How do you scale sales coaching?

12 min read

Shruti Kapoor is the CEO at Wingman. Shruti enjoys working in the interface between technology solutions and business needs and has worked in leadership and business development roles. She is also a member of the Modern Sales Pros, one of the world’s largest communities for leaders in sales, operations, enablement and related disciplines.

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  • Sales coaching is helping the salesperson, improving their performance as a salesperson that includes different activities. They need to do prospecting, they need to do the initial qualification and discovery process, they need to handle the deal all the way until it is closed and all other interaction processes.
  • The large part of sales coaching is the interaction with the customer and how do we help the salespeople get better at that interaction. 
  • The often the sales coaching is conducted, the more the improvement in the salespeople. 
  • The important thing that is missing in today’s sales coaching is Personalization.
  • In terms of peer to peer coaching, the power of sales coaching comes by using a tool that allows you to go in and listen to calls at your own time and pace and to be able to listen to anyone’s calls. 
  • A lot of sales knowledge exists within the organization and within different salespeople heads. If they can get the tribal knowledge out and make it more democratize, the whole organization can benefit.
  • Sales coaching doesn’t always have to start with tools, a lot of the basic starts with making sure that the intent and the process is set right. 
  • To become better at coaching, rather than being a mentor and providing solutions, try to get the person to dive deeper to find their own answer.

Transcript of the podcast:

Speaker: Shruti Kapoor

Host: Sanjana Murali

Sanjana: Hello everyone. Welcome to another weekly episode of Limitless Podcast, a place where we bring together global leaders in sales and marketing. My name is Sanjana and I am the host of Limitless Podcast. Today we are talking with Shruti Kapoor, CEO of Wingman. Hello Shruti. Welcome to Limitless.

Shruti: Hi Sanjana. Great to be here! 

Sanjana: Thank you so much for joining in today, Shruti. I’m really excited about the conversation that we’re going to have. 

Shruti: Likewise 

Sanjana: The topic that Shruti and I are going to talk about today is how do you scale sales coaching? I have vague knowledge about sales coaching. So like a curious student, I have prepared a list of questions that I want to ask you today. Shall we get started, Shruti? 

Shruti: Absolutely! I’m very excited to bring the world of sales coaching to someone new today. 

Sanjana: All right, that’s interesting. But before I start shooting my questions to you, Shruti, I’m really interested in digging into some of your background. I went through your LinkedIn profile and I saw that you have a degree in Life Sciences and went on to become an analyst at Morgan Stanley. That’s quite interesting! I want to understand a little bit about that. 

Shruti: Yeah, careers are never linear paths unlike what we’d like to plan for. So I say I did my undergrad in Life Sciences and I had a strong passion and I still continue to have a strong passion for Science and Tech. And at that point, I really wanted to work in curing the world of diseases. 

I worked on dengue, I worked on cancer and I soon realized that while that world was exciting one thing that I couldn’t control was, you know, the pace of the experiments. I couldn’t sing to my bacteria to get them to grow faster to give me results faster. And that kind of became a reason for me to say that I wanted more control on my destiny and on the pace of things and taught me to look at other avenues outside of vet lab research in biology. And that got me to the business world. 

So I did my MBA from the Indian Institute of Management and after that, you decided that I enjoyed numbers and I enjoyed analysis and went into Morgan Stanley Investment Banking. And that was back in 2008, just before the financial crisis hit so this is in some sense my second crisis as a working professional. 

Sanjana: That’s great. I think we are similar when it comes to the background. Because I did my Electrical Engineering and then on to become a business analyst. From there I became a content writer and from there I became a marketer. It’s not linear for me as well. This makes me more curious, Shruti. Did you plan to get into sales? What led you to be in the position that you are today? 

Shruti: So, you know that was another series of events and career paths, Sanjana. I worked for a long time in early-stage tech investing. And given my background in technology, take investing and finance, I took up a job in fintech at a company called Payoneer, what was basically a role in helping Payoneer enter a new market which is when they were entering India, became a role of figuring out go-to-market, figuring out hiring salespeople, setting up a sales process and all of that was very new to me. I never did any of that and I think while I did that I looked at it from an outsider’s perspective as a curious student like yourself and that got me thinking about what are some of the things that could be done better in sales. 

And that’s what inspired me to start Wingman and ensure that you know everybody could do better sales and more sales people could get better at the trade. I think it’s very exciting and great. And today it’s at a cusp of, it’s always been definite about humans and relationships and dealing with emotions, but I think today there is a very interesting mix of technology coming into it. Yeah, that’s what brought me here. 

Sanjana: Interesting life story there, Shruti and that is totally inspiring as well. So let’s quickly jump into our discussion today. Let’s start with the basics. What is sales coaching and what is not?

Shruti: I think that’s a great question and especially the second part of it. Because a lot of times people confuse sales coaching for any activity that goes into telling a salesperson on how they could hit their quota better. All right, and given how transactional sales generally is and how numbers driven it is, the same comes into play with sales coaching which is what people often call sales coaching is really deal coaching. 

All right, so as a manager, can I go in and say okay, these are the 10 deals that we should try and close and can I coach you to make sure that you close these all right, which in my mind is not sales coaching. 

Sales coaching is helping a salesperson improve their performance as a salesperson and that includes across different activities. So what are the different activities that a salesperson needs to do. They need to do prospecting, they need to do the initial qualification and discovery process, they need to, if they are closer to closing the deal, they should go ahead and do the deal all the way till close.

And, of course, along the way they need to do other tasks like making sure that the CRM is up to date, making sure that they’re communicating back with other teams who might need to help in getting the deal closed. Sales coaching is helping people do each of these things better. 

And of course a large part of this is the interaction with the customer and how do we help salespeople get better at that interaction and that’s kind of where a large part of the sales coaching becomes, you know coaching people on how to either write emails or how to have better phone conversations.

Sanjana: Got it and that was spot on. Sometimes managers only set aside a couple of days with sales coaching and want to maximize how much information is pushed out in that short time so that the sales rep can get back to their work which is dispel. 

However, the problem is that when there is so much to learn in such a short time, most of the knowledge that sales reps get usually goes unabsorbed. So in your experience, how do teams do sales coaching? 

Sanjana: That’s a great point because it’s definitely a challenge to retain and actually use any of that knowledge. I will give you a small example. Today if someone told you that you need to change the way you speak or maybe you know, somebody came and told me that I use a phrase. Maybe I had a lot of my sentences with the word right. Right? So, even if you told me that maybe five times over the next five months and if you’re only setting aside, you know, one day to coach salespeople that you’re probably doing that right? You’re probably only giving them feedback. Maybe once a month at best. I said, I’m not going to be able to change that habit, right? I will continue to use that same phrase because every time I get on a sales call, I am still going to be in that stress situation. So much is going on and I will not remember what I was told a month ago. 

Unfortunately, that’s how a lot of teams do end up doing sales coaching today. And, what you pointed out was, you know, where people bring in maybe an external trainer to do sales training once a year. It’s a great event for motivating people as a great morale booster, but the impact after the 30-day period is almost zero. 

The teams that are most successful and teams that are able to bring that content and that feedback loop into a more regular cycle so that people are actually able to change that behavior and keep it going throughout so that it’s not just sporadic, it’s not patchy, something that happens once a year or maybe you know once a quarter. But it’s something that actually sustained on every sales call. Yeah. 

Sanjana: How can teams stand out and what’s missing in today’s sales coaching?

Shruti: So I think there are two things that are missing. One is definitely personalization. Somebody needs to give me feedback that I use the word right at the end of every sentence right now that is not going to come from doing a group session with 50 sales people where an external sales trainer is coming in talking about techniques. For that you really need to understand what are the different things that each salesperson does well or badly and see where the maximum gains are and maximum improvement is all. So personalization is definitely important when it comes to sales coaching. It has to be something that happens one-on-one apart from the group sessions. 

Sanjana: Are there any tools available for that?

Shruti: Okay, so, you know, I think the first thing where it starts is in just understanding the communication that each sales rep is having. So on the email side, of course, it’s easy to review emails. What has been a challenge for the longest time is getting insights from the calls salespeople are having. That’s the problem that we solved with Wingman which is how we make it easier for both managers and the salesperson to review their own conversations and then not just have to go through call by call but get the broader trends. This a phrase or word that I use more often, you know to my going to long monologues. 

Things like that make that data much easier, but we don’t just stop there. So as I said, I will take some post-mortems and great. But if they are going to happen with the frequency of once a quarter, nobody is going to change their behavior. 

So what we also do at Wingman is we help people by giving them real time prompts that remind them of the good habits that they want to do or take them away from the bad things that they don’t want to do. Like you can set up a prompt for the phrase does that make sense and every time that you say that phrase and if you want to stop using it it’s going to show up and remind you it’s going to be like a punch in your face telling you, ‘Damn, I used it again’. 

And that’s where it’s most effective because one you don’t need a manager to spend so much time and two, it’s happening when the context is strongest. It’s the moment when I can actually make a change or I can actually register that much more strongly versus if I was listening to that call a month later and I saw the phrase. Does that make sense?

Sanjana: So you spoke about personalized coaching and group sessions. Where does peer to peer coaching stands and how does it work?

Shruti: I think for the longest time, people who are in sales teams, unlike most of the professionals, they know which sales reps are doing well, who’s meeting quota, and who’s exceeding quota. People always been curious about what can I do to be more like that person? What are some of the good practices that I want to follow from that person? 

And, I think the challenge there has been, it’s not very scalable for a salesperson to sit in on someone else’s calls regularly, and I think that’s where the power of sales coaching comes by using a tool that allows you to go in and listen to calls at leisure, at your own time and pace.

And to be able to listen to anyone’s calls, right? So people also feel hesitant in asking their peers to say, you know, can I sit in on your call? But they don’t have to feel hesitant in going to a platform and say, you know what? Let me listen to five calls of this person today. See, you know how they’re doing better. Let me just listen to five calls of my peers to see how they are handling an objection around pricing? 

And, I think that peer-to-peer has a big part to play because honestly beyond a point sales managers are kind of out of the game very often. They haven’t been making calls. They don’t understand how they need to immediately respond to some of the customer questions and I think a lot of that knowledge exists within the organization and within different salespeople heads. 

And, we want to help get the tribal knowledge out into the open and make it more democratized so that the whole organization can benefit from it. 

Sanjana: Interesting conversation there, Shruti. I am thoroughly enjoying this. I also want to know the tools that are available for sales coaching. I mean the list of tools. 

Shruti: So I think it doesn’t always have to start with tools. I think that a lot of the basics start with making sure that the intent and processes set right between the manager and the salesperson which is that you need to have a good cadence for coaching. You need to have some sort of format for saying this is what we are trying to work on. This is I think anyway of improvement and there needs to be a way to monitor whether or not that has improved. 

I think where the tools help is in identifying the areas that can make the most impact if they are improved. And also in helping track whether or not they’re getting improved and the third thing where the tools can help is in getting a buy-in from everyone on what are the important things that I need to improve. 

An example is how do I make sure that if I give someone feedback saying that whenever a pricing objection comes, don’t or when somebody asks for pricing in the first five minutes, don’t talk about the price. Now I can tell my sales reps that you know many million times but they might not still adopt it because it is uncomfortable. 

But if I give them data and say ‘Listen, these are hundred calls where pricing was asked in the first five minutes and people gave that answer and here are a hundred calls where pricing was asked but people deferred it and said, let’s talk about it at the end. And you know in these hundred calls only 5% closures and these hundred calls 25% closures. 

Everybody is going to get the buy-in because sales people fundamentally want to make money. So I think that’s kind of where the tools come in and what kind of tools, of course, Wingman is right up there. It belongs to a category called conversational intelligence and what it does is it enables people to identify these patterns, but more importantly, like I said, it also enables people to go ahead and use those patterns as coaching aids in real-time during the calls. So you need minimal external support you need minimal involvement from the manager to actually get a lot of gains going. 

Sanjana: I will definitely check that out, Wingman, right?

Shruti: Thank you, Sanjana. 

Sanjana: Let’s chop it up, Shruti, with just one last question that I have. What does it take to become a great sales coach? 

Shruti: That’s a tough one! So, yeah, I actually, apart from my background in sales in technology and investing, I also did a certification program as a coach. Right? And this is like a general coach not specifically a sales coach. But I think there are a few things that I learned from what is important to be a good coach. 

And maybe one takeaway for everyone who’s looking to implement any type of coaching in-house is not to put on the hat of being an advisor or a mentor when you’re trying to coach someone. And the difference really is if someone comes to you with a problem as a mentor, you would want to give them a solution to it. 

If I tell you that I find it really challenging to build rapport and my calls you might tell me you know, why don’t you try these three things. Yeah, right and that’s useful in a very intuitive reaction. But the challenge there is that the adoption doesn’t happen. 

If you were to approach the same thing as a coach, what you would do differently is you would get the person to dive deeper to find their own answers. 

Maybe the answer is not to give them a suggestion on saying why don’t you talk about these three things about coronavirus or you know, these two things are about work from home to build rapport with the answer the person will come from the person saying ‘You know what when I try to build rapport, I am very self-conscious or maybe you know, I have these hesitation that I’m taking up this person’s time’ and when they start to fundamentally question and understand what their own hesitations are, they will come up one with better solutions. And they will be completely personalized to them and two they will be much more likely to stick with the suggestions. 

The biggest challenge that people have as mentors as they feel that I gave such great advice and nobody followed it, and I think that’s the distinction between being a great sales coach worse than being just a good sales manager. 

Sanjana: This is interesting. I personally liked this. I think it’s a wrap, Shruti. Thanks much for this lovely conversation. You sure have given us a lot to think about sales coaching and I’m looking forward to learning more from you. Thank you so much for spending your time with me today.

Shruti: Great, Sanjana. Likewise! I enjoyed the chat as well. 

Sanjana: Thank you, see you again. Bye.

We are available on Apple Podcasts, Spotify, and Google Podcasts. Subscribe to our channel for your daily dose of quality learnings and insights into the world of sales and marketing.

Sanjana Murali is a Marketing Specialist at Hippo Video. She is an award-winning blogger, one of her articles on “Customer Success” was selected from worldwide participants and won her MVP 2019 award. She has learned the knack of ranking her blogs and website pages in the 1st result of Google Search from her 6+ years of writing and marketing experience. She is also the host of #Limitless webinar and podcast series at Hippo Video. She loves to talk about branding and marketing with videos. An eternal writer, words are her lifeline.

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