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8 Sales Coaching Tips From Top Sales Leaders

8 Sales Coaching Tips From Top Sales Leaders
Phillis Chang
June 23, 2023

Training and coaching a sales team requires patience, consistency, focus, and commitment— requirements that can feel overwhelming without proper support and guidance!

With that in mind, we’ve compiled some invaluable sales coaching tips from top revenue leaders like John Barrows, Jen Spencer, Ollie Sharpe, and others.

These tips cover various topics that sales leaders and sales managers encounter while leading their sales teams. From what to expect when transitioning into a sales leadership position to how to coach different sales reps to be successful in their unique roles. We're about to dive deep into the best resource for sales knowledge, experienced sales leaders!

Get ready to learn from the best and gain the insight you need to create sales coaching programs that lead your team to success!

Top 8 sales coaching tips:

  1. It takes time, structured planning, and discipline.
  2. Stay consistent and drive for excellence.
  3. Objectivity is the key.
  4. Focus on the individual and the most pressing issue.
  5. The power of coaching, not telling. Help your sales reps find the answer themselves.
  6. Be empathetic to your sales reps and prospective customers.
  7. Be a learner and model that to your sales team.
  8. Create an environment of trust and transparency.

1. Moving into a leadership role

“The top-performing AE may be bringing in a lot of leads, but when moving into a leadership position they might have more trouble supporting the growth of others. 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)

If you are new to coaching and training, you may already recognize the difference between being a seller and a sales leader.

The transition from focusing on your own sales performance to being a sales manager can be jarring if you aren’t adequately prepared for the shift. Suddenly, developing your own selling skills and hitting your numbers isn't your focus anymore.

Instead, as a sales leader, you are now measured by your team's achievements and success. This means that you need to shift your mindset from focusing on individual success to team success.

Focus on team success
Focus on team success

Additionally, a sales leader needs to be able to think and plan strategically. An individual contributor is usually focused on achieving short-term goals such as reaching their immediate targets and closing deals.

A sales leader on the other hand must think long-term, and develop strategies that not only have their team's best interests at heart, but also align with the company's goals.

Seek out mentorship and growth opportunities

Your network can be a great resource when it comes to learning how to build a successful sales strategy. Seek out mentors for advice and guidance. Ask for help when it comes to setting up your own sales coaching programs. And remember that your struggles most likely aren’t unique to you.

So don't hesitate to reach out and utilize the insights of others to help with your own personal transition and development.

Every seasoned sales coach needed to start somewhere after all! And as someone new to the role, you aren't expected to know everything. Take this opportunity as a new sales leader to lay down a solid foundation for your sales team that places an emphasis on sales training and sales coaching.

Emphasizing the importance of coaching and training in your sales strategy, will set a precedent that you consider the growth and development of your sales reps to be a priority on your team.

Demodesk sales coaching guide
Download to help reps consistently reach quota with better coaching

2. It’s a marathon, not a race

"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 Vice President - Inside Sales (EMEA) at Dataiku)

One of the keys to effective sales coaching is establishing a secure environment for your team to be successful and continue growing in their careers.

Sales reps, especially those who are new to the role, need to know that that they aren't expected to know everything and be able to do it all from day one.

It's important that they feel comfortable with taking chances, innovating, trying new things, and ultimately failing in order to improve their sales performance. Sales coaches are invaluable during this onboarding stage for new reps because this is the time that they are most in need of guidance and most receptive to sales coaching.

Consistency and driving for excellence trigger regular wins
Consistency and driving for excellence trigger regular wins

Practice makes perfect

For pretty much everything in sales, practice makes perfect. And it will take some time for reps to get the hang of the activities they need to carry out in order to successfully fulfil their roles.

It is a rare rep who is able to confidently cold call someone or make an effective sales pitch on their first try. So work on creating a positive sales culture that encourages continuous improvement.

This will give your reps the space they need to grow, and will result in a stronger sales organization with happier reps.

Grow and evolve alongside your sales team

Just as sales reps don't become superstar sellers overnight, sales coaches also need to consistently learn and fine-tune their sales coaching techniques in order for their coaching to be effective.

As a sales coach, you should constantly be evolving and maturing alongside your team. This means that your sales coaching techniques need to be flexible and adapt to the needs of your team.

It’s therefore important to stay focused on your team's long-term goals and get their feedback on your sales coaching. In regular 1:1 meetings for instance. This may seem like a small implementation, but over time built-in feedback sessions like these will help you measure the effectiveness of your coaching.

3. Coaching should be tailored for different roles

"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)

When setting up sales coaching programs for your reps, hone in on each team member’s role within the ecosystem of your sales organization.

Take the time to understand how each rep determines success within their role and then coach to their specific metrics and goals.

For example, coaching a Sales Development Representative (SDR) is not the same as coaching an Account Executive (AE). These two roles are distinct and each has their own sets of KPIs measurements, goals, and challenges for which they are held accountable.

By establishing a baseline understanding of the different roles and their responsibilities on your sales team, you will be able to effectively coach and train your sales reps to be successful in their unique roles.

Sales coaching: reps have their own sets of KPIs measurements, goals, and challenges
Examples of sales KPIs for specific sales reps

Here are some examples of sales KPIs for SDRs and AEs that can be used to track the progress of their sales performance, and consequently, your sales coaching:


  • Outbound activities (cold calls, emails, Linkedin connections, etc.)
  • Response rate
  • Number of meetings set
  • Number of qualified opportunities
  • Lead conversion rate


  • Sales conversion rate
  • Average deal size
  • Sales cycle length
  • Revenue generated
  • Customer Acquisition Cost (CAC)

4. Don’t try to fix everything at once

Focus on the individual and the most pressing issue. Observe their development and then move on to the next challenge. 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)

Successful leadership doesn’t necessarily mean that you are able to solve all the problems on your sales team instantly. In fact, that's a pretty unrealistic expectation.

Rather, it can be a lot more effective to focus on one aspect at a time. This applies to all aspects of your work. Whether it be your sales coaching program, your overall strategy, or the training of a specific sales rep.

Let’s say you are working with a sales rep who is struggling with hitting their daily outreach numbers and is also unsure of their overall career goals.

Instead of overwhelming them by trying to address and improve everything at once, focus on one thing at a time. Perhaps start by addressing why they are hitting roadblocks with their outreach first.

Once you work through this obstacle, then you can begin to work with them on their longer-term challenges.

4 sales playbooks for real-time sales guidance
Increase quota attainment with real-time sales guidance

5. Recognize the power of guidance instead of control

"I think my biggest learning around sales coaching, or at least the thing that made the most impact, was when I realised 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 they will learn a lot better in the future."

Ollie Sharpe (VP of Revenue EMEA at Salesloft)

Trust your sales reps

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 for employees. Furthermore, 80% of 30-44 year old employees find the situation to be a dealbreaker.

When you guide your reps through their problems, don't try to control the conversation or the resulting decisions. Instead, show that you trust in their ability to improve and do their job.

Empower your reps to take ownership of their roles, career growth, and overall success. This is an essential part of effective sales coaching.

This means trusting your sales reps to make their own decisions and encouraging them to self-assess their own progress. Help your reps understand that you are there to support and guide them, but ultimately they are the ones responsible for their own career growth.

When sales reps feel that they have more autonomy, they are likely to be more adept at finding creative solutions to their problems.

sales coaching advice: 1000 employees found that having a boss who doesn't trust them is the number one cause of frustration
Having a boss who doesn’t trust them is the number one cause of frustration

6. Lead with empathy

"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 has started thinking differently about the buying process and are encouraged to think more critically about our prospects' "why."

Jen Spencer (Chief Revenue Officer at SmartBug Media)

Being empathetic is one of the most fundamental characteristics of successful sales coaches. As a sales coach, you need to be able to give critical feedback, celebrate wins, and acknowledge the individuality of each of your reps.

Empathy is necessary for all of these and helps to build trust between you and your reps.

When sales reps experience empathy from their coach, it establishes a precedent on the team that it is an important characteristic for both internal and external communication and relationship building.

This can result in a trickle-down effect. So that with some guidance and encouragement, reps can learn how to be empathetic with customers on sales calls by being more understanding of their challenges and pain points.

Be a trusted advisor

Just as empathy has the positive effect of helping sales coaches build relationships of trust with their reps, customers can also sense when a sales rep empathizes with them and understands their situation. This empathy enables reps to lay the groundwork for a relationship with the customer that is built on trust.

This is especially important because the sad reality is that the sales profession is still generally considered as being not very trustworthy.

In fact, in a 2020 LinkedIn survey, only 40% of buyers found the sales profession to be trustworthy.

However, 88% describe the sales reps they do business with as "trusted advisors." These stats indicate that it is possible for a sales rep to break through the negative perception that people have of salespeople.

When a sales rep is able to demonstrate a genuine understanding of the customer's needs, challenges, and goals, they are able to establish a deeper connecting with the customer by showing them that they are not just focused on making a sale. They genuinely care about the customer's success and want to help them achieve it.

Leading with empathy as a sales coach can lead to encouraging compassionate behavior across your team. And you can expect that this will result in sales reps building stronger relationships with their customers.

In a 2020 LinkedIn survey, only 40% of buyers find the sales profession trustworthy
Only 40% of buyers find the sales profession trustworthy

7. Consistently learn and grow as a sales coach

“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 changing in the company, the industry and the world that is impacting sales. 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 that don’t work. You have to be the one who knows what is working and help salespeople learn new methods of customer engagement.”

Alice Heiman (Founder & Chief Sales Energizer at Alice Heiman, LLC)

You can’t know the answer to every question or the solution to every problem — and that’s completely normal!

The key is to view it as a growth opportunity and to have the willingness to learn and improve. This means accepting critical feedback, creating a space for open communication, and accepting help when you need it.

No business or organization can prosper with an incompetent boss or leader. So it’s important for sales coaches to consistently learn and grow alongside the sales reps that they are coaching. Utilize the resources available to you and don’t be afraid to ask for additional learning opportunities.

Consider joining sales communities such as Pavillion, or a program like the Sales Leader Development Program from DSG. Communities and programs like these provide support to sales coaches and leaders looking to enhance their skills and knowledge. And they can be an invaluable resource for you as you work on developing a sales coaching program for your team.

Consistently seeking out growth opportunities, gives you the room to improve your current sales coaching techniques. So invest in your growth as a sales coach and watch as both you and your team reap the benefits of successful sales coaching.

8. Be open, honest, and communicative with your sales reps

“As a sales leader, it is important to create an environment of trust and transparency. One of the top concerns that sales reps have is job security. So providing an environment where they feel confident they can share without consequences, and being able to listen to their concerns as well as course correct when they may have the wrong end of the stick helps create a healthy team culture and makes sure everyone is moving forward together through challenges and obstacles.”

Stephen Williams (Director of Business Development)

Creating an open and honest communication channel within your sales team is crucial.

As a sales coach, you need to be straightforward and transparent when communicating with your reps. For example, if your reps are not adequately aware of the sales expectations or their monthly quotas, then it will be much more difficult to coach your sales team toward success.

In order to avoid miscommunication around quotas and expectations, try implementing something like a real-time centralized dashboard or reporting system that your sales reps can access in order to view their quota expectations and attainments. This can help them keep track of their progress as they work toward reaching their quotas.

Be open to feedback

On the flipside, it's also important to be open to feedback and listen to your reps if they feel that the expectations and quotas they are expected to meet are unreasonable.

Unrealistic quotas and expectations can seriously damage a sales team's motivation. So if this is the feedback that you are getting from your reps, it may be necessary to acknowledge that they need be reassessed or adjusted.

A strong internal communication system allows for an effective feedback loop within the sales team that encourages sales reps to have open communication not only with sales coaches and sales managers, but also with one another. This will not only enable you to make timely course corrections to your strategy when necessary, but it will also result in an inherently more unified and high-performing sales team.

Be open to feedback and listen to your sales reps
Be open to feedback and listen to your sales reps

Final Thoughts

When transitioning into a sales leadership position, remember that sales coaching is one of the most crucial components of the role and should be prioritized.

Embrace the feedback you get from your team, because it will provide you with valuable insights into how effective your sales coaching is. And remember that it's not only important to invest in the growth and development of your reps, but also in your own growth and development as a sales coach. This will result in more effective sales coaching on your part.

Consider going through sales leadership training or seek out a mentor. Because learning from an experienced sales leader will help you to navigate through the many challenges you will face more effectively.

Moreover, remember that successful sales coaches take the time to build strong relationships of trust with their sales reps. It's important to set up a culture and environment where your reps feel that they can be open with you and rely on one another. This will benefit your team overall by encouraging everyone to work together toward the common goal of building a successful sales team.

For more in-depth sales coaching advice, download our Sales Coaching Guide here!

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