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Help Reps to Consistently Reach Quota with Better Coaching

Type:
Ebook
Help Reps to Consistently Reach Quota with Better Coaching

Chapter 1: Introduction

Coaching is one of the most imperative and critical 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 coaching structure, you are setting up your team for success and growth.

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 sales organization.

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

improve the performance of your core sellers up to 19%

Your role as a coach is also heavily reliant on acting as a teacher for your reps. Educate them on how their role within the sales cycle impacts your organization as well as reinforce open communication & teamwork across all departments.

It’s important to remember that sales coaching is not the same as training or managing. While all of these are necessary to lead a successful sales organization, to coach a rep is to specifically work on long-term improvement and growth.

“Coaching is way more important than we give credit. 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 an efficient sales coaching program see 28% higher win rates.

efficient sales coaching program see 28% higher win rates

Unfortunately, 73% of managers spend less than 5% of their time coaching their sales teams. And only 50% of organizations invest in continual training and development of their sales managers.

The lack of investment and attention on coaching within companies can lead to a long string of problems within the sales teams. These can include failure to reach quotas, inconsistent guidance, and lack of transparency.

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

Here are a few more reasons why coaching has such a profound impact on business:

  • Improves productivity and performance
    Coaching sales teams means encouraging successful habits and increasing resiliency among your reps. These factors not only lead to higher levels of productivity but also stronger long-term performance and accountability.
  • Boosts revenue
    Organizations that provide an effective and dynamic coaching structure can reach 7% greater annual revenue growth.
  • Increases job satisfaction
    Great sales coaching helps 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 coach.
  • Prepares your team for growth
    Being aware of your team’s pain points will help you address current issues. This will also prepare you for potential challenges as your team grows and evolves.
60% of sales reps are more likely to leave their job if they feel like their manager is an inadequate coach

Chapter 2: Tips for world-class coaching

Establishing a systematic coaching process is essential to leading a successful team. When a comprehensive structure is created, it builds a foundation for a more prepared and effective sales team.

Here are some essential sales coaching tips for you to integrate into your organization:

Tip 1: Create a sales coaching structure

Oftentimes, a coaching system involves integrating a specific coaching model or goal-setting method. Sales coaching models are structured guidelines that can help you lead your sales rep to a particular goal.

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, acknowledge the current situation. Then create a strategy or roadmap to reach that goal. SMART goals are a great integration with this method as well.
  • OSKAR (Outcome/Objective. Scale. Know-How, Affirm and Action. Review)
    OSKAR is a solutions-based, behavioral approach that encourages progress and incremental achievements, as well as positive affirmations. It also spurs self-reflection, which improves an employee’s 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 the coach are paramount within this model.

When creating your coaching structure, review your sales data and consider feedback from your team. This will help you create a customized structure that will match the specifics of your reps and the company’s objectives.

Tip 2: Be flexible

Once you’ve settled on your coaching structure, it’s important to be flexible. As the industry and markets change, the way you coach your reps may change as well.

Every manager has their own style of coaching. Every sales rep has their own way of learning. So, it’s important to incorporate a program that’s adaptable for all types of teams and unique to each rep. Take your time to get to know each of your reps. Then adapt the strategy that will fit their needs and preferences.

Tip 3: Set up team touchpoints

Own the coaching structure that you create and make it a priority — effective coaching takes time and patience. On average, 70% of new sales training implementations fail to achieve their goals. It’s imperative that you remain focused on helping your reps succeed and grow through your coaching methods.

70% of new sales training implementations fail to achieve their goals

Implement recurring 1:1 meetings
Implement both 1:1 weekly check-in meetings as well as structured coaching calls with your reps to ensure you are making the most impact as possible.


With individual coaching 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 & connect with them in real-time to talk about ways to level-up and understand how they perceive their performance.

Understand what is happening every sales call to identify best practices & coaching opportunities. Coach in real-time with Demodesk shadowing or review rep performance on your own time with call recordings. See how it works!

For remote reps specifically, disconnection, lack of communication, and unclear goals can be some of their top challenges. Ensuring that they have that set time on your calendar each week is an important reminder that they are a priority.

Tip 4: Trust your reps

Trusting your reps is crucial throughout the coaching process. Give them the resources and support they need. Then trust that they can move forward with confidence. Focus on maintaining open communication without being overbearing. Instead, discuss with your reps how they prefer to communicate their challenges, victories, and progress.

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. This situation is a dealbreaker for 80% of 30-44 year old employees.

“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 on how to address them. Too many 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! Instead, as Demodesk’s VP of Sales Lauren says in her article on World-class Coaching.

“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.”- Lauren Wright, VP of Revenue 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. When you coach with intent, then you are setting the rep up for success in the long run.

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.

87% of millennials say that their professional growth opportunities are very important to them

Chapter 3: Tailoring your coaching to different reps

When you coach different types of reps, it’s critical to first understand each rep’s place within your company's sales ecosystem. For every type of rep, you need to determine which specific metrics to track for measuring performance. Then compile the necessary materials required to adequately coach each team.

Sales Development Reps (SDRs)

The sales cycle generally starts with SDRs — as they build a large amount of the future pipeline. Make sure to instill their importance within the sales team. SDRs are usually the first point of contact for a prospect. Encourage them to do research and educate themselves as well.

  • Onboard efficiently
    Create a streamlined onboarding process providing them with standardized sales playbooks and mentorship programs. You can help them understand the goals of the company. And show where the SDR department fits into these goals, and the expectations of them, individually.
  • 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. If your SDRs are struggling due to a lack of communication or transparency with the AEs, implement a post-meeting assessment framework for consistent feedback opportunities.
  • Pinpoint the right metrics
    An SDR’s quotas and goals are generally communication-based, including building up the pipeline with quality leads. Their success is typically measured by the number of calls and emails made, as well as the number of meetings scheduled. However, it’s important to help them distinguish the difference between the number of meetings booked versus their quality.

Account Executives

It’s important to coach to AE-specific & individually-set KPIs. They are responsible for closing sales and bringing revenue into the company. AEs will have the most interaction with prospective clients. The main focus for you as a coach is to work with them to improve their metrics and processes.

  • Pick a coaching model
    Since coaching an AE relies heavily on the individual, it’s important to select a coaching model that will best fit with their personality and your management style.
  • Review your compensation plan
    The right compensation plan can motivate your AEs to increase their productivity and boost their overall sales performance. If you notice that your AEs are lacking incentives, review your compensation model and see if it’s the right fit for your particular organization.
  • Focus on the customer meeting experience
    AEs will have the most interaction with prospective clients, so working with them to improve their sales skills will also be the main focus for coaches. Shadow sales calls or create a role-playing exercise for your AEs during your 1:1 meetings. Actively observing and reviewing their selling style will give you more insight into where they may need additional training or guidance. Utilize automation analysis as well — a combination of firsthand insight and AI-based feedback will give you a wider view of how the AE is engaging with their clients. This way you are able to coach to their specific needs accordingly.

Sales Enablement Specialists

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

  • Setup 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 so your specialists can have more insight into the common conversations and challenges between sales reps and their customers. Solid communication is also essential when it comes time for your sales enablement specialists to train reps on their content — if the understanding between the teams is already solid, then it helps make the specialist’s training responsibilities more effective.
  • Create a centralized content library
    The main goal for enablement teams is increasing revenue through smarter and more effective marketing and sales collateral. Create a centralized library where your enablement specialists can own all the available sales content, like training materials, case studies, and eBooks. This autonomy over a centralized hub of information will encourage more collaboration between the enablement, sales, and marketing teams. In addition, making these resources easy to access for all reps (remote and local) is the best way to guide the enablement team towards greater success.
  • Understand the difference in their metrics
    It’s essential to understand that sales enablement success is typically measured by a combination of indirect and direct metrics. For example, a direct metric would be sales content usage and an indirect metric would be conversion rates when the seller is using the sales content. You’ll always want to focus their attention on the effectiveness of the content — encourage them to analyze additional engagement metrics like clicks, downloads, and views for a better understanding of how their material is working for the reps.

Chapter 4: Coaching your reps to reach quota

Coaching your team to reach quotas 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.

actively coaching a sales team showed a 21.3% increase in quota attainment and a 19% increase in win rates

Set attainable and realistic quotas

Document and communicate the quotas with your team on a regular basis and be sure they understand their expectations. Consistently refer to these numbers in your 1:1 meetings with your reps. 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. Listen to your reps to ensure your quotas are realistic and attainable.

Document, Communicate and Be Consistent

What if your reps aren’t reaching quotas?

Despite consistent coaching, there is always a chance that 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 you giving your reps proper training?
  • Are they fully prepared for selling your product?
  • Do your reps thoroughly comprehend the specifics of your sales cycle?

If any of these areas are lacking, then pinpoint the issue and adjust your process accordingly — invest in automation tools to better prepare your reps and then track their performance improvements.

69% of B2B Salespeople do not have enough leads in their pipeline to meet their sales quotas

Review your sales collateral

There is a possibility that your sales reps are either not utilizing all of the sales content at their disposal or there is not enough quality material to assist with their sales.

Aside from your individual and team conversations, 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.

This allows everyone within the team to stay in the know with the most up-to-date content, helping close deals more efficiently. By analyzing how they use this content, you can see where they may need more support or clarity.

With Demodesk Playbooks & Battlecards you can make sure that reps are using standardized content, from one central location. Explore it for yourself!

Demodesk Playbooks & Battlecards

Chapter 5: Analyzing the effectiveness of your coaching

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

It also helps you determine if your other internal systems, like mentorship programs, onboarding processes, and training structures are providing the right resources for your sales reps.

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

Sales metrics are one of the most common and informative ways to measure performance. Automation and other reporting tools will help to organize sales metrics on a macro and micro level. This will allow you to measure success for your team overall and individual rep performance.

Sales performance metrics

Here are some examples of Team KPIs and Individual KPIs for tracking:

Individual KPIs

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

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 coaching, you’ll need to accurately measure the sales metrics that you’ve set for your team.

Ask the right questions

Based on your 1:1 conversations, track their progress and behavior changes to see if they are incorporating your suggestions and notes. 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 or create a reliable reporting system to always have a streamlined hub of information and insights. Make this system accessible to your reps so they can have transparent visibility into their metrics.

It’s also important that you receive feedback from your team so you can continue growing in your coaching role. This means having open communication with your reps and the willingness to be flexible to their immediate needs.

While sales metrics alone are incredibly effective resources, you also need to understand your reps on an individual and personal level. Make sure to provide your reps with reliable and clear insights, as well as honest feedback and encouragement.

Keep a 1:1 file to document feedback & individual progress. Review how far they have come 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.
  • Integrate automation
    Automation is important for analyzing performance and helps make your coaching methods more productive. AI-based software helps you better understand the challenges and offers an applicable solution to the problem.
  • Give consistent feedback
    Make sure you provide time to each of the salespeople to address their goals and where their performance could improve. This is best done through feedback sessions, 1:1s, and performance reviews. In addition, you should include room for self-assessment opportunities. It’s also important that you receive feedback from your team so you can continue growing in your coaching role. This means open communication with your reps and the willingness to be flexible to adjust to their immediate needs.

Chapter 6: Sales coaching tools and resources

Sales automation helps coach your reps by adequately preparing and training them to enhance their performance and overall skills. Plus, research shows that some automation systems can help increase sale closure rates by 30%, while simultaneously reducing administration time by 14%.

Automating coaching for sales reps

In short, sales automation streamlines manual and time-consuming tasks like data entry, report generation, and email communication. In addition to increasing productivity and performance, automation encourages consistency and efficiency. When certain tasks are automated, it ensures that everyone across the team is using best practices when selling and documenting their progress.

Analyze your sales data and determine areas of improvement. Then incorporate sales automation to help improve consistency and accuracy in those areas. Also, take into account feedback from your reps — what do they feel like is missing from their seller toolkit? Where would they like a more streamlined process?

“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 on 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

For example, is your sales team struggling with setting meetings or scheduling mishaps? Invest in an integrated calendar tool to make the entire process easier for all parties. Focus on your team’s main pain points and implement an automated resource for a better outcome.

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

Other tools that are helpful are ones like Demodesk. Using call recording and meeting shadowing allows you to coach more reps efficiently by reviewing their performance in real-time without disrupting their calls. See how it works!

Demodesk: call recording and meeting shadowing allows you to coach more reps efficiently

Coaching management platforms

Sales coaching tools and programs are not only for the sales reps. As a coach, you should also pursue additional training to become the most beneficial coach for your team. You want to ensure that while you’re helping your reps improve their sales skills, you’re continuing your own personal growth and development as well.

For example, if you are a new sales leader and coach, then joining Pavillion or a program like the Sales Leader Development Program from DSG would be a helpful tool to assist with this transition. This program includes role-play, one-on-one coaching calls, and individual exercises.

Invest in growing your skills as a coach and you’ll see the positive impact it has on yourself 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

Chapter 7: Growing as a coach

Although automation tools help support you as a coach, it’s also important to thoroughly understand the qualities that make up a capable coach.

Characteristics of a good coach

  • Empathetic
    This is an essential temperament when it comes to being a coach — you need to be able to acknowledge challenges, celebrate wins, and adequately support every individual on your team.
  • Knowledgeable
    An effective sales coach has a wide range of adaptable skills and fully comprehends the sales process from all angles. A good coach also knows that they don’t know everything and seeks out additional support and education when needed.
  • Transparent
    Communication is key for any type of coach — you need to be able to communicate with transparency, awareness, and directness. Otherwise, you run the risk of creating a difficult environment where reps don’t feel like they can thrive and flourish.
  • Reliable
    To be the most efficient coach, you need to 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 you through each of their challenges.

Succeeding as a coach

  • Create an internal support system
    Sales leaders can often feel overwhelmed and alone when it comes to coaching their team, so work towards creating a connection with other leadership teams at your company. This instills a more unified and supportive system within the organization.

  • Utilize your network
    Join leadership organizations and seek out advice from mentors or other sales coaches. This support might also come through external experts in the coaching or sales world.
  • Always pursue additional learning opportunities
    Don’t be afraid to utilize your resources and ask for additional education opportunities. This way you can stay up-to-date with the current sales coaching techniques and improve your current coaching methods.
“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 encourages them to think more critically about our prospects' "why."- Jen Spencer, CRO at SmartBug Media

Chapter 8: Final thoughts

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

Coaching your sales team is more than simply guiding your reps to achieve their sales goals — it’s about helping them grow into their role, enhancing their skill set, and working to develop their career path. With a supportive and effective coach, reps are not only set up to reach their goals but the entire sales organization is better prepared for continued future success.

“Sales Success doesn't happen overnight, lead from your heart and use emotional intelligence in every decision. Daily efforts, sharing feedback and perfection in tiny details will grow your coaching culture.

We often say that we are running a Marathon; Consistency and driving for excellence in your Sales routine will trigger regular wins for yourself, your team & Company."- Doreen Pernel, Regional VP Inside Sales EMEA at Dataiku
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