Kushal: Hi there. Welcome to “On the Flip Side”, a podcast for anyone who wants to live their best sales life. We're going to be talking to buyers, sales managers, SDRs and AEs about things like, what does it take to be a great sales manager, or how can you go home happy month after month? So let's dive right in. 

I'm honestly so excited and a tiny bit nervous to be hosting today's podcast recording live today. We've hosted over 30 episodes of “On the Flip Side”, had some amazing guests actually. We decided to take this live. And even further that I'm super excited about the topic for today. And of course our guest for today, the topic itself is a bit of a tongue twister, “Should sales shut shop in the last two weeks of December”? And that's exactly what I asked our VP of sales at Wingman. And we decided to make it a conversation for everyone to join in. Pradeep, welcome to the show. It's so great to have you here today.

Pradeep: Hey, thank you, Kushal. It's great to be here as well, right, and more than a tongue twister. It's a very kind of like, controversial topic as well. I could see the world getting divided, right, into like, but not exactly divided, like I see other controversial course. Here, it's like a different kind of divided, we'll get to that soon. But very happy to be here, and nice to meet all of you.

Kushal: Great. For those folks who don't know, of course Pradeep is our VP of Sales here. And he's also a very well regarded and well-loved sales leader both in India and of course globally. Pradeep, first off to sort of tease this section, will you be going on leave, say the next two weeks or so? 

Pradeep: In normal cases, I wouldn't, right. But I've just become a father, right, so I'm going on a paternity leave, the last week, right. But if that's not been the case, right, then, no, I wouldn't have been.

Kushal: Congratulations on your good news, of course Pradeep for the addition of a little baby boy to your family. So Pradeep, to get right into this right, we of course ran an interesting poll on your LinkedIn today about you know, the same topic, should folks really kind of shut shop, go home and just come back maybe refreshed in January? Like there are a few suggestions around that. So tell us what are the people saying, is it time to go back home and come back?

Pradeep: Very interesting results to the poll, right. Like, from the start of the poll till the end, right. So I could see from 4 people to 40  the people. It's not a huge amount. But still, it's not a lesser amount as well, right. But given the fact that we ran the poll only for like, say, seven hours or so the results are pretty interesting, because like, constantly 70% number was not broken, right, from the start of the finish, right. That's 70% of people are for shutting the sales function for the next 10 days or so. And generally, like with such kind of like polls, I see people getting exactly divided, right, so like 51% for and for, like 49% ish against, something like that. But here, like 70% is like a really good number to be like, clearly, it's the North star metric. 

So I was looking at the persona as well a little bit deeper. And there, I found an interesting insight, right. So among the 70% who voted like, hey, yes, let's shut down the sales team, right, like we had a mix. Like we had a mix of sales leaders, we had a mix of like reps, individual reps as well, right. And then some middle managers as well, right, but 50%, right, of this 70% are sales leaders. And one of the interesting fact is, among the rest 30%, right, 90% are still sales leaders, which means that the sales leaders are now divided. They're like 30% of the sales leaders are like, yes, they shut it down and 50% of the sales leaders are like, no, no, let's keep it running, right.

Kushal: Yeah. I was going to ask you, if it's, you know, great news for all of the sales teams and sales reps, right like if the leaders feel it's time to shut shop sales, let's just go home.

Pradeep: Exactly, right. So that was a very interesting fact, right. And that is a very interesting insight as well, right. As to, Hey, why do leaders think this way? And that's an important question to ask as well, we can't straight away neglect saying that, yes, sales should function all the time, because customers will be there all the time and neglect the importance of the personal space that people get as well in sales, right. So I think that is one of the reasons why the sales leadership is divided on this fact as well, because generally this season is seen as slow and sales leaders like tend to think that okay, now is when I should really like put my team to ease.

Kushal: Got it. So Pradeep, if I know we have some more hard hitting questions around what people should really be doing, you know, if they feel this is downtime for the teams, and what should they be doing? But before we go to that, I think Jen Ferguson commented, I think on your LinkedIn post or on you know what, it's okay to give your people some time off. It's also a time of relaxation and rest and celebration for a lot of folks, so it's okay to kind of say, you know what, it's time for me to just go home, you know, and relax for a while. So is this maybe a time for sales leaders to also be showing a little more empathy, possibly towards their sales teams or what their, you know, different folks on the team might want?

Pradeep: Great question. First of all, thank you, Jen, if you're watching, that was a great comment, right. And I know how much hard work you're putting into the ecosystem to make sure that a leadership is being more empathetic towards the team members as well, right. So thank you for that. And yeah, to answer that question, right. I think Jen's comment was more around, analyze your business first, right. That is what I would recommend as well, right. Where, look at your business trajectory, because I've seen businesses where they, like, kill it in December, right. Like, suddenly the graph is shoot up heavily in December, right? And that is because their business is more around getting the leftover budgets that companies have at the end of the year, right. And at the end of the year, like some teams like revenue operations, or DevOps, like they are much more like, what do you call they have time to investigate to deeper technical tools or technical infrastructure, right, that they can go ahead and implement. So that leads to a ripple effect of having a huge demand and that spikes up the sales as well. 

So her comment, the best thing that I liked about that was, do you have a demand, right? Do you have a demand spike in December or do you have a demand spike in November, just a month before, right? That can lead to a ripple effect. So analyze a business first, if your business is not demanding that particular spike, right, or that particular indicator, right, where your team should be like much more reactive to your customers or prospects, then go ahead, give your team a little bit more relaxing space, right. Give them time off, right. So they don't burn out easily. And that is not just so… typically the like… since this is a holiday season, we all generally like normalized and tend to think that okay, we should shut it down, right. And that is the thought process that we need to break, right, what we have to do is, we have to analyze business by business. And understand, which is a downtime, like there will be a downtime for every business. For example, right now with Omicron, right, speaking again, that might be a downtime for travel business. Again, that might come up, or companies or technologies that are tied to the travel space or who knows, right, a month later, the demand might peak again. So it's good to analyze this trend that the business is following understand what are the few days or weeks are the time, right, where your business can be a little bit more relaxed, and give your people, right, a time to go ahead and release their like kind of stress, because it's a stressful job, nobody can deny that sales is not stressful, and nobody will say that. So you can give your people the time as well to go ahead and relax and get their mental space and mental bandwidth as well. Generally, I've seen companies as well tell that, hey, take time off whenever you want but that whenever you want will never come, right. And when leaders are somewhat like telling people that, okay, you can now go ahead and take your time off, it will look much more as a positive indicator to your teams and businesses as well that, okay, right now, they are caring enough about us as well and not just the revenue numbers.

Kushal: That sounds like a lot of intelligent sort of calculation between what our business demands, and then really what our team members need. And so I think there's a fair bit of, you know, data crunching, but also then sort of emotion crunching as well to be done there. Pradeep, going a little ahead, right, given that 70% or so folks do feel like you know, maybe this is going to be slow so it's okay to maybe take some time off, is the best way to take some time off fordo you think for folks who are still at work? What's the best way to sort of utilize this time?

Pradeep: Got it. That’s great. So the important slogan that we all should remember is, “you don’t stay at work and take time off,” right. And that generally happens these last two weeks, even when I was in AE, right. Being completely candid, and not sure if my ex-boss is here and watching it. But when I was in AE back then like seven to eight years back, I used to like sit at work, December like last two weeks, I used to chill, enjoy, enjoy time, have the great fun of my life. Sometimes it happens, right, because like, I used to get like four or five calls. And now I used to like sit and wait around for calls. And maybe I'll get even just two for a week, right. I used to be very happy about that. 

But the reality is if you're staying at work then the only thing that you can do to be a lot more productive is prospecting, right. And that is what I would recommend, right. Because mostly like 90% of the cases, if you have not seen the deal before the 20^th of December, you will never see the deal come through before the end of the year, right, because it's extremely hard, right, because people will go on leave and it's like you have to like move mountains for your product to be the first priority when somebody is returning from the vacation, right. Because like when somebody is returning from vacation, there's going to be a ton of things on their plate. And they'll, it will take time to check things off, right, of the plate. So what you can do at best, I also saw one of the comments to my post where I think a sales leader has mentioned that they got like 50 plus demos during this time.

Kushal: Right. 

Pradeep: And that's basically because their ideal persona would have been much more attentive or much more receptive during this particular space. That's why I tell always analyze your persona, always analyze a business first, right. And based on that, you can go ahead and tailor make your prospecting strategy, right, because now that you have a lot of time, you can go surgical, right. It's always about, like whether you're going ahead for a net fishing, or a rod fishing, right? And during other times of the business, you can go ahead and do net fishing, right. But now you have a lot more time, bandwidth and mental capacity to do a rod fishing. So you can get and the exact customers who you would like to talk to in the next financial year right now, right, and that's the best strategy to do.

Kushal: That sounds like sales teams should, sales reps especially, should really be using this time to sort of get in touch with their ideal customers, establish that trust, set up all of those steps so that when you know as soon as January kicks in, then those folks are, you know, you know, your product or service is top of the mind. And that's hopefully a priority for the other person as well.

Pradeep: Exactly right. Because like anyway with Jan, majority of teams, again, we'll be a little distracted with sales kickoff, right. And for the viewers, we'll also be doing upcoming sessions on sales kickoffs, as well. So feel free to follow this on LinkedIn live. And generally with such distraction, Jan also demands a good month, right. Because that sets the precedence for the whole year. Not numbers wise or not factually, but more or an emotional side, right, when Jan is great, your business by itself, the people within the business also will tend to think that, okay, now this financial year is going to go great. Let me just put in my best efforts to make it happen, right. And that just sets emotional positivity to your team as well. So since both are striking at the same time, your sales kickoff and the expectation of great Jan, right, you need to really work on your pipeline during the last two weeks of December. 

Kushal: So Pradeep, talking of teams, and maybe adding a little bit of controversy to this discussion, I'm just going to ask on behalf of you know, all of the sales reps and the AEs, should sales leaders be giving their team's quota relief over the holidays, especially after the 20^th as you put it?

Pradeep: I'll add a little bit of diplomacy to the controversy as well, right, where I'm not going to just rule out by saying it depends upon the business again, right, because I've told that enough. But I would say it depends on mostly the financial and the culture that you want to build as well. Basically, the quota relief is an indicator that drives the behavior for business, right, and it can be taken either ways, right. So if people are giving a quota relief, then right now, my 70% becomes 100%, right. And people can either perceive it in two ways. If a person has already done 70%, they can perceive it that okay, I'm now done with my numbers, let me just close the month or year out, right. Or people can think like, Okay, now 30% is 100%. Now, if I do more, I'll get more accelerators on it, right? So it depends upon the way you want to like you want your business to think, your reps to think, right, and your overall dynamics to work as well, right. And for this to work, like effectively, the only two things that you got to analyze is the people who work for your team, and also the business dynamics as well, right. So if your business is under a good pressure that you have to like deliver a solid result before the end of December, then I wouldn't suggest quota relief, that's the last thing you want to do. But the business is already doing really well, right. And you just want to like give more flexibility to your people, then I wouldn't be against it as well, right. It's a great thing to do, right. And 50% of the people will always be like okay, now I'm done with the quota and for 50% will be like, okay, now's the time to overachieve, right. So that mindset will always be there. You just got to mentally prepare for that, and then go ahead and do it, right. But there's no harm in doing it if your business is sound and solid and you're almost at your quarterly numbers.

Kushal: So clearly all sorts will make a sales team, like I said, right, it could be like super ambitious folks. It could also be people who've sort of done some part of the quota, there's still some distance to go. And I guess that's, it's probably, it makes sense to kind of take it one team at a time and not to use a blanket approach necessarily across the board. Going a little ahead Pradeep, for those who want to focus on building their pipeline, what are maybe the top ways that you suggest for people to really focus their energies on?

Pradeep: Got it, great. So now's the time, now's the right time to experiment a few new tactics as well, like video prospecting, right. And going heavy on LinkedIn. Like if your persona is available a lot on LinkedIn. For example, in our case, in Wingman, our principal persona will be a lot on LinkedIn, right. And now, I've been telling my reps that this is a great time to go heavy on LinkedIn, right now you can go ahead and do a quick loom video and share it on LinkedIn, right, or test out the LinkedIn voice feature as well, right, and these kinds of like creative methods could be adopted to go ahead and generate prospecting, right. Because obviously, obviously when somebody's celebrating a holiday, or they're going ahead and calling them in between, right, they will be like somewhat pissed. When you especially, when you ask the question, how are you doing, right? Yeah, the last thing that they will expect is like, oh, okay, Pradeep is there on the line? I'm very excited. Like, really? Like, no. So yeah, and instead like, now's the chance to be like more genuine as well, right, or try different other methods like sending gifts to your prospects, right, seeing how that's working, right. And trying out a little bit more ABM approach, right, where you're tying closely with marketing as well, right, especially at the end of the year, and going surgical on your approach with your prospects, right. And that is some of the tactics that I'll recommend, especially during this particular time of the year, right, because it's not good to be too aggressive, right. And if you're passive, you will always be left behind. So you got to understand that fine balance and attack on the right channels, where your prospects can engage a lot.

Kushal: Pradeep, you spoke of video prospecting, right. And that's one of the trends that we're seeing across the board. A lot of other sales leaders have also spoken about how folks are increasingly sort of responding to video prospecting. It will be great to hear about maybe some of the best examples that you've seen, or you know, what your guidelines would really be for someone to do video prospecting well?

Pradeep: Got it. See the why video prospecting will work or why will it fail? I'll just give one example for both, right? So why it will work is if you're very genuine in the video, right. If you're striking a conversation very casually, right, with genuinely, like, you're genuinely trying to help out a person, right. Not… not a fake pitch, or a fake talk track or a script that you talk about, right. And that will generally not work, right. So why video prospecting is becoming a trend or increasingly like drawing a lot of attention is because like, imagine, you start and end your day looking at emails, right. And you suddenly get something different. You will obviously have the curiosity to go and look, watch it. So you're getting open rate easily, right. That is the first way to go ahead and get a reply, right. And second is the quality of your content, right. And I would say extremely short and extremely genuine, like get to the point immediately, right. If you say something like, hey, you know what, I saw that you love football, and keep talking about football for the next two or three minutes, right. Obviously, the person is going to figure it out, right. They'll read between the lines, right. Versus like, you can talk about the direct pain that you're solving, because people know that you're reaching out to them to do business, right. But what value do you add is the principal thing that you need to focus on. And keeping it really short to the point concise and precise, right, that will get you the final thing, which is the most important thing that I played it, right. And like being, if you're again, like going with videos really strong. If your CTA (call to action) is really soft, like, hey, respond to it, like it, comment it, right, that's soft, right, then it's not going to work again, right. Instead, you just asked for 5 minutes or 10 minutes on a call, right, then it's a hot CTA, but it'll work. Because people will appreciate you being upfront and asking for their time as well and telling them how you're going to utilize it.

Kushal: I think it's really key that you spoke about making interesting sort of videos, concise and precise as well. In fact, one of, I think the best pieces of outreach that I've also received as a marketer came from someone called Mitch Pelroy, shout out to him as well. Video very interestingly, he had about I think two or three dogs in his background, and I’m a dog person for those of you who may not know this already, and he had about, you know, two or three dogs in his background kept it very casual, very honest as you pointed out, like there was no pretense there was no okay, you know what? Here I am sitting in a suit and a tie in my office. There was none of that this was you know, a couple of months ago, everyone was working from home, no exceptions. And it was a very honest sort of portrayal of what working from home really meant for a lot of folks. And that video just caught my eye. Because in a sea of even videos, right, although video in itself is not entirely overused yet, I think there's a lot of potential if it's done right, as is true with a lot of mediums. But with this one, it was especially a very honest, fresh sort of very real approach. And I think that's really what stood out in that video and really made me respond to that piece of outreach. So I think there's a lot to be said about really being creative, thinking creatively when it comes to a lot of you know, this prospecting content and basing a lot of that based on who you are as a person and keeping it very real. Because it's, I know it's a cliche, right, but it's like they say, you're literally the only person that's unique. And that's going to be the most unique piece about you, whether that's a person or a brand, the fact is that there's only one of you, whether that's one of your company or one of you. So it makes sense to kind of base a lot of your content. And this is from the perspective of someone who receives a lot of it, but it makes sense, it makes no sense to sort of base off a lot of it on who you are, and keep it really honest and authentic. 

Pradeep, just to go ahead also to you know, your point around LinkedIn, we hear a lot of reps getting a lot of flak, you know, for sort of what they typically call, you know, connect, and you know, pitch and immediately do a bit slap, right, and I've received some of those as well, someone connects with me, and that the next minute I get, you know, an outreach for them. I might even be interested in the service, but I'm probably so cheesed off with that experience of how transactional that feels, in some sense that I might not respond. I get why people would do it though, because if one wants to meet their targets, right, they've been told to reach accounts, message them, get responses, what needs to change here? Is it sales leaders who need to change their mindset or, you know, is it sales reps who really need to kind of be mentored to do better?

Pradeep: Yeah, great question, right. So when this happens more often than not, immediately, I've seen people like blame the sales reps right away. I've also seen like, some sales leaders openly shout out sales reps, who are actually doing this by name calling too right, and those are like some pretty bad stuff that are happening in the market, right. If you think with some level head, right, then the reality of this is the people who are doing this are not being coached enough or coached correctly, or the… to think even ahead, just go ahead and look at the profile of the sales leader who's leading them, right. And you will often see some people who are like very antiquated or out of touch from the market, right. We're actually reading these. And more often than not, like 10 years before this could have worked. It could have worked, right, because like people were all out on sending emails, and then like activity rate is directly proportional to your demos or your orders, right. And that was the kind of sales people were doing, like a decade to the get back, right. And people will, people are still following it, like some people are still following. And that's mostly because the playbook is defined like that. If you see if you look at that email, like I used to, like, look at those emails, look at those messages, right, in detail to understand why people are even doing this. And the very reason I can see is, they're clearly written down, they are being given to them, right. And when you give something to them, it's more often than not like one person's brain that's acting, right. So what I would generally recommend sales leaders to do is trust your people, right. Get yourself really updated in the market, right. And three years, give them a framework, not a pitch or a talk track, right. So it's very easy to give a pitch, or to give a talk track out, right. And, like very honestly, you give a pitch or you give a talk track only dumb people, right. People who are extremely smart will figure it out, right. And make it a point to hire extremely smart people, right. So whenever I give talk tracks, I do give top tracks I do give pitch, but everything will be framed as a framework, nothing will be a hard and fast rule that you have to use the exact same words, exact same line, exact same punctuation and all that, right. Because that could break the creativity, right? There is still a human connect to the profession that we are doing. That is why we still exist, right. Every other day, there are tons of tools that just come up in the market that say that, hey, we are going to replace and that is the fundamental like people are now calling it what… I was watching a show that Nathan was posting yesterday, and I could see like one of the founder come in and tell that, hey, the future is going to be like customer-led buying, right? And salespeople are going to go like salespeople are going to be eradicated around the world. People have been saying this for three decades now and still we exist, right. The thing is we evolve with time, right, that is my point, right. Right now it's all about creativity, like letting your people think clearly, right, and getting yourself updated with the trend and with the market as well is very, very important as a sales leader, right. Just like how it is important for a developer to understand the new technologies out there and getting themselves updated, it's also important for salespeople to understand and catch the latest trends that are happening in the market and getting themselves updated with.

Kushal: Great points, Pradeep. And I just reminded of this segment from Friends. I don't know if you've watched a segment of this episode where Phoebe gets, you know, cold calling job at, you know, an office, and she just has a script that she needs to go through. And you know, she calls up someone and the poor guy I think has just lost his grandmother or you know, he's in a bad shape. And she's because… she's like, I need to get through my script, right. Because that's literally what she has in front of her. So she doesn't know how to kind of get off that and just that entire experience, of course tells her that she's maybe not the best person to be in sales, or at least cold calling, right because we know it takes heart. Cold calling was also an art and it takes a lot of heart to do as well. So I think great points around creating guardrails and really framework for your team to use and encouraging thing to kind of, you know, fill in the blanks and you know, to kind of grow and make that better, I think really great point around kind of upskilling ourselves as sales leaders as well and keeping up to date with what's really happening in the… Great conversation, Pradeep. I think this has been incredibly useful. One last question for you. As a sales leader, right, what will sort of give me, you know, if this is a time of reset for you, what do you think you want to kind of double down on, or what will your priorities be as you kind of get into the New Year?

Pradeep: Great question. So the core priority will be to understand, reflect on the mistakes that I did personally, not connected to any business, right, but personally throughout the year. Like, we will go wrong multiple times in multiple areas, right. And more often than not, it could be like, as simple as owning your reps' trust, right. And as complex as, okay, winning against your comp, and people can go wrong all the way, right. And the one thing that I would recommend for sales leaders is always be paranoid about the market, right. Because like, market flips you over in no time, right. And that is something… and always be grounded to reality as well. Sometimes, like when you get exceptional results, it's possible that you're on a spike, right. And then like, I see sales leaders like jumping all over, like, instead of like, it's okay to be grounded to reality, and then understand what will come and kill you tomorrow so that you can kill it right away.

Kushal: Yeah. Got it. Get it before it gets you.

Pradeep: Exactly right. That is what I will be focusing on as well, right, reflect on my mistakes, right, and then see what I can correct, right, as I'm going through the next year. 

Kushal: Thanks so much, Pradeep. I think this has been an amazing conversation. This has also been one of our first “On the Flip Side” podcast lives. And I'm sure there'll be many, many more interesting episodes. And of course, we have amazing plans as well for all of our audience in 2022. So yeah, we will come back with some more amazing content when we see you back in 2022. Thanks so much Pradeep. We've had a great conversation with you.

Pradeep: Thank you, Kushal, and thanks to all the viewers. Bye, bye.

Kushal: Bye, bye.