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World Class Sales Coaching Advice from VP of Sales

World Class Sales Coaching Advice from VP of Sales
Lauren Wright
May 14, 2021

As sales leaders, it is our responsibility to empower and cultivate our teams. This is why coaching is one of the most imperative aspects of being a manager.

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. This enablement should filter from the top down — the more coaches can feel prepared, the more sales reps can feel equipped to succeed.

As the current VP of Revenue here at Demodesk, I am the sales leader for multiple departments including the SDR, sales, and customer success teams. As the leader and coach for these teams, I have to consistently check in to ensure that I am setting everyone up for success in the best possible way. I typically ask myself the following questions:

  • How can I enable my team to ramp up efficiently and find success quickly?
  • How can I ensure that they improve every day?
  • What are the systems I need to put in place to promote this improvement?
  • What are the coaching mechanisms that are working and what needs to be fixed?
  • Importantly, how can I make sure people are enjoying their job?

I recently participated in a webinar called World Class Coaching, hosted by Modern Sales Pros (check it out here!). In this conversation, along with Caroline Bray of Iterable, we talked about all facets of coaching a sales team and the importance of establishing an overall coaching culture throughout the entire organization.

I wanted to compile some of my insights and recommendations for becoming a world-class coach. These include how to implement a structure, why technology is helpful, where to incorporate your methods, and some key coaching tips.

Demodesk sales coaching guide

How to create a coaching structure

Where to start

I like to begin by focusing on the people and then creating a process around them. People need to have a willingness to be coached and to coach others. This is all about having the right mental mindset, which means it actually starts during the hiring process. Therefore, it is essential to create a hiring framework where you ask the right questions — this will ensure you find the most suitable fit for your team.

Once you have the right people in place, you can begin to build a personalized sales and coaching process. Figure out what the “North Star” is for your company and create a system around that focal point. Then determine which tools you can utilize to implement your blueprint.

How technology can help

Technology is a great tool to help build your coaching strategy. Automated coaching software is your friend when it comes to adequately preparing your reps. Ask yourself, what type or piece of technology can I leverage to best enable my reps? Automated coaching tools can range from AI-based conversation feedback to centralized battle cards to video practicing capabilities. Utilize the best technology for your team where it’s most essential for their success.

Automation also enables documentation consistency throughout the sales process — crucial for when you need to compile CRM data. Implementing automatic input systems will eliminate the time spent performing these administrative tasks. This gives sales reps the space to focus on the job you originally hired them to do.

For example — with Demodesk, information can be entered directly into the rep’s playbook throughout a meeting. Once the call has ended, that data is funneled into our CRM with one click. Investing in automation software helps to implement a thorough sales process and enhance your ability to coach the team.

As much as technology can be helpful, it’s important to remember to create a sales system first, then incorporate the automated coaching tools as a way to help streamline the process.

coaching with real time sales guidance

Where to incorporate coaching

Once you have your coaching framework created, you can begin to create space for incorporating your methods. Here are some ways you can integrate your coaching strategy:


During the onboarding process, quality coaching is all about reducing ramp time and getting reps active in the selling process as quickly as possible. To do this, you first need to understand your own expectations and goals for their progress. Ask yourself the following questions:

  • What are your expectations for their first few months?

Create a clear 30-60-90 onboarding plan so you have a guidepost for your expectations — and a way to tangibly measure their progress. Don’t forget to share this plan with the rep as well! They need to know what is expected of them as they move through their first few months.

  • How can I enable them throughout the process?

Determine where you can help ensure their success. Which tools can you use? Is the system in place working for them or can it be adjusted according to what they need? Every sales rep learns differently, so be logistical about each individual onboarding experience.

For me personally, Demodesk is a great example of how to successfully onboard new hires. I know that a new rep can walk in the door on their first day and have all the information they need in one place. They can be fully equipped for their first client-facing meeting, which means they can hit the ground running faster.

Implementing a mentorship program can also enhance the onboarding process. Offering peer assessment and coaching opportunities is valuable for both parties — it encourages the overall value of feedback and self-improvement from the very start.


As a sales leader, you will want to find areas where you can increase visibility. This is a necessity for both you and the sales rep as it instills clarity and communication. One way to achieve this is by shadowing meetings. Shadowing creates an opportunity to observe the sales process in action and provide direct coaching feedback. As a result, you can have more transparent conversations with your sales reps about how to adapt the process and where they feel they could use more assistance.

Shadow the meeting Demodesk

‍Shadowing is also a great way to see what collateral is being shared across the team — discovering firsthand if the narrative that has been put in place is actually working.

Pipeline meetings

Through shadowing, you already have direct knowledge of meeting details to approach pipeline conversations with more understanding and awareness.

In addition, utilizing data can assist in painting the overall picture. These metrics can help determine where the gaps are within the process — then, importantly, share these findings with your reps.

Transparency is the only way your team can make changes — without the ability to self-assess, they won’t be able to improve. Instead, these conversations can be an open discussion about the sales process. Is our content working? Is it engaging? Where can we get better?

This is another example of where automation can be a helpful coaching tool. For instance, Demodesk measures customer engagement in real-time. These types of in-depth analytics are essential for reassessing my coaching strategies and our sales process overall.

Career development

One of the best parts of coaching is helping sales reps grow to their full potential. To achieve this goal, create a career development plan that coexists with your coaching structure.

Have open and honest conversations with the reps about their goals and then coach to their specific objectives. Encourage them to take on projects or other opportunities that align with their ambitions and then coach them through their experience.

Effective coaching tips

Coach to one aspect

You can’t fix everything at once (though you might want to!). Instead, focus on the highest impact issue and coach to that problem. 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.

Create clear competencies

Transparent and direct expectations are key to a successful team. Everyone should have a clear understanding of how to thrive in their role. Being a coach means helping them determine the management of their day — what are the most important tasks and how to best complete them with efficiency.

Stay consistent

Coaching is the easiest task to drop when your schedule becomes overloaded. However, staying consistent with your coaching is fundamental if you want to lead a successful sales organization. Even during those busy periods, be sure to own the structure you have created and ensure that all leaders are leaning into the process.

ramp time ebook

How to set up new sales managers for success


I think that one of the most difficult aspects of moving from a sales rep role to a sales manager role is understanding that it’s a completely different type of position. Becoming a sales manager means you are working in people management, not number management. And that is a big shift! By sharing these distinctions with your new sales managers, you are starting them off with a clear understanding of what lies ahead for them.

Don’t be afraid to ask for assistance

Something I wish I had done earlier was lean on other coaches in my position. Encourage your new managers to join a leadership organization and utilize outside networking for assistance. Peers are a substantial resource for information, advice, and feedback. New managers aren’t expected to know everything right out of the gate, so other sales leaders can be some of the best educators.

Coaching across leadership teams

Create a connective string across the other leadership teams at your company. Instill a coaching culture environment and unite your managers under this principle. Sales leaders can often feel overwhelmed and left out on their own when it comes to coaching their team, so enforce the importance of coaching across all leadership. This creates a more unified and supportive system within the company.‍

Connecting Leadership Teams

Early insights

Have any of your current sales reps expressed interest in becoming a leader? Using the career development system you put in place, assign them to projects where they can start to incorporate coaching methods. Opening up these opportunities will give them insight into the role — if they decide to continue on that track, they will be even more prepared for the transition.

An established coaching process is a key to a productive and valuable sales organization. Creating a solid, yet adaptable system encourages success throughout the company. An effective coaching structure can also enhance onboarding progress as well as individual improvement, motivation, and career development.

Additionally, automation is paramount when it comes to enabling your team to succeed. Leverage your tech tools to coach reps through the entire sales process — allowing them to improve, grow, and reach their potential.

Lastly, stay transparent and consistent even when your schedule fills up. Instill the notion that a coaching culture is advantageous across the board. This ensures that everyone can move collectively and productively towards your company’s aligned goals.

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