Limitless: A Sales and Marketing Podcast

S3 E4: Tried and Tested Tips to Prospect Like a Pro Ft. Cory Bray

Episode Summary

Hey Listener! Wanna learn the tried and tested methods to prospect like a pro? We brought you the prospecting leader whom the sales world admires! Give it up for Cory Bray, 8x author and co-founder at CoachCRM. He has built high-performing sales teams in industries that range from manufacturing to technology. Corey is passionate about making sales accessible, actionable, and scalable with coaching.

Episode Notes

The key takeaways are...

Grab a copy of Cory's sales works: 
Book 1: Triangle Selling: Sales Fundamentals to Fuel Growth - https://amzn.to/3yIMBnp
Book 2: The Sales Enablement Playbook - https://amzn.to/3fMpf9M

Episode Transcription

Hey, all! Welcome to another episode of our Limitless Podcast series. I'm Nisha, a product marketer, at Hippo Video and your podcast host. We have with us today Corey Bray. Hey, Corey. Welcome to Limitless. 

Thank you so much for having me today. 

Great to have you here. It's completely our pleasure. So a little bit about Corey.

Corey is the co-founder of CoachCRM and the co-founder of ClozeLoop, and a partner in 2.12 Angels, which is a seed-stage venture fund. He has also written 8 top-selling books on B2B sales and sales management. He has built high-performing sales teams in industries that range from manufacturing to technology.

Corey is passionate about making sales accessible, actionable, and scalable with coaching. So today, Corey will be sharing with us some tried and true tips to prospect like pro. So let's dive right into the questions. So, Corey, here's my first question for you. Most sales reps are little bit self doubt when it comes to cold outreach, how can they overcome that fear of cold knowledge?

I think what people are scared of is not winning, and maybe that's not necessarily losing, but maybe it's being stagnant. And what we often find is that the best cure for hesitation, concern, and for call reluctance is winning. So the thing that organizations can do is equip people with the messaging, the lists, the technology, the tools, and everything that they need to do.

So they can sit down, do their job and win. Because if they're not doing that, then it's gonna be hard to keep people motivated. And that's really the answer here. It's not something that you can just snap your fingers and do. But if you're not winning, if you don't feel like you're winning, then things are gonna seem harder than they are.

After like maybe losing out on, I don't know, like 5 to 6 consequently, there's that inherent confidence drop. Right. So how do they overcome that? How do they get their feet back up? 

Well, losing a deal isn't something that you can control. And I think there's only two things that salespeople can control. They can control their quantity of activity and their quality of activity. And if that's all that they focus on, they're gonna be in a great position. They can look at what they're doing and, and maybe if the deal didn't go their way, well, did they do the right quantity of that could be preparation for the meeting.

It could be the number of questions that they ask. It could be a lot of different things that they can measure. And then in terms of the quality of activity, what could they have changed that could have impacted that deal? And if you can take learnings away from one deal you might not have won and apply those in future situations, that's great.

And that can help you feel like maybe you didn't win the deal, but you got better and you're putting yourself in a better position to win the next.

Okay. Yeah, that makes sense. Okay. So onto the next one. So what's one phrase or line sales reps can open with that will make the prospect want to talk to them.

Like it didn't be specific to any industry any product, like just a generic line. And are you talking about in, in what type of meeting? Uh, the first call. Oh, in a cold call. Well, in a cold call, there's people who get hit with cold calls all day long, and a lot of them are ranging from your auto insurance to what, what do they, the warranty renewal . And so they're, you're getting these things on your phone pop up day by day by day or all, all the time throughout the day. And I think one of the best-recognized ways to get past that is to interrupt the pattern and do something a little bit different and throw the prospect off a little bit, pique their curiosity have 'em think, uh, who is this?

What do you want? And then they can hear you out. I think that's the thing that we see work the best when you can, you can throw 'em off a little bit at the beginning with some kind of interruption. Okay. Like, say something unconventional on something that hasn't been said before. Well, yeah. And it's something like there are a million ways to do this.

There's not a right way. One of the ways, that we advise people to do this, we do internally is we'll say, Hey, this query from closed loop, that probably didn't sound familiar. Does. And when you say that in the negative format, it makes people think, oh, does that sound familiar? I don't know. And they're thinking, and then they say yes or no, if they've heard of us before.

Great. If they haven't, they'll say no, what's this all about? And then we can move into the next phase where we're getting closer to delivering our elevator pitch. That tells 'em why the heck we're here. I think that, again, lots of ways to do this. The what, what you don't wanna do is just sound like every single person that's calling them all day long.

Yeah. That, just gets them. It's like, when you walk into a store and someone says, can I help you find anything? Even if you're there looking for something, most people are gonna say, no, thanks, I'm just looking. Yeah. And you're doing that because people are scared of salespeople trying to sell 'em something to donate.

Yeah, that's very true. I mean, we recently did a webinar with, you know, Beck Holland on how to use video as a pattern interrupt in sales. Like, so that term was yeah. A little familiar, I guess. Yeah. Yeah. Okay. Thank you for that. So the next one is, uh, a good chunk of these leads grow cold after discovery calls.

So what are some questions that reps should ask prospects on the call? How can they ensure that, you know, they end with something that guarantees them the next meeting? 

Yeah, meetings go cold after the discovery call, typically because there wasn't enough pain uncovered in order to justify the prospect investing more time.

When we think about emotions that drive a buying decision there's usually three main buckets there's pleasure or reward in bucket one, there's fear in bucket two, and there's pain in bucket three. And if we're able to find pain, then prospects will prioritize what we're talking about more.

And they'll also make a decision on a compressed timeline. Okay. That's what's gonna drive a, a faster decision. So if you're on a call and you're unable to uncover pain based on what I just said, you're extending the timeline and reducing the priority, which is often what gets them to shove you aside and think, oh, well, we'll work on something else now.

And then we might come back to this in the future. Or we might not. And so that's the key and, and the way to get there is for the salesperson to really understand what pain points does my company solve, for which personas in which market segments. And then if it's a platform potentially with what use cases.

And if you thoroughly understand that and know where you're uniquely positioned to win both against the competition and against do nothing, then when you're in that discovery call, you've got pretty good guidance around what to talk about. I can go to you. And I say, Hey, look, we're working with folks who are concerned about this pain point, struggling with this pain point and anxious about this pain point.

Does any of that popping up in your life over there? And what I've done is delivered specific winning pain points that if we, if they have them, then we're gonna be in a pretty good position to at least create some velocity with the deal and have a chance if not. 

So this is all the research that has to be done before the discovery call, defining your ICP, identifying the audience, the problems you solve for your audience and all that.

Yeah. If a salesperson shows up to a meeting and they don't know what pain points they solve for which personas and which market segments. Yeah. Then they're not set up for success and they're not gonna win. And like I talked about earlier, the best cure for a bad attitude or motivation is winning.

Yeah. That's absolutely true. Okay, so the next one is trust is one of the most crucial factors in pushing prospects along the pipeline. How can sales reps build trust in communications throughout the process? 

Yeah the framework that we use for trust is the scale framework. And this is something that we've adapted from some other work that's out there in the human knowledge corpus world.

And there's really five key drivers here. A couple of them that are really relevant to sales processes are certainty people knowing what's going to happen next. Autonomy, having the ability to say no and likeness ensuring that social proof is tied to things that are similar to the prospect.

For example, I'm a large company and you're telling me how you help small companies. I don't care. And if I'm a small company and you're telling me how I, how you help large companies, I also don't care. So there are a few different levers that we can pull to really establish trust there. Those are some of them.

And then the salesperson just keep an eye out. If they feel like the prospect stops opening up, doesn't talk as much. Isn't accepting a calendar invite for next meeting. Then there's one of two things that's probably happened either. We haven't uncovered enough pain, so they don't understand why this should matter to them or we haven't established enough trust. And so they're not going to, to open and be honest with us. 

Okay. Got it. So this is tying in with my previous question. How important is personalization in cold emails? 

You know, because personalization is usually equated with trust. So how can sales trust, personalize emails at scale. I don't know that they need to.

I think that if someone sends an email that shows how they solve specific pain points for a specific persona, that's in a specific market, the fact that you layer on, Hey, you know, go Ohio State Buckeyes, or I enjoyed your speech that I listened to in in the podcast, the other. I, I haven't seen any evidence that that substantially moves the needle.

The evidence that we've seen is that if you tailor the message relevant to the pain points you solve for the persona in the market in which they operate, then that absolutely moves the needle. But if you get into deep personalization, I don't know. I just, I would love if anybody has any real research around this.

I'd love to see it. It's something that we can sit here and talk about and say, yeah, we need to do that. But it's also something that takes a substantial amount of time. Now, granted, if there's a, an individual that just won an award or published a book or something like that yeah. Send him and personalized note.

Absolutely. But feeling like you have to force personalization with each interaction, I think it is flawed. But again, I'm open to learning. If someone's found some real research there, I just haven't seen it. Okay. So I think there are some controversial opinions, controversial opinions on it. Like some, you know, advocate, personalization, like, and you say like, it's just pain points that matter.

It's not personalization. That's what matters. I don't care that, you know, okay. I went to Warr and I'm founder of a couple companies. I've written some books. If anybody mentions that in a message, it doesn't change my motivation to buy something from you. I'm only gonna buy something from you if it solves the top business problem for me.

Yeah. Fair enough. Yeah. Okay. So this next question is because yeah, we are a video sales enablement platform. So I have to ask this. Yeah. Have we used to consider using video and cold outreach? So do you think, you know, having a name to a face would play a role in building trust? What is your opinion on that?

I love video throughout the sales process in cold outreach. One of the ways that I like to use it is have your face down in the corner, over the top of a case study, talking about how you solve specific pain points for a specific persona in a specific market segment. And for these again, it's not personalized, but it's persona-lized. The person that's receiving the video, looks at it and says, oh, wow, that seems relevant to me. Do I have that problem? Do I not? And then they can make a decision whether or not they wanna meet with you. I think that's key. I'm not a huge fan of just your face up on the screen saying, Hey, how's it going? Yeah. I don't think that adds nearly as much value as having a backdrop of something that's relevant to the individual that you're prospect matters more to the face.

Yeah, totally. I mean, it's nice to have people are visual people, like things moving around and if you go to Moravian's law, If I can do this off top of my head, I think they said that professor Marabi and said that communication has three components and 7% of the impact is from the words we say 38% is tone of voice.

And then 45% is a visual piece. So if I just speak the words, just the words, just the words don't do anything. The tone of voice adds a lot of context. Adding a visual element helps even more. So having that little, little face on there at some point in the screen, alongside the content that does bring things to life and there is a ton of value there.

Yeah. That makes absolute sense. Okay. So this is a very general question. So how different to sales and a small business from an enterprise, like does the approach or the process differ. 

When you're selling to a small business versus enterprise, or when you are a small business versus an enterprise,? 

When you're selling to a small business or an enterprise, your audience.

Yeah. Well, when you're selling to a small business, there's usually one person that can make a decision. They can put it on their credit card, they can do whatever they want. In an enterprise, there's lots of people because there's politics and regardless of ego to the top person, they need to ask people below them or the person below them.

They need to ask people above them, get a lot of different stakeholders. And then they've got finance, legal procurement, our favorite sales prevention departments inside of companies. Whereas small business. Yeah. If the business owner or the CEO wants to make a decision, they will. And if they come back and say, Hey, I've gotta talk to my team about this.

It's funny. I was talking to somebody about this. I don't, maybe it was on LinkedIn. Maybe it was at 10 or the other night. And they said, well, sometimes the business owner or whoever it is says, I've gotta talk to my team and let them help make the decision. If that's happening in a small business, it's, it's either resistance or objection where the business owners saying, I don't think this is that important, or they just don't wanna deal with it.

They've got other things to focus on. That's something that we see quite often and then enterprise deals they take, they take longer. And they've got all kinds of risk. I think one of the, when it, when it comes to the longer term idea of sales, meaning not just getting the contract signed, but making them fully, fully successful.

A lot of times the person that signs the contract is not the person that's doing the work. Yeah. And that can cause friction because then the people that are supposed to implement it might have other priorities and it might not even get off the ground. We see that in enterprise sometimes not, not with our business, but with some of the folks we work.

Okay. So the sales cycle is usually shorter with this and these right than it is with. Oh yeah. Well, they should be, but they can be long to, I mean, I'm a big fan of long sales cycles. 

That's interesting. Okay. Why is that so? 

Well, because it's, it's not always a 30-day buying window or, or a 60-day buying window.

I've closed a couple of deals recently on one-plus-year sales cycles with not gigantic businesses. Things just take time. And, I think that assigning a reasonable length to the sales process for a deal. If someone's got a compelling event, then the sales cycle should be short if they don't have a compelling event and they've got some pain, but they've got other priorities, then you've just gotta stick around and be there to solve the pain when the other priorities get solved for and the triangle selling methodology.

That's referred to as energy. They just don't have the energy to do all of the things at once. So you've gotta wait until they have enough energy to, to bite off something new. In terms of, of video sales, for example, maybe they're implementing a new CRM, a new sales methodology, maybe they're hiring a bunch of people.

Maybe one of the sales leaders left the company they've gotta solve for all of those things. And then they can tighten up tech stack. That may be an example, and it might take six to nine months to get through that at which point, boom. Now it's time for you. And I don't think that people should disqualify deals just because it doesn't fit into a 30 or 60-day sales cycle.

Yeah. But at the same time, you've got a close revenue. I think just understanding what a reasonable sales cycle would be given a deal, giving the attributes of a deal. That's smart. Trying to force it. Isn't it. But the revenue you get from, it also matters, right? Like if it's worth it or not. So, yeah. So if, if they're not, if they're not being honest with you, then I, you just disqualify it.

If they're telling you that they wanna do it, then they don't, then they do. Then they don't. That's a mess. But if there's a reason to believe that, Hey, they will buy in six months or they'll seriously consider it in six months, work the deal. That's my opinion. 

Okay, great. So this is a question based on the current environment. So the world is slowly entering a recession. What is it for salespeople to weather the storm? How can they sustain their deals and build their pipeline? Well my opinion, again, I'm not an economist. Okay. My opinion is that we're slowly coming out of recession out of recession. We entered a recession January 1st, technically, which means that we were entering a recession in Q4.

So it's almost been a year since we started entering the recession. And I think this is, there's an old saying that says when your cab driver starts telling you to buy stocks, sell stocks. And I spend a lot, I have a dog. I've got a 10 pound shitzu and she's great. Oh, okay.

She'll be going for walks. So whenever I go for walks with her, I listen to podcasts typically hosted by venture capitalists. And the things that I'm hearing on these podcasts are more and more positive, especially for early stage companies. Obviously some late stage companies raise money at just ridiculous valuations.

And they're not having a great time right now, but, what I'm hearing is more and more positive things for early stage, some somewhat positive economic indicators. But then on the internet, on LinkedIn, that's kind of like the cab driver telling you to sell stocks. Everybody's freaking out that we're entering a recession, but I think they're nine months behind the curve and yeah.

Will it last for longer? Maybe? I don't know. But it's definitely in the middle to late phases. If history holds, if you go back and look at historical recessions, they don't last for six quarters, you know, they'll typically last for 1, 2, 3 quarters. They can last longer. I think in, in 2001, we went for upwards of six quarters.

But we're, we're in the third halfway through the third quarter of it right now. So I think that just like when COVID started and everybody started freaking out well, yeah, the economy was booming three to four months later. At the same time where people were saying that the sky was falling in the general public forum.

So I think it's, it's important for folks to be very careful of that and not just follow what random strangers say and, and maybe invest in energy and hearing what the experts have to say. Again, I am not an expert economist. I'm just referring to what I've heard. Some folks that are way smarter than me say.

So when it's uplifting to know that you are out of danger because you know, people keep saying, oh my God, we're entering it to a recession. And they're all in panic mode, but you so insane. No, I mean, I just, I just went to the, I was, I was a couple of minutes late cause I was in my car. I had to go to the bank because I just got the biggest check we've ever received as a business.

Wow. Okay. Congratulations on that. It wasn't a million dollars, but it was, it was into the six figures and the biggest one ever. But the economy's terrible. No, I mean, Definitely. Yes, there are, there are bad things going on, but there are always bad things going on. Um, I live in Texas. The oil business is booming right now, so it, it feels pretty good down here too, just because of that.

Okay. So that's great to know.  I'm sure the audience will also be, uh, yeah, pretty happy hearing this. Okay. Uh, so this is my penalty. My question for you. So what is your advice for sales leaders? How do you, or how do they, how can they set their sales team up for success? And how do you coach sales leaders and what metrics do you make them track when you coach them?

Well, I think that for, a sales leader, let's, let's talk about two different groups of people. Let's talk about manager managers that manage individual contributors and managers that manage managers. So there's because there's two different, there's two different answers to this. So the, the folks that manage individual contributors.

The thing that we're seeing folks have the most success with with, uh, coach CRM. That's that's my, my software business. We, we focus on coaching, helping people become better coaches. Okay. Is that if every manager has one specific thing that they're coaching each person on their team on at all times, working towards resolving that, holding the person accountable to doing something, to resolve it, and then moving on to the next.

that's how they can just consistently up level their team and help everybody on the team consistently be better. Just one thing that they're coaching, that's going to move the needle. That's going to have an impact. And then from the manager of manager's level, their job is to hold the managers accountable to doing that, looking across the organization and understanding.

Yeah, I've got six different frontline managers. Let's look at what they're coaching. Are they coaching at all? Are they coaching frequently? Are they coaching on the things that matter? Getting visibility into that helps senior leadership operate the human capital of the organization, much like they do the, the financial capital by getting, getting insight into where the, the specific skill or mindset gaps are across the team.

And then understanding if things are being done to address those or not. And so they can get better. I think that with, with your point about the economy, Again, my point was that we're things look like they could be getting better, but people are still nervous. And when folks are nervous, they double down on operational efficiency.

They wanna ensure that they're getting more out of their current team. And the number one way to do that is coaching. Got it. Okay. So what about the metrics that, uh, should track, like apart from the obvious metrics of revenue and deals close? Like what other metrics are they supposed to. Yeah, the going back to the point that salespeople can only control two things, their quality of activity and quantity of activity.

It's important for managers to have a good set of leading indicators. You mentioned revenue and, and quota attainment, things like that. Yeah. Those are lagging indicators. Those are good. We need to hit those. The leading indicators are things like how many deals have we uncovered a, a pain point that's worth solving.

Do we have next steps? Has the prospect agreed to them? Are they in the future? Mm, what's our pipeline coverage ratio. How many, how much revenue do we have in the pipeline versus what we, we need to close in order to hit our goals. But I think the, the thing that I drift towards is focusing on those qualitative metrics, such as have we documented the pain is the pain compelling is the next step.

Yeah. Agreed to by the prospect. And is it in the future? If those things happen, they drive all of the other quantitative metrics. To move towards where you want them to be. But if all you do is focus on lagging indicators and quantitative metrics, then you're coaching something that the salesperson can't control.

They can't control close date. Yeah. They can't control legal red lines. They can't control any of that type of stuff. So only coach do things that people can control is the big takeaway here. So this is something that salespeople can improve on the leading metrics that you. Yeah. What, and, and for each role, obviously I think the examples I was using was for an account executive for customer success manager, it might be, do we have quarterly business reviews?

Are we identifying pain related to upsell opportunities, things like that. Are we getting the right people involved for cross-sell or upsell conversations? What, whatever those leading indicators are per department, then for sales development, you know, obviously number of accounts, being targeted, number of people enrolled in sequences, things like that.

Those, those help you get, get an insight into are we positioned to hit those outcome metrics that are so important? But you can't just tell somebody, Hey, book, more meetings. You there, there's a gap there between what you want them to do and what they're gonna sit down and do at 2:30 PM today. Yeah.

Thanks. Absolute sense. Okay. So Corey, this is my last question for you. What are some books or podcasts that you recommend? Every salespeople, every salesperson read or listen to. Well, I've written 8. I've written 8 books. They're all pretty good. So if you're in sales development, we've got sales development and 46 reasons your cold calls fail and how to fix 'em fast.

Okay. For managers, the five secrets of a sales coach is part of the best book, but we've also got hiring onboarding, and ramping salespeople and sales. Playbook's a builders toolkit along with the sales enable playbook. And then for salespeople, triangle selling and the triangle selling field guide.

And the reason we wrote these books is we saw a gap in the market. Yeah. There's, there's tons of great content out there around mindset and go get 'em and motivational that type of content. But in terms of sitting down and doing something that's framework oriented, that's where we saw the gap. And that's why we started writing these books.

In terms of podcasts, the ones I like this weekend, startups all in acquired, and the Andrea podcast is the ones I've been listening to. Okay. I'll make sure to listen to the recording and no on all the books and listed down. Yeah. I'm sure our listeners would also get, you know, great value out of your books since, you know, I think everyone has a problem, right?

Like they all have those big motivational speeches and all that, but it's the tiny gaps that. Yeah. And if anybody lists this once a book we'll send you a copy. Just send me an email or a LinkedIn message. Yeah. Yep. That'll be great. Okay. So I think we can have the conversation after the recording.

All right. Uh, sari. Yeah. That those were all the questions, I had for you. Thank you so much, Corey, for giving our business, those memorable and actionable tips. And thank you, listeners for tuning in today. We'll be doing many more of these podcasts with more such stellar sales leaders from around the globe.

So stay tuned for our upcoming episodes. We are on Apple, Spotify, Google, and well subscribe to get notified when a new episode is out. And please leave a review of you're on Apple. Thank you for listening bye-bye and have a great day. Thank you