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Sales Coaching Advice: 8 Valuable Insights from Top Sales Leaders

Polina Davletshina
October 18, 2021
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Sales Coaching Advice: 8 Valuable Insights from Top Sales Leaders

Sales coaching requires patience, consistency, focus, and commitment— requirements that can seem overwhelming without proper support and guidance!

With that in mind, we wanted to compile some key pieces of sales coaching advice from top revenue leaders like John Barrows, Jen Spencer, Ollie Sharpe, and others. Keep their insights in mind as you develop your coaching skills. With these tips, you’ll be set up for success as you learn to lead your team.

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 & The CEO of Tenbound)

If you are new to coaching, you may have already recognized the differences between being a seller and being a sales leader. The transition from focusing on your individual quotas to people management can be jarring if you aren’t adequately prepared for the shift.

This is where your network can come in handy. Seek out sales coach mentors for advice and guidance. Ask for help when it comes to setting up your specific coaching structure and how to maintain consistency. Remember that other coaches have most likely made this shift as well, so utilize their insight to help with your own personal transition.

Demodesk sales coaching guide

2. Coaching is 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 most important aspects of coaching is creating a secure environment for your team to be successful and continue growing in their careers. This means that your coaching structure will constantly be evolving and maturing, just like your sales team.

Make sure to also remain focused on long-term goals for your team as you create a coaching structure. For example, setting up weekly 1:1 meetings may seem like a small implementation, but over time these built-in feedback sessions will also be a helpful tool for measuring the effectiveness of your coaching.

3. Coach specifically to different teams

"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 a coaching system for your reps, hone in on each team’s role within the company’s sales ecosystem. 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 Rep is not the same as coaching an Account Executive. These reps have their own sets of KPIs measurements, goals, and challenges. By creating a baseline understanding of each team, you will be able to coach more effectively to their unique roles.

Sales coaching: reps have their own sets of KPIs measurements, goals, and challenges

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’ll solve all problems instantly. Instead, when it comes to coaching your reps, focus on one aspect at a time.

Let’s say you are working with a rep who is struggling with hitting their daily outreach numbers and is also unsure of their overall career goals. Instead of overwhelming your rep with all possible improvements at once, focus on why they are hitting roadblocks with their outreach first. Once you work through this obstacle, then you can begin to work on their longer-term challenges.

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 will learn a lot better for the future."

Ollie Sharpe (VP of Revenue EMEA at Salesloft)

Empowering your reps to take ownership of their role, career growth, and overall success is an essential part of being a coach. This means trusting your reps to make their own decisions and encouraging them to self-assess their 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. Furthermore, 80% of 30-44 year old employees finding the situation to be a dealbreaker. When you guide your reps through their problems, instead of controlling their decisions, you are also showing them that you trust in their ability to do their job.

sales coaching advice: 1000 employees found that 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 starts thinking differently about the buying process and encourages them to think more critically about our prospects' "why."

Jen Spencer (Chief Revenue Officer at SmartBug Media)

Being empathetic is one of the more fundamental characteristics of being a successful coach. In this role, you need to be able to give critical feedback, celebrate wins, and acknowledge the individuality of each of your reps.

Empathy helps build trust, which is an important aspect of internal and external relationship building. This temperament from you as their coach filters down to your team. Through empathy, reps are encouraged to be more understanding of their client’s challenges. They will also be more adept at finding creative solutions to their problems.

In a 2020 LinkedIn survey, only 40% of buyers find the sales profession trustworthy, but 88% describe the sales reps they do business with as "trusted advisors." Leading with empathy as a coach means encouraging compassionate behavior across your team. This leads to stronger client relationships across the board.

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

7. Consistently learn and grow as a 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 the willingness to learn how to be a better coach to your reps. This means accepting critical feedback, creating a space for open communication, and accepting assistance when you need it.

Utilize the resources offered to you and don’t be afraid to ask for additional learning opportunities. By seeking out consistent possibilities for growth, you are creating space to improve your current coaching methods and techniques. Invest in your growth as a coach and both you and your team will see the benefits.

8. Be open, honest, and communicative with your 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. By providing an environment where they feel confident they can share without consequence and being able to listen to 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 critical. As a coach, you need to be straightforward and transparent with how you communicate with your reps. For example, if your reps are not adequately aware of their sales expectations or monthly quotas, then it’s much more difficult to coach your team towards success.

A strong internal communication system also allows for effective feedback loop opportunities between teams, as well as between you and individual reps. By encouraging regular open communication, you are also inherently creating a more unified sales team.

Final Thoughts

When transitioning into a sales leadership position, remember that coaching is one of the most crucial components of the role. Invest in your growth as a coach, whether it’s through sales leadership training or simply seeking out a mentor. Most importantly, understand that becoming a successful sales coach takes time, commitment, and focus. Be open to feedback and continue to grow with your team.

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

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