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The Outbound Playbook: Problems, Signals, Execution
Episode 68411th June 2026 • The Daily Sales Show • Sell Better
00:00:00 00:44:42

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Outbound rarely fails because reps are lazy. It fails because nobody told them who to target, what to say, or how often to say it.

Will Aitken ran this one solo, walking through the outbound system he builds for teams. Almost every broken outbound motion fails at one of three points: weak messaging, targeting that is far too broad, and execution with no system behind it.

Your buyer never asked what you do

Ninety-five percent of the market is not buying right now, so leading with your product lands on nobody. Will's fix is to work out the buyer's status quo first. Competitor, doing it themselves, spreadsheet, or outsourced? Each breaks differently, and those breakages are what you reach out about.

His shortcut for any role: every function exists to make the company money or protect the company's money. Work out which, then how that person is measured.

The problem identification chart

Will's core tool, borrowed from Gap Selling, which he notes he can use since he wrote the sequel. Three columns: the business problem, its impact, the root cause.

You fill it in by asking what goes wrong next, repeatedly. His worked example ran from nobody trained to handle a mental health incident, through someone getting hurt, litigation, a PR problem, employees leaving, being unable to hire, to lost revenue. That last link is what a buyer actually cares about.

Three kinds of signal, and they are not the same thing

Catalysts are events that create the problem. Layoffs mean the remaining team cannot maintain policies across twenty systems. An acquisition means two IT environments getting blended into more chaos.

Symptoms are observable directly. A job posting mentioning policy updates across networks tells you they have a capacity problem today.

Intent is someone showing interest, in you or a competitor. Downloads, profile views, an old deal cycle, site visits.

Start with the people who already half know you

Will ranks prospects by familiarity, not fit alone: past users who changed companies, old deal cycles, webinar attendees, anyone connected to your executives or customers. The version that scales is building your list from lookalikes of existing customers. Reach out to Coca-Cola on the back of your PepsiCo work and they do not know you, but they know PepsiCo.

He caps research at five minutes for mid-market, and is blunt about personalisation theatre. You cannot connect someone's interest in hiking to a cybersecurity audit. One good business reason beats a full account brief.

Know your math before you change anything

His example chain: two hundred calls, twenty connects, ten conversations lasting over thirty seconds, three meetings booked, two that showed up qualified.

Each gap points somewhere different. Few connects means contact data, call timing, or spam flagging. Connecting but not converting means your opener is not creating curiosity. Conversations that do not become meetings means the problems you raise are not the ones they have.

Resources mentioned

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Thank you to our sponsor: Outbound Sales Pro, First Orion, Replay, ZoomInfo

Transcripts

Will Aitken:

What is up, beautiful people? Welcome to the Daily Sales Show, brought to you by Sell Better. My name is Will Aitken, I'm going to be hosting today's show, and we're going to be talking about building an outbound playbook. problems, signals, and how to execute with best practice. Gonna wait a few minutes just for everyone to jump in the room, but while we wait, I'd love to hear from you in the chat. Let me know where in the world you are, what you sell. In fact, if you tell me what you sell in the chat, I might be able to use your company or what you sell as an example somewhere along the way, because I'm pretty darn good at improv as well. Now, to help us break down this topic, we've got…Oh, it's just me today! For those of you who don't know, I obviously host the Sell Better daily sales show, but I also run a sales training company, often working with teams to build their systems, playbooks, help them fix problems they're having, and of course, train their sellers as well. I'm also the author of Gap Prospecting, if you haven't read it yet, jump to Amazon and grab a copy of that.

Will Aitken:

But today, I'm going to be sharing how I typically go about doing this for a team, and sharing some of the best practices that I encourage their reps and sellers who I work with to use along the way as well. As I mentioned, let me know what you sell in the chat, and if we have any questions along the way, use the Q&A, because I want to make sure I stop and address things, and I move quick when I'm by myself. So if you need me to slow down, you need me to talk louder, you need me to talk quieter, let me know. I'll be keeping an eye on that as we go. Now, before we jump into the main content of today, let's do some housekeeping. Yeah, the show is recorded, they're always recorded. So much so, in fact, that you can go back and see any daily sales show recording on SellBetter.xyz, or by scanning that QR code on your screen right now.

Will Aitken:

You'll also be able to see all of our upcoming shows. For example, next week we have a show with the team over at Nooks, talking about how some of the best reps are executing on their cold calls, on their emails, and what they're actually doing on a day-to-day basis. That's with the director of sales over there, so he's actually going to be sharing some of the best practices they're using, which might overlap a lot of what we do here today, based on my knowledge of how they do things at Nooks, but will probably be a little bit more on the tactical side, more focused on, like, the actual subjects and the bodies and stuff like that. We will get into a little bit today, but it's gonna go deep, so be sure to check that one out. I believe it's next…Thursday or Wednesday. One of those two, I'm sure my host will help me out in the chat with that one. Now. We couldn't do these shows as often as we do them without our wonderful partners, and today the show is supported by a fair few of those partners. We've got a fair few partners working for us today. We've got Outbound Sales Pro. If you don't know, Outbound can be kind of tough. You might need it today, and some of this stuff takes time to build the skills, build the systems, stand things up. It could be expensive, and you might need results, like, next week.

Will Aitken:

That's where you might consider using a lead generation agency. But a lot of lead generation agencies out there do a horrible job of protecting your brand, and just go with the spray-and-pray approach, which can actually do more harm than good, oftentimes. Outbound Sales Pro is not one of those agencies. They do really good work, and they've booked over 10,000 meetings for their clients, so if you're looking to get set up faster, or without having to do quite as much work, then do consider checking them out. There's a link in the chat. To have a look at them. What's next? First Orion, first Orion. So yesterday, I made a cold call. I'll tell you a little story. I was making cold calls from my mobile phone yesterday. I don't normally do that, I tend to use a dialer, but I only wanted to make 5, so I didn't want to, like, log in, get into the matrix and all that stuff, so I just made some phone calls from my phone, and someone picked up and said, I picked up this phone call because it said, it's Will Aitken calling at the top of my screen. I knew your name from LinkedIn, therefore I picked up.

Will Aitken:

That is a big, big challenge that we often don't think about as sellers. 9 out of 10 Americans say they will not pick up the phone to an unrecognized number. What First Orion does is allows you to brand your call with your name or your company's name, so that people know who's calling beforehand, and are therefore actually more like to pick up. There's some awesome research data on this, and you can check out more info with the link in the chat. Whew, replay! Replay! So, guys, when I used to be an account executive, I was not good for a little while. I was really bad. And I would say one of the most impactful things that, helped me to sell better, whether it was my cold calls, my cold emails, or my discovery calls, most of my discovery calls, to be honest.

Will Aitken:

was going back and reviewing my game tape. Reviewing my own calls, listening for the filler words, having a manager who was willing to jump in there and help me and tell me where I could have done better, where I missed stuff, where I could ask another question. Now, the thing is, a lot of sellers out there don't have a manager who has the time to do that, or if you're a manager, your reps might not be as open to feedback. Replays allows AI best practice to give every feedback on pretty much every single call a rep has, so they can improve their game without feeling like they're under a microscope or being micromanaged. So check out replays, link in the chat. And then last but not least, ZoomInfo. A lot of what we're talking about here today is going to be related to what ZoomInfo helps people do. ZoomInfo is not just a data tool that you might know it as, that's not just con- emails and phone numbers, but they also have an entire platform that allows you to research buyers, look for intent signals, and level up from there, and do that at some element of scale as well, without having to go onto every single prospect's LinkedIn profile and look for that information.

Will Aitken:

They have a new GTM workspace, I think it's called, that you can check out with a link in the chat. There's some really cool stuff in there. It does a lot of the complex stuff that other tools in this space do, but does it for you, so you don't have to feel like you're a data scientist just to pull it off. Be sure to check that one out. There's a link in the chat so you can request more info on that if it sounds interesting. I'll touch on some of these as we go, if they come up during the content here today, but with all that said. I'm gonna just take a breath. And again, if you're arriving, shout yourself out in the chat, let me know where in the world you're calling in from, and let me know what you sell, and I'll try and use what you sell as an example somewhere along the way. Once again, if there are questions, use the Q&A tab, it helps me spot them quicker as well. Shout out a few people, John King in Minneapolis, Sam over in Atlanta, we got Irulin, Hunt, Warehouse Optimization Software. That's an interesting space. So those are some good examples that I can pull on later on.

Will Aitken:

So, what are we going to be talking about today? Well, we're going to be talking about how you can build an outbound system that works. Now, why do you need to build one that works? Because a lot of them don't work. They're inconsistent. They're hard to maintain, you might have… it might just be you doing the prospecting, or you might have a team of prospectors. But where I've seen most of them fall down comes down to one of these three areas. First of all, they have weak messaging. This is kind of like the stuff that seems basic, but a lot of people gloss over, and then because they have a weak message holding up everything else, it doesn't matter how good the templates are, how good the cold call opens they are, they're not going to be saying something that their prospects actually care about, and therefore, it doesn't resonate, and they have a hard time with it. The next one is bad targeting. Everyone says they have an ICP, but most people go way too broad, try and troll for fish instead of using a spearfish, so you gotta be able to know who exactly you're helping. And then also be able to identify who's the most likely to be in a buying window right now with the use of intent and signals, which we'll talk about a little bit later. And then finally, inconsistent execution.

Will Aitken:

This can be because they're not doing it often, or when they are doing it, they don't have a system to do it, so it takes a lot more time and effort to actually make a call, or it might be that they don't have a process or script laid out, and therefore, they might have a bad script they might just generate from ChatGPT or found online 5 years ago. So, inconsistent execution is the last way that I see this fall down. Even when reps aren't hitting their numbers and KPIs. it's often not because they're lazy, it's because they haven't got a clear idea of who they should be going after, what they should be saying, and how they should be doing it, which leads to inconsistent execution. So…Let's start with this first piece, weak messaging. So, I think most people out there Despite thinking they might do, really don't know their buyers as well as they think they might.

Will Aitken:

And the problem is, most buyers out there haven't actually asked what you do, so by reaching out to them and telling them more about your product or service, you often go full on deaf ears. If they wanted to know what you did, they would have already reached out to you, and they'd actually be actively buying right now. But 95% of the market is not buying. So by talking about your product, you just kind of…being ignored, essentially. To speak about something more relevant, though, you need to actually know what your buyers care about. So, let's say we use that warehouse optimization software example that I think we heard from a name that I remember mispronouncing just a moment ago. irrelelyn. what metrics… I'm assuming that you probably sell to warehouse operations managers, plant managers, those types of folks. What metrics actually gauge their success or failure? How do they know if they're doing a good job operating warehouses, or if they're doing a bad job? A lot of the time, with operations folks, it's

Will Aitken:

reducing costs, it's avoiding incidents, those types of things. But knowing those for your individual buyer will allow you to have much better conversations and write much better emails and outreach to these folks as well. You've really got to immerse yourself in their world to know what they care about, what they're doing on a day-to-day basis, and the kinds of things that actually get them in trouble, or get them loads of praise from their boss as well. Now, here's a clue for you guys. Almost every single company function, regardless if it's cybersecurity, sales, marketing, operations, HR, they are all there to do one of two things. Number one, make the company more money, or number two, protect the company's money. So, if you know that, then you just need to be able to figure out what… how they do that, and that will allow you to immediately understand their role a little bit better, and that's the kind of things you want to be speaking to when you reach out to them, the impacts that you can have on what they're doing today, and of course, that final number, how they actually get measured.

Will Aitken:

outside of that, I'm gonna guess, and I'm gonna pick on you one more time, Ariel, and I'm gonna move on to another example. Most people are probably optimizing their warehouses in some way today. Or they're not doing it, and they're just managing everything in spreadsheets. You need to know what's the likely status quo that someone has long before you get to them. Are they using a competitor? Are they doing it themselves? Are they using a spreadsheet? Are they outsourcing it? And then from that, you can derive what problems go wrong with that, that you can speak to, that your solution, service, or offering is able to actually help them solve. So in the case of a warehouse optimization thing, I'm gonna imagine that most warehouses are probably managing Excel files. That means that when they're managing them in Excel files, there's a lot of things going wrong. They're not being able to identify, get a big picture of things, they're missing potential opportunities to save on costs, whether it's power, employees, headcount, times… time,

Will Aitken:

payroll, whatever it might be. Maybe they're not using their space as effectively as possible, they just don't know, and therefore, that could be the meaning that they're losing money in that sense. However they're managing things today, you really need to have a good idea of what that looks like. So an example of ZoomInfo, let's say, is someone using another lead tool. And then, if they are using another lead tool, which is likely they are doing outbound, what are the problems that go wrong with those? Is it inaccurate contact information, which leads to wasted time and missed opportunities? Is it that reps aren't using the tool because it's too difficult to use? Is it that…The data is there, but it's, it's expensive, let's say. They're probably spending too much on the data in some cases. Knowing the problems you helped solve and what's wrong with their potential status quo will allow you to speak to those things long before you start telling them about your product, because coming back to this piece again, the buyer did not ask. So, how can you do this well? One.

Will Aitken:

go to the same kinds of events as your customers, look into their world, listen to podcasts. If you sell to lawyers, you probably don't know as much a lawyer does, right, about their field and whatnot. But you can still listen to some of the resources, you can understand their language. problems they run into, the ways they tend to do their work today, the way they speak about things, and that way you can come across much more like a peer when you reach out to them, and immediately be more relevant with any outbound messaging, whether that's a cold email or a cold call that you make to them as well. I'm gonna pick on someone else for an example here. We've got, Michael Peristine. I hope I said that right. Peristein, maybe? He's based in San Francisco, awesome. Silicon Valley. Workplace services and technology. I might need a little bit more than that just to help understand what you fully sell there. Someone else said high-tech software. By the way, be specific when you share what you sell, because I quite… don't quite know,

Will Aitken:

I'm gonna look for one that I can actually use. Freight service, okay, it's alright. I'm just gonna use another example in just a moment. Packaging sales…digital dental platform to HR benefits teams, like Virtual GP, common in UK, but for dental. Okay, okay, that's an interesting one, alright. So, in the case of Callum Brown, who sells digital dental platform to HR and benefits teams, it sounds like that's sold as an employee benefit for their teams. This is something that, again, most people feel like they don't need. They're like, yeah, we have a benefits provider, right? But by understanding what they're doing today and what often goes wrong with that. you can better position your product or service against what you can assume they're probably doing. So, if you sell to American teams. then almost every single American employee provides some kind of health insurance. And they often don't provide dental insurance as well. Same for Canada, same for the UK as well, because dental often isn't covered by public health services.

Will Aitken:

So, most people are going to probably be providing something, unless they're very small and they're just hiring their first few employees. But, even though they're providing something, that coverage may be inadequate. People might run out to it, run out of it. Employees might not feel like it's adequate enough for them to get their and their family's healthcare done, and therefore, that could be creating churn risk. What's more likely is, people aren't actually using it. So, oftentimes you're playing for these benefits, but people aren't making use of them, which means they're having zero effect, and you put these benefits in place in the first place to better retain employees and keep them around. So, by offering, a virtual GP, it's more convenient, and therefore people are more likely to use it, and therefore you're going to improve the retention and adoption of said benefit. So the problems I'd be speaking to in your case would be People aren't using the benefits platform, which leads to…retention issues or, paying for, benefits that people aren't using, right? Wasted fee… money, basically. And the impact that has over time is that people leave.

Will Aitken:

Or people feel like they're not getting benefits, or they don't feel appreciated work, or wasted funds on benefits and things for employees that they are not using that could be dedicated to things that they would like to use, which again, links back to retention initiatives and keeping people around. So just by knowing that. really well. Most people have that. You can even call out when you reach out to someone, hey, most people have dental coverage as part of their plan, but they're finding Either this is happening, people aren't using it, or this is happening. The coverage isn't enough, or it's not convenient enough. For their, their needs, and therefore they, they, again, maybe max out or don't adopt it at all. There's an example for you. One of the best tools you can do to do this is what I call a problem identification chart. It's borrowed from Gap Selling, but obviously I'm allowed to use it because I wrote the sequel to that book, Gap Prospecting. It's called a problem identification chart. Very simply, you would put your business problem in the left-hand column, you'd put the impact that can have on a business in the middle column, and you'd put the root cause on the right column.

Will Aitken:

So in the case of this dental benefits platform. The business problem might be low retention or low adoption of benefits. The root cause of that is that benefits are hard to access, maybe because they're using a peak provider. Maybe they can only go to certain, Maybe only certain, practices are in their plan. and their benefits… current benefits provider is restrictive on which practices, so they have to go out of… out of service to get dental care. The other root cause might be that they used to work at… the root cause of the retention issue might be that they used to have better benefits at a previous company. And they don't have them anymore. And the impact, then, would then be the retention, risk. wasting money on benefits people aren't using, negative Glassdoor reviews, which makes it harder to hire people in the future as well. But by mapping that out, this gives you kind of a bit of a roadmap to say what to speak to in your prospecting, in your outreach to people.

Will Aitken:

I'll use another example in just a moment. As I mentioned, folks, if you have questions while we go here, use the Q&A. In fact, what I might do here is drop you a link so you can build one of these yourself, because we do have one. I highly recommend everyone do this, exercise up front. I'm just gonna drop a link in the chat so you can download a template for that. And make one, you can do it after this or during the chat here today. And if you want feedback on what you end up making as well, there's some good instructions in there. You can connect to me on LinkedIn and send it to me, and I'll happily record you a one-minute, 2-minute voice note, just sharing my initial thoughts on that. Because by doing this right up front, you're gonna have a much easier time Reaching out to the right people, and saying the right things as well. So, what comes after you've figured out those problems? Well, again, this can come down to knowing why those things are important, and if you can't do this exercise, you might struggle. So…

Will Aitken:

For example, let's just hear, real quick in the chat, someone say, why do people buy what you Cell. Okay, Mental First Health is a workplace training program that equips employees and headers with the skills to recognize and respond to sport colleagues experience mental health or substance use challenges while helping create a more mentally healthy workplace culture. Okay, so, Deanne, hope I said that right, you mentioned that you sell mental health first aid at work. So, it's a training program that allows People in the office. To be more, better equipped, so that if there is a mental health or drug crisis, they can respond to that more effectively. That's the gain of using the training, or taking the training, or training your employees to be able to respond to those incidents better, right? So…if that's your feature slash gain, I'm getting about a million emails right now. If that's the feature or gain, why do people care about that? At least the first question to ask about.

Will Aitken:

Well, because if people don't have that, then what goes wrong? Well, they might be having an incident in the workplace, and no one knows how to respond. Which means that person maybe doesn't get the care they need. or there's a larger incident at work, or in some cases, someone could get hurt, especially with mental health crises. Someone could be aggressive, someone's having a drug problem, they could be having an overdose, whatever it might be. If that happens and someone's not trained to do it, what goes wrong? A lot of things that can go wrong, but I'm gonna pick on one. Let's say…They don't get the care they need. And they… Hurtful to other employees. Okay, let's just say they might end up harming another person other than themselves in a mental health crisis or a drug crisis. In those cases, what's wrong with that? Well, that then creates, what's the word?

Will Aitken:

the employer themselves would… if someone gets hurt at work, they're gonna get sued, basically. It's gonna be an incident. Even if someone doesn't end up suing, it's gonna be a huge, traumatic event for maybe a lot of the co-workers there. They may no longer feel safe at work, they may want to leave work, they may take, litigation against the company. They may… this might become a PR nightmare, especially if it's a company that's publicly facing. Let's say if you are Dunkin' Donuts, just use this example, and one of your people at work is having a mental health crisis. or they could do so, it could be crazy. All it takes is someone to pull out a mobile phone and film that going down, and that's potential brand risk to your company. If you don't have anyone who knows how to adequately respond to that, that could escalate and become a PR nightmare as well. If that happens, well, we're gonna… if our employees leave, we're gonna have to pay to replace them, we might not be able to hire new people. If we get a reputation as being an unsafe employee, we won't be able to attract new people. If we can't hire people, then we can't produce for our company, and therefore, our company's gonna lose out on revenue, essentially.

Will Aitken:

Right? So that gets you to the real pain, instead of just saying, we help people train their teams to better respond to mental health crises, you look at what the status quo, not having people trained to respond to those, could be, and the impacts that could have, and that helps you understand that this is why someone actually might care about it, instead of going, oh, well, that sounds nice, but we don't need that. Well, if they're willing to see, oh, hang on, there is a risk that if this happens, it could be a PR nightmare, it could lead to retention issues, it could cause litigation. Well, in those cases, that's something they probably do care about, and they're at high risk of, especially in high-risk industries, like. I don't want to stereotype, but let's say there's industries that do have more mental health issues, for example. Nurses, places where they're exposed to a lot of traumatic, stressful environments, let's say. Hope that was a good example there. As I said, pick a problem identification chart link in the chat, use that, map that out, because that's going to help you speak to the right things in your message as well.

Will Aitken:

So then, it comes time to target. And I mentioned most people at this stage go way too broad. So you have an idea of the problem you used to help solve. You might solve 2 or 3. And then it's a case of who do you sell to? So, in the case of… I'm gonna pick someone else to chat right now. I hope this has helped when I pick someone out, because I have examples in my head, but I don't like to use my examples, because they're all sales training related, and I know that a lot of people have don't sell to salespeople like I do as well. Concealed weapons detection systems. Okay, interesting. You're based in… John sells concealed weapons detection systems. Interesting. So, John over in Virginia, that's an interesting one. So, when it comes to targeting, obviously, you could say, well, we sell to…Hmm. Let me think about this.

Will Aitken:

I have to imagine your primary audience is pretty clear, so maybe it's not the best example, but you probably sell to large event spaces, airports, stadiums, theaters, maybe movie theaters, Anywhere where large crowds gather, and there's a higher risk of a potential, violent attack. And therefore, concealed weapons, identification. detection is of more importance, because if there's not, someone could get into those events, and this is a risk sale versus a status quo problem sale. It's like a… something that could happen instead of something that is happening today. So, your ICP is probably quite clear, any large kind of venue or space like that, especially if it's a private venue, governments are often much harder to sell to, they have a lot more white tape around their buying process, but for private companies…any kind of event space, but I'm gonna choose someone else.

Will Aitken:

AI data security, okay, that's an interesting one. Okay, here's a good one, actually. You know what? I'm gonna use the data security example. So I recently did a training for a team who was in the cybersecurity space. They provide a software that allows people to get a better visibility into what firewall policies they have out there. The challenge is that a lot of companies out there have loads of different systems stacked on top of each other, and therefore, when they need to update a policy in any of their tools, whether it's a firewall policy or a compliance policy, they have to basically go to 10 different places to check it, and make sure it's most up-to-date. If it's not up-to-date, then what happens is, they open themselves up to compliance risk, obviously maybe failing an audit, or they are having to dedicate a large portion of their team just to checking this stuff and getting up to date. Or anytime they have to do kind of any kind of infrastructure update, or they have a ticket, they have to go double-check all these different places manually. Which creates a big, long delay in how fast they're able to resolve any issues or tickets in those cases. Then, of course, there was the audit risk side of things. And…

Will Aitken:

Yeah, so the idea was that their software allowed them to get better visibility into where all their policies were, so they could make sure those are all up-to-date at any one point in time, but also see which policies are where, and which ones might be out of date, which ones are restricting people, that type of thing. In those cases, we know the situation that creates that is complex IT environments. If you only have one tool, you don't need a tool to go and look at all the different places where your, policies might or might not be up to date. So instead of going, okay, we could sell to any company, with over, let's say, a billion in revenue, we said, okay, what companies are more likely to have more complex environments than others? Well, obviously, large consumer data, high-risk industries, those high compliance and high-risk industries are an obvious place to start, but what other things happen frequently enough That would tell you if someone is dealing with this challenge already, or could soon be dealing with this challenge.

Will Aitken:

So we talked about some things that create more chaos and more of that problem for companies. So a catalyst would be something that… and these are all different types of signals… a catalyst might be they are hiring someone, or they've made an acquisition. Sorry, let me just say this again. A catalyst might be that they had some layoffs. If they laid off half the team, then that means the rest of the remaining of the team doesn't have time to be going around and looking and updating policies in 20 different places. They'd need to be more effective, otherwise their ticket time is… resolve time is going to go way down, and that's one of the metrics we found they would actually measured on. If they had an acquisition, well, that often means that you end up blending a lot of IT environments. If you acquire a small company, they come with a bunch of tech stack and systems, and therefore it's even more chaos and more chances. So by looking for companies that had layoffs and had just been in acquisition, we found those were places where they could be much more relevant, because it was more likely that those people would be facing the problem of that chaos,

Will Aitken:

the chaos and high-ticket response times. A symptom would be something you can observe directly. Now, this is gonna… these two are gonna be different for whatever you sell, so what I recommend doing is maybe going to AI, and asking for some ideas, and seeing which ones make the most logical sense, depending on what your industry is. But a symptom is a sign that someone is actually running into that problem. So, for example, if someone is hiring a role, and in the job description it said, updating policies across networks. That would tell me they're actually hiring that person because they're having capacity issues today with that. I'm not saying they shouldn't hire that person, but it's basically telling me that's a… that's something they need help with right now. Another symptom might be, and this is something that might be very observational, If you sell marketing software.

Will Aitken:

and you can see that someone's getting low traffic using a tool like SimilarWeb, or maybe even ZoomInfo's web analytics, and you can see that they're having a high bounce rate, well, that's a signal that maybe their website isn't as optimized as it should be, and if that's something you have with, or you're a web design agency. then that allows you to come in and say, hey, I've seen that you've had a quite high bounce rate, and focusing on those people is going to yield much more fruit than just trying to speak to everyone out there who has a website, basically. And the last category is intent. So this is when someone actually shows some level of interest in what you offer, or maybe even one of your competitors. Again, ZoomInfo's a tool that can allow you to see intent of people searching things online, but if someone downloads something directly from you, if someone views your profile, if someone maybe even bought from you guys, did a deal cycle with you in the past. If someone's on your website and you're tracking that, these are people who are worth looking into, because they're basically showing that they're looking into solutions, potentially, for that problem, and therefore you can assume that they're more likely to be running into that problem.

Will Aitken:

Beyond that, these are the things you want to be looking for when you're researching people, when you're building your lists, using whatever tool you end up using, LinkedIn even. You also want to make sure you're focusing first on the people who are most likely to recognize you. So, if we went from a scale of warmest. to coldest, you'd want to start with the people who are most likely to be aware of you. One of the biggest challenges with prospecting these days is that we don't have access But you know who you give access to in your life? People you know. So, starting with people who are already familiar with your company, maybe they're past users of your company who moved company, maybe they engaged your deal, went through a deal cycle with your company a couple of years back, so they're aware of you. If they are attending your webinars, again, they're aware of your company. If they are in your network. They were of you. If you met them at a trade show, you already know them by name. If they are connected with one of your executives, well, that's a good potential for an intro there. If they're connected with your customers, then maybe that's another referral opportunity. But it doesn't necessarily have to mean that they even know you personally, or even your company. They might just know someone that you already work with.

Will Aitken:

So if I'm working with PepsiCo. and I want to reach out to Coca-Cola, but they don't know what my company is and what they provide, I'm much better looking in the places where I have that PepsiCo case study, because if I can reach out to Coca-Cola and say, hey, been doing some work with PepsiCo, although they don't know me, that is going to activate some level of familiarity in their brain, going, okay, I don't know who this is, but I do know PepsiCo, this is making me more curious, and therefore I'm more open to the conversation. So even just starting with lookalike accounts, competitors, and adjacent companies to the companies you're already working with is warmer than just pure cold, where you might just be using these catalysts and symptoms that we went through beforehand as well. When it comes time to do research, it's not one size fits all. A lot of people say, how much time should I spend researching a company? Well, if you're doing 500K deals, million dollar enterprise sales.

Will Aitken:

Probably a little bit longer than if you're selling something for 10K, right? So that's not a one clean answer to it. What I would recommend is not spending over 5 minutes if you're in that kind of S&B mid-market. what I think you can do oftentimes is build your lists ahead of time to include some element of research. So instead of going out to, oh, I want to reach out to Coca-Cola, which similar company do I have that I can use as a warm intro or reference? Instead, what I might do is start with PepsiCo, and then go look at all the different competitors and adjacent companies who are going to recognize PepsiCo. And then I've been starting with 10 companies who I all know are in a similar spot to PepsiCo, and that becomes my reason for reaching out. And I don't actually have to research them that much. I can just… because I already have that one thing, the rest, I can ask them in a conversation if I cold call them, or I can just leave that in my cold email. You don't need to know everything about an account before you reach out to them, is what I'm trying to say. Sometimes you just need to know one good thing. So in the example of the cybersecurity company we mentioned beforehand. If they can build a list of 100 companies who recently made an acquisition.

Will Aitken:

that's enough. You don't need to do any further research on that company, beyond just finding who the right person at that company would be to reach out to. Now, a lot of people do this cutesy thing where they go, hey, I saw you went to this university, or you're really into hiking. I don't love it. You can use it if you want to put, like, a PS in an email or something like that, but let's be real, it's very hard to connect someone's interest in hiking to Cybersecurity threats and audits. So I'd much rather see something that's going on in the business than lead with that, versus anything personal about them. There are obviously some fringe cases where that can stand out. I've had a couple done to me, where someone went from my job history and found my first employer and used that. That got my attention, but it didn't get my interest. It didn't mean that I was actually interested in what they were selling. Whereas when they said, hey, you've been in a company, been running a business for 2 years now. there might be, grants available to you in Nova Scotia. Well, that was interesting to me, because I know there are grants available, I just don't want to go on the website and do all the forms and stuff, and they were offering to do it for me. So…

Will Aitken:

Don't feel like you have to go personal, don't feel like you have to go deep, just need one good reason to put a company in… prioritize reaching out to them. Alright, let me just take a breather for one minute, and make sure I'm not missing any questions or anything in the chat here as well. Sending… selling event offices to local organizations. Good to hear that I got… I guessed right, Steve. We must work with a lot of company warehousing. Let's go into the actual tactical side of things. So, once you've figured out what you're gonna say, what people in your market care about, and who's the most likely to be caring about that right now, with those signals, catalysts, triggers, intent, and warm intro scale that I showed you, what do you actually do when it comes to reaching out to them? So… I love cold calling. I've always enjoyed it. It has its challenges, it's very hard to master, it's kind of scary, and it's very easy to avoid doing it as well, much like anything that's hard in life. Going to the gym is hard, but if you want to get buffed, then you go to the gym. If you want to sell stuff, I recommend making cold calls. Especially where you can. Make branded cold calls using today's, sponsor and partner.

Will Aitken:

Right? But I cold call because it's one of the fastest ways to get in touch with someone, and it allows you to get a lot of information back from them, even if they're not the right fit prospect to have that account. It's a two-way conversation, so I can ask some questions, and I'm pretty good at it, so therefore, it works quite well for me. Yesterday, I got three connects, booked one meeting. And that was in an hour of calling. That's super effective, and I could have sent 100 emails, sure, but it would have probably been quite bad emails if I tried to send 100 of them, and frankly, I got a lot more information than the one that I booked. I basically did a full discovery call with him. It was, like, a 20-minute long conversation, asking about everything his team was doing. He was very open to sharing with me, and then we ended up booking as well. So, here's how I structure my cold calls. I'm gonna use another example here. Charlotte, Cher, you sell learning development technology. Okay, I'm gonna try this. So, for my opener, I might say something to the effect of this. Hey, name… Let me just make sure I get this right. Hey, name!

Will Aitken:

Spotted some growth you've had in your learning team recently. I had a question for you, it's Will over at learningprovider.com. You got a moment to help me out? So, that might be an example of an opener I might do. If I was being a bit more fun with it, I might say, what's up? It's Will over at Sales Growth. Just reaching out because I saw that you're in a similar space to one of our clients, and I wanted to see if you might be running into some of the same challenges that they are, when it comes to prospecting, or the same challenges they're running into with close rates, whichever target I've decided to identify in this space. There you go, sure, who did you say this is? A lot of people start freezing up at this point and say, who is this? Because they've never heard of you or spoken to you before. So if you go, it's Will from Sales Growth, they're gonna go, hmm, no, don't know who you are. Just roll straight with it. Thanks, it's Will from Sales Grove. So, like I mentioned, I noticed you're in a similar space to a handful of the clients we're working with in the e-commerce… Technology space.

Will Aitken:

They've been running into challenges, especially with the outbound prospecting. They were doing really well a couple years ago, but over each quarter, they've almost seen a decline in outbound results and the number of meetings being booked. At best, it's been very inconsistent, which means that it's making it very hard to forecast how much pipeline they might have, or coverage for on any given month. Is that something you're seeing, or do you feel like your team are nailing this, and they've got more pipeline than they could even hope to ever close? Right? So that's my reason for the call. I'm gonna share one of those problems from the pick that I created earlier, and a root cause, to give it some more context, low close rates. maybe they're running into… a lot of people have been running into challenges with low close rates because their buyers are much more skeptical to spend money right now due to economic uncertainty. Oftentimes, when the rep can't find something during the discovery phase, that deal often ends up tied to something that's nice to have versus something that they need to have. Is that something you're seeing, or would you have… do you have a lot of confidence in your… the deals that your reps are forecasting to close right now?

Will Aitken:

So I'm kind of giving them an out, but I'm sharing a problem I'm putting in front of them and seeing if it's relevant to them. If they end up telling me, yeah, I would say that's a problem, or maybe if I put two wrongs around them, they say I can relate to that, or they go, well, what do you do? I might say something to the effect of, well, we typically train teams who are challenging this. You said that you are having a problem with that, can you tell me a little bit more about that? And then I'm just gonna get them to tell me more. Oh, okay, how long has that been happening for? Okay, is that something you've tried to do something about so far? What have you tried? Alright, that makes sense. So, if I'm hearing you right, you're having challenges with low close rates due to a lot of buyer indecision right now, often being… you feel being charged by the economic uncertainty in your industry and specifically? And that's leaned to some low close rates on the team. Would you be… have I got that all right? And they go, yeah. And I go, would you be open to hearing a couple of ways that we've helped other teams improve that problem, or overcome that challenge by doing XYZ? And they're gonna say yes or no. If they say yes, great, book the meeting, get their email, move on from there.

Will Aitken:

Now, that's a perfect call. A lot of the time, you're gonna get some objections along the way. The thing that I think most people don't realize is most objections are just knee-jerk reactions. Some are going, I'm not interested. Well, they're not not interested, because they probably don't even know why you're calling yet, right? Or they go, just send me an email, that's just a quick way to get rid of you. What I do in those cases, when I get one of those kind of brush-off objections, I agree with them. Yeah, I'm more than happy to send you an email. Say, last thing I want to do is send you some junk. Do you mind, given I've got you on the phone right now, I'll take turns 20 seconds to just share exactly why I was calling, and you can tell me if that email's worth sending. If it's not, I'll lead you to it. Oh, could you call back later? Yeah, more than happy to give you a buzz back later. Say, given I've got you, do you mind if I briefly share why I was calling, and if it's relevant, I'll call you again later. If it's not, I can leave you to it and won't call you again. Right? If they say, I'm not interested, oh, for sure, I'm sure if you were, you probably would have given me a buzz already. Figured that might be the case.

Will Aitken:

the, let me just make sure I get this right, sorry, I went… had a brain fart there. You're not interested, that's the… I'm sure that…I figured that might be the case. Hang on, I'm having a bit of a meltdown here because my brain went too quickly and now I'm stumbling over myself. Figured that might be the case. Is it that you get a lot of calls like these, or is it that you feel like, then maybe insert the problem, isn't much of a challenge for your team right now? So, it's like, are you trying to get rid of me, or is this really something that you're not going to be interested in? You kind of give them a couple of choices in that one. Sometimes you get some real objections as well, like, we don't have a budget, I'm not the right person. In those cases, again, I would agree, but ask a more open-ended question versus a yes-no question to try and continue the conversation. Totally understand a lot of people are cutting back on budgets right now. Is it… would you say that…It's that you can't spend any money no matter what it is, or…

Will Aitken:

this thing just isn't a priority that you think you would even want to invest in, it's not a big enough challenge that you need to fix it, right? Going down that road, I like giving a couple of options, because you often get a little bit less, what should happen to me, like, people with deer in headlights, when you give them options, they can pick one and kind of go over that, and then you can explore further. So with objections, agree. Get on their side, say, hey, totally understand, that might be the case, and then basically give them a couple options to choose from. I would go further into this, but we could do a whole show on cold calling, and we just do not have time, so I'm going to quickly, briefly touch on cold emailing. I like to just do a, We've had some formatting issues here. The formula for an email would be, I've seen this about you, I can't be sure if this is the case for you, but some people are finding challenge, problem, which is leading to impact, going back to the pick. We've been helping companies solve it with this asset, this…

Will Aitken:

tool, this offer, or this. Does that sound helpful? Would you like to know more? Can I record you something to give you an overview? Does that sound interesting? Basically, just try and start a conversation with a cold email. Keep it nice and short and brief. I might even be able to pull one up that I sent yesterday, got a response, while… because this slide has been absolutely butchered as well. Gonna double check we don't have any comment, questions here while I do that as well. Do you have a suggestion on how to build a play based on the familiarity in EdTech? Yeah, so… In EdTech, a lot of learning and development providers go to events, they may be past users, it depends how big your company is, but let's say you sell for…I worked for a company once called Mentimeter. They sell to learning development coordinators and universities to help with their learning experiences. they had a lot of free sign-ups for their tool, or people just accessing guides and tutorials. There was a big market there. There was also a market for people who

Will Aitken:

Maybe they taught at one university, or were teaching at one company, and using Mentimeter, and they moved to another company. Well, those people are likely to be familiar with Mentimeter because they use it at last role as well. Those don't change that much. In fact, I have a list of signals that you might be able to use as well. Feel free to reach out to me afterwards, and I think there might be an email going out after this, which will share some of those resources with you as well, to make it really easy for you to use them as well. It's a startup, so you probably don't have that many customers to rely on, but…if your executives are connected with anyone, I think that's always a good one as well, or even if they ask… if you have one customer or two customers, go familiarity play, even though it's not directly competitive. in learning development teams don't care about this as much as go-to-market teams, for example. You could say, hey, I saw you're in a similar space to this company we're working with. And they were running into this challenge. Wanted to see if that's relevant to you as well. If it is, I'm more than happy to share some of the ways that we helped them solve it. That could be a really good cold email right there. beyond…

Will Aitken:

some of the email tacticals, and I probably was a bit ambitious trying to get to all that, you're gonna need to have a system to actually deliver on all this, because doing this once…Is the inconsistent execution piece that we mentioned beforehand. So to do that well, I often recommend just having a sequence. This isn't, like, the fully automated sequences that used to go around, like, 2021, that's just gonna book meetings on repeat for you. It's just a way to track what you've done and how much you're reaching out to a customer. So I've found the most success reaching out to a customer, like, 2 or 3 weeks long period, giving them 4 or 5 calls in that time, leaving maybe one voicemail in that segment, and then sending them an email. The first email could hit on the first problem I helped solve, the follow-up could share some more context, or a case study, or a story, or a resource for them. And the second email could start a brand new thread and hit on the second problem that I think they might be experiencing. And then I might end with, hey, we've been reaching out because of this. is that, I'm even going to assume that either you're not the right person at your company to speak to about this, or this isn't relevant right now. Let me know, would be helpful, but if not, I'll just assume, assume you're good for now and leave.

Will Aitken:

And then I can retarget them again in the future as well. To do that, you're gonna need a good system. To one, get the data in, two, track what you've done. I personally just use HubSpot, and then I have a few data providers, ZoomInfo is one. I also use some of Clay, and I've been using a couple of other tools and testing them recently as well, just to get contact information in and do some of that list building research that we mentioned earlier as well. To set my activities, you gotta know your numbers. If you're an account executive, you know what you have to hit a year, you know how many opportunities are sourced by marketing. You now know how many sources… opportunities you're gonna have to source yourself, based on your close rate, to hit your goal. If you know how many opportunities you need a month to hit your goal, you can back that to your qualification and show rate, and say, okay, I need to book 10 meetings to get 5 qualified opportunities, and to book 10 meetings, I need to do, let's say, 2,000 touches.

Will Aitken:

This comes back to tracking your math, and by having a system that does your sequencing, or at least allows you to track your tasks well, you can calculate this math much more reliably versus just guessing or using industry standard best data. So, that's where I might say, okay, I made 200 calls today. I got 20 connections. From those 20 people who picked up the phone, 10 of them lasted longer than 30 seconds, and from those 10 conversations I had, I was able to book 3 meetings, and from those meetings, 2 people actually showed up to the meeting and were qualified, right? I can then look at this and know my math and say, okay, if I'm making 200 calls, and I'm only getting, let's say, 10 connections, and that's… if I can get 20 connections. then I can look into maybe better contact data, or I could change the time of day I'm calling, or I could think about branding my phone calls, or I could, it might show me that I'm having, spam-likely issues as well, I'm not getting a very high connect rate. Or I could try and switch up my AI gatekeeper script as well to try and get through to more people as well.

Will Aitken:

If I'm getting connected to a lot of people, but I'm not having conversations with many, well, that tells me my opener might suck. I might need to do a better job of creating some curiosity there, maybe leaving something a bit more relevant about them so they'll stay on the phone with me. If I'm only booking 3 meetings, then that tells me that these problems that I'm putting in front of people probably aren't resonating enough for them to be interesting, caring how to solve it. So is it the questions I'm asking? How I'm positioning those problems that we helped solve? Am I, positioning if we could show you a way to do this, would you be interested? Am I getting objections? Am I handling those well? So by knowing your numbers really well, you can start to diagnose what's going wrong in here, and start to fix it as well. But to do this, you need to be recording your numbers somewhere. That's why it's really important to have a good prospecting system. Like I mentioned, I just use the sequencing in HubSpot. I don't use it to send emails, I have Instantly and Aurum. And my dialer, the plugin on top of that. So I can make my calls from Aurum and use instantly send my emails, because otherwise you can have some deliverability issues as well. More than happy to share about that later as well.

Will Aitken:

So, a couple of takeaways that you can do. Build your pick, that's gonna be the basis. Identify some signals that can help you refine your market a little bit better, and then, of course, design your sequence to be problem-centric around some of those things, and then actually do the work. We can sit there spinning our tires, talking about this all day long, but ultimately, until you get out there and test some stuff, oftentimes you won't actually know what's working and what's not. So don't feel like it has to be perfect before you hit go, and don't let overthinking get in the way of doing. Sometimes it's just you have to fall flat on your face and have a couple of bad cold calls to feel good at…Using a new script or approach, whatever it may be. So guys, I just spoke for 45 minutes, pretty much straight there. It's been fun. If this was helpful to you, normally we have a guest, we kind of do a bit more interview style, then let me know. We're going to be sending out some resources afterwards. For example, I have a playbook template that you can basically make your own that follows this kind of methodology and practice. Also, Be sure to grab a copy of the book, because it's…

Will Aitken:

Gonna take you longer than 45 minutes to read that, and I just tried to basically cram this into this, and as you saw, we had to talk pretty quickly just to cover the stuff we did cover, so please, if you haven't already, grab a book, it's on Amazon, you'll get a follow-up email with all those details in there as well. If there are no questions, though…This has been fantastic. I had a blast, I hope you did too. Keep it real. Peace, love, and sales.

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