effectiveness of your sales coaching, you'll need to accurately measure the metrics that you've set for your team.

Ask the right questions

Based on your 1:1 conversations, track their progress to see if they are incorporating your sales coaching tips.

Document any challenges and changes:

• Are they improving in a certain area?
• Are they overcoming their challenges?
• How often am I checking in on their progress?
• Do I need to adjust the way I am coaching to better fit their needs?
• Are they taking the initiative to reach their long-term goals?

“Being in a leadership position, you need to take the coaching role seriously. It takes time, structured planning, and discipline. For your team to perform well, you have to put a sales coaching structure in place to help your team grow.”- David Dulany, Founder & CEO of Tenbound

Build a reporting system

Invest in creating a reliable reporting system for a streamlined hub of information and insights. Make this system accessible to your reps so they can have visibility into their metrics.

It's also important to receive feedback from your team so you can continue growing as a sales coach. This means having open communication with your reps and being flexible with regard to their immediate needs.

Keep a 1:1 file to document feedback & progress. Review their progress on a quarterly basis – it's just as important for them to see their growth as it is for you.

• Centralize dashboards
  A centralized dashboard is the most direct and accurate way to see overall achievements, pipeline trajectory, lost opportunities, and individual quota attainment. ‍
• Give consistent feedback
  Make sure you set aside time for coaching sessions with all of your reps to discuss their goals and how they can improve their sales performance.

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Chapter 6: AI-based sales coaching and workflow automation

AI-based sales coaching

The integration of Artificial Intelligence (AI) into sales processes has revolutionized the way sales teams operate, providing them with powerful tools to enable a scalable sales coaching approach. Demodesk Coaching & AI offers a suite of features designed to help you automate call reviewing and scoring, automate manual tasks and focus your time as a leader on the things that really have an impact.

Demodesk provides immediate, personalized, and actionable feedback for reps after each and every sales call. Demodesk is a personal, AI-based sales coach who is always at the seller's side to help them improve their sales skills with every call.

There is no setup required – just select our ready-to-use scorecards (MEDDIC, BANT, SPICED and more) or set up your own scorecard that matches your company-specific sales process and your team members will automatically receive feedback on how well they've followed the playbook. We'll tell them if there's anything they can do to improve, and give you actionable advice that they can apply directly in their next sales call.

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Demodesk aggregates the information across meetings and calls with AI to help you identify trends, opportunities, and areas for improvement.

Review meetings 10x faster with a powerful X-ray view with a single, searchable recording library for all your meetings-video calls, phone calls, and uploaded recordings (yes, it works for offline meetings too!), so you can quickly assess what was discussed and where to intervene. Demodesk analyzes each call based on company-specific objectives and key selling points. Just give us your playbook, and we'll tell you how well your team is executing it.

See all conversation stats and metrics at a glance, and instantly understand what's good, what's bad, and where to improve. Drill down from a bird's eye view to a specific minute of the meeting in seconds and identify areas for improvement with individual coaching area reports that analyze patterns across sessions and show continuous improvement over time.

Demodesk also helps you understand trends across all interactions and sales reps, such as top objections, frequently asked questions, or feedback on specific product features. Gain insight into the skills and behaviors that differentiate top performers, or turn sales best practices and methodologies into call scripts.

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Workflow automation for sales coaching

Sales automation helps you coach your reps by adequately preparing and training them to enhance their sales performance and overall skills.

Plus, research shows that some automation systems can help increase sales closure rates by 30%, while simultaneously reducing administrative time by 14%.

Sales automation streamlines manual and time-consuming tasks like data entry, report generation, and email communication to improve productivity and performance.

When certain tasks are automated, it ensures that everyone across the team is using best practices.

For example, if your sales team struggles with setting meetings or experiences scheduling mishaps, it could be worthwhile to invest in an integrated calendar tool that makes the entire process easier for all parties involved.

“The number one coaching tactic for a sales leader is to be a learner and model that to the team. Stay on top of what is happening in the company, the industry, and the world that is impacting sales. That includes what new automation tools are out there to make your team more efficient and make buying easier for your customers. Be aware of how the buyer is changing and most importantly, what approaches are working. You can't be an effective coach if you are coaching using old methods and tools that don't work.

You have to be the one who knows what is working, what automation to use and help salespeople learn new tools and methods of customer engagement." - Alice Heiman, Chief Sales Energizer & Founder of Alice Heiman, LLC

You do not need to integrate an assortment of new automation tools into your process — be selective about the areas you choose to automate to ensure it actually helps your team be more productive.

Features such as call recording and meeting shadowing allow you to coach more reps efficiently by reviewing their performances in real time without disrupting their calls. See how it works!

Other resources & platforms

Sales coaches should also pursue additional training. As a sales coach, you want to ensure that as you help your reps improve their skills, you're continuing to improve your own as well.

For example, if you are a new sales leader and coach, then joining Pavillion may help you through this transition.

Invest in growing your skills as a sales coach and you'll see the positive impact it has for you and the rest of the team.

“I think my biggest learning around sales coaching, or at least the thing that made the most impact, was when I realized the power of coaching, not telling. To me, coaching is where you help them find the answer or the solution, or even what they should have done, by asking the right questions. Rather than saying 'you should have done x', help them to work out that they should have done x. This empowers them but it also helps them to understand why they should have done it and will learn a lot better for the future.”- Ollie Sharpe, VP of Revenue EMEA at Salesloft

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Chapter 7: Growing as a coach

It's important to thoroughly understand the qualities that make up capable sales coaches.

Characteristics of a good coach

• Empathetic ‍You need to be able to acknowledge challenges, celebrate wins, and support every individual on your team. ‍
• Knowledgeable ‍Effective sales coaches have a wide range of adaptable skills and fully comprehend the sales process from all angles. But they also know that they don't know everything and seek out additional support and education when necessary. ‍
• Transparent ‍Communication is key — you need to be able to communicate with transparency, awareness, and directness.
• Reliable Be consistent with your coaching structure. It's important that your team knows you are available to them for guidance and that they can depend on your support through each of their challenges.

“One of the best things you can be as a coach is empathetic. Not only to your sales reps, but to your prospective customers as well. When a member of my team asks me a question, I stop myself from answering directly with what I would do in their situation. Instead, I ask questions that the sales rep can only answer if they are also equally empathetic to our prospect. Since I do this consistently, my team starts thinking differently about the buying process and is encouraged to think more critically about our prospects' "why."- Jen Spencer, CRO at SmartBug Media

Succeeding as a coach

• ‍Create an internal support system
  Sales leaders can often feel overwhelmed and alone when it comes to coaching their team. Make sure to build strong relations with the other members of the leadership team at your company.
• Utilize your network
  Join leadership organizations and seek advice from mentors or other sales leaders and sales coaches.
• Always pursue additional learning opportunities
  Don't be afraid to utilize your resources and ask for additional learning opportunities. This way you can stay up-to-date on current sales coaching techniques and learn new coaching tips.

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Chapter 8: Final thoughts

Studies have shown that quality sales coaching can increase win rates by 28% – leading to improved sales skills, more engagement, and a higher level of retention across your team.

Coaching your team is more than just helping your reps achieve their sales goals — it's about helping them grow into their role, enhancing their skill set, and helping them develop their career path.

Supportive and effective sales coaching not only sets reps up to reach their goals, but also prepares the entire sales team for future success.