Episode 4: Who's the best sales coach?

 Jen.

Oh God. Are we just both...? You know, your LinkedIn posts are so dramatic. It's like, I feel like you could turn a grocery list into a TED Talk. It's like, come on. Oh my God, it's so awful. It's not that fucking serious. Jen. We gimme an example. An example. Gimme an example, gimme you. Okay, I'm gonna open up LinkedIn right now.

Remember? When LinkedIn didn't track impressions, none of us spent a single second thinking about people. How many people saw our posts? We thought about how many thoughtful conversations happened in the comments, pace, pace, pace, pace, TED talk, how many new meaningful connections it drove, how many dms it initiated.

In my opinion, I think the introduction of the impressions metric is what changed LinkedIn. For the worst. Do you disagree? Do you disagree with me up? If you disagree, do you disagree with me? I will say Will. That was a very close impression, but your posture was insane. Yeah. Well, what do you want me to do?

The camera doesn't point at the ceiling. Uh, Rayna. All right. You were curved. I, that's what I look like. You curved. Just as I'm tall, I just crawl around stages. Yeah. Jen's tool as well. You like walking through door frames like this. I'm so short. I gotta use every inch of my spine to. Yeah, sure. Shut up, shorty.

All right. Okay. Don't, don't be happy to go at us 'cause you're, you're, you're vertically challenged. Unlike Jen and I, you're like one statement away from getting canceled. That's generous. Today's competition is a good one. You are both sales trainers in your own right, but which one of you is the better sales trainer today?

One person will decide. So you're gonna meet close's lovely and brilliant senior account executive, Kate Pet. You'll both be given the same video sales call from Kate and now she's a known badass seller at close. But this is a recent call that thought went well, but the pro. Ended up ghosting. So she'd love to learn what you think she could have done different.

And remember the two of you at the end of these competitions, were either gonna be donating to some dogs or some more salespeople. So up to you two to make that decision. Let's go ahead and watch Kate's sales call and we'll get your coaching feedback and we'll see what people are actually paying you for.

So spicy. Did you write that? I felt, I felt like it had a little sting to it. Jen, what do you think? Oh,

what is up Kate? My name is Will. If you don't know who I am or even aware of me, I just wanna start off by saying good on you. Being open to having two complete strangers provide coaching feedback on one of your calls. Like being open to coaching is, it's tough sometimes, especially when it's not someone you know.

And to, on that note, I don't know exactly how you like to take feedback. What type of coaching is the most helpful for you? So what I'm gonna do is I'm just gonna share the observations I saw watching back the school, and hopefully there's something in there that's helpful. You can take everything from a pinch of salt.

I've never sold clothes before. This is just from an outsider's perspective. There's nuances I probably don't understand overall notes. Number one, I wanna say. You have incredible active listening skills, like the fact you're willing to ask a question and then just, there were a few times where you asked a question.

There was like a good 3, 4, 5 second pause. A lot of sellers like to jump in there and feel that silence 'cause it's uncomfortable, right? There was some times where this guy was talking and he stopped and you just sat back and let that silence ride and he carried on and told us more, right? So first of all, kudos on that side of thing.

I want to also compliment the fact that you have really good, uh, you seem really informed on this space, on your solution, on other solutions like HubSpot, and you just have a very good executive type of presence on a call as well. And then finally, it also sounds like he's probably looking to a couple other solutions.

You probably picked up on that as well. He said, oh, we were looking at you or deciding. Who we're gonna go with. And then at the end he said, I wanna compare this to a couple other solutions as well. Really good opening. I like the fact that you skipped all the small talk. Definitely mirror style. I dunno if that's what you do every single time.

I like how you just get straight to business. That's my personal style as well. Aspo, the things that I think could have been a little bit better in the opening. There is a question here, which I'll just highlight for a second. Not everyone likes saying agendas. I like to love us and just say, Hey. Just to make sure we're on the same page.

The purpose of this call is to really figure out how you're doing this, then see if we can help, and then figure out if it makes sense to keep trying. I think that just helps us keep us aligned. It might be worthwhile adding that to your talk track, but either way, your question kind of did that. Four questions in one.

I think the questions we ask, the more clear we can be, the better. So compound questions often end up getting us like compound responses. They often just end up responding to one of the four questions we asked. So it was like insight into your business problems with HubSpot, ideal solution, and what led you to start looking into this.

So I think, all right, let's start there. You said things aren't going as well as they could be a HubSpot. Tell me more about that. That could be a great way to launch this into the call and save some time on this stuff where he starts giving us unnecessary background information that you probably already know.

My second favorite question you're about to ask, my first favorite question of the whole call. You asked for clarification. You said, I'd like to dig deeper into that manual side of things. What do you mean by that? Clarifying? That was awesome because he was very vague, so. By getting to clarify, he gets very specific on what he actually means by that.

And this is the most important problem to him, obviously it's the one he mentioned upfront. So he is saying basically the biggest challenge is that they're not filling up the forms, the fields in HubSpot. And that's the challenge. First favorite question is this next one. What is the reason? I love that question.

'cause this starts to tease into like, sure things aren't being filled out. What's the reason that's important to you? 'cause that leads you on to something that's a, a real business case at that point, right? It's a great question there. So then we get into the demo section of the call. The challenge that I found when he got into the demo portion, I can find a few examples, is he started peppering you with questions and certainly one of my old managers told me that stuck with me for a long time is the person who is asking the questions during the call is the one who has control of the call, and there's a point where it kind of flips.

Almost at the moment, you start sharing your screen where he's the only one asking questions, and there's a few questions he asks like, oh, how about task management and sequences that Weren mentioned before? And I don't think we really understand why he's asking those. I think that was a great opportunity to dig deeper.

Oh, you mentioning you're talking about task and sequences. Like I'm happy to show you what that looks like. How do you manage that today? So I feel like that was worth drilling into to understand what the need was there that was driving his curiosity into how those things look and work. I think the best thing you can do in those is sometimes just, oh, you mentioned sequences before.

You know, maybe you kill your screen. To make sure it's clear that you want to understand that, that you're not just gonna show it to him right away. We haven't spoken about that piece yet. How are you doing that today? What does that look like? What's the problem with that? Is that something you're struggling with?

Figuring out that piece before we, we give answers all the time. Just throwing the question back, Tim, so that way you maintain some control and obviously learn some more information about why is looking into this, ideally something that you can sell to as well. Super brave for having two complete strangers jump in and review one of your sales calls.

It feels like a very personal thing to do, someone I don't know, but it's been great getting to know you over the past 33 minutes. Awesome. Cool. Keep it up and uh, if you have any questions about any of this feedback, I'm happy to clarify anything. I'll send over the doc with some notes as well, just so you can read that, just in case you don't wanna look at my face anymore.

If not though, keep it real. Hopefully we'll get to chat properly soon. Kate, I just finished listening to your call. I'm a big believer that good coaching comes in three, so I'm gonna give you three things I really love that you did, and three things to work on for next time. So let's start with the good number one.

You are a phenomenal active listener. You didn't interrupt him once. You let him complete his thoughts. You picked up on really small cues of things he said, and then you didn't let it just float by. You went back and revisited it. Number two, I think you got into the conversation in less than 60 seconds.

I personally am a huge, huge fan of this. I think sometimes we do excessive report building for our own security and our own confidence. I, if I think about it, like someone who's going from meeting to meeting this person was traveling a ton, they probably just want us to get to the damn point. So I like that you didn't do any weird, small talk about the weather or things like that.

The other thing I really liked that you did in the open is that you gave him confidence to know that you read his request. Again, seems minor, but a lot of times sellers will show up and say, all right, so tell me why you're here. What you did that I loved is you said, it sounds like you're trying to do this and this is why you're here at the call today.

And then you gave the floor to him to kind of correct it. So I really liked how quickly you got into the conversation versus doing, you know, rain talk. And then number three, you asked some really great why questions. So one of the examples I wrote down was. He was talking about, one of his motivations was for sellers to stop manually filling out CRM fields.

A lot of sellers. Would probably just fly by ba bat and say, okay, cool. That's a problem. The time it takes to spend filling out, you know, serum fields. Instead, you sought to understand why you sought to understand how much time on average. And I think you got to something really interesting, which was, it's actually not a matter of how much they're spending on filling out CM fields 'cause they're not doing it at all.

And that opened the door to a much more significant problem. You wouldn't have gotten to that if you had just. Settled for the first answer he gave you. So I really liked your use of very thoughtful why questions when you heard things that. We're incomplete in your mind, moving to the three areas of constructive feedback.

Things I think you can work on for next time. I am personally a big believer in treating inbound, really no different than I treat outbound. And what I mean by that specifically is I think sometimes with inbound we give over, I hate to say control 'cause I don't think we should ever be trying to control prospects, but we end up putting ourselves in the shoes of kind of like a recipient, like I'm here to answer your questions.

What is it you've come here today to learn and then it can be really difficult, I think, to pivot the conversation if the prospect comes in at a much lower elevation than we'd like, or they're asking like really, really small nuanced or not nuanced product questions and we really need to get to a higher level of pain to understand this is even a problem we're solving.

Or if this is just a lookie Lou. So one way you could do that is in your open. Like I said, I loved your open. It was short. It. Punchy, but you could add something to the effect of like, Hey, when I saw this come in, I took a minute to look at the business. I actually have a couple other clients that are similar in regards to this, this, and this.

So maybe it's the fact that they are about to get seed funding. Maybe it's the fact that there are less than 10 employees. Whatever you think that would draw parallel to typical problems that others see that are similar, I would kind of draw upon and say, so I have a couple ideas for you, but before we get to that, I'd love to understand.

What prompted you to come to the call today? So I think that does a couple things. One, it shows that you have ideas, not just like product, you know, answers for them, but it also allows you, as I noted before, to pivot the call if the call kind of goes into a little rabbit hole, which I think at some points it did.

So it allows you to lift back up and say, I had a couple ideas. Is it okay if we take a few minutes and I can share those? 'cause I think they're in line with some of the things I hear you trying to achieve. Second thing is, I mentioned this, and this is something you did really well, which is you asked Great why questions.

I think when you do a good job of that, it opens the door to reframe how they're thinking about a problem. So I think that was the door to a much larger problem than he ended up gravitating to, which is like, do you have this feature or should we stick with HubSpot for this? And so what I would've loved to have seen you do there is then take a little bit more ownership of that conversation and say, okay, so it sounds like the larger problem isn't necessarily the time it's taking reps to input things manually.

It's actually about how do we make sure these conversations don't go to waste because we know x. Percent of our previous conversations convert into revenue. Have you looked at that? Do you know if there's a conversion number or can we talk about some other things that would help you in that pursuit of getting to a finer segmentation of that list?

Okay. And number three, I think towards the end of the call, there were some elephant in the room things he said. So one of them I wrote down was like, we're not dying with hub. Spot. Right. And this was something he said later. So he started the conversation by being like, Hey, we'd like to move off HubSpot.

And then towards the end he is like, well, we're not dying on HubSpot. And that was screaming like there just is an urgency in his mind of the need to change, I think might burn an opportunity to do a high value trial because they're not in the right head. Space for it. So instead, I think if you think about what was being asked of them, maybe it would've been a different kind of next step if you had gone back to that higher problem elevation.

And we could have said, you know, let's take a look at how we're approaching, you know, re-engagement campaigns today, or how we might do that without information like this. And then I think you can move into a trial conversation if you get buy-in that this is a problem worth solving. So those are my three things to work on.

But again, I just wanna say like beyond everything else, your ability to act. To do great active listening and ask why questions got you to a place where I could see those opportunities. If you hadn't done those things, I would've probably struggled to give you good feedback. So well done. This job is hard and I'm rooting on you and don't see any reason this couldn't be a win back conversation.

All right. All right. What's up you two? I'm in a new spot right now, so quickly explaining. I'm on an offsite for coms store, but that's not stopping me from doing Will versus Jen. So how did you feel about the feedback that you gave Kate? Like what was your approach and all of that? I hit every minute of it.

Um, frankly. Um, Jen, Jen, I'm, I'm curious to hear what you think, because I think you've got a, you hated her call or you hated coaching. Uh, I, you've got a lot higher EQ than I do. Um, I'll give you a compliment right there. Coaching is a very intimate fit, you know, to give someone feedback. It comes better when it's from someone you trust.

No, at least, you know, in the coaching sessions that I do with one-on-one with reps, I often get to know them a little bit better, break the ice, make sure I know where they're open to, what they really want to focus on so I don't talk about things that aren't important to them. That was really challenging doing that someone I haven't met and who doesn't know me, and frankly, I, I feel Kate was really brave for even being open to this in the first place.

That was my first. Thought I was like, oh wow. Having two randos, just comment on my work. Oh, the. Good honor, focus on one thing if you got a direct concern. So that's kind of where I chose to take it as well. The last thing I would say is I, I wanted to make sure there was something there that Kate could actually do versus wallow in, in, in, in critique.

So I made sure to give like, okay, overall I. Things you might be able to still do for this deal. I'm kind of glad you didn't do that. Well, now you have one compliment and I have one compliment for you so we can be done with complimenting each other. Fuck you see now I'm taking now from the other end. I'm Jen now we are being coaching our coaching.

This is how it felt for Kate. Oh my gosh. I mean, will, if you wanted to know what it was like having you as a coach, a boss, a mentor, you could have just asked me. I wasn't even trying, I wasn't even trying with you. Rayna, you don't need coaching. You're already perfect. Okay.

Hey Will. Hey Jen. Nice to officially, unofficially meet you. Um, I just wanted to share a quick video to say thanks again for the feedback on my recent sales call. You both start the time to provide honest, constructive, non-judgmental and empathetic feedback, which I greatly appreciate. Um, it's not easy being super vulnerable, but I can tell you both.

Been in my shoes before, um, and really both had some great pieces of advice, so thank you for that. I thought it would be fun to do a little spinoff of this, sort of a feedback inception and give you feedback on the feedback you left me on the call. Um, and I'm actually going to score each of you individually and see who comes out on top.

So Jen, what I loved. I loved your approach to the call. Um, I love how you broke it into three different parts. Um, so that structure made things super digestible. Your delivery was also very warm and empathetic, which I really appreciated. Um, so it made it easy to absorb the feedback without feeling defensive or critical at all.

So it really felt like you were on my side. I could tell that you've been in my shoes before and done this before. So what helped me the most? Um, I loved how you pointed out the difference in the inbound versus outbound mindset that I shouldn't just be an order taker. I feel like this is something I constantly struggle to balance, especially in an inbound role.

Um, just. Finding the balance between getting folks what they need in order to make a decision, if poses the right fit, while also still meaning control, maintaining control of the call. So I, I, you know, feel like a lot of times they're looking to us almost as product experts, so I love that, um, tactic to sort of, um, approach the call as a product expert.

Effort and bring new ideas that they may not have thought of before to the call. Um, as a way to like take back control if I feel like I'm getting in the weeds, which I feel like I did a couple times during that call. So that's really helpful. And then where I would've loved to see you go a little bit deeper on the call.

So on the topic of lack of urgency, I love that you flagged that and picked up on that in the call, which was great. But I would've loved your thoughts on how I could have handled that live. So what could I have said to bring some momentum back? Um, I love the idea of calling out the elephant in the room, but like, how do I get sort of that sense of urgency overall, it was really solid feedback.

Um, again, you brought some really great points to the table and gave me some really good tactics that I can use on future sales calls. So I'm going to rate it a solid B, so thank you again for that. Now will over to you. So what I loved, I really appreciated how strategic and practical your feedback was.

I love the way that you broke the call down into four different parts, similar to Jen. But you did the opening discovery demo and then close. I think breaking it down that way allowed me to see where I started to lose control of the call. Um, and then you also picked up on the same strengths that Jen did, like active listening, um, but added more tactical ideas that I feel like I could put into my next calls right away.

What helped me the most? You gave me real usable tactics, so telling me to pause the screen, share and flip questions back when I feel like I'm losing control. I love that sort of. Break in visualization. I think that that would be a really great moment to sort of take a step back and reassess. Also, love when we get to pricing.

You had a really great idea about like asking, once you sort of, you know, frame the conversation to say, this is what we recommend based on what your needs are, how does that compare to what you're paying with HubSpot so we can really actually see what that gap is. My favorite thing that you mentioned or tactic that you recommended was just simply like, for a deal that's sort of losing momentum.

Put a calendar invite on their calendar and just see if they're gonna be. You know, moving forward. Um, so I did that in this case. I actually put a calendar invite on his calendar for tomorrow, so we'll see if he shows up. I'll keep you posted, but I love that it really feels like a way to get back into the driver's seat, especially since he mentioned like end of May.

Let's hold him to that, you know, let's see if we can move this deal forward at this point and just put the meeting on the calendar and um, you know, go from there basically. So, where I would've loved to see a little bit more, I think when it comes to assumptions about. Deal readiness. I would've liked to hear a little bit more on how I could have kept that deal warm.

Like if I did put the calendar invite on his calendar, he didn't show up. How would you approach the deal from there? Would you consider it lost? Would you continue to try to advance that deal? Like what are your thoughts? What are some tactics I could use when it comes to just like a ghosted deal too?

Because that's sort of what's happening in this case. So overall score, I'm going to give you an A, which means the winner is will. So this was a really tough one. Honestly, I took a lot back from both of these calls, so I like. It was a really tough decision, but I think in the end, the tactical suggestions and the strategic lens and the way you made your coaching actionable just edged it out a bit.

I really appreciate you both taking the time to provide feedback. Jen, your emotional intelligence and just clarity we're top notch, so I honestly feel like I walked away better. Thanks to both of you again. I appreciate you both taking the time. Great to officially unofficially meet you and I hope that our paths cross again in the future.

Thanks again. Well, she is just the sweetest. I love I team Kate. Team K or crap, I mean, Kate, champion, happy Champion. I mean, listening to her feedback, I knew I was losing it. I was like, damn it. Ultimately, uh, he's not just on the board anymore. He's equalized, he's equalized. So beyond k just being an amazing sport, obviously you and I doing some great job here.

Uh, I just wanna say he's back. He's back. This is well deserved. This is well deserved. I will give you your credit. As much as I wanna talk trash to you right now, you clearly outperform me. I can take a loss. Unlike some people on this screen, there's maybe considers using hyphen, like a normal person, right?

Angry marker. You have to hold down a key on a phone. You have to hold down a key for like two seconds and then select the M dash. I'll take it. I'll take it with pride. I will learn from what you did well. And I will play in the future. And I feel good that my win was earned, um, as well. So what does that mean?

Nothing. I, it's not like the AI human thing was like a complete coin toss or anything like that, you know, I'm just saying that is such a low road. You're taking the low road. We were on the high road. Should we play rock paper, sci again? You know, that's a hugely skill focused game. Uh, if you, if you wanna really equalize again, uh, or leave deal, deal.

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