If you have a fear of cold calling, or you manage people who do, then this is the interview for you. Allego’s VP of Sales Richard Smith and I discuss one of the main factors holding sales people back from being truly successful: cold call reluctance.

We discussed:

• How a fear of cold calling manifests itself, both within us and in the staff that we manage
• Some of the factors that increase and decrease that fear of cold calling
• How Rich got over his own cold call reluctance when he was starting out his sales career
• Leading from the front, creating a culture that embraces cold calling
• Getting great fit hires and managing expectations around cold calling from the start

Here’s a transcript of our conversation.

How to Overcome the Fear of Cold Calling

George: Rich, welcome. How are you doing?

Rich: I’m very well. How are you?

George: I’m good, thank you. I think what we should do is just start off by having you introduce yourself, give us a bit of background on your career and what’s led you to Allego.

Rich: Yeah, sure. I’ve been in sales not too long in the grand scheme of things, coming up to ten years. I started in sales as an SDR, fresh out of university, and worked my way up in the chain at a previous software company. When that company was acquired about three years ago, Kevin Beales, Allego GM, said, “Rich, do you fancy coming along and leading on the sales side of things?” I thought it was too much of a great opportunity to turn down.

George: We’re not going to talk too much about the Conversation Intelligence product specifically, because the website does that, but I am interested in what you and Kevin saw as the perceived problem that led you to create this software solution. What was the problem that you guys saw in sales that led you to think, “How can we solve this for our customers”?

Rich: I think so much of it was born from our experiences, and if I look at it on a personal level, it’s fair to say that, in my early-stage sales career, the amount of personal development I got was limited at best. It was probably a very similar situation to how a lot of sales people kind of learn, just by almost doing the job and making mistakes, sometimes now knowing all the mistakes I’m making. Are they actually mistakes? What am I doing well? Really, the problem was never really having that consistent exposure to getting feedback from somebody who was more senior or more experienced.

The coaching that I got was really restricted to what I would describe as “back of a taxi” feedback after a meeting. That kind of five-minute journey back to the train station, getting that sort of debrief from my manager. The problem was, even when I did sales calls and demos and side-sales functions, a lot of those calls and demos were happening behind closed doors in meeting rooms, meeting booths. Nobody ever really got the chance to listen to how I sold and give me recommendations on how I can improve.

It felt like there was a better way here, and thankfully, my situation’s very similar to thousands of others, globally, where the amount of personal development they receive is limited at best. Part of that is, in my opinion, in order to actually help salespeople improve, the first stage is observing what they’re doing today, and Allego provides a vehicle to observe how sales people are selling in practice and then using technology and tools to really start to take people to the next level.

George: One of the things you and I spoke about when we were planning topics for this episode was the idea of the cold call and often how fearful people can be of making those types of calls. How do you see the problem? How do you see other people experience this fear of cold calling?

Rich: First of all, there’s no getting away from it. Cold calling is a daunting experience of pretty much any sales professional out there. As somebody who’s been doing it for some time, the first one of the day is always the hardest one to do. It’s not easy. There’s a lot of sales people who have never really done cold calling, and part of that is because it’s completely out of their comfort zone. In my opinion, I think if you can become accomplished at cold calling, then you really set yourself up for success for the rest of your career.

There is a genuine reason why cold calling is daunting. First and foremost, it’s an interruption to somebody’s day, somebody who doesn’t have a clue who you are, who your product is, why you’re calling them, and you’ve just rang them out of the blue. Going from somebody not expecting your call, not knowing who you are, to then getting that person to want to give you more of their time feels quite a daunting task. I think, ultimately, that’s where it stems from. The foundations of why people have fears over cold calling is fearing that they’re an interruption and that they’re almost a thorn in the side of the people that they’re looking to call. I think, coupled with that, the fact that they have such a short window of opportunity to make that cold call a success just adds to that pressure.

I think there’s maybe an element of cold calling in that it’s long been seen as this high-volume activity game and can be, in that sense, quite mind-numbing. You could sit there and you could make 60, 70 dials and have nothing to show for it at the end of it. Yet, from my experience, while cold calling is still a numbers game to some extent, so much of what you can do with cold calling is actually increasing your chances of success.

I think, ultimately, the fear and the anxiety around cold calling primarily stems from being that interruption and making sure that you’re making the most of that person’s time when they actually answer the phone.

George: I want to come back to some of the reasons why people might find it a daunting prospect, but before we do that, maybe let’s take a step back and actually define the cold call. When you talk about cold calling, are you talking about calling somebody up with no prior interaction, or maybe they’ve downloaded some class or form a website? How do you define the cold call?

Rich: In my opinion, a cold call is calling somebody on the telephone who has little to no idea of who you are or your company is, who isn’t expecting your call. I’ve often heard cold calls being described as a correlation of somebody who has an element of expectation of the call, but in my opinion, a cold call is exactly that. It’s somebody who you haven’t spoken to before, who wasn’t expecting your call, who doesn’t really know who you are and much about your company, and that is my definition of a cold call.

George: Let’s jump back to some of those reasons why people might be reluctant or reticent to do a cold call. You mentioned sort of them thinking of it as an interruption, but talk about some of the other factors that may exacerbate that. I’m thinking in particular of maybe people who are self conscious about being overheard on the phone or being criticized by colleagues. In terms of the hierarchy of the things that make it even worse for people, what are some of those? Top three, top five?

Rich: Well, I’ve seen this firsthand. I remember when I started my career in sales, I was pretty much the only person in my sales team at the time who would cold call. I’d never done the job before. I had very little sales experience. I didn’t really know what to say when I made the call. I kind of just tripped myself in the deep end. However, there was … if you imagine, as an individual salesperson in quite a quiet office, not a lot of background noise, sat in a sales desk with others around you, feeling unsure about, “Am I gonna say the right thing? What happens if they hang up on me? What if I whittle my words?” The whole concept of being in that quiet environment, thinking that everybody’s listening in on your calls just kind of adds to the anxiety.

I’ve seen this before when we started building the sales team at Allego. There were times when we were a smaller company, we had a much smaller sales team. Those same concerns of feeling like people are eavesdropping into your conversation is something that can really hold salespeople back. I think there is that mental block that a lot of people have, especially in a quiet or close-knit office environment, feeling that they’re very self-conscious about how they sound on the phone, and also they maybe get a sense of anxiety or embarrassment if they get hung up on by a prospect and feeling that everybody knows that that happened.

George: Were there times in your career where you were new to cold calling and you had that reluctance, or have you always been prepared to pick up the phone, not necessarily hampered by any of the things we’ve spoken about? What’s been your take over the years with cold calling?

Rich: I’ve definitely had cold call reluctance in my life. I think particularly in those early days, not necessarily at Allego, but when I was learning the ropes and maybe in sales environments that didn’t really have that really culture mindset of really solid prospecting. There were mornings where I’d walk in and the thought of making a cold call at 9:00 in the morning in a quiet office was almost petrifying.

I think over time, I kind of removed that mental block from my head, and I think for a lot of salespeople who are feeling the same thing about cold calling and that same kind of … they look and stare at the phone for the first hour of the day, just trying to psych themself up or to pick it up. It is a mental block, and there are things that I think can be done for sure that can really help to remove that mental block, which I’m sure we’ll come onto. Part of it is the cold, hard reality of sales is sometimes, with mental blocks, it is just getting over it, facing your fear, ultimately, and saying, “I’m never actually gonna get over this fear until I just do it.” That’s the reality.

George: On an individual level, we’ll come onto culture later and how, as a sales leader, you can foster within the team a greater acceptance and a greater enthusiasm for cold calling. On an individual level, then, how did you get over some of those initial roadblocks, those things that held you back from making that initial call first thing?

Rich: Some things I did was choosing the times that I did cold calling. The reality is, nobody really wants to make cold calls at 8:30, 9:00 in the morning. People are still warming up. Like any salesperson, we warm up during the day. Once we start talking more, we start getting our heads in the game more. Maybe a switch to prospecting at times of the day when there was bit more of a buzz in the office, and feeling that myself, I warmed up the vocal cards if you like, just as any sportsman would do in the stretchers and getting over the rustiness and getting into the swing of things later on.

I think as well a big part of what I did was really trying to optimize the cold calls I did. Rather than just calling blindly number after number, I had a relevant opening statement to use with prospects. I quickly learned that you don’t need to make 70 cold calls before you get one meeting on. You can become more effective in what you’re saying to increase your chances, but you could make 10 dials and you could end up getting one meeting out of those 10 dials because you have one conversation and you know how to nail that conversation.

As well, little things like putting music on in the office just to create more of a background noise. It sounds quite simple, but it removes that deathly hallows silence from the office and just provides something a bit more comforting as you’re actually making calls.

George: Talk about culture as well. If you’re responsible for a team of sales professionals, how do you lead from the front when it comes to identifying somebody who’s really strong at sales but maybe there’s a bit of reluctance there in the cold call? How do you engender a culture where that enthusiasm that you have is shared amongst the team?

Rich: For me, one of my big principles is leading from the front. I think if you’re a sales leader and you’re demanding your team to make cold calls, which is daunting, is hard, if you can’t show that you’re prepared to do it, too, then people won’t necessarily follow suit. I’m a big believer that, as a leader, you set an example. You might not even, as a sales leader, be the best person at cold calling in your sales team, but I think you have to show that you’re prepared to do it at times. One, to kind of get people following the lead, but also as a way for you to maybe set a standard as well.

I think as well, for me, a lot of it stems from the outset when you hire somebody on. I think there’s a lot of expectations that you can set around what the culture is, for example, prospecting is. I think a lot of sales people, when they’re hired, they need to understand that that is part of their routine, and if they have total fears and concerns of cold calling in a company that has that as part of their prospecting mix, then they may wanna question whether they are the right fit for that company as a starting point.

That’s one of the things that we actually measure for when we recruit here at Allego is we do physical exercises based around things like cold calling to really see if someone really is comfortable doing it.

George: I had a conversation with one of the SDIs here at Allego earlier today on exactly that subject. What she said to me was how refreshing it was in that roleplay, in that preparation, was to not roleplay an entire call but to roleplay segments of. The open of a cold call, for example, is a good way to do that. That’s something you and Kevin, in particular, have consciously thought to implement over time. Have you found that to be a successful way of doing it, of honing in on isolated components and then having the perspective SDR run through that with you?

Rich: Yeah, for sure. Even though cold calls are traditionally very short conversations, you might question, “Well, how many facets to a cold call really are there?” Well actually, when you break them down, you could have a two-minute long cold call that could be made up of five or six or seven individual attributes, which you can coach around. That could range from the very first thing you say on a call, the opening gambit, as I say. It could be on the first question. It could be working on pauses, which are so crucial to success in cold calls. It could be understanding how to handle objections. It could be around knowing the specific moment in the call when to try and close someone for a meeting.

There are so many facets, which to try and coach all of those in one go at an individual is very difficult. It’s not as easy as saying, “Let’s just practice cold calls.” When you break it down into those segments, the way I think about it, it’s almost like piecing together the perfect jigsaw. That’s where tools like Allego have been really powerful because you can share literally five seconds of a cold call with somebody else on the team because that was the part of the call that maybe they need to improve and tune up on.

Definitely, I think, coaching and breaking things down in bite-size chunks, especially for young, inexperienced salespeople who are trying to learn the ropes is key to just really refining and practicing those skills.

George: I want to come back to overcoming the fear of cold calling because I think, ultimately, that’s what people are gonna be listening out for on this episode in particular. Are there any specific tips? You mentioned sort of embracing it and just almost taking that leap of faith and making that first call. Are there any other tips that you would give somebody who shares that fear of cold calling but is still reluctant to do it?

Rich: There’s a number of things that I can think of here. First of all, if you work with other salespeople, I come back to this facet of … it’s called the silent sales floor is how it’s been named, and a lot of it comes from the quiet offices, and encourage, if you work as part of a sales team, get other people to make cold calls at the same time as you. Everybody on the phone, making dials, having conversations, not just creates general background noise, which makes people feel less self conscious about how they sound. It also just creates an amazing buzz in the office and an amazing energy as well. It really encourages people to keep on going.

Secondly, one thing we’ve done at Allego, which I’ve written about, is creating days that are completely dedicated to cold calling. We call these hard call prospecting days, but ultimately, it’s where everybody on the sales team, no matter what your job function or role is, comes in and makes calls together. The idea is making an element of gamifying the day as well. We have things like building in prospecting Battleship, Play Your Cards Right, all these little games which foster just a culture of people wanting to do more activity, want to turn something which is traditionally seen as quite a mind-numbing activity into something that’s actually quite fun and energetic.

Finally, I encourage practice and review. Nobody becomes good at cold calls overnight. It probably took me five or six years before I thought I was really effective in doing it. Practice through roleplay, recording calls, listening back to them, and getting other people to give feedback. Listen to what your other colleagues are doing and try to pick up on the things they do well or things that they could improve on. Nobody ever gets good by not practicing. Unless you have that culture of practice, experiment, feedback, and repeat, you’ll never ever improve. I’d say all those things really foster a culture of more positivity and less anxiety when it comes to cold calling.

George: Give me your take on how that initial cold call should be approached. Is energy, is enthusiasm good? Is there an upper ceiling to it where it becomes too much? What’s your take on how you approach that call in your own mind and how you come across?

Rich: A little story. I remember, just very recently, as someone who leads the sales team but still does cold calling and prospecting when I have time available, I remember doing a cold call recently, and I almost felt, as I was doing it, I was almost boring myself the way I sounded. I knew I was doing it. It was just one of those days. Lo and behold, the call went absolutely nowhere. I just thought at the end of it, I was like, “There was no way that prospect was ever gonna wanna gie me any more of their time because I haven’t enthused them at all, just by not enough energy in my voice.”

Definitely prospects can resonate from your energy that they get on the phone. I think maybe there is a ceiling there. I think you don’t want to be too over the top because I think that might sometimes be construed as your being the typical pushy, over-the-top salesperson, but I think certainly, having some level of energy and sprightliness in your voice is key. I think as well, just trying to sound natural. I think why we have so much success here at Allego is because everybody just sounds so natural when they’re on the phone. We’re not following scripts or anything like that. We’re trying to make, even a cold call, a conversation.

I think there are definitely some facets and how you sound on the phone is definitely important. Again, none of that is measurable until you listen back like I did and have that second perspective. Sometimes how we think we sound on the phone is very different from reality.

George: In terms of how cold calling culture can have a positive and negative impact on a business, give me your perspective on where it can go, both on a negative side and a more positive side? In terms of, if a business is doing cold calling and doing it well, where can that take them?

Rich: I think we all became bored of the ongoing debate online that’s been around for ages. Is cold calling dead? From our perspective, the reason we embrace it so much is because it works. We have conversations with the prospects we wanna speak to. We book appointments. For me, that’s the pure evidence of why cold calling is still very much alive. Actually, I think, from a wider perspective, so few sales teams are cold calling, and they’ve become too reliant on sending emails or sending Linkedin messages. What it’s come to be is just too much noise in those arenas. As a result, they’re missing a trick. I could count on one hand the number of cold calls I’ve received from salespeople in the past three years, and that’s the genuine truth. Ask me how many emails I’ve received, and the number is enormous.

I think a lot of it, again, comes down to the fact that many people have a misconception around how cold calling is received by prospects, but also a feeling that they have had it hammered into them that cold calling is dead. For me, long may it continue for people to come to me saying that because that just means that it’s easy for companies like us to break through the noise and stand out.

Going back to the other side of what the negatives of cold calling could be, I think, really, it comes down to whether you do it effectively or not. I think you can be incredibly ineffective at cold calling and find that you literally waste, as a sales person, as a sales team, hours and hours and really have not a lot of return on your investment. With anything to do with prospecting, the best approach is a blended approach. It’s using all the tools available to you. Knowing your audience; some prospects respond better to certain methods of outreach than others. Certainly, just as it is a waste of time to send hundreds of generic templated emails, the same can be said for making hundreds of dials and not being effective at having that conversation.

Part of that as well that is quite crucial that we’ve found is having the right data. We use some brilliant tools, like ZoomInfo, that we’ve been a customer for for a couple of years as one example, who provide direct dials, which is transformative in relation to navigating gatekeepers, getting through to prospects, increasing connectivity rates, and not wasting time hitting switchboards and hitting people who will never put you through to the people that you want to speak to.

George: In terms of touchpoints, cold calling is sometimes seen in isolation. The call happens, there’s no followup. What’s your take on what is a typical cadence? Even if there is a typical cadence, does it involve just calling? Does it involve calling and email? Is it blended? Give the listeners a little insight into how you see it working. Does it work by itself, or should it be used as part of a blended approach? What might that start to look like for some other businesses?

Rich: It’s a really interesting question, and I don’t particularly feel I’ve got the magic bullet here. My philosophy on touchpoints and follow ups is: follow up sensibly with regularity, but don’t go over the top. Too often I see salespeople going over the top with the follow ups. They’re ten plus touchpoints, but I think where they often fall down is most of those touchpoints tend to be the same methods; it’s like ten emails, one after the other. By the second, you’re completely bored of receiving them and there’s probably a reason why you didn’t respond to the first one, anyone. That’s a bit of a side topic.

I think having a cadence which includes multiple touchpoints, whether that’s a phone first, email second, social third. I know a lot of people are starting to get into writing handwritten notes as part of their cadence. When it comes to the phone part of that cadence, the key to it has to be around the time of day that you’re making the calls. I think it’s quite key. We have to become smart at understanding when we can best catch our prospects, and often that’s first thing in the morning or lunchtime or even later on in the day when people tend to be at their desks more or not head down at their day job.

Follow up sensibly, follow up diligently, but I think we salespeople need to understand when no response typically means there’s no point wasting more time in that prospect.

George: You’ve already shared an example of a time when you yourself said that you felt bored on a call, and you weren’t surprised when the prospect was bored. Let’s look at the opposite of that. Let’s think of the reverse. Can you think of a time or share a time when you were maybe hesitant about going into a cold call, but it ended up going very well?

Rich: Yeah, pretty much every time I make one. I think there’s always that level of uncertainty. Just like funny things with salespeople, I’m sure this will resonate to lots of people, where you can look at a prospect up on Linkedin that you’re gonna prospect, and you suddenly make weird judgements in your head, or this person looks like a particularly scary person or this person’s got VP in their title. I’m a bit nervous calling them. We make these weird … they’re just mental blocks about the look of the person or the job title and just feeling that that’s gonna change the dynamic of the conversation.

I was in that boat. I used to be in that boat. Anybody that had a really senior job title, I used to get more anxious about calling that person. Again, I think it’s a facet where you just kind of have to laugh it off and think, “That’s just silly.” One method I used to do is to put together a calling list, but I wouldn’t put their job title on that list. I’d just have the name of the person and the company. I knew that they fit the profile of the person I wanted to talk to. I knew what they were called and the company that they worked for, but that mental block of seeing their really senior, big, flashy job title was just removed from my vision. To me, that springs to mind as things that I think often we feel that this is gonna be a more dangerous cold call, but things that are pretty meaningless at the end of the day.

George: Excellent. Last question to wrap things up then, top three tips. What are the top three tips that you would recommend somebody follow if they are currently in a position where they fear cold calling or they’re managing a team of people who they know are fearful of cold calling? What would be the top three tips that you would give somebody in that situation?

Rich: From a management perspective, I’d start with addressing it full on with the team. I’ve had conversations with sales people before where I address the fear of cold calling before they’ve experienced it, before they get to that stage of staring at the phone and not wanting to pick it up, of me saying, “Listen, this is a very real thing. It affects so many salespeople. I understand firsthand the challenges and how daunting it can be and the reasons why it can be daunting.” And just getting people to appreciate the fact that I, as a sales leader, appreciate the anxiety that people have over it. I think it is a great way just to get sales people on your side and almost start to overcome that fear before they’ve actually got it.

Secondly, I really think having a team of people who are doing it at the same time and having that culture that everybody can just be on the phone at the same time is so crucial. That also provides opportunities for instant feedback. You’ve just come off a bad cold call. The person next to you can ask you, “What happened? What went wrong?” And you can even review the call afterwards as well. Just having that shared experiences of people all in it together.

The third one is a great call opening that we use here at Allego, without giving away the company secrets, the opening line we use in the call which never fails to let us down, “Hi, Mark. It’s Richard from Allego. Have you got 23 seconds so I can tell you why I’ve called today?” We often, nine times out of ten, get very positive responses. There’s my secret sauce.

George: Rich, thank you very much for your time. Really appreciate that. There’s some great tips in there as well.

Rich: Thank you, George.

Learn More

Download The Complete Guide to Conversation Intelligence to learn how Conversation Intelligence can help improve sales coaching, content, and training.