Episode 46: Jenn Haskell on Effective Techniques to Motivate and Coach Sales

Shawnna Sumaoang: Hi, and welcome to the Sales Enablement PRO podcast. I am Shawnna Sumaoang. Sales enablement is a constantly evolving space and we’re here to help professionals stay up to date on the latest trends and best practices so they can be more effective in their jobs. Today, I’m joined by Jenn Haskell from Monotype.

I would love for you, Jenn, to just introduce yourself, your title, and your organization.

Jenn Haskell: Absolutely. Thank you, Shawnna, for having me. My name is Jenn Haskell. I am the global sales trainer and sales enablement person here at Monotype Imaging. Monotype is based out of Woburn, Massachusetts, so right outside of Boston. We’re a global organization and we’re actually known for two parts of our business.

We have typography — selling fonts and types, that’s actually our business. We also have a technology that allows companies to collect and curate user-generated content, and then use that for different promotions, marketing mailers, advertising, and things of that nature that they may have on their website. So, at the end of the day, Monotype is a brand company. We’re here to ensure that companies are on-brand across the board.

SS: Excellent. Well, Jenn, we’re very excited and honored that you’re able to join us today. You’ve done a lot of writing and speaking on sales enablement, particularly kind of around the training and coaching components.

So, you’ve even said in the past that sales enablement leaders are part trainer and part psychologist. In your opinion, why is that the case and how can psychology skills help sales enablement professionals be more effective?

JH: You can’t see me because it’s a podcast, but I’m kind of giggling on the inside. I have a big smile on my face. When I first said that Shawnna, I actually was at a Sales Enablement Society local holiday event that they had several years ago. Each vendor that was there got about five minutes that they could get up and say something. And I wanted to do something funny to lighten it up a little bit. So, I created this meme about sales enablers being the ultimate psychologist. And I don’t think I realized how real that was and how true that was, but I definitely realize it today.

To get back to your question, why would it be important for a sales enabler to sort of understand the psychology? I look at it this way: sales is a tough business. You can be the top of the leaderboard one day and not closing a deal for multiple quarters in a row the next day. And one of the things that I hear a lot from sales leaders, and I get it, it’s their business to drive the revenue. But I do hear a lot, “it’s not personal, it’s business,” right? Well, I believe for an enabler, you have to make it personal because you have to gain credibility and you have to be perceived as a trusted advisor. You’re the person that’s going to be working with your sales reps to coach them and to mentor them and to provide them with foundational learning or continuous learning.

I’m also aware of the fact that at the end of the day, there isn’t one salesperson that is exactly the same as the next. They all share a lot of the same characteristics. I bet if you put them on a DISC assessment or a predictive index, they would probably fall within the same category. But I know that they all learn differently. They all receive information differently. And so I think the psychology part comes in handy because it allows me to build programs that are going to resonate with everyone across the board and not just certain individuals. At the end of the day, people are motivated by different things.

People learn differently, people accept information differently. They have different levels of emotional IQ, and those are the types of things that if I can tap into it for myself as an enabler, it actually benefits me one of two ways. I can have more effective sales enablement programs and I can make that personal connection. And I think it also allows me to demonstrate what my reps might be able to do when they’re having conversations with clients.

SS: Absolutely. I think you are spot-on that one of the core values enablement brings is really humanizing the sales team and the culture within an organization. From your perspective, what are some of the other core competencies that you would say sales enablement leaders need to have to be successful and what skills have helped you most in your career?

JH: Well, I would start with communication. And having strong communication skills, whether it’s in a one-on-one environment, whether it’s facilitating actual learning, we have to be able to be well-spoken and well-written, that’s the thing that allows me to connect with my reps and to be transparent about things like, “here’s why you’re doing this, this is the benefit for you.” But it’s also what allows me to connect with my senior sales leaders and my executive teams so that I continue to have that executive sponsorship.

So, communication first, and a little bit of project management, because I don’t think there’s a sales enablement professional out there that wouldn’t tell you they’re under-resourced. We’re constantly trying to prioritize 15 different things at once. And I know for me, as obnoxious as it may seem, I actually have a calendar that I will create at least six months out in advance. It’s so OCD, it’s color-coded, but it’s a Google Doc and I share it with all of my sales managers and sales leaders, my marketing leaders, and they basically know from week to week, day to day, everything that a sales enablement team is working on and delivering. It actually helps to keep me in check as well.

I think the ability to coach is one thing, but you need to be able to provide feedback that is constructive, thoughtful, and helpful. So, that kind of ties back into the second question around the psychology piece. Your reps are gonna expect that when you do provide feedback, you’re not just copy and pasting your answer from one rep to the next. They’re going to feel better when they know that it’s tailor-made just for them. And I also think having some basic soft skills around empathy and emotional intelligence and those types of things are really going to take you a long way in that enablement role.

SS: Absolutely. I think empathy, communication, these are all things that I think are the soft skills that sales enablement leaders really need to help kind of motivate and inspire their sales teams. What are some of the ways in which you’ve done that kind of motivated and inspire the sales teams at Monotype?

JH: The first thing that I do is I do my best to empower them on a regular basis. They are stakeholders in their own success. I personally don’t want to be viewed as the sales enablement person that comes in with a program that worked in another organization and was effective and successful and just say, “well, it worked there, so it’s going to work here.” I always have conversations with my leaders, my managers, my reps — I want to know what their daily activity looks like. I want to know what the conversations are that they’re having, the objections that they’re receiving. I want to know how they feel.

One way that I motivate and inspire is I connect with them and I give them the time that they deserve, and I let them know that I take it personally if they leave the organization or if they’re not successful. To me, that’s my failure. It’s one of the first things that I say to reps, because that’s how important they are to me, and it’s motivating and inspiring.

I know every single rep. I know not just about their accounts and the money and revenue generation side of things, I know about them personally. What keeps them up at night that I can hopefully help with? What process isn’t as efficient as it can be that I can hopefully streamline? What areas of the business are we just missing that I can advocate for them? I make them stakeholders in their own success. The second that you enroll them in having a say, right then and there, is inspiring to a sales rep.

SS: I really love that approach, Jenn. I want to pivot a little bit because you had mentioned coaching and feedback being one of those critical skills, and you’ve also written in the past about the importance of coaching. From your perspective, why is coaching so important and what should enablement’s role be in coaching sales?

JH: Yeah, I mean, I’m a former college athlete, right? So I have been coached since I was four years old. It’s been such a critical piece of my life that I think it’s just entwined in my DNA. But there is a connection there because a lot of people that end up in sales probably at some point in time had been coached, whether it was by a professor, or their parents, whether they played a sport. I just think coaching allows us to feel like we’re worth the investment. We’re not making an assumption that you’ve already got the skill-set. We’re acknowledging that the skill-set is there, but we’re going to tap into it. We’re going to hone your craft, and we’re going to take it to the next level.

I know a lot of people, myself included, actually expect to be coached and they’re open to being coached. And I actually think as you see the generations change in the workforce, millennials want to be coached, the Gen Zs want to be coached. That is something to go back to the previous question that motivates and inspires them.
Enablement’s role in that is a couple of things for me. I want to be able to do the coaching as well. I think I can offer a different point of view than a sales manager. I tend to be the one that plays a little bit of devil’s advocate. Let’s look at this from a lot of different directions. Let’s do a lot of roleplaying. And build up your confidence so that when you do have that call with a client, you’re ready to go. But on the flip side of that, I also want to make sure that my managers are better coaches as well.

A lot of the time in sales, you’ll see sales managers be very successful sales reps in the past that had been promoted to that manager level. And we can’t make the assumption that the people management skills are there. So enablement really should own that manager enablement piece and showing them how to conduct effective coaching and how to give thoughtful feedback.

SS: Absolutely. In that same article, you also mentioned two effective types of coaching, the manager-to-employee, which is why the frontline manager enablement is so important today, as well as peer-to-peer. So how do those two types differ in terms of the value that they deliver and from your perspective, is one more effective than the other?

JH: I actually don’t think one is more effective than the other. I think they’re both absolutely required. And what I like about the peer-to-peer — so I’m going to start with the second one first — is one, you’re learning best practices from a rep that might have different experiences. They’re talking to different customers, they’ve been in different sales plays. So you’re really learning from that rep. I love peer-to-peer because it creates a sense of teamwork and collaboration, but there’s never any walls going into that, right? Not too many reps are nervous about talking to a fellow peer about a deal or a strategic approach to a conversation they’re about to have. So it’s very natural and you’re not feeling like you’re going to be put onto the microscope.

If I have a program where there’s a certification piece involved, it’s a really great way for the reps to practice with each other so that by the time they do get to the manager or the sales enablement coaching piece, they already have so much more confidence going into that. So, I like peer-to-peer because I think it really promotes the practice.

Then as far as the enablement-to-employee or the manager-to-employee at that point, hopefully there’s enough of a foundation where you’re basically just fine-tuning through the coaching and offering more of that strategic leadership point of view.

SS: And beyond those two types, what else have you found effective by way of coaching strategies that you might recommend?

JH: Yeah, so sometimes I’ll take a really informal approach to coaching. I’ll give you a perfect example. I have your standard BDR inside sales team that I actually sit with in the Monotype office. They are slightly junior reps, a couple of them are straight out of college. They’ve never sold before. They do call blocks on Thursdays. I’ll go over. There’s a little bookcase over there. I’ll go over, I’ll sit on the bookcase with my laptop while they’re doing their call blocks, and I’ll say to them, “guys, I’m here. I’m listening. I’m not judging. I’m just learning from you. But if you get off a call and you have a question, I’ll help you because I am listening. But I’m not going to force my coaching on you.”

That team absolutely loves it because now what I’ve done is I’ve enrolled them and I’ve given them the opportunity to accept the coaching or not. There’s no right or wrong answer in that situation.

Another technique that I think is wildly successful that every organization should have is some means of video-based coaching. A lot of us have sales readiness platforms or learning management systems, but to me, that’s only a check on a checklist, right? It’s great if you complete a module or a curriculum or an assessment, what I really want to know is out of what you learned, can you put this into practice? Can you be effective? And a video-based coaching assessment tool is going to allow you to do that.

SS: I love those recommendations. So, I want to close with one question. I just want to kind of understand some of the upcoming sales enablement initiatives that you might have in the pipeline that you’re really excited about.

JH: It’s the end of 2019, so I’m excited about end-of-year activities. I like to see the buzz. Going back to your question previously about motivating, I’m the one walking through the office and high-fiving and fist-bumping my sales reps and getting them excited as much as I can. I always love to see that end-of-year buzz.

But right now, the biggest initiatives that I’m working on would be sales kickoff. I want sales kickoff to be something that my reps walk away from and they just feel ready to crush the next year. So, I want it to be really effective as well as motivating.

And personally, here at Monotype, I’m excited about the fact that we did just recently get acquired by a private equity firm. Our company dynamic is about to change, and hopefully that’s going to work in the favor of the sales organization as far as just having better alignment, having some strategic initiatives and being able to support them through that change.

SS: Well. Thank you so much, Jenn, for joining us today. I really appreciate your time.

JH: Great. Thank you so much, I appreciate it.

SS: And to our audience, thanks for listening. For more insights, tips, and expertise from sales enablement leaders, please visit salesenablement.pro. If there’s something you’d like to share or a topic you want to learn more about, please let us know. We’d love to hear from you.