EPISODE 631: A Deep, Honest Look at Empathy in the Sales Process with Kyla O’Connell

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Today’s show featured an interview with Kyla O’Connell with Win-Win Sales Training. Kyla will be a speaker at the IES Women in Sales Leadership Elevation Conference on October 12. The interview was conducted by Gina Stracuzzi, chairperson for the conference.

Find Kyla on LinkedIn.

KYLA’S ADVICE:  “Explore how empathy is really emerging as a superpower in business. Not just because of how we’re going to influence our customers to want to buy from us, not just because we’re going to influence our teams to work harder to hit their goals because we’re influencing them. Having that empathy for yourself so that you can recognize when you’re having an off day, and forgive yourself, and get back to the next play. Because again, it’s the kindest thing you can do, but it’s also the most effective thing you can do for your career.”


Gina Stracuzzi: Thank you. Kyla is founder and lead facilitator for WIN WIN Empathy-Driven Sales Training, and I am super excited to talk to her about that and what she’s doing now. I will say, Kyla is leading the session at the conference on Have Sellers Lost Their Edge? Using EQ and Empathy to Help Sellers Revive and Elevate That Selling Feeling, which I love. Welcome again, Kyla, and tell us about yourself.

Kyla O’Connell: Thanks, Gina. Similar to a lot of sales executives, my career started as a sales representative early in my career, and I noticed that I was having a lot of very quick success in those roles. I just thought, “Okay, this sales thing is easy.” That was wonderful and then I realized that it was one of my positions, in maybe my late 20s, probably my fourth sales role, happened to be in DC with the Capital Society. My job was to convince very prominent Washington DC professionals to upgrade their private club membership, from whether it would be Tower Club, or the City Club of Washington, to a higher level of membership that they would obviously pay monthly dues to per month. I was able to increase the value of that membership by 40% within the first six months of being in that role. That got the attention of a lot of very prominent people in the area, which was wonderful for my career. Probably one of the reasons I took the position.

I kept hearing from people that I had a ton of respect for, business owners, and CEOs, and key executives, “Hey, Kyla, if you ever start your own business, I’d like to maybe hire you as a consultant. I see what you’re doing here. This is really great stuff. Maybe you could help our company.” When you hear that about 10 times, 12 times, you start to listen. My 30th birthday present to myself, I started Driven Sales and Marketing, which was just a boutique sales and marketing consulting firm. I was going to just focus on small businesses that maybe weren’t ready for a full-time marketing executive yet, and help them not just strategize their plan, but sometimes execute it as well.

That started the relationship with one of my clients, which is John Asher, who’s also one of those prominent DC professionals, as well as a prominent sales professional and speaker, and just one of my dearest mentors in my life. We just had such great synergy, and after two years of working as his contractor, he said, “Maybe we should merge our companies and work together.” That was the beginning of a more than 15-year relationship. I just loved what we did. We are sales trainers. I remember the first training that I went to with John Asher, and I said, “Oh my, I’m definitely going to do this one day.” That’s where my passion really got into training and coaching salespeople, and eventually some of the top sales executives and leaders in rather large companies.

It was really with that assistance merging my company with Asher that I was able to get that experience, which led me to training and coaching thousands of salespeople, hundreds of sales executives all over the world, including Europe and China. Then our relationship, it’s still a beautiful relationship, but I wanted to go in a different direction. I wanted to go into this more empathy-driven direction, and I just felt like it was the right time in my career and also in the world today to get this message out and to join other really prominent sales thought leaders who are much bigger platforms than I have. But I wanted to join their conversation about the power of empathy. That was really what drove me to go out and start WIN WIN. I can’t think of any title or name of a company that really just amplifies empathy-driven sales training more than we both win.

Gina Stracuzzi: Boy, if there was ever a time, it is now. Empathy came to set prominence during COVID, but I think it’s even more important now perhaps because now we’re in this world that’s half hybrid, half real life, and being empathetic of people, meeting people where they are, and trying to help them keep doing what they’re doing and doing it well, is really critical. But knowing what they’re dealing with is a big piece of it, and being empathetic is really how it’s going to happen. I think that’s brilliant timing, if I may say so, Kyla.

Kyla O’Connell: Well, good. Thank you.

Gina Stracuzzi: We’ll talk a little bit during this interview about some of the things that you’re going to be talking about at the conference, but they fall into the training that you do for others, which is why I wanted you to do this session. Can you talk to us about some specific examples where you have used empathy-driven techniques to achieve results?

Kyla O’Connell: Obviously, I spent the first half of this conversation speaking about the sales career and working with the sales representatives and executives. When I was selling, and I am always selling, of course, now I’m the founder of a company, so I’m selling every day, as you know, we’re all in sales all the time. Whether you’re running your own company or you’re the first person that picks up the phone in an organization, anytime that one organization is communicating with another, or one person’s communicating with another, is an opportunity for that relationship to either increase in value or decrease in value. That’s a passion of mine to really help people understand that one, we’re all in sales.

Now, also, what does that mean? That means we have to show up with empathy, and we have to show up consciously, very competent about how we are harnessing that empathy to the other person, whether that other person is a customer or a member of our sales team, or any team. It’s really about putting that a hundred percent focus on the other person, and also a hundred percent focus of not making this conversation about me, and making that conversation about the other person. As humans, that’s not something that necessarily comes natural to us. People who have natural high levels of empathy do tend to be better at this. My empathy levels I think are in the higher range, so it is a little bit of an easier process for me, and that’s probably why I’ve always sold this way, and managed and led this way. But it’s still work. It absolutely is still work, and it requires a hundred percent focus.

Really what that means is when you are speaking to, let’s say in a leadership situation, a sales executive, EVP of sales, or sales manager, director, is speaking to one of their sales team members, that means that they’re bringing to that conversation the perspective of who they’re speaking to, and they’re not thinking about anyone else. You said it, everybody’s story is different. I can’t lead each person the same way. How I show up for Jim, who needs constant mindset training and constant listening, and helping him maybe control some of his anxiety, because sales can be very stressful, is completely different than how I show up for let’s say Amber, who needs a lot of recognition. Those two conversations are completely different. The one-to-one meetings are completely different. The strategies that I’m going to help Jim with look completely different than what I’m going to help Amber with, because they’re customized to where they need that help.

Once you really listen and ask a lot of questions, which is of course what we teach in sales training, what we should do for our customers as well, because we do the same approach with our customers, then we can really harness, “What does this person need from me? Let me help them, if I can. If I’m not the right person to help them, let me find somebody who is,” and then give them the strategies, support their efforts, give them a lot of support, and then here’s the big one, then get out of their way. Let them be them. Let them see their own success. In those two examples specifically, there wasn’t a lot of sales training needed. They had great natural aptitude for sales. They were industry professionals. They didn’t need more product knowledge. They didn’t need more software or process. They just needed what they needed. I helped them get it and helped them see what they needed, and then they were off to the races. In those two situations in one year, those two individuals doubled their sales from three million one year to seven million the next year. Now they’re on their way both to do 10 million a year in sales. It was exciting.

Gina Stracuzzi: Really, I’m excited about what you’re bringing to the conference along those lines, because I think when I talk to different salespeople in my work with IES, and this is true a lot for women, they’re feeling like they’ve lost a little bit of the hustle. I think part of the reason we’re doing the conference is because we’re not talking enough about this transition back into real life, so to speak. One minute anybody is a potential killer, and the next minute everything’s okay. There’s been an emotional impact on all of us. If you are a seller and you need to be on, and you need to be considering the needs of other people in your job, then I think it wears you down and burns you out a little bit faster if you’ve lost that selling feeling, as the title of your session goes.

I’m eager to hear what you’re going to talk about in that session, because I think we had that hustle going prior to the pandemic, where everybody was at like 90 miles an hour. Now, we’re trying to rev back up to 90, but it doesn’t feel authentic. Because we’ve got this new way of life that’s a little more casual, not quite as driven, at least outwardly-facing. I think it’s left people in this in-between place, if that makes sense, of not really having the same level of drive, but still wanting to show up, still wanting to be really good at their job. But there’s a little something that’s been lost, and I would think that empathy to that situation is exactly how to come at it.

Kyla O’Connell: Yeah, absolutely. Whether you’re a sales leader inviting your team to come back to the office, or you’re a sales professional and you’re now inviting your customers to come back to the office, or have in-person meetings again. I think sales, and management, and leadership business, it’s always evolving. The pandemic just forced that evolution, I think, a little faster than where we were headed anyway. There’s no secret that the younger generations are forcing business owners and business leaders to be more empathetic. I’ve seen that play out in my life and in examples of my clients’ companies where their leaders have had to really change some of the ways that they’ve been managing for years, because people will just leave. They just want a different management style, and our customers are too smart today. They expect a more empathetic selling environment as well.

During that evolution, and maybe again, it’s throwing some people off of it because it happened so quickly, I think the key there is, one, to recognize, yes, the world’s a little different now, and we’re also on the launching pad of this AI. It’s going to evolve this again. It’s just about hanging on in some ways. But I think that the key word after recognizing that things have evolved is strategy. What we’ll talk about in the conference are strategies that salespeople can use to show this empathy through their selling process with their customers, and also strategies that sales leaders can use with their teams to show empathy to their teams. The beauty of these strategies, and I’m happy to get into a few of them if you want, or we could just tell them, “You have to wait till we get to the conference.”

Gina Stracuzzi: Well, give them one as a teaser.

Kyla O’Connell: Well, again, nothing that I am teaching has not been said before. I wish that it was, or else we would have a whole different level. But it’s packaged in a way, like you said earlier, at the right time, where we’re in the middle of this evolution, that I think that these strategies need to be revisited, repackaged, and thought about differently, and leveraged differently. One of the strategies, and it’s very simple, and any salesperson, or leader, or trainer, or coach has certainly said this on your programs before, but it’s probably the key foundational strategy of empathy-driven leadership and empathy-driven training, is to show up in a conversation with a mindset and perspective of, what is in it for them? We call it, with it. What’s in it for the person that I’m speaking with to be speaking to me?

That foundational approach, obviously there’s many strategies within each stage of the sales process that we’ll get into in the conference, but the foundation is always about whether you’re prospecting a new client, okay, what angle are you taking? Because if you’re taking an angle that isn’t important to the person that you’re contacting, don’t expect a response, especially today. Or if you’re a leader, and you’re in that one-on-one meeting with somebody who’s struggling, and you don’t come to that meeting with an angle that that person resonates with and can feel psychologically safe with you, that they may open up and tell you what’s really going on, and that maybe you can help them in a way that if they didn’t feel psychologically safe with you, they wouldn’t share. Then how much influence did that manager really have if that salesperson left just as frustrated, if not more, or god forbid, even fearful after that meeting?

It’s not anything new that people haven’t talked about before, what’s in it for them, but again, going back to being consciously super competent, meaning you are completely harnessing what’s in it for them as you’re preparing for that meeting, the questions that you’re asking, the mirroring of that person’s personality and communication styles so they feel comfortable with you. All of these things, again, have been said before, but to harness it all together in a purposeful, conscious way takes practice, and it’s not easy, but it’s extremely effective. One of the things that people who work around me, or my clients and coaching clients, and even I was training yesterday in Buffalo, I always say, leveraging empathy isn’t about just being nice. That’s a byproduct of it, but it’s actually about being effective. There’s just been too much proof of that effectiveness in my career and the people that I’ve helped succeed that I know it works.

Gina Stracuzzi: Well, that answers my next question, which was going to be why empathy is so powerful in business today. I think that it’s like so many words. Empathy, authentic, innovative, they get used to death. But if you can step aside from that, the power of empathy is something that cannot be denied and is going to be critical moving into this new evolution that you mentioned. As younger people become the biggest mass of workers, there’s still a huge transition period where some companies have as many as three generations working with them. If there isn’t empathy there, it’s going to be a struggle for them to get along. I know that some companies are doing it better than others, from stories we hear. Can you talk to us a little bit about that in terms of your own training? Have you come across situations where you are training multiple generations, and how do you use empathy to help them?

Kyla O’Connell: The beginning of how I coach or manage a salesperson, or even a sales leader, because sometimes they need to hear this too, and it starts with having empathy for yourself. What does that mean? It means if it’s challenging to get back to the office, if it’s challenging to get that hustle back in, there are going to be days where that is going to be more of a struggle than others, and that’s okay. You need to have that empathy and forgiveness of yourself and say, “Okay, tomorrow’s another day.”

One of the things that’s been interesting, I was talking to my husband about this, all of the coaching that I’ve done over the last 20 years, has really been helpful in starting my own business, because I’m coaching myself. I literally am saying to myself the same exact things I’ve been saying to others, “It’s okay that maybe today wasn’t a 10-task day,” that you got 10 major things done today. Maybe you only got two things done today, and that’s okay, because you got tomorrow. One of your other speakers, Alan Stein Jr., I’m a big fan of his, and I want to give him credit for where I heard this, and I’m sure he gives credit from where he heard it, but you want to focus on the sand that’s in the top of the hourglass, and not the sand at the bottom. Another strategy that Alan talks about is focusing on the next play.

I was an athlete in college, in high school, and I know that he talks about how he’s worked with some of the top athletes in the world, and that next play mentality is empathy for yourself. It sounds like drive, and it is drive, but it’s also empathy. It’s saying that missed shot, or this day, or missed sales month does not define me. My next play is where I’m going to focus, and let’s see what the next play is. If it’s fantastic, then I’m going to build on that success. But you have to have empathy for yourself first to really be able to have a chance of showing up and having empathy for others. It comes across as self-confident, but it’s actually probably the kindest thing you can do for yourself.

Gina Stracuzzi: Going back to what we were talking about previously, where people are struggling a bit to get back to that ambition level, the intensity level, the drive level that they once had, but still loving sales, that is a good piece of advice for those people. We all have those days where it’s just like, “I’d rather just plop on the couch and do nothing,” which is for me one of those drawbacks of working from home. Because as I look out from my office at the couch, some days it’s calling to me, but it’s having that empathy for yourself to not beat up on yourself for even wanting to go to the couch, is I think really profound advice. It’s something that as humans we’re not always very good at. We would not say half of the things we say to ourselves to another human being. I like that. Self-empathy is a good one. Well, we are at the end of our time. Is there one piece of advice or closing thought you would like to leave us with?

Kyla O’Connell: Well, sure. I think that come to the conference to explore how empathy is really emerging as a superpower in business. Not just because of how we’re going to influence our customers to want to buy from us, not just because we’re going to influence our teams to work harder to hit their goals because we’re influencing them, but also because of what we just talked about. Having that empathy for yourself so that you can recognize when you’re having an off day, and forgive yourself, and get back to the next play. Because again, I mentioned it’s the kindest thing you can do, but it’s also the most effective thing you can do for your career.

Gina Stracuzzi: Well, that is great parting advice. Thank you very much, Kyla. If you want to hear more Kyla, which you should, join her and I, and Fred, and many other people at the Women in Sales Elevation Conference on October 12th. Thank you very much everyone.

Transcribed by Mariana Badillo

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