You know what? It’s OK to be yourself with your peers and your prospects. It’s OK to let them know if you’re feeling intimidated, or if you are having a bad day. That kind of openness and honesty can really help build trust and form instant connections with people. Most of us just focus on the hard skills of sales and ignore the soft skills at their peril. However, taking advantage of them may just help you make that next sale.

In this episode of INSIDE Inside Sales, Darryl is joined by Ashleigh Early, Sales Development Leader at Vendition and co-host of “The Other Side of Sales”.  Darryl and Ashleigh discuss using soft skills to make you a better, more connected salesperson. For example, embracing your humanity to make yourself more relatable, as well as the power of using radical honesty to establish a deeper connection with your prospects. They also talk about being both self-aware and truly knowing your audience so that you can close those difficult deals. Learn how to take advantage of soft skills, only on this episode of INSIDE Inside Sales!

Not in the mood to listen? No problem, you can read the transcriptions below.

Host:  Darryl PraillVanillaSoft

Guest: Ashleigh Early, The Other Side of Sales


Darryl Praill: It’s a wonderful day in the neighborhood, boys, and girls. How you doing folks? I’m feeling pretty good. It’s been a productive day for me so far. I’ve already kicked butt with a wonderful webinar. I had the joy of having a conversation with the Institute of Sales Management, and I was joined by Chris Beall of ConnectAndSell.

Darryl Praill: He and I addressed their whole association. They’re based out of the UK if you don’t know that, and if you’re in the UK listening, then hats off. Great institute. We had a conversation about the anatomy of a cold call, so check it out at the VanillaSoft website or the ISM website. All that matters. But it’s kind of interesting. You know, we were in the green room prepping for the show. And the nice thing about before you go live, in any kind of event, is you get a chance to talk to your cohost.

Darryl Praill: And that always leads to some interesting conversations, and one of it is we get talking about the folks of the ISM. They were actually very complimentary and they were like, “Wow, you guys have great energy, you’re really full. You really know how to engage the audience.” Which was very nice of them to say because trust me, when I go home. Sometimes my wife and family doesn’t always feel the same way about my skills and that led to a conversation. Tell me if this is a conversation you can relate to that you’ve ever had. Where I was saying just what I kind of just said now, which is, “Thank you. That’s nice of you to say.”

Darryl Praill: And part of the reason I have fun, like I do in this podcast when I’m talking to you guys, I get jazzed and get excited. It’s the whole idea of just connecting and sharing. But there are times when my skills are less robust, less capable. And so don’t let this fool you, this persona fool you. My public image, don’t let it fool you because I struggle. I personally struggle with this. A real-life story on that front. One of the reasons I was hired at VanillaSoft was because they actually wanted an individual who can not only do their job but who could push back. They intentionally wanted to hire somebody who would challenge them. Now I don’t get that logic, although I do get that logic clearly they had a lot of people who were similarly aligned and they wanted to mix it up a little bit. Some who could come in and say that the emperor is wearing no clothes or that glass is half empty, not half full, whatever it might be.

Darryl Praill: And that was one of the reasons they hired me and it’s worked out really, really well. Kind of. Because when I say kind of, what I’m really saying is there had been many times when I have delivered that truthful message, that hard message that needs to be said, the elephant in the room and people have not reacted well. So full disclosure, whether you’re doing this on a sales call or you’re doing this with your colleagues, you’re not the only one who struggles with this. It was funny, I was talking to my son yesterday, if you don’t know my son, he’s actually in the broadcast game and he was being interviewed for a job he would love to have. He really wants this job. He’s got a killer job now. But you’re always looking at other options. And I said, “How’d the interview go?”

Darryl Praill: He had a phone interviewer and he said, “It went generally well,” he goes, “But I think I might, some of the answers I gave might’ve not been received well. Maybe I came across as cocky, maybe I came across as all-knowing and that wasn’t my intent. So I’m kind of left going, I don’t know. I don’t know how to read this situation.” And I said, “Dude, I have so been there. Here’s some tips and tricks I’ve learned over the years, many, many years of doing this, whether I’m talking to my spouse, lovely Tracy of 30 years or others, colleagues, coworkers, employees, bosses.” And I said, “I struggle here too.” I was talking to my boss the other day and I said, I want your advice on how to talk to this individual because this individual, and I haven’t always connected.

Darryl Praill: He doesn’t always hear what I’m putting down. What I’m saying. I mean it in the best of intents. And his response was, “Well Daryl, you need to understand, you have a reputation.” I know I have a reputation. “Yeah, well sometimes because of your reputation when you speak, no matter what you think you’re saying, they’re hearing it a different way.” And I said, “I know that that’s why I’m here. That’s why I’m here talking to you saying how can I deliver this message?” Recently I went to my head of HR and I said, “I’m looking for some advice. You know, I think I do a pretty good job connecting with most people, but there are some I don’t. So how can I do this differently? What tone, what trips, what tricks can I use?” This is my way of being vulnerable and transparent with you guys.

Darryl Praill: Because I want you to know this as much as I love talking to you. Like you, I struggle with my softer skills. I struggle sometimes reading every single individual and I know from my own personal side that your career in sales depends on you navigating not only your quota but also how you engage with your boss, engage with your coworkers, how you connect with that sales prospect. They’re all softer skills, so how do you do that? Well, isn’t that a nice segue? I brought in somebody who’s all about the softer skills. Have you met her? Her name is Ashleigh Early. She is the apprenticeship director at a wonderful company called Vendition. I met Ashleigh recently at the TenBound conference, it was the sales development conference, TenBound with David Dulany and we connected right away.

Darryl Praill: She’s actually a pretty cool chick and I’m saying chick because I think I can say chick with her. I’m not trying to say chick to be derogatory. I quite like Ashleigh connect right away. Part of the reason we connected was on hockey. Her husband is a goaltender. He had dreams of making the big leagues. He didn’t achieve that goal, but he had a pretty good runner up. He met Ashleigh, so, Hey, you can’t complain with that now. What I like about Ashleigh is that she’s got her own podcast. Check this out. I know I’m talking to the right person, her podcast of what she’s the cohost is called The Other Side Of Sales and you need to go follow this for no other reason than let me read this to you. It’s the B2B sales podcast for the rest of us. We tell the stories and share the insights of B2B sales professionals that do not fit the stereotypical mold of air quotes. Can you see me doing it? “Sales, bros.” They’re speaking to non-sales bros. How can you just not automatically like her? Ashleigh, welcome to the show.

Ashleigh Early: Thanks for having me.

Darryl Praill: Oh, how’s that for a build-up? Did I do okay? You yelled at me.

Ashleigh Early: I’m blushing a little.

Darryl Praill: Are you blushing a little bit?

Ashleigh Early: I’m blushing a little and you can totally do chick. I can rock a chick.

Darryl Praill: I knew you would. I knew you would. All right, and for those who are offended by chick, I apologize in advance. I’m trying to be politically correct, but she and I, we just bond. So now with that said, softer skills. This is something that is a challenge or an issue that you see as you architect Vendition’s, sales development, apprenticeship program. I mean, talk to me. You deal with SDRs every single day.

Ashleigh Early: So, in my role at Vendition, so we are a sales apprenticeship company and the apprenticeship program means that all of our apprentices get at least 30 minutes weekly, one on one with myself, or a member of my coaching staff, which right now is myself and the incomparable Sam Schooley who you should also go take a look at. But when you talk about soft skills, I do somewhere between five and 10, 30-minute one-on-ones every day with SDRs who are in typically their first three months of the role. I would say 80% of those sessions includes some form of soft skill coaching because this is hard and no one talks to you about how to do this stuff or building this out in school. You do not use soft skills in the business world, in school, or in any other facet of your life. So it’s one of the biggest learning curves. It’s not just learning how to sell in an SDR role. It’s learning how to get along with everyone. And not that people are antagonistic because salespeople are inevitably people pleasers. But it’s that walking that fine line of advocating for yourself, pushing prospects beyond their expectations, but not coming across as a used car salesman while at the same time making sure your boss and all your coworkers like you. It’s an incredibly fine line to walk.

Darryl Praill: So were you using your soft skill, voodoo magic when we met each other for the first time?

Ashleigh Early: Yes.

Darryl Praill: Because you were engaging. I love it. All right, so let me ask you this. What would be some symptoms? So for those listening who may not think they have a soft skill issue, they may think everybody likes them, they know how to read people, they think they’re pretty confident. What are some common things you see, especially in the sales profession that would be indicators that they might have a soft skill problem? You know, it’s the Jeff Foxworthy, you might have a soft skill problem if. All right, so what would that be?

Ashleigh Early: I think one of the most common ones, and I’m seeing this more ironically enough with women than with men. Overfunctioning and what I mean-

Darryl Praill: I have no idea what that means. Go for it.

Ashleigh Early: Yeah, so specifically I see this a lot with, like I said, more with women, but I do see it in men. But when you feel very uncomfortable, when you feel internally like you have to prove yourself and to compensate for that, you end up coming across as overbearing, cocky, telling everyone else what to do and entitled. So I’ll give you an example of this. I did this. So I mean we talk about soft skills voodoo. Most of this comes from me putting my foot in my mouth over the years and trying really hard to learn my own lessons and then help other people not to repeat my mistakes. But when I started at a company called FireEye, it was a really unique program from an SDR perspective and I was an SDR because I was in my mid twenties and I was the youngest person on the team by about five years.

Ashleigh Early: Everyone else in this team and there’s six or seven other people, we’re all their early thirties if not in their early forties and they were amazing, brilliant, eloquent, mature human beings who were just so impressive to me that I walked in there and I was terrified. I was absolutely terrified and to compensate what I ended up doing was building out a hyperlinked PowerPoint script for myself and I did it because I felt like I had no idea what I was doing and I had to play catch up and I sent it to my boss just to say like, “Hey, is this on track or not?” And she forwarded it out to the whole team saying, “Hey, check out this cool thing Ashleigh built. We should all use this.” The net result of that was one of the other SDRs pulling me aside and saying, “Girl, you need to cool your jets.” And I was like, “But what? I didn’t ask her to send it out. I just built that for myself.” And she was like, “Oh okay. Because it looked like you were coming in and being a cocky little 20 something and telling us all how to do our job.” “Oh that was not, no, no, I’m scared of you guys. You scare me.”

Ashleigh Early: I don’t want to look like a fool, so I’m creating things for myself, but I see this at a lot of people in terms of it more often than not comes across as cockiness and an inability to be coached. So it’s kind of like I say, overfunctioning because this comes out more often than not as people just doing too much and everyone else looks like they’re just or running ahead of it. But it’s really being motivated by fear. So if you feel scared or really intimidated more than about 30% of the time, you’re probably doing this. So if you feel like you need to take a break in the middle of the day just to go shake in the bathroom, you might have a soft skill problem.

Darryl Praill: I love it, I love it. Okay, so with that visual of shaking in the bathroom, we’re not done. I’m going to leave you to contemplate that while we slip away for a brief commercial break. Don’t go anywhere.

Darryl Praill: All right. Welcome back folks. Hopefully you are no longer shaking in the bathroom and you have recognized you might have a soft skill problem. All right. What other attributes do you see in soft skills? So let me give you context that may help the audience. I’m assuming some of this might be interactions with my fellow colleagues on the sales team. It might be interactions with my boss. So what are some examples there where you might have some soft skill challenges? We’ll set that stage and then then we can start talking about maybe some classic tips and tricks to address those soft skill problems. So that my audience can apply your wisdom.

Ashleigh Early: Okay.

Darryl Praill: I can hear it already. “How much time you got there.” I can almost feel that in your voice.

Ashleigh Early: Yeah, so I think there’s two things here. I think there’s the internal soft skills and the external soft skills. So I’m going to focus on internal, which I mean like inner kind of inner company politics and politics is a dirty word for many, many reasons, but kind of addressing the internal stuff first. We can talk about how we handle prospects later, which is the external side. First of all, every company has politics. Every company has politics. Any company that says they don’t have politics is in denial about the fact that they have politics. So that’s not a dirty word. I mean, I’ll say this, I’m someone who studied politics in college. I have a BS in political science. I completely nerd out over every, specifically I can date when we record this, but I’m flipping out over what’s going on with the parliamentary process in the UK right now.

Darryl Praill: In the UK? I know it’s crazy, isn’t it?

Ashleigh Early: I’m living for it. It’s horrible, but it’s so much fun. It’s a great slow motion car wreck.

Darryl Praill: I’ve already had three conversations with three of my British colleagues already today about Brexit and it’s amazing how each of those conversations were completely different about what’s going on with Boris and everybody else. Anyway, it just blows my mind. Okay, I’m done. Back to you.

Ashleigh Early: Oh no, I know. I love watching the livestream of parliament. I actually watched the livestream so I can see the votes and watching the representative defect from Johnson’s party last week, like by literally just walking across the floor. Oh, you can’t make television like that. It’s brilliant.

Darryl Praill: And isn’t it crazy how just different the UK scenario is just playing out just versus even the US scenario? I mean, there’s a lot of conflict in both of those scenarios. It’s amazing to watch, which is ironic that we’re talking about internal conflict. So, carry on.

Ashleigh Early: And this is kind of the whole point. Politics is not inherently a bad thing. Politics is by its very definition, just the science of human interaction. So every interaction you have is political in some form. Just in terms of power dynamics, persuasion techniques, there’s always interactions going on and there is a science behind all of it. So every company, every relationship you have is inherently political. So one of the things I talk a lot about is like, I want to de stigmatize that because politics is not a bad thing. Internal politics is not a bad thing. When they get toxic, that’s where it’s bad. So what you can do to protect yourself from getting into a toxic environment, the ultimate prevention against a toxic environment is radical honesty. So being incredibly transparent with your boss, being very transparent with your coworkers.

Ashleigh Early: And I’m not saying overshare, so there’s a difference between telling your boss, “Oh my gosh, I went out last night, I had oysters, I got food poisoning. I might be running around a little bit crazy today. So, if you don’t see at my desk, that’s why.” And just telling your boss, “Hey, I’m not feeling great. I’ll be at my desk as much as I can, but I might not make it through the day.” Different thing versus saying nothing. And then your boss walks by and wonders, “Hey, it’s 10:00 AM. It’s prime call hours. Why isn’t John at his desk?” So radical honesty is a huge thing because especially in your time as an SDR, you can’t fix what you don’t know about and nobody knows you. You have no reputation, you have no credibility. You need to earn everything. So especially being honest with your boss around what you’re thinking and what you’re feeling is super, super, super important so they can understand how that ties into your behavior. Because if you don’t tell them what you’re thinking and feeling, all they have to go on is your behavior. And that’s how you can end up with that thing where you look cocky, but really you’re terrified.

Ashleigh Early: The same thing on attendance, which is something I see way too many people confused by attendance in an SDR role. And I always tell people every boss handles attendance differently. But if you have a boss or you have an environment that is very structured and they do want you in your seat at a certain time, to be early is to be on time, to be on time is to be late and to be late is unacceptable. Just straight up. If you have a boss that is more lenient like I was when I was managing SDRs, my role for the team was just, “Look, I want you to be in by this time. If you’re going to be late, just let me know. That’s fine. We can handle it. If you’re late a lot, we’ll have a conversation, but stuff happens. I want you guys to be focused and relaxed and doing your job and having fun. So I don’t want to be a hall monitor.” Every person in every company manages differently. But again, it comes back to this idea of over communicating and that radical honesty of telling them kind of where you are and what you’re thinking.

Ashleigh Early: So those are kind of the quick things. And that also goes for your, I think one of the best things you can do is either in your office or reaching out to other SDRs in the area, have an SDR BFF.

Darryl Praill: Oh, I love that.

Ashleigh Early: Yeah. Have an SDR BFF, someone who you can text and say, “Oh my gosh, I just got chewed out. I hate this job. Why am I doing this? What am I doing with my life?” And at the same time have that person respond back and be like, “Oh my gosh, it just happened to me too. You’re not alone. We both suck at this, lets stuck together, whatever.” Maybe edit that line out, but you can figure these things out and having that someone to commiserate with that you can be fully transparent with without worrying about, is this going to go to my boss or what are they going to think? Kind of having that fully unfiltered relationship can be super, super, super therapeutic.

Ashleigh Early: Like I said, if you’re at a company where there’s a team of SDRs finding who your BFF is going to be in the office and it doesn’t always necessarily have to be on the SDR team. Several of my SDR BSFs were actually ops people, where I just kind of go down and park next to their desk and be like, “Oh my gosh, I’m really getting sick of this system. Can you please explain to me why we’re using it?” And then just having fun conversations because I just got along with those people really well. But having somebody that you can kind of have those unfiltered conversations with and then they can help you strategize around how to bring ideas and stuff like that to other people is super helpful.

Darryl Praill: So it’s funny I’ve heard you say at least three things, and I know you’ve said more, but the thing that jumped out at me, was a couple things. You said have a BFF, which I would use a different term. Same premise. I use the term of having an accountability partner. So somebody that, yes they’re the BFF you can go and dump on, blah. “I got my butt handed to me. Am I wrong? Am I, let me just vent. Blah. Because it’s a safe place to vent.” We all need to vent. So it’s better you have the ability, the capacity to vent to somebody who’s trusted than not having that because what will happen is all your frustrations will boil up inside and eventually you will blurt out at a frustration to an individual, maybe your boss and you will say something likely bad that will not help your career progression. So it’s no different than in the classic, “I’m going to draft an email and I’m going to respond to them and I’ll show them,” and then you don’t send it, right? You kind of vent it out. You get your stuff out. Okay, cool-

Ashleigh Early: I’ll tell you this, I actually had to fire someone once because this happened to them and I took a bit of responsibility for it too because I didn’t see it coming. But it’s one of the things that helped me get very good at spotting this. An SDR had that happen to them. They were keeping everything in and they exploded because a prospect was rude to them and they responded by sending the prospect a message on LinkedIn saying, “I hope you get what’s coming to you.” And that’s a threat. I had to fire him on the spot, which sucks because he was a really good guy and he’s doing just fine now.

Darryl Praill: But he learned.

Ashleigh Early: He learned. But that was a perfect example of, if you bottle these things up, they will explode and you can’t predict when they’re going to explode. So it’s that whole idea of shaking a carbonated can. Like you’ve got to make sure you release that some way, somehow, somewhere. And it’s knowing yourself well enough to know when and how to do that. And if you don’t know when and how to do that, that’s a conversation to have with your boss. And if your boss isn’t somebody who can have that conversation with, hit me up on Twitter, if nothing else or LinkedIn or something. Hit one of us up.

Darryl Praill: Oh my gosh. Professional shrink right there with Ashleigh. I love it. So you’re right. The reason I call it an accountability partner as a opposed to just a BFF is because it’s also somebody who needs hold you accountable to say, “You know what, I love you. You know we have a great rapport. You know I’m looking out for your best interest. So with that as the premise, you were out of line there. What you said or how you approached it, you were out of line. I’m just giving you that context. I’m not lashing out at you, I’m not judging you. You were out of line.” And accountability partnerships are two ways. So there are BFF, so you can vent, but they’re also an accountability partner to hold you accountable because you’re trying to achieve something, right? You’re trying to achieve control my temper, control how I engage, control my dialogue, control my voice, control my intonation-

Ashleigh Early: Stand up for myself better.

Darryl Praill: Stand up for myself. Whatever it might be. An accountability partner is going to do that in the good and the bad. You said something you shouldn’t have said or you didn’t stand up for yourself and you should have and that was the perfect chance because it’s only, this is the big part, it’s only when you’re self aware that you go, “Oh.” So perfect story. I had multiple bosses, but one in particular stands out for me where he would say, “Darryl, you’re doing this and it’s bad.” And I’m early in my career and I would argue, “I don’t see it. I don’t see it. I don’t see it.” And he would get so frustrated. And finally we had this epiphany and I said to him, I said, “You have permission, the next time I’m doing that to interrupt me, stop and say, you’re doing it right now.” Okay.

Darryl Praill: Fast forward a couple of weeks, middle of something. He said, “You’re doing it right now.” And all of a sudden I went, “Oh.” Mind blown. Poof. I see it. Now I see it. I’m in the moment, I get it. And so I asked my boss for that help. So my boss gave me that permission back. So that was that accountability part of it, self awareness, proactively seeking guidance. I opened up by saying I went to my boss, I went to my head of HR and said, “How do I, Darryl, interact with these people differently? Because I know I have this nuance and I know I have this reputation so I’m going to preempt it.” You can’t bust me for having a bad style if I’ve come to you first and said, “I know I have a bad style and I want your help.” So just getting in front of it.

Ashleigh Early: Absolutely.

Darryl Praill: Politics, getting in front of the message, right. That’s what it is.

Ashleigh Early: Radical transparency.

Darryl Praill: Radical transparency and it freaks people out. All right. And when it comes to prospects, we’re running tight on time, but are there any considerations here that I need to be aware of as a rock star sales rep that I am.

Ashleigh Early: The biggest thing I think people fail to do when it comes to kind of keeping this theme of radical transparency and self awareness when you’re calling, it’s know yourself and know your audience. So a really good example of that is when I’m cold calling and everyone’s got their different ideas on how they open. I typically will start off conversations with usually a very bad joke and it can be everything as simple as, “Hope your Monday is going better than mine is. How’s your week going? Mine’s kind of, this is one of those weeks, I’m kind of looking forward to the end of it.” or “Hey, things are going great. I got my coffee, the sun’s out, everything’s good. How about over there?” Making jokes about Monday night football, making jokes about the weather, anything like that. But they’re very quick. But that kind of radical honesty and not being afraid to start off a conversation with a prospect saying, “Yeah, I am in the midst of the morning. The caffeine hasn’t kicked in yet. Forgive me if I stumble over my words here.” It makes you human and especially when you’re dealing with cold calling or cold emails, anything that can make you human will instantly stand you out from the pack and help you create a better connection.

Darryl Praill: What I love about what you just said was you nailed it. You turned your possible vulnerabilities and your issues into a strength. You were vulnerable, you were transparent and you embraced it, but you were speaking the truth. It’s not like you’re a used car salesman or a snake oil salesman. This is you. You used it for good. I love that.

Ashleigh Early: Totally. And I mean it comes out as simple as I actually figured this out because I got really horse pretty early on in my SDR career and I actually have a blog post coming out soon on how to take care of your voice. Given my previous life career as an opera singer, I didn’t follow my own advice. I lost my voice and I was calling people and rather than my boss was like, “I don’t know if you should be calling people, you might scare them.” And so I just started off the conversation saying something along the lines of, “Hey, I’m sorry. I know I sound like death but I’m just getting over a cold. I’m calling you because I’ve got a number to hit this month.” And I got tons of meetings.

Darryl Praill: Sure. Because it broke the ice and it was funny and it was disruptive but it was very personal. And you recognize the elephant in the room. You were the interruption and this is why. I love it.

Ashleigh Early: Yeah. All right.

Darryl Praill: We’re out of time.

Ashleigh Early: And I’ll say this too. One more thing, really quick.

Darryl Praill: Yeah.

Ashleigh Early: You’d be surprised how often people love being a hero. Any chance you get to have the other person on the other side of the line feel like they’re being a hero. It’s one of the most powerful closing tactics you can do.

Darryl Praill: That is so true. People are actually genuinely good if you give them a chance. If they can help you out, you can leverage that. It’s a win-win. You all know what’s going on. Everybody feels good and who doesn’t want to feel good? So I love it. So we’ve just scratched the surface of soft skills. You’ve heard her say if you have no one else to talk to, she would be available and the only way you can do that is if you follow her on LinkedIn and it’s really simple. It’s Ashley, A-S-H-L-E-I-G-H. That’s the Ashleigh spelling she has used. Early. Not late, Early. I know she’s never heard that joke before. So Ashleigh Early. She’s a rock star. She is the rockstar coach, advisor, apprenticeship director there at Vendition. She of course also is the co-host of The Other Side Of Sales, which is for the rest of us who are non-sales bros. Check it out, both of those. Ashleigh, any final words, thoughts, wisdom, or just parting sentiments you want to share?

Ashleigh Early: I actually have a favor to ask.

Darryl Praill: What’s that?

Ashleigh Early: I want to ask you and everyone who’s listening just with The Other Side Of Sales podcast, we’re trying to highlight all of the amazing people out there who are doing great work but who don’t necessarily fit the general mold. So we need more people to talk to. So if you go to there is a nomination form. I want to hear from anyone who’s been a huge impact on your career or who you look up to, who is a beacon of individuality and learning to lean into that self-awareness and is doing things in an incredible and fantastic and an individual way. So, nominate the awesome sales pros who you think we should talk to and highlight.

Darryl Praill: That’s it folks. We’re done. We’re out of here. Speaking of podcast, please go like, share, comment, review On The Inside, Inside Sales podcast. We will see you again in one week’s time. Take care. Bye bye.