Episode 244: Jess Rodriguez on Improv Techniques to Boost Training Effectiveness

Sales Enablement PRO Podcast

Shawnna Sumaoang: Hi, and welcome to the Sales Enablement PRO Podcast. I’m 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 that they can be more effective in their jobs. Today I’m excited to have Jess Rodriguez from Beyond join us. Jess, I would love for you to introduce yourself, your role, and your organization to our audience.

Jess Rodriguez: Thanks so much. My name is Jess Rodriguez. I am the senior sales enablement manager at Beyond, and what we do is we work in the short-term vacation rental space and we help property managers and hosts grow and keep their revenue.

SS: We’re excited to have you here, Jess. Now, in addition to your sales enablement experience, one of the things that I thought was really cool about your background is that you’re also a professionally trained actor and have coined yourself as The Improv Girl. How does your experience in improv influence your approach to sales enablement?

JR: This is a great question and there’s a lot of ways that I can answer it, but really both improv and enablement are about creativity and the willingness and the ability to adapt and learn to really see and feel and embody whatever project or program that you’re working on. Anyone that has done improv gets into it for a different reason. Some really like the opportunity to create something, some people want to make people laugh, others do it to build their confidence, and I think mine was a combination of the three. Regardless of why you do it, what you get out of improv are these magical moments of experiencing what it’s like to take an idea or a concept, and not only bring it to life but to see how far you can go with it.

In improv, you go from, let’s say, talking about taking a trip to the beach. That’s maybe the scene that you’re provided with, and you are then tasked with acting out this trip to the beach. If you want it to be good and you want the scene to really resonate with your audience, you have to make yourself believe and act like you are at the beach. Maybe you’re thinking through the details about packing, you are holding your figurative beach hat when the wind blows, and you’re feeling your toes in the sand, but it’s just like a real trip to the beach where you could experience a tidal wave mid-scene and you have to roll with it.

Having the familiarity and taking things from an idea and putting them into an action to really just embrace every part of that idea and learning to pivot has made a major impact on how I actually approach sales enablement and the programs that I work with.

SS: I think that’s fantastic. Now, what are some improv skills that could help sales reps improve their performance?

JR: I love this question. It’s one that I get a lot and I think people hear improv and sales and they automatically assume we’re going to use improv to teach people how to be better at a specific sales skill, like negotiating or objection handling or demoing a product. You can absolutely do that, but I think we have to look at what it takes now for someone to be a great seller. I actually read in the Sales Enablement PRO report on enabling the future of selling, it stated that some of the top priorities for salespeople would be learning to collaborate and how to create very personalized journeys for their prospects and customers.

What we know is that it actually takes something quite different today for sellers to be really great and it’s gone beyond these very standard sales skills. It’s really about having the ability to connect with that prospect or that customer to understand their story, their motivations, their pain points, and their goals, and then be able to communicate how their product or service not only fits into that story but actually makes it better.

What better way to improve that ability to learn that story, and tell that story than with improv? I think about the skills that improv has taught me and what I’ve applied in my career, and I think what really comes to mind first would be listening, which sounds very basic, but is so essential. I think about something called characterization, and as I mentioned, I think about storytelling as well.

SS: I love those elements. What are some of your improv techniques for training salespeople to be more effective at listening and responding to customers?

JR: Great question. Let’s start with listening. There is one technique that I use consistently during every workshop and keynote presentation that I’ve done that starts with explaining and demonstrating something called ‘yes, and’. One of the first things that you’re taught at improv is this concept of ‘yes, and’, and it represents the mindset that no matter what someone says or does in a scene, you have to accept it with a literal or figurative ‘yes’ and then you add to it.

The reason it’s so important is during improv, it prohibits you from going into a scene with this premeditated agenda of how the scene is going to go because you can’t control what your scene partner will do or say. That’s like the fun in improv. That means you go into this scene with zero expectations. When I think about why sales reps struggle with something like listening, I think it’s because they go into this “scene” or their conversations with an agenda and with an expectation of what’s going to happen.

They’ve done this before, maybe it’s their eighth demo of the week, and they feel like they know what Susan from Company A is going to express as pain points or obstacles, so they’re anticipating how this will go and they’re unintentionally closing themselves off to something that could be a really great conversation. When you go into a scene with zero expectations, it forces you to be what I call powerfully present in that scene. You will naturally start to pay attention not only to what is being said, but the body language, those nonverbal cues that you’re getting, and when you think about listening, that’s what you have to do. Listening means you are really just powerfully present in what is happening in that scene.

Now for the second part of your question, responding to customers’ needs, what I didn’t tell you about ‘yes, and’ is the, ‘and’ part of that means that there has to be this logical connection for what you add to the scene. Let’s say, for example, you start out the scene in the kitchen and you decide that the kitchen has caught on fire. That’s logical, quite unfortunate, but it’s logical. If you start in the kitchen and then you decide you’re on the moon, that’s not a logical connection, so at that point, you’re doing what we call going for the laugh, and you’re not actually thinking about the common good of the scene.

Let me kind of bring it all back together here. As a seller, I think about how to respond to a customer’s needs in a way that is for the common good of that scene, and the common good of their goals, their objectives, not my own objectives as a seller, and that can be really hard because we want to feel prepared. We want to be viewed as the expert, the consultant, the one with all the answers, so we think about maybe how you do this. How do I go into this conversation with no agenda or expectations, but still be able to act as that expert or consultant?

My response to you would be that you prepare. In improv, they tell you to expose yourself to as many cultures, references, characters, news articles, and happenings in the world as you can because it makes you well-rounded. It will set you up for success when you’re in a scene, someone throws something out there at you because you have to accept it and you have to know what to say and do next to effectively respond in that scene.

In sales, I think about all the resources that we have out there for us, like talk tracks, playbooks, competitor news, or information. Lean on the resources that your marketing or your enablement teams have given you to prepare for those conversations, but overall, when you’re going in, don’t go in with that expectation or that agenda and that will make you a better listener, and make you more equipped to respond in a way that really makes an impact for the person you’re speaking to.

SS: I think that is phenomenal advice. I can’t tell you how many times I feel like that’s exactly what reps struggle with because they’re more concerned about what they’re going to say next than actually listening to the customer and expanding upon their needs. I think that’s fantastic advice, and I love the analogy that you drew there. Now for sales enablement, one of the tools that we use is that manager/rep role play. This is a relatively common tool to use in the sales training world. I would love to understand from you how improv can be used in those scenarios to help managers better coach their teams.

JR: Yeah, that’s a great question. Let’s talk about roleplaying. First of all, it really breaks my heart for roleplaying because it just seems to have a very bad reputation and people don’t seem to like it. I have a theory, but I’m curious, like, as a sales enablement person, why do you think that is?

SS: Well, for me personally, I think I get a little bit of stage fright, but for others, maybe it feels a little scripted. It feels unnatural because it’s something that we’re not used to doing.

JR: Yes. I completely agree. The stage fright element is very valid for many individuals. I remember the first time I did role-playing in sales training as a salesperson. It was my very first, real onboarding with an organization. It was classroom style. There were probably 30 people in the class, and when the instructor said we’d be doing role-playing, my actor self was thrilled. I was so excited. I was like, this is my moment, I’m so great at this. Give me the scenario and a minute, and I’ll be ready. Then about 30 seconds in, I was like, wait a minute. This doesn’t feel right. This is uncomfortable. I don’t understand what’s happening right now. When we finished, the instructor threw all this feedback at us.

I think you hit the nail on the head, Shawnna, when you said that it feels so scripted because when I think about why that experience is really bad, there are two things that took place. One is that it wasn’t a real-life scenario, right? We’re told that it’s supposed to be this creative exercise designed to help you practice, but it’s not uncommon for the person on the other side to be either silly or not fully invested or say things that a prospect or customer would never say.

We’ve all experienced that, and/or your instructor has very specific things they’re looking for as far as responses, which doesn’t make sense either because every prospect and customer is different, so how can someone say with confidence, this is absolutely how you should have responded? Are you with me for those two reasons?

SS: Absolutely.

JR: I agree that oftentimes roleplaying is a challenge because it feels like a waste of time and what I would tell a manager or any sales enablement person is that your reps will only get out of roleplaying as much as the sales leader is willing to put into it. There are a few techniques on improv that come to mind. I actually have a whole guide about this on my website for anyone that would like to dig in further (JessRod.com), but the three things that I would look at first are to lean into that character. That means that the person acting like the prospect or customer needs to embody the prospect or the customer.

If you don’t have buyer personas to work from as a sales manager, I would encourage you to go create your own. In one of my previous roles, there was an activity where we had our reps create their own buyer personas they had this whole backstory and they named their prospect and we let them google a photo and pick a random photo of a person, we let them identify their pain points. We really let them create this persona. Then we used those personas throughout the onboarding kind of as a round robin, so everyone had experience with different personas, but it gave the person playing that character some strong roots and foundations in who they were embodying.

The second thing I would tell a sales manager is to be self-aware. One of the first things I always do after any performance, even after training, is I go back and I watch the recording. Let me tell you, Shawnna, it is painful and it is not fun, but you make notes about how you can improve. I look at my delivery, my demeanor, my facial expressions, and then of course specifics of what I said and then I know what to work on because I’m seeing it for myself. I’m not just being told by someone else like, hey, your training would’ve been a lot better if you would’ve done X, Y, Z.

What I would recommend for a sales manager is to have your seller listen to a call or watch a recent demo, and then come to the session for role-playing with notes on where and how they would like to improve, and then use that time, that role-playing session time to practice those areas. This not only will help them really take ownership, because they’ve spent time prepping, but it also just gives them some control of what they want to work on versus being told by someone else where they’re struggling.

Then the last thing I would say is really embrace this idea that there are no mistakes in roleplaying, there are only opportunities. I think we have to remember that roleplaying really should not be about assessing or looking for required outcomes. We’re not looking for the reps to say specific things or ask specific questions. It should be about providing this very positive, safe, and supportive space for them to practice this skill.

I always tell people to think of their favorite person to hang out with. They’re probably the ones that make you feel smart and funny and interesting and important, so make your seller feel like that, and role-playing won’t be as daunting.

SS: I love that and I think you’re absolutely right. A psychologically safe environment also I think would produce tremendously better outcomes in that role-playing scenario. Now you have experienced designing improv-based team-building activities. I would love to learn more about how that type of team building drives collaboration and communication between team members and whether there’s actually anything I can, you know, maybe try at my next team meeting.

JR: I love working with teams. It’s a lot of fun. There is a lot of that scary part of being in front of people sometimes for attendees. When I think about the workshops, have you ever attended a training or a workshop where, let’s say the focus was communication, and they put together a deck and you’re talking through what it means to communicate different styles of communication, how to apply in the workplace, but it’s, it’s mostly like a presentation? Does that sound familiar at all?

SS: Yes.

JR: Yeah. When you’re trying to drive something like collaboration or communication, a slide deck is not the way to do it, and that’s because collaboration and communication can be, I think, very vulnerable things to acknowledge a team is struggling with. If you give them this slide deck that explains five things they need to do to collaborate or the top four communication styles in the workplace, that’s not going to break down that barrier of what got them there in the first place. That barrier that’s causing them to not communicate or collaborate. They need to experience it.

What’s really magical about using improv for team building is that you start off by breaking down those walls. In my workshops, the first thing we do is play an improv game. Before we’ve pulled up any slides, any presentation within the first five minutes of the start without even being told how to do it or that they have to do it people are laughing together, they’re working together, they’re being creative together. They’re starting to experience what it actually feels like when they do communicate and they work together.

By the end, they’ve had 45 minutes of that experience and again, have felt and seen what happens and what it looks like when they are working effectively, and because of how the games are structured and the content is structured, they’ll also experience what it feels like and the impact it has on everyone when they don’t actually work together and communicate. It’s really about getting them to experience it for themselves, put themselves in that seat, and not just tell them how to do it.

SS: I love that. Jess, last question to close for you. In your own career, how has this improv training helped you advance your career in enablement?

JR: Thank you for that question. I owe a lot to my improv training and the directors I’ve had, the teams I’ve worked with. I mentioned earlier in our conversation that regardless of why you do improv, what you get out of doing improv are these magical moments of experience. In my keynote, I speak about having what I call an improv mindset and how I’ve used these foundations like ‘yes, and’ to really be a driver throughout my life. Improv has given me the confidence to take on new challenges and new opportunities because through those magical moments and through those experiences, I’ve been able to see how incredible something can be when I say yes to it.

SS: I love that and I love that say-yes approach. Well, Jess, thank you so much for saying yes to being on this podcast. I greatly appreciate the insights that you share today.

JR: Thank you so much for having me. It’s been a pleasure.

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