Humanizing Sales in the Age of AI: Strategies for Success
What separates the best sales teams from the rest in today’s unpredictable market? For David Ashe, director of sales development at Allego, it’s about ensuring your SDRs retain their human approach. In a world where AI and automation are causing buyers to question if the person calling them is even human, sales reps must humanize their approach.
“We try to humanize ourselves by leaving voicemails, by having the emails be a little more authentic and written by a human,” Ashe said during a recent interview with me. “There may be some spelling errors, or there may be some abbreviations of words or street lingo in there to show that we’re human and not a bot that is well polished. And then we use social media to show that, ‘Hey, this is a human. Look at my profile. I’m a human.’”
And during today’s economic climate in which buyers are risk-averse and reluctant to meet with a seller, let alone purchase anything, SDRs must act like therapists, he said.
“We have to lead [buyers] down that path to understand they have a problem that they didn’t know about, even if they don’t have any obvious ailments,” Ashe said. We’re opening up different channels to say, ‘This is happening. You didn’t know it, but it is. And we can help you.’”
Your team’s success also depends on you, the sales director. Are you motivating your sellers? Do you provide personalized coaching? Do you allow peer-to-peer coaching? Are you staying on top of new sales techniques?
Just because you’re in a director position it doesn’t mean you should stop learning. Learn how to be a better leader, but at the same time, learn how to be a better salesperson.
“Just because you’re in a director position it doesn’t mean you should stop learning,” Ashe said. “Learn how to be a better leader, but at the same time, learn how to be a better salesperson, and take that information and give it to your team.”
Ashe shared even more during our candid conversation, including practical advice and insights gleaned from years of experience at the forefront of sales leadership. From dealing with economic uncertainties to the role of technology in building genuine connections, Ashe offered a roadmap customized for sales leaders searching to find a balance between adaptation and innovation.
Continue reading to learn how Ashe’s GEAR methodology enhances sales training and leadership by providing a definitive path for SDRs to thrive in any future sales environment.
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Michelle Davidson: What are the biggest challenges that you face as a sales development leader these days?
David Ashe: I never think about just myself as the leader. I think about the team. So when you say, “What do you face as an SDR leader?” I’m going to think about my team’s challenges and, overall, what’s stopping us as a team from succeeding or even over succeeding? And I would say right now, it’s the economy. It has made it difficult because a lot of companies aren’t looking to add tech right now. Companies are saying, “We’re not adding any more tools. We’re using the tools that we have. And if we don’t have any tools, we don’t have the budget to add any more on.” Usually, people would be open just to having a conversation and learning about tools they could add later on, but … now we’re finding people won’t even have a conversation because they’re scared to take those conversations, since their higher-ups have said, “Please don’t do this. We’re not adding any. So why are you taking time out of your day looking at tools when you can be doing other things?” So, some people used to be risk-tolerant, but we’re finding a lot more people are risk-averse to having even a conversation about a new tool. It’s like, “I’m not going to waste my time because I can’t add anything.”
Then I would say another thing that is making it harder for the team, and it kind of goes into the challenges the SDRs face, is AI. AI is fantastic. It helps the SDRs be efficient in areas where they could be slowing down, but it’s also made the SDRs’ job a lot harder. The reason why it’s made it a lot harder is people already have their walls up when a salesperson calls. And now, they automatically think we’re not human, or that we didn’t write our emails; it was done by a bot, and there’s no real human connection anymore.
And then when you get into AI-powered dialers or parallel dialers—which are not really AI but machine parallel dialers—people are getting more and more phone calls. The volume of calls that you get on a daily basis has increased. In the past, you may have gotten two or three sales calls a day, but now you may be getting six or seven of them a day. So people are not picking up their phone as frequently as they did in the past.
How do the SDRs get around that? How are you coaching them to get around that to be able to reach somebody?
Ashe: We’re using different channels, and we’re continuing the message that we started via email through the phone, social, and voicemails. When people are doing the parallel dialers, they’re not looking to leave voicemails. They’re just ghost calls; they’re hoping someone picks up. Their connect rate is still 4 to 5%, but they’re making 900 calls in one day. They’re just churning and burning through people, and they’re calling them multiple times throughout the day.
We try to humanize ourselves by leaving voicemails, by having the emails be a little more authentic and written by a human. There may be some spelling errors, or there may be some abbreviations of words or street lingo in there to show that we’re human and we’re not a bot that is well polished. And then we use social media to show that, “Hey, this is a human, look at my profile, I’m a human.” And sometimes we’re sending voice notes or we’re sending videos.
When thinking about the qualities or skills that make a successful SDR, what are the top ones?
Ashe: There is no real order, but you’ve got to have I would say 80% of them or 75% of them. So the first would be being coachable. You have to be coachable as an SDR. Talent can only take you so far. So, if you’re not learning new things inside and out, you’re going to create a glass ceiling for yourself. So you have to be able to take some coaching from either your SDR leader, or the account executive (AE), or even your peers and be able to apply it.
The next one is being a strong communicator. If they’re not a strong communicator, it makes it really, really difficult to make a prospect or customer change the way they think. We’re finding that the majority of SDRs are finding success through the phone. So, if you can’t be a strong communicator on the phone, it’s going to be really difficult to exceed your number.
You have to be coachable as an SDR. Talent can only take you so far. So, if you’re not learning new things inside and out, you’re going to create a glass ceiling for yourself.
Next I would probably say active listening. There’s something that we talk to the SDRs about as soon as they start. It’s that you’re not listening to respond; you’re listening to understand. And when you’re a good active listener, you can pick things out and really dig into them. And then try to connect the dots on what they said, like the challenges they’re experiencing and how our solution can help. If you’re not listening to what someone’s saying and you’re just ready to, what we call, pitch slap, you’re missing an opportunity to really connect. So active listening allows us to connect with a prospect, and it allows us to position the solution as something that they need rather than something that they just need to hear about.
Then the final one, and it’s a big one, is curiosity. They have to be naturally curious. We need people who want to learn about our prospects, learn about our product, and ask a lot of good questions. Not just ask questions, but ask good questions that will help uncover intel that we can use. And that goes back to active listening to help us leverage that information to get us into a conversation about our solution. So, if they’re not someone who likes to ask questions and they just want to talk about our product, it will lead them down to a lot of dead ends and people won’t want to learn more. Because our job is to get them to pique their curiosity, to get them to have a conversation with an AE.
It’s not too different from being a reporter.
Ashe: Yeah, very true. And I tell my SDRs it’s like the old way of selling. You can kind of still do this with inbound. But inbound, as you know, has kind of slowed down. But back in the day we’d say, “You’ve got to be a doctor, you have to take the doctor approach.” But with the doctor approach, someone knows they have something wrong with them, so they’re coming to you to figure out what’s actually wrong and want to know how you will treat that symptom or how you can solve that problem. But right now people don’t want to spend money or have been told, “We’ve got to button down the hatches.” So, SDRs have to be more like a therapist. We have to lead them down that path to understand they have a problem that they didn’t know about, even if they don’t have any obvious ailments. We’re opening up different channels to say, “Yeah, this is happening. You didn’t know, but it is. And we can help you.” So it’s moving away from the doctor approach to the therapist approach.
I would assume that your SDRs have different styles and personalities. Do you coach them differently? Is there personalized or customized coaching for them?
Ashe: Yeah, you have to treat every individual differently because they all learn differently, and they all respond differently. I know with some of my reps, I can use a little more carrot with them. With other reps I use a stick approach, and they respond better. But if I’m dealing with someone who values steadiness, cooperation, and calmness, I can’t use a stick approach with them. This means I can’t be overly harsh or forceful, like saying, “Hey, you’ve got to do this. You’re failing. What’s going on here? We need to push harder.” I have to be a little softer with that person.
You have to treat every [SDR] differently because they all learn differently, and they all respond differently.
You mentioned the GEAR methodology. What is it? What is it for?
Ashe: I’m a big planner. I really took the cheesy saying of “if you fail to plan, you are planning to fail” to heart. So every month I have a document, and it has the four things I need to make sure I am ready for that month. One of those four things is gamification–the G in GEAR. So, as an SDR you’ve got to have some sort of incentive, that extra fuel to get them way across the finish line. In slower months, we have to step it up and consider offering additional money.
There are different games that we can play or different competitions that we do. This month, we’re doing some March Madness. Similar to the NCAA bracket, we’ve created an SDR March Madness bracket, where each SDR is paired up against each other in the bracket format. And it’s a winner takes all tournament. So, having some sort of carrot to keep them motivated throughout the month helps drive them a little harder without having to say, “Work harder.” We’ve also done an SDR Kentucky Derby. We’ve done SDR Battleship, SDR Monopoly. We have a contest where the person who has the most meetings booked on a Friday gets a drink sent to them by Dash. So there’s different things, different levers that I try to pull when it comes to gamification.
The next thing I consider is enablement. We’re dealing with what I call the video game generation. These are the people who have grown up on video games, experiencing multi-players, and still play games released a decade ago. These games continue to engage them by releasing new content and providing ways to level up, keeping them engaged. So for me, it’s like, “How do I provide them something to sustain their engagement each month? How do I level up their skillset?”
For example, a few weeks ago, we did some email training with different types of email formats SDRs can use when they’re reaching out to their prospects. And a few months ago, we did some social training. Different types of training are designed to help give them more than what they’re used to doing to make their job exciting again. They’re doing a job that is very repetitive. What new little trick or tactic can I give them this month or this week for them to try on the phones to have some fun?
[SDRs are] doing a job that is very repetitive. What new little trick or tactic can I give them this month or this week for them to try on the phones to have some fun?
And then the A is accountability. What am I going to do to make sure my team is held accountable? I think that’s one of the things that a lot of leaders struggle with—how do I hold my team accountable without being micro-managey? So, I use different tactics. I leverage peer-to-peer accountability where I pair them up in teams for competitions and say, “We gotta get this job done. Lean on each other. It’s a no person left behind mentality.” So if they see one of their teammates failing, they help out.
Or I have a KPI sheet, I call it my heat map, where it has all the KPIs and it ranks them against their peers, and it uses some color coding to say, “Green is you’re doing well, yellow is you’re close, and red is you’re doing bad.” And when they look at that against their peers, they say, “Whoa, I got to pick it up. I’m not doing as well as my peers, I don’t want to be the last.” You don’t have to be the fastest, but you gotta be faster than the slowest. So, instead of me saying, “Do your job, do your job.” and staying on top of them, I use different types of levers to have the team hold each other accountable. Or I use technology to hold them accountable. And I use the KPI sheet, but I’ll also build out different formulas in Excel, and I’ll show them how they’re doing. I use their numbers to provide constructive feedback and guide them towards meeting their targets.
And then the last part in GEAR methodology is reassurance. How am I going to show the team that they’re doing a good job? How am I going to be that cheerleader this month? What is a different tactic I can use to really get them excited that they feel like they’re having an impact on the business? Does that include doing a shout-out on the Slack channel? Is that asking my CRO, or my founder, or my CEO to write them a note saying, “Good job.” Is it doing a shout-out on LinkedIn? Is it going to LinkedIn and giving them a recommendation, or endorsing them for something. Or is it calling them out in a team meeting or quarterly review?
So that’s the GEAR methodology. It’s gamification, enablement, accountability, and reassurance.
Is training delivered to SDRs in the flow of work?
Ashe: We time block to help provide training in the flow of work. This includes listening to calls and sharing best practices. Like if someone has a good call, they send it out to the team, and the team can listen to it when they want. Or if someone’s doing something different on the phone that’s finding them success, they share out to Allego for everyone to watch on their own.
Can you recall a challenging situation you encountered while coaching SDRs? Or a success story of an SDR that you coached?
Ashe: I’ve had some great stories over my career, but I can tell one from here at Allego. There was a rep that was struggling, and they were on a pre-PIP [performance improvement plan]. And the reason why they were on a pre-PIP is they weren’t hitting their numbers. They were kind of just floating. They weren’t doing any of the extra things that they needed to do, and they didn’t really have a strategy for their day.
In a pre-PIP meeting, we talked about things like, “How are you planning your day? How are you organizing your day?” So, we organized their day with time-blocking, doing 45-minute call windows, prospecting windows, emailing windows, and then rinse and repeat. But the thing we saw that was hurting them the most was their messaging. And I think one of the things that a lot of sales organizations struggle with is consistent messaging. They allow people way too much autonomy on how they position and pitch the product.
This person wasn’t using consistent pain probes. So, we started having this person listen to A-player calls. We started doing some role plays with this person with another SDR, and giving coaching on that recorded call. They would send us the role play that they recorded in Zoom via Allego, then the manager and I watched it and gave the person coaching. We gave them the compliment, “You’re doing good here and here, but you need some improvement here.” We gave them the score-sheet and then started scoring over that 30 days at least two calls a week, so we could really understand where this person’s gaps were.
And then it came to the body of the call. So we have our introduction, or open, our intro, body, and close. They were doing well introducing who they are, and the pattern interrupters, and the upfront contract. And they were doing good with delivering the pain probes. But they weren’t doing well finding pain, digging into it, and connecting how our solution could help.
We were able to see that by coaching their calls. One time they did really well on the body, but it wasn’t consistent through every call. So, by using the Allego scorecards and using the profile, we saw they were really weak in this area and were scoring about 50% in the body of the call. Then we started doing more role plays where we just focused on the body. We said, “You already got through all these things, this is the pain probe I picked. Now, let’s go into the pain funnel, and really dig into it.” And we would record that, and we gave them a simulator so they could practice.
By the end, they got themselves off the pre-PIP by working with their peers, getting coaching from their manager and their director, and then putting it all together. After doing all of that, this person was a quarterly all-star and SDR of the Year.
Oh, that’s awesome. It must make you feel good that it works.
Ashe: Yeah, I love seeing them succeed. That’s why I took this job. I want to teach people a lifelong transferable skill that can make them very successful if they’re willing to put in the work. Someone did it for me, and I want to do it for others.
One last question: Any advice for your peers, for other directors of sales development?
Ashe: Just because you’re in a director position it doesn’t mean you should stop learning. Learn how to be a better leader, but at the same time, learn how to be a better salesperson, and take that information and give it to your team.
About David Ashe: David is director of sales development at Allego. In this role, he oversees a sales team responsible for growing the company’s customer base, revenue, and profitability within the United States.
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Download The Sales Coaching Handbook and learn what top sales coaches do to boost motivation, increase focus, and supercharge the performance of sales teams.
