Your Personal Call Coaching Wingman with Shruti Kapoor
31 Jan 2026 · 46 min
This content was created by Kevin "KD" Dorsey. This content was uploaded by Kevin "KD" Dorsey. This is a podcast episode titled "Your Personal Call Coaching Wingman with Shruti Kapoor" (PODCAST, recorded 2021-05-17). It is an English interview-style conversation hosted by Kevin "KD" Dorsey with guest Shruti Kapoor (CEO/founder of Wingman, YC startup, and certified life coach). They discuss practical call coaching for sales teams: building a coaching culture, call recording and review, peer vs manager-led coaching models, how to give effective feedback (ask questions, limit scope), agenda-setting, using customer stories, handling objections, in-the-moment prompts/battlecards and tooling (Wingman) to copilot calls, practice/repetition strategies, KPIs/frequency for coaching, and applying life-coaching techniques to leadership. The episode is aimed at sales reps, managers, and sales leaders looking for tactical ways to improve conversion and coaching effectiveness.
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Thanks so much, Kevin. That was a great intro. Thank you.
Absolutely. And what makes it great is it's all true. It's all true, right? These are things that you're doing and you know about. And I think that's why I'm so excited to talk, because funny enough, as much as I talk about call coaching, we haven't really covered it that much on the podcast yet. So this is a fun topic for us to dive into. And so now one of the reasons why people tune into the show is they like that we get to the point is straight tactics and the fluffs. Let's talk about the impact of call coaching. Right? What have you and Wingman seen, like in the data or revenue about the difference between teams that do call coaching and teams that don't?
You know, I think the irony of it is that, you know, I think people who choose the tool are people who are already somewhat committed to call coaching. And that's why we choose to even, you know, buy a tool and invest money behind it. But, you know, even despite that, what we see is that a lot of people, you know, they will record calls, they will do some of the nice and easy to do stuff, but not actually spend the time, you know, in call coaching. What we've seen, though, is that people who do call coaching and, you know, if you have very clear ideas around what's really going to make a difference or you want to explore those ideas and then implement them, people have even as much as double their conversion rate in just a quarter. All right? And this is mind blowing. Like, even for us, what we see is that especially if you're able to get your entire team aligned to a particular team, it works really well because then you're no longer competing with each other, but you're working, you know, as a user and everybody is trying to get better at something and everybody is sharing their tips on how they did that same thing better versus, you know, you feel that you're being called out. So, yeah, I think it can be both a great way to. Of course, you Know, improve performance, but also a great way to kind of build a meaningful team bonding.
I mean, I think you nailed it. So I have now implemented call coaching on four different teams. And your data holds up after getting in. Great call coaching almost every single time. I've seen a 2x increase in conversion rates, both on the close side, but then also on the prospecting, like DM conversion side. Like when you know what you're looking for and coach to it, those numbers go up, which I think is amazing. Now I want to take a step back though, because he actually says something that's very important. You said, you know, the people that are coming to wingman right now are ones that are kind of already doing it a little bit and looking to take it to the next level. How can a team get started? Right. Maybe I have a team that we aren't doing call coaching yet or we're not reviewing this. Like how, how should I get started to kind of get that culture in place?
Yeah. So I think I would say while I make wingman, which is of course a software platform for doing this, I would say that looking for a software is not the first place where you should go. Right. I think the first place you should go is to inculcate that as a culture. And, you know, how do you do that? Right. So one of the things that a lot of themes we've seen are hesitant about is, you know, I give feedback behind closed doors, but that doesn't scale. And that also maybe isn't as impactful because it's harder for me to hold people accountable. So ideally what you want to do is you want to do it as a group session, but then you also want to be aware that you don't want this to become something which makes people feel threatened. So a good balance that we've seen is you can have, I always tell teams you can have three models of coaching. You can have something that is the manager decides the agenda, the manager picks the calls and does it everything right. And you can have it at the other extreme where you know, it's completely peer run, right. So you have the reps themselves choosing the calls, the reps themselves sharing the best practices, and you can have something in between. I would say that if you want it to be least threatening, you start with, you know, a very peer based approach. And the thing is that it might not be perfect on day one. Like you as a manager might have different ideas that might not be what your team picks up on, but what it does is it creates that openness and it creates the culture of giving and accepting feedback in a non threatening manner. So that's one part right on the culture part. That's what you need to solve for. Right? And you can start from kind of the most lenient and then maybe bring it to some sort of a happy medium where maybe the manager sets a team for a period of time and then the team gets together and iterates on that team. And then the second part of it is, you know, what do you need to do to even put it in place? And in fact, I was just listening to a podcast episode that you'd had with Mike Lever and one of the things that you both agreed on was if you're shadowing calls as a way for coaching, that's a really bad idea. Right? And I completely 100% agree with that. So you do need to put in something in place to be able to record those calls and observe them after it's done. Right? Because if you're sitting there, then of course your rep knows that you're there. One of two things is going to happen. Either he or she is going to change the way they would usually answer the question, right. Or they are going to defer to you whenever something sticky comes up. Right? Because they know you're there. And so even for reps who are very early in their onboarding process, what we recommend is like, you know, let them be, give them some good fallback, like, you know, phrases that they can use if they don't know the answer to something. But then, you know, let them kind of run the call the way they are and you should record the calls. Right? So if you don't want to invest in technology on day one, what you can do is, you know, you could just use like a zoom recording, put it up on a shared folder and then over a period of time, as you start using those recordings, you'll realize that you absolutely would want to invest in technology because you can't spend like 45 minutes reviewing a 30 minute call and giving feedback, right? You'd much rather spend 10 minutes doing that and be much more effective so that you can review like five, six more calls.
So yeah, I think that's so important and kind of what I covered in the intro. Like it actually still is mind blowing to me that we even have to have this conversation about why you should be recording calls and listening. Like you have companies spending millions on millions and millions of dollars and they have no idea what's being said by the customer or the salesperson on these calls. So I Think that's just an absolute no brainer for people to do. But you actually used a word. I didn't have a question ready for this. So we're going to go down this path, feedback. Because I actually do think there is an art form to this too that a lot of managers also go wrong with. Okay. They get a tool like wingman, they get all these calls and now they're like, oh, let me just give all the feedback, right? Let me just say all the things. What would be some of your tips to the coaches? Right on. Like what types of feedback should they be giving but also how to deliver feedback because I do think that is important because if you deliver it the wrong way, well, there goes your coaching culture, just like that. So what would be some of the feedback tips on how to deliver feedback on a call.
I would like to draw some lessons from life coaching here. Right? So one of the things that when you're actually doing any type of life coaching, coaching, etc. Is you always work with the belief that the other person has the resources to make things better for themselves. And I think that if we use the same when we are doing call coaching or sales coaching in general, what that would mean is you would not give suggestions, but instead you would ask more questions. Right? So instead of saying that, oh, you know, instead of talking about discount like this or showing ROI like this, you should have done it differently. The better approach might be to get that person to come up with an alternative approach, to critique the approach that they took themselves. And once they have come up with the alternative approach, you can kind of work with them to refine it, maybe bring in a few of your suggestions. But if they feel that they own that alternative approach, they are much more likely to go ahead and implement, which is what you see time and again in life coaching. The reason if a coach shouldn't suggest to you what is the right path for you is because if they suggest to you, and I'm sure you've gotten the same advice from your 10 well wishers in the world, you're not going to implement that advice. Because that's, yes, you think that that's a great piece of advice, but you are not committed to it. It didn't come from you. You don't feel that if you did that, you know, you kind of take ownership for it. So I would say that that's definitely one part of it. And which is why even if you don't get the same person to come up with the advice, if you do it in a Peer group session. That still works. Right? Because they are much more likely to kind of iterate, brainstorm with their peers, then they might be to challenge their manager's advice.
In a lot of cases, I think that's key. I work with my managers a lot on this too. It's like three to four pieces, tops. Yes. You might have had 100 things that you wanted to talk about on that call. Three to four, tops. And if you can split them good and bad, that's even better. A couple of good things, a couple bad things, and then go work on those. Right. And so I think that's something that I hope people listening understand is you have to limit that feedback of how much you give them. But one thing I'll follow up here because I feel like I've noticed a difference between reps in their careers. I feel like reps that are earlier in their careers actually like more of the directive feedback, hey, do this. Whereas reps are a little bit further along are like, you know, you kind of guide through the questions of like, hey, like, what could you have done there? Have you seen any or noticed difference there?
Yeah, you're right. I think reps who are earlier in their career, of course, often don't, you know, this kind of find it hard to even imagine what is the best possible scenario there. Right. And I think it's also a matter of just general experience and exposure to life. I think one way to actually expose your reps is to put them in buyer shoes wherever you can. Right. And then ask them feedback on calls where they were a buyer, not a seller. All right. And you would see them come up with the best possible feedback. Whereas when they are put in the spotlight, you know, it's. It's always much harder, then they kind of go into the defense mode. So I think even for seller sellers who are just starting out, I would say, you know, wherever possible, create opportunities for them to be in buyer shoes. That really helps. And I agree with you. Like, they might not be able to come up with the best possible solution or even with good alternatives, but I think it's still useful to get them to start thinking about it. Right. And it's okay if you ask them the question, you know, get them to think about it and then come up with the suggestion rather than straight away come up with the suggestion. Yeah.
Now there's definitely. There's definitely a balance. And I love that, putting them in the buyer's shoes. Because even as I'm thinking, like, I used to do it, decent amount of reverse role Plays right where they were the prospect and I or a manager would pitch. Right. So they could put that buyer's hat on for a second and throw the objections out and throw out the questions to kind of do that. So I think something I have to get back to, I think I've done one recently, so I need to go back and get. Get my reps into some of those buyers shoes there. So. Okay, so now let's say you're better, actually. Oh, go ahead. Yeah, go ahead.
So, you know, the other way to do it is if you're actually evaluating tools for your team, get them to actually go do the research and get them to actually be on the calls as buyers. Right. And when they hear somebody else pitch to them, even if. Even though it's a different product. Right. So it's not about the product knowledge, but they will just notice these little things about how the person greeted them. Did they smile? Did they actually mean when they ask a question, did they actually use that question to kind of change the rest of the call? All of that becomes really clear to.
That's a great call. We talk about this with our team pretty often, actually. It's like most salespeople don't get sold to. They don't know what it's like to get a cold call for real. They don't know they're not getting all these cold emails. They're sure as hell not sitting through these product demos. It's like, yo, go sit through some of these and you'll get it. You'll understand why you have to be different. Because if you sound like everybody else, that's when you're rolling your eyes over the zoom because you just can't stand it anymore. So. No, that's true. Like, and I do, like, involving them in the buying process I think is huge because getting them to think like a buyer is missing in a lot of places. And it's also full circle. Why even, like, the call recording is so valuable, One of the ways that I leverage it heavily is I want to listen to the prospect almost more than I want to listen to my own reps. I want to hear what they're saying, what they're asking, what do they get excited about, what questions do they ask? Right. Because if I can pick up on that, I can help better craft what the reps are looking for. So let's take that next step. Right, so, okay, say I have a decent culture in place. You know, I'm recording my calls now. What are some of the things I should be looking for or what are some of the best practices out there in terms of prospecting calls and closing calls that I really should be paying attention to make sure that either they are there or certain things that you've noticed that are in a lot of calls that really should not be there anymore.
Yeah, I think one of the things that we notice which seems to be so, so simple and so obvious and, you know, doesn't happen often enough, is setting an agenda. Right. And what we've seen is that if you set an agenda for a call, right, your win rates on those calls are more than double your win rates on other calls. And that's just kind of mind blowing, right, because it's not hard, it's not, you know, probing, etc. But it still doesn't happen often enough. And I, I've spoken to sales reps on why would you not set an agenda? And they feel that, listen, that sounds too salesy and that's not my style and that sounds too formal. But I think that there are maybe nicer ways to do it. But at the end of the day, I think it does a few things. One is it makes you come across as professional, you know, that the other person also has limited time. So while they want to build a rapport with you and get into a relationship and all of that, they do want to feel that their time is being respected and they know what they're getting into. The other thing that it does is that it allows you to actually kind of state upfront what the next steps are going to be. Right? So the idea is, listen, if we do this, we're going to do this during today's call, and if everything goes well, this is what we would expect to happen. And do you agree with that? Right. So what happens is that they don't kind of get into the call with like a bowl of popcorn in their hand just watching a demo, right? They're kind of invested in saying, oh, shit, you know, at the end of the day call, I need to be able to make the decision whether it's A or B. And so let me, you know, kind of pay attention. So that's definitely one best practice that we've seen. And that kind of holds across the different stages, right. What we've also seen is that customer stories have a great impact, right? And what we do see is that again, those are things that happen in like, less than 5% of all the calls that we see. And I mean, I think there are a few reasons for that. One is if you didn't Close the deal that you want to tell the story about, you always feel like it's a little bit kind of fake or you're not able to kind of give it the full credibility that somebody else would be able to. So I think that it makes a lot of sense to almost do like a storytelling workshop around the customer stories that exist within the organization. And then, of course, there is a bunch of different things on the objection handling side. And something that caught me really by surprise, and I was actually speaking to one of our early customers, and they were looking at their dashboards and seeing, you know, what are interesting trends. And what we noticed was that their win rates were double on calls where they had objections versus where they didn't. And initially that came out as a big surprise for them and for us. And, you know, later we realized that, you know, this makes a lot of sense because when a person is actually telling you an objection, they're actually trusting you enough to share more information. Right? And that means that you've crossed the biggest hurdle in any sale, which is the lack of trust. And so you have to kind of build on top of that, and you have to treat the objection as a sign of respect that they're showing you, rather than a. Rather than as something that you should get defensive about. So I think those are some of the things that we've seen have a huge impact. Right? So I mentioned, like, you know, in the case of agenda setting, it more than doubles win rates. We've seen that, you know, calls with Objections have a 30% higher chance of closing than calls without objections. Similarly, we've seen with customer stories, that number is, I think, like, 60, 70% higher if you kind of talk about customer stories. I think the other thing that a lot of customers initially asked us was, listen, what are the knowledge gaps that my team has? And, you know, what they were curious to know is listen. We've given everybody these standard phrases like, hey, you know, my product specialist will talk about this in the next question call, right? So if they didn't know the answer to something, they would use that as a polite grudge to kind of not have to say that, I don't know this. But what we saw was that very few people actually use those. Right. Like, even though they were coached to use them. I'm not sure what your experience has been. Would love to hear how your team handles, you know, situations where they don't have the answer to something.
Well, my team's perfect. They always execute all the things perfectly, every single time.
Of course.
But Hypothetically speaking, what might happen on my team, right Is either they completely fall apart, right? Like oh well, and they go down a, there's a rabbit hole, right. Of just rambling as they try to find the answer. Trying to the classic salesperson, talk my way to the answer, right. Or very similarly, right. If they're not prepared, they don't answer it or they can't. And then there is sometimes that lack of trust on the buyer. But it's also why with my teams I focus so heavily on the 80%. There are always going to be objections out there or questions out there that you're not ready for. We don't spend that much time on those ones. And like my reps and managers know this, right?
Like oh well, what happens if they.
Want a left handed engineer for their team? And like no, no, no, no, I'm not, I'm not, I'm not even going to worry about this because you still don't know how to handle the what do you do? Objection. So we really try to steer them back to it. But also, you know, for some of the in time learnings, we were working on this for 2020 and then of course 2020 jacked up a lot of things. So it's actually being done again now. I was getting battle place mats made, right? So these laminated placemats that had the call scorecard on it and our top objections, right? And like the one liners there and the top questions, right? So like it's flippable, it's laminated, just you have it there. Also the beauty of inside sales is.
You can have it in front of you, right?
So to give them some of that in time learning because I think it's really important actually a good segue to the next point here is, you know, post call is still post call. It's already happened. The good or the bad has already happened, whereas getting in front of it is really the key. So this is going to be kind of a two part question. How can we empower reps in the moment? How do we get them to be able to execute in the moment? Then also how do we make it step, right? So okay, you reviewed the calls, you know where to improve. How do you actually help the reps get better? So it's a two part question. Start with like the in time learning, like how we can do that and then we can talk about, well then how do we actually make it stick in the long run?
Yeah, I think that's my favorite topic. So one of the things that you know When I was building a wingman product, I realized was I spoke to a lot of sales leaders who all believed strongly in call coaching. Right. And that's why they were talking to me. But what they would often say at the end of that discussion was, you know, it's something that I love, you know, I'd love to do more of, but I don't do enough of, right. I don't have the time to do it. And it's not surprising because I've hardly seen any organization have KPIs around call coaching. Right. All the KPIs for sales managers around quota. And so what we realized was that there were two parts to the problem. One was that managers weren't doing enough call coaching, or they were not doing it frequently or regularly enough. And the second part of it was that some of the metrics that people were now able to measure, like even things like talk to listen ratio, while they were able to measure it, that didn't necessarily mean that those metrics were changing. Right. You know, if during this conversation, I have no idea what percentage of time I've seen spoken, I have no idea what percentage of time you've spoken. So it's unfair in some ways to expect the rep to be able to say, you know what, I want to improve this metric and I'm going to go into the call with that objective. Right? So I think that one way that you can improve call coaching and, you know, have impact on some of the things that you actually want your team to change is by doing it in real time. Right. And that's the whole reason why we built Wingman and we actually renamed it as Wingman because that's kind of the position that we wanted the product to have as something that someone that helps you copilot those sales calls. And, you know, my own observation was that, you know, when you're going in for maybe a prepared speech of some sort on a stage, you can rehearse that 30, 40, 50 times, you can go and deliver a perfect speech, but that's not what a sales pitch looks like, right? You can go and practice your sales pitch, you know, 100 times, but at the end of the day, there is somebody else on the other side of the table who's going to stop you, who's going to ask questions, who's going to have a different use case than what you prepared for, right. And so your pitch needs to keep adapting and it becomes very quickly overwhelming for a sales rep to kind of keep track of all of the information that they're gathering from the customer, remember the pitch that they need to deliver, Be able to, you know, give the most obscure piece of information that the customer might be asking. And so of course, the Wingman product does all of that. Right. And you're right. I mean, I think the closest equivalent to that is kind of the battle card placemats. Right? So that's something that you can refer to easily while being on that call without losing your train of thought.
I think that's key. And you touched on it. And you know, I've talked about this a decent amount publicly, but even with my own managers, it's like the amount of things that we expect a rep to remember is actually pretty ridiculous when you start to put it all out loud, right? So they need to remember the opening to a script. They need to remember the tonality they're supposed to use. They're supposed to remember the Personas. They're supposed to remember all the features and benefits of a product. They need to apply the features and benefits to that specific person. Oh, yeah. And then they also need to remember objections. They need to remember how to follow up. They need to remember how to ask for the meeting and confirm, like all of these. We're asking our reps. And then they have to do it in the moment when oftentimes too, they're afraid, right? They have a stranger on the phone and now they're in a fear state or they need that deal. So they're pushing hard. Cause they have to hit quota and all that goes out the door. And I think that's why I love the concept of what y' all are building, is that in time is like just the prompt, just a prompt. It's something that we have. So we have a system internally we call bps, right? It's behavior, process, and skill. And, you know, so if someone is struggling in a certain metric, we like, what's the BPS score? Is it behavioral? Like they're just not doing it? Is it process, meaning we haven't taught. We don't have good prompts and prompts. Is there like, do we have prompts, reminders for them to be able to do it, but also too old school? Is there a sticky note? Do they have a sticky note on their monitor? Right? So you are clearly taking prompts to the next level, which is way better than my sticky notes. But I do want to follow up a little bit on practice, right? So. Because in time can only go so far too, in terms of are they. Can they recall it? Right? So like, do you have some best practices on practice because I think that's where it does start to stick. A little bit is okay, we recorded it, I got the feedback, I have the prompts, but I do need to go rehearse it 30, 40 times to make it sound natural. Right. So what do you guys encourage around practice and repetition?
You know, it's not very different from the kind of, you know, little flashcards that you might carry when you're going to go up and give a speech on stage. Right. Like it's supposed to be something that you can quickly glance at and that, you know, helps you refocus your train of thought and like, you know, what's the most important thing that you want to be talking about next? Right. You're not expected to kind of read end to end from those flashcards and they're not really meant as, you know, the full speech. So I think that's probably the intent with which people should think about battle cards in general. But what that means is that there is of course, a lot of practice that needs to go in for it to sound familiar. So the way we would encourage teams to do this is you have your kind of detailed notes or detailed scripts around a particular topic. Take the example of handling an objection, say around timing. Right now you have a few things that you want people to say. Maybe you want them to talk about, okay, what is going to change between now and, you know, whatever is the proposed time that you have, right? You want them to maybe dig deeper with a couple more Y questions. What you would therefore want them to do is to be familiar with it, to understand why they are supposed to ask that questions, what should happen when those questions are asked. But use little prompts or cues to help them just get reminded on what is it that they should be doing. And so the thing that we've seen to be most effective is like if the team chooses together and say, you know what, we broadly think that we are pretty bad at handling the timing based objections. Why don't we choose that as the theme for the next two weeks of this month? And what we are going to do is even when you're doing call coaching, we are going to pick up examples on those, we are going to iterate, come up with better scripts for that, and we are going to iterate on our flashcards, etc. Based on that. So what we've seen is that if you kind of choose a theme and work on it, and it goes back to what you said, if you give somebody feedback on 25 different things on a call, it's probably as good as giving them feedback on nothing. So if you just actually decided as a team that this is just the one thing that we're going to make sure everybody gets feedback on for this two weeks, we actually see that that improvement is much more dramatic.
Yeah, I think. Well, you know, we talk about aim small, miss small a lot with the managers. It's like aim on one thing, aim small. What is the one thing you're going to work on for the next two weeks, three weeks, two months, until they get that down and then it can become a strength and then you can move on to the next. I think oftentimes as managers and as leaders, we're anxious to talk about the next thing, right? So we know they're still struggling with whatever objection, but we're tired of talking about it. So we move on to the next thing and we don't cover what we should have. And I do actually want to take a step back here a little bit. You mentioned something earlier about KPIs on call coaching, right? How often should reps be coached either by their peers or by their management and leadership team? Like what could some of those KPIs do? Like for my team, my managers are responsible for listening to three calls per week per rep and my reps are responsible for submitting three calls per week with self feedback. Right. Like that is built into our one on one doc. The links have to be there, right? It's like this is happening, right? So like what are some of Those, I guess KPIs that you know, you would track for, like a call coaching culture or how often do you think it needs to happen for it to actually, you know, I guess become a culture. Really?
Yeah. So I think there are two things, right? One is how frequently should it happen and you know, based on how many calls should it happen, right. So I think the frequency, definitely at least a weekly frequency, right? Because beyond that you're trying to change somebody's habits, right? And if you're doing that, you know, once a month, you're not going to make any impact, right? And I think we've all kind of read enough books about how to adopt new habits, how to change habits, and what it really boils down to is that you kind of have to do something till it becomes muscle memory, right? So I would say that ideally if you can, and if you're trying to maybe bring in something that's pretty dramatic or pretty, pretty damn important, maybe you should even do that as like a 10 minute stand up coaching every day, right. For that period of time when you're trying to really bring on board a new habit. Right. So I think frequency wise, at least a week, right. And then how, how many calls should a person review? I think the right answer is probably as many as you can. But of course the way to maybe amplify that fact is by doing it as a group coaching session. All right. And there is probably a balance that you want to do between group and one on one coaching. But I think a lot of things, if you do them as common themes, etcetera, can have a huge impact in a time efficient manner, even as a group coaching session. So, yeah, that, that would be my recommendation.
I like it. And I think what you've done throughout this too is you've talked about, you know, rep led, peer led, manager led. I do think that combination of three is so valuable to actually get to that feedback. And also for people listening to the earlier point, you know that people tell me, I just don't have time. If you have a team, you have time, right? You have a team that can help you with this, right? You've got 5 reps, 10 reps, 20 reps. Spread it across, right? Get some of that peer learning. We call it tribal training on my team, right? The tribe teaching the tribe, right. And like how to. But we also do. We train the trainers, we teach them how to give feedback, we use a scorecard, right. So we're all looking for the same things because that can go wrong, right? You got five managers looking for five different things and then no one's getting coached the right way, which never goes the way that you want it to. I've made that mistake many a time. So. All right, so as we start to kind of wrap up here, I did actually want to touch on a little bit of like this life coaching thing, right? Because I do think there's so much overlap between leadership and life coaching. Right. In a lot of ways, like management is half psychology, if not 70% therapy, right. Like there's a lot of life coaching that goes on there. And so like, I mean, I guess how do you leverage, you know that when you lead your own team or how do you encourage your leaders or other leaders of like how to be a better kind of life coach, then it also probably carries over into being just a great coach.
Coach. Yeah. I think my own motivation in some ways for going through the whole process of training as a life coach was how could you actually be a better leader and manager? And I think that translates actually into every aspect of life. A few things that I've seen and that I think every manager can easily adapt for their own teams. One of them is to actually, you know, it's start with the basics, set aside time, which is led by the person that you're coaching, right. Don't, don't set up your one on ones with you setting up the agenda, right? Be very clear that the agenda has to be brought by the person, you know, who you're having the one on one with. Because what that does is, you know, it starts with giving them the power and, you know, making them feel that they have the ability to kind of improve their situation. Right. The second is to kind of keep the discussion open. Not everything should be related to the work directly, right. A lot of times what happens outside of work impacts what we do at work and vice versa, right. So it's important to create that space where people are actually okay to talk about work, things that are unrelated maybe directly to work. And one of the best examples I've seen of this is a sales manager was once telling me that, you know, a lot of the sales reps are actually comfortable discussing their financial planning scenarios with him. And he feels that that is in so many ways part of what he should be doing or discussing with them because he feels that at the end of the day, you know, everybody in the sales world is in it for the money. And therefore, if I can help them kind of think about it more productively, then maybe that also helps their performance. Right. Again, it's just an example of something that doesn't necessarily relate to work, but it does. And then I think the third part of it is to constantly ask people for what they think they could be doing differently. Right. And kind of go deeper into breaking this up. So there are of course a few different frameworks that exist in the coaching world, and one of them that I find really effective is kind of the ABCD thing, right? So you have, you're put in a situation, but then often people think that they are reacting to that situation, but what they're actually doing is there is a whole layer of beliefs, right? So they're interpreting the situation based on the internal beliefs that they have, and then they're using that interpretation to actually how they feel about that situation. And then that feeling is causing them to kind of think about it and then take actions. Right? So I think just being familiar with some of those basic frameworks, you know, helps in help, you know, in helping the person that you're trying to help. So I Feel that, you know, broadly this applies even when you're trying to give advice to people in, you know, social circles, etc. But a few kind of tricks, if I can say so, right, that have really helped me. One is not to use the hot button, right? So the hot button is basically, you know, somebody tells you something and you're like, oh, shit, I have experienced the exact same thing before. And, you know, this is what really worked for me. And you should go and do that. And it never works, right? Because everybody's situation is different. And as soon as you say, oh, I've experienced the same thing before, you've lost them. Right, right. And then this. And the second thing is that I found personally very helpful is getting people to give themselves advice from the point of view of somebody that they really respect, right? So if I say that, okay, you know, you're facing this tough situation, tell me who you would go to for advice, right? And let them pick, like two or three people that they really value and respect in their lives and say, okay, you know, so if you went to that person, what would they tell you to do in the same situation, right? And what it does is because they are able to kind of then distance themselves from that situation a little bit, and they're trying to give the best possible advice that they think they would give in that situation, they actually come up with really great ideas that they might not have, you know, while they were going through it. And because they feel that that advice is, that advice is now coming from somebody that they respect, they're actually much more likely to follow it. And so, you know, those are just kind of some simple things from Life Coaching World that I've taken and used in many different scenarios.
I love that. It's funny that that second one, we joke about it a little bit internally with my management team, right? We have a little acronym, right? It's like ww kda. Right? So not wwkdd. Right, not what would KD do? What would KD ask? And that is something that I really prime my managers and my reps for. Like, okay, what would I ask in this situation, right? Because you know, I'm coming with questions, right? To your earlier point. Like, very rarely am I immediately directive, here's what we're going to go do. It's almost always starts with questions, right? It's like, what would I ask? Take that pause and think, like, all right, what would Katie ask me here? He probably asked me if I actually observed it happen. Well, no, I didn't observe it happen.
Great.
Well, then you better go observe before you go bring it back to me around it. So I think that's really good. Are there, are there any good resources out there, books or courses that you'd recommend people look into around, like, how to become a better coach? Because you said it very well. Like, coaching covers all aspects of your life. Yes, your work life, your leadership life, but then also relationships, friends. Right. Social circles. Right. Like, being a better coach and communicator, I think is just an amazing skill set. Like, are there any good resources you could point people towards for that?
You know, I've been reading the book the Trillion Dollar Coach. I mean, I think it's a good starting point, but I think a lot of things are maybe somewhat dumbed down and hard to execute the way it's written up. You know, it's easy to understand what the takeaway is, but maybe it's hard to execute, but that's probably a good starting point. Of course, I went through this program called Ericsson Coaching, and I think it's available, you know, globally. You know, so if somebody is willing to kind of do a deeper dive, I would encourage them to. To maybe check out Ericsson Coaching. Awesome.
Well, we are almost there. I got two questions left for you. We've been going for almost 40 minutes already. Like I told you, this is my favorite topic. We can do this all day long. I still got questions we could dive into. I got two last questions for you here. The first one's just called the Big three. Right. So we've been talking about call coaching for over 40 minutes. That's a lot of information to not break our own rules. If you wanted people to remember only three things from our conversation today, I, how to better coach calls or how to instill a call coaching culture. What would the three takeaways from our conversation be today you want people to remember?
Let me think about it. Yeah. So I think one, definitely don't observe while a person is doing it. Right. Go back, do it later. Two, it's really hard to execute on sales coaching feedback because you're in the hot seat and there are so many variables. So do you know, kind of keep it simple, Change one thing at a time and wherever possible, provide little cues and nudges to the person who's on it. And three, believe that your reps have the ability to and, you know, and the motivation to get better and use that when you're doing coaching. So incorporate that into how you give feedback, into how you get them to think about how they would Modify a script and get better at it.
I love it. I love it. And then the final question here, right, so the name of the podcast is Live Better Sell Better, right? We have this really weird idea that if we took better care of ourselves, that if we had more joy and energy and fulfillment in life, that our sales would also improve. And now I'm speaking to a life coach here. So what would your live better advice be for people in terms of how to get more out of life as a person? What would that party advice.
Think about, you know, what would matter five years down the road or 10 years down the road, and use that as the lens to decide on your overall priorities and what gives you joy and so sorrow. And I think in a lot of sales scenarios, people get too caught up with, you know, their monthly quotas and stuff, and, you know, that can give them a lot of stress, a lot of little highs and little big lows. So, yeah, kind of take the bigger perspective. And, you know, I think that will get you both to be better at sales because you'll probably not be as pushy, and it'll probably help you understand your customers a bit better as well.
It's so funny. Just this morning I read a quote. It was like the rule of five, and I think it was on the lines of, like, if it's not gonna matter in five years, don't spend more than five minutes worrying about it now. And, like, I just thought it was just very succinct and powerful way, like, if this is if the latest episode of the Bachelor or the person that cut you off in traffic, it's not gonna matter in five years. So why even waste five minutes with negative emotions around it now? So that's so key. So, Trudy, this was. This was amazing. I mean, where can people get more of you? Where can they learn more about Wingman? Like, obviously, I've been talking about it more now as I've been learning, like, where can they get one more of you? Because you have a lot of great information to share. And where can they learn more about Wingman, the tool that you built?
Sure. I'm on LinkedIn. Not as active as I'd like. You can look for Shruti Kapoor. And, you know, if you search with Wingman, you'll definitely find me. Wingman is, of course, the website is www.thrivingman.com. you can also check us out on LinkedIn. But, yeah, would love to hear from all of you. Would love to also get some more suggestions on how you do your coaching sessions and what works and what doesn't.
Oh, yeah. So we will be talking. We've been trading emails or. I'm gonna keep showing you what I'm doing. I'm loving what y' all are doing. I'm excited to kind of get my team's hands on it sometime here soon. So, Trudy, this was amazing. Thank you so much for your time, your insights and energy, and we will be in touch again soon.
Awesome. Thanks, Katie.
You're welcome.
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