Episode 40 – Andrea Flack-Wetherald – leveraging concepts from improv to strengthen relationships between sales and customer success teams

Here we go! Episode 40 of The Talent, Sales and Scale show features Andrea Flack-Wetherald, Owner at &Beyond Improv. Andrea has a diverse background, has a deep understanding of what motivates teams, has spent lots of time in the improv world and talks to Bryan about how those skills translate to improving your business.

On Episode 40, Andrea and Bryan go over:

-how her structure around improv translates to success in business

-concepts from improv improve teamwork and company culture

-dialing in on traits that must be present from every part of a business to truly see success

Plus SO much more! This episode is a ton of FUN!

&Beyond’s website:

You can connect with Andrea on LinkedIn here:

Read Full Transcript

Bryan: Hey, everyone. Bryan Whittington with this episode of The Talent, Sales and Scale Show. Today we have Andrea Flack Wetherald of And Beyond. So this should be fairly interesting.
So the reason I asked Andrea to be on is that I took Improv a while back because I’m too flat-footed. And I couldn’t adapt in a sales conversation quite enough. So Andrea and I had a couple conversations. And so the topic for today that we’re going to be handling is how in the world do we take any leverage—the idea of Improv—and then help that to eliminate the clash between sales and the delivery of the brand promise or the customer success with that brand promise, where the sales people (they never do this), but they say that some people over-promise. With customer success some people have some grief. But that never happens, does it, Andrea?
Andrea: Oh no; that never happens. And the customer success and delivery people, they’re never sticks in the mud, yeah.
Bryan: They’re all good as a hood. So welcome, Andrea. It’s so good to have you on board with us today.
Andrea: Thanks so much for having me; I’ve been looking forward to it.
Bryan: Yeah; me too. All right, so let’s jump right into this. I mean Improv, sales, business, customer success. You do leadership and culture stuff. I mean, what makes you an expert on this? You’re in Improv, for goodness sakes.
Andrea: Yeah. So one of the things that I think is aboutFfold-up Improv is that it’s actually just a really approachable, really effective content learning system. Improv makes it easy to learn things that are really important and really, really applicable. And so my background is in addiction and smoking cessation n behavior modification coaching. That’s a lot of words all in a row. (Laughter)
I’m a social worker; that’s what my degree is in. That’s what my license is in, it’s in social work. And when I was first done with school my first foray into the adult world of work was doing behavior modification coaching on a research study that was here in Pittsburgh, looking specifically at addiction and smoking cessation.
But what I learned during that time of working with scientists on the medical end, but also learning from social scientists who have studied ways that people change, like what’s happening in your brain when you attempt to make a change, those things that I learned about how people can make effective changes that last over the long run. You’re not just changing to appease somebody, to get your boss or a judge or your wife or your doctor, or whoever off your back. You’re changing because you’ve tapped into your own internal motivation. And you’ve tapped into your own internal understanding of what you want and what your purpose is. And you’ve understood that this change is in alignment with your best interest.
So this framework of how we help people do that is powerfully transformational in the leadership and HR spaces as well. And delightfully enough Improv is a really fun way to learn those skills, because a lot of the same skills that it takes to lead effectively to change effectively, to grow and be the leader that you intend to be on a consistent basis, those skills are happening in Improv. And so it’s a real time way and a fun way to do something that can absolutely change your life.
Is it helpful to give examples of how Improv does that? Or is it immediately obvious to you and all of your viewers why Improv is such a powerful mechanism for learning this content?
Bryan: Not even close because I was not expecting that answer. (Laughter) Geez, Louise! Let’s unpack that. So first, a learning system? It’s Improv, for goodness sakes! How is it a learning system?
Andrea: Yes. So I have built some backbone around it to help it to be a system. On its own it’s still a great learning method. But what makes it a system is kind of the infrastructure that I put in place alongside it to be clear on the use of that word system.
Bryan: Okay.
Andrea: But as a method, they say that with Improv there are no rules. But really there is a ton, because what you’re being asked to do is to be present in this moment. That’s mindfulness. Stay present in this moment and choose curiosity instead of judgment. Stay present in this moment and listen actively to what is happening around you, because if you’re not listening you can’t add anything. If you’re not listening you can’t contribute. You haven’t earned the right to “and” if you haven’t “yessed.”
And so the foundation of Improv is this idea of “yes and.” And when I teach it in my corporate work I teach it as humility and courage, because “yes and” tends to make people kind of glaze over with “We can’t say yes to everything.” That’s the whole point of our class. We can’t say yes to everything.
But what we’re really talking about is equal parts of humility and courage. And it’s this dance that we do in Improv of listening and valuing others’ contributions, being opened in getting surprised by your theme partner in a delightful way, albeit unexpected, but at the same time realizing that it’s not enough just to listen and observe what’s going on everywhere else. At some point you have to summon the courage to contribute your own perspective and your own input. Otherwise you’re in the audience. You know, if you’re improvising, if you’re participating, you have to have that equal measure of adding your own perspective. And it’s that dance—listen, build, listen, build. If that sounds like Agile Development to any of your listeners, it’s because that’s also how Agile Development is very similar in spirit to that yes and, and humility and courage.
So in real time in Improv, these skills that make software work for users, these skills that make teams produce effectively, that help people engage conversations about racial justice at work, and diversity, equity and inclusion, with those same skills it’s vulnerability; it’s courage. It’s listening; it’s present focus. It’s sacrificial support of your team partners. I could preach on this all day.
Bryan: All right.
Andrea: So those same skills are present in Improv.
Bryan: So that’s really interesting. So I jotted down a couple of high levels. We call it being present. The buzz word in the business community is mindfulness, right? We have to be mindful, whether it’s just showing up and being present. Active listening is a part of that so we can repeat back. And then it seems like curiosity.
Andrea: Mm-hmm.
Bryan: And correct me if I’m wrong. But that curiosity is that open-mindedness, that respect and valuing of others. You brought up value. But value is really the respect of others.
Andrea: Mm-hmm.
Bryan: And really what you didn’t say—I don’t think you did!—this is really based on trust, then.
Andrea: Oh, yes. It all comes down to trust.
Bryan: Yeah. And the reason I was thinking of that is that if I’m going to lay out and if I’m going to have courage, I always reference Kim Scotts. I love her book, Radical Candor. It really gets to can you challenge somebody in a caring way, right?
Andrea: Yeah.
Bryan: Be confrontational; I’ve heard it put this way as well. And so that courage, that radical candor to get out there, yet to be humble enough to open up to others. So it’s really just human relationship skills that you’re talking about.
Andrea: Oh, absolutely. And that trust factor is obviously critical for teams to perform well together. But you know, what I realized in my work is that I started out really focused on sales. I had been the director of marketing at a company where I was getting calls from sales people all day long. And I was thinking that boy, I would be less irritated by these sales people that are calling me if it didn’t feel like they were just reading from a script. (Laughter) I felt like they were actually listening to me. That had been the impetus for this work. I could teach sales people Improv skills and that would help them so much to be better at sales. And it absolutely would.
What I realized though, as I started coming into companies and trying to address really specific things like this is that people would think to call me for anything related to sales or creativity types of stuff. Can you help us at the beginning of our meeting to get our brainstorming juices flowing? We need help with collaboration or communication.
And as I started having these conversations with leaders in HR team members and going into a few companies there at the beginning, I realized this. Is there ever a time that someone needs me when the problem isn’t really about confrontation? It’s not really in some way about that I am afraid to advocate for myself. Or I let it fester so that I’m blowing up at people. Or I just start writing people off. So then I’m not communicating well because I’ve decided what “kind of person this is,” you know?
And all of that is obviously about trust. So the more I was unpacking on what helps people yield trust, it’s seeing them as whole persons. It’s seeing them as more than Joe, the bean counter, or Beth, the sales lady. I’m just making names up at this point. (Laughter) But it’s seeing someone as a whole person, and realizing as Maya Angelou says that “We are more alike than we are unalike.” Tapping into that human energy will help you to be braver. This is really about being a brave team member.
And when you’re brave you know that your voice matters. And you also know that so does your theme partner. Theme partner is an Improvism for whoever you’re communicating with in that given moment.
Bryan: Yes. So let’s talk about that. Let’s take the antagonistic view.
Andrea: Yes.
Bryan: That’s not being brave; that’s just being an adult—showing up and having a good communication. What would you say to that person, that it’s not about bravery; it’s just having a conversation?
Andrea: I mean, if it doesn’t feel like you’re summoning some level of courage or vulnerability, then you’re not saying what really needs to be said.
Bryan: I like that.
Andrea: Because if you don’t feel like you’re being vulnerable, then you’re taking the upper hand. And you know, what you’re really saying is that this person needs to conform. If it doesn’t feel vulnerable then it feels like I have power. And if I have power then we’re not on an equal playing field.
Bryan: Yeah, and so that’s really curious, because you probably see it all the time. But there are so many business leaders, so many managers, so many supervisors that they lead through title.
Andrea: Mm-hmm.
Bryan: It’s my way or the highway; do it this way. And then they bemoan the fact that nobody is sharing ideas with them, that they are a paid audience because why isn’t anybody coming? I have to solve everybody’s problems. My sense is that it’s probably because it’s self-induced from the environment that you created.
Andrea: Absolutely, and usually with the best of intentions. If you could see an FMRI of my brain right now it probably looks like fireworks. (Laughter) Because there is so much here.
Bryan: Yes.
Andrea: So let me start with one thing, which is that typically when people say “No one is giving me their ideas,” this is often the same person who will say, “Okay, but no one is giving me feedback either. I asked for feedback and they’re not telling me what I can be doing differently.”
So I often end up almost in this impasse of someone, where they’re like “Well, no one is pitching the ball of ideas.” And I’ m like “Well, there are reasons for this.”
But then they say, “Well, it’s not me. We do our 350s. We do our Myers/Briggs and all this stuff. No one is giving me feedback and I’ve done all this stuff.”
So the thing is that with someone who is wanting that feedback there are good intentions there. It was a good intention that put that idea in their heads. I want to fix this problem. It’s not good that no one is pitching their bold ideas.
So usually my advice in that situation is to ask more specific questions. Specifics are goaled in Improv. And they’re also goaled in these feedback conversations.
Bryan: Can you give a couple of examples there, because—
Andrea: Absolutely. Yes, thank you. So for example I had a client who was in a similar situation, actually the exact situation. (Laughter) And I gave him a template. Instead of saying, “How am I doing as a leader?”, say, “A month ago we rolled out this change. And I noticed that there was some friction in your department on that. How could I have communicated differently? Did you feel that I was approachable? Did you feel that you could speak to me about what your ideas were? Could I have been onsite more frequently? Did you feel that I had enough face time with you?”
Ask specific questions. And part of it is that when you jog someone’s memory about a specific thing, then he will be like “Oh yeah; I remember that.” And then he can say something like “You know what? You were here, but it seemed like you were busy the whole time. So I didn’t feel like I could get your attention. I felt like I was bothering you if I tried to get your attention.”
We are not a caricaturization of a boss. We are human persons. You know, I am a human person. And so if even with the best of intentions I show up at your location and I’m trying to be present, if I’m busy, nervous, upset, I don’t seem approachable.
This is where I talk about listening hygiene. And I talk about it as a skill, because it’s not the same as in fifth grade or fourth grade, or whenever kids learn about hygiene in gym class. You don’t just get to be sweet. Now I know about that and I’m clean now. It takes proactive effort every day or you’re going to stink. And it’s not because you don’t know enough about it.
Bryan: I didn’t tell my ten-year-old son this. Oh my gosh!
Andrea: Yeah. And there’s also not something wrong with you. I can’t even tell you how frequently people tell me. I come onsite and they’re like “So-And-So is a narcissist.” People are ready to diagnose folks left and right. They’re so ready to tell me who’s the problem.
And it may not be that there’s something “wrong” with this person. It could be that we need to brush up on our listening hygiene, because, you know, if you’re booking your meetings back to back to back to back, then people feel like there’s just time scarcity anxiety. Do you understand what I’m saying?
Bryan: Yes, because there’s a lot to unpack there. I was expecting this to be a little bit lighter and more fun. But I really like where you’re going because I didn’t realize how voluminous this was going to be. (Laughter)
Okay, so let’s talk about listening hygiene. Let’s define it and give a couple of examples there. And then what I’d really like to do is to put some application to this, because there’s application from a prospecting/marketing perspective, from a sales perspective, from a leadership perspective, not only from this customer success sales side.
And that’s the beauty about this, right? So for the listeners, if you learn these skills, they’re ubiquitous across every facet of life. So let’s really go back to this listening hygiene. What is listening hygiene? Can you give us a couple tangible examples, please?
Andrea: Yeah. So listening hygiene is about how consistently you deliver at the caliber of your intentions, which is a very wordy sentence. But what that means is that listening hygiene is about all of those active listening skills that probably you and every person that watches this says, “Oh great; yeah”—open body language, you know? I’m asking good questions. I’m showing with my nonverbal communication that I’m listening.
People know from however many tiny things they’ve been to what the behaviors are. But at some point it’s almost like your body can learn those skills with muscle memory, right? Those skills are like driving a stick shift or playing an instrument. At some point your body just knows how to imitate that. Your body can just do that without being checked in.
Listening hygiene is about your present focus. It’s about being in this moment—really present and not distracted. The advice that I give my clients is to just notice. If they’re being really honest, the times that their wives want to smack them upside the head and be like “You’re still not listening!” What causes good people to do that?
Bryan: Marriage.
Andrea: Right. So first of all I’m glad you said that to me. So, marriage. When people say that what they really mean is that I start taking that person for granted.
Bryan: Very true.
Andrea: I start taking for granted the honor of their attention. I start taking for granted the privilege of sitting across the table from this person and hearing their perspective on life. I’m forgetting the gold mine that is across from me, of a potential for us to build something beautiful together in this moment.
So part of it is these Improv skills. I call them “the core five.” I promise that I won’t get into all of it because I know you didn’t ask me for a full Web&R. But—
Bryan: I like it. What are the core five?
Andrea: So in the core five we talk about honoring your theme partner.
Bryan: Okay. I was just going to try to translate. So honoring your theme partner would be mutual respect, active listening, bla-bla-bla.
Andrea: Yeah. Honoring your theme partner to me very specifically means remembering who this person is, remembering who they are to you as valuable contributors. I didn’t start with the first one, so I’m out of order in my brain.
But choosing curiosity over judgment is one of them. It’s listening beyond your comfort zone, present focus, as I’ve said a few times, and then gift orientation.
So gift orientation means that no matter what pops up, it improvises like that’s okay; I receive this as a gift. It’s not a deal breaker; this doesn’t ruin it. This is a gift; there is something here for me.
And so that is especially critical when it comes to confrontation, because folks get worried. I’ve done a whole variety of different applications of this concept when I’m working with leaders and teams, depending on what the need is. I’m talking sexual harassment, diversity and inclusion, brainstorming, overcoming a new owner. There’s a leader in a department and there’s just stuff that comes up, you know?
So when we have gift orientation, no matter what somebody says, you realize that oh, that painful thing, that difficult thing I just heard, that’s pointing in the direction of my next question. You know, it is giving me clarity on what needs to happen next.
So if we don’t panic, and we don’t feel like uh!, now it’s ruined, because if we think that’s what will happen, then when we hear something difficult during confrontation we’re likely to start avoiding it. We’re likely to start avoiding things or questions that desperately need to be said and asked if we’re worried that the answer or that kind of person would break it, and would put us in a situation where now there’s no coming back from here.
Bryan: Now I want to go back to what you said—listening beyond your comfort zone. Is that what you said?
Andrea: Yes.
Bryan: What in the world is that? (Laughter)
Andrea: I am a Mennonite. And every time I perform I’ve got one foot in the comedian canoe and one foot in the Mennonite canoe.
Bryan: That’s a big divide.
Andrea: If you drew a Venn diagram of things that happen at the Mennonite church and things that happen in a dive bar during a comedy set there’s just no overlap. (Laughter)
Bryan: You’re one step away from Amish, for goodness sakes.
Andrea: Yeah. So for me listening beyond my comfort zone, I am strong enough to be uncomfortable. Uncomfortable is not the same thing as unsafe. And if I keep listening, I can talk about this for an hour; this alone I could talk about for an hour.
Bryan: Sure.
Andrea: This is about resilience. Listening beyond your comfort zone is about resilience. It’s about knowing that when somebody says something, and then you’re like “Uh! That’s the kind of person I’m dealing with!” Or “Oh, maybe this is not the right person to hire,” or “Maybe I’m not the right fit here,” then it’s the narrative you check into most readily when you’re uncomfortable. It’s about me or it’s about them. Listening beyond your comfort zone means oh wait; no, no, no, no, no. I’m not going to do that. Instead I’m going to stay present with this person and I’m going to keep listening. I’m going to actively choose to be resilient. I’m going to choose to recover from whatever just now happened because I trust that I am enough and I trust that this person is enough.
Bryan: Right.
Andrea: I trust that they’re both more than whatever just now happened. It might be true—something painful or unprofessional, or whatever just happened. But when we’re resilient beyond that, then we can get to wherever we need to get to. And that doesn’t mean that we never part ways. It just means that we don’t part ways prematurely.
Bryan: Okay. So let’s try to bring some application of this or tactics to this. So on the listening beyond your comfort zone, (how do you say that again, please?)
Andrea: Yeah; listening beyond your comfort zone.
Bryan: Okay, so listening beyond your comfort zone. So what you said here is that we have to have such self-confidence that no matter what they say, we’re not going to take it personally.
I had a guy by the name of Lempen Trencosta. He and I butted heads a lot. I’ll have to send this to him whenever we’re done. But he went through some rough times. And you talk about resilience. But one thing that I learned from him, which has fundamentally changed my life, is to take nothing personally.
Andrea: Mm-hmm.
Bryan: And for you not to take something personally you have to have such an inner strength that I’m okay no matter what anybody else does.
Andrea: Yes.
Bryan: So it’s having that inner strength and inner confidence that I’m not going to take it personally, but then also going to your curiosity statement. Let your inner voice go, “Well that’s interesting. I would not have thought of that,” right? If we take it that it’s interesting to intentionally drive that curiosity,--
Andrea: Absolutely.
Bryan: We can stave off that emotional involvement, because if we get emotionally involved, I think that the place—and you can correct me if I’m wrong here!—but it seems like the place where listening breaks down is that as you’re talking, if you can see me on the video, I’m just itching to jump in,--
Andrea: Mm-hmm.
Bryan: And you say something, and I’m rebutting you in my mind, instead of taking it in and then thinking of a way to respond.
Andrea: Yeah; mm-hmm.
Bryan: So is that kind of all wrapped into that listening beyond your comfort zone?
Andrea: Yeah. And you’re thinking beautifully to the way that these core five dovetail into each other. And this is the reason why I love using Improv to teach these things so well, because it’s one thing to hear me say this, and to be like “Ooh yeah; I can see how that would absolutely be helpful!” But it’s another thing then when we’re in person someday, in a post-pandemic world. (Laughter)
Bryan: Right.
Andrea: And you hear these skills. And we’re going to practice some Improv games together. You should see the look on people’s faces. And they’re just like “Oh! I don’t want to do that! I’m Pam from HR; I’m not Tina Faye! Why is she here? Why is she making me do this?” You know. (Laughter)
Bryan: “I’m the CFO!”
Andrea: Right! And so it’s like “How dare she!” You know, that’s part of it. And so I try to encourage people not to drop that bomb as a surprise. But sometimes people feel like that’s the only way that it will happen. I encourage people not to surprise their staff with that. (Laughter) But the point, regardless, is that even if they know what’s coming there’s this fear. I have such an impact that sometimes I start getting fearful as well. I feel there energy. Oh my Ghosh! What if I do something foolish? What if I embarrass myself? There’s just this heavy, heavy reluctance. And then to watch people overcome that together and realize that oh, this is okay. This is what it feels like to say something out loud in front of the group. For some people that is a powerful milestone, you know?
Bryan: Yes.
Andrea: For other people it’s noticing when you’re not needed on stage. For other people it’s knowing how to hang back a little bit. But Bryan, I can’t tell you to watch people navigate that in real life, noticing when to hang back, noticing when to let somebody else shine, feeling what it feels like to get out there and put your idea out there in this Improv game and be like oh, that didn’t land like I thought it would, and then to have somebody else come out and add their ideas on top of it. And then it becomes the funniest thing that’s ever happened.
Bryan: Yes.
Andrea: And they’re double over, crying with laughter. And then you’re like that’s what it feels like when someone has your back. That’s what sacrificial support looks like. Instead of judging your idea that it didn’t go how you thought it would, I’m not sitting over here like “That’s embarrassing for them; good thing it wasn’t me!”
I jump out there because I’m remembering to honor my theme partner. I’m remembering to use curiosity instead of judgment. I’m remembering to listen beyond my comfort zone. You know what I’m saying? These skills go into practice so immediately. And then at the end it’s like this incredible moment of asking what well of resilience did you tap into in order to decide that you were going to commit to this, in order to decide that you were going to get out there and do this?
That’s the same stuff that you’re going to tap into when you start noticing that uh-oh, I see confrontation brewing in this meeting; I see this happening! And I could sit back and be like “Ooh; good thing I’m not the one on the chopping block!”
Or I could remember that’s my theme partner. What an honor I have to be in the room with this person! What an honor I have to be the recipient of their passionate, creative input!
Bryan: Yeah.
Andrea: You know, it changes everything about the way we treat each other in those vulnerable moments.
Bryan: Yeah. You were saying something and I didn’t jot down the note that I had. So I’m quickly trying to go back and remember the point that I had. But it was something along the lines towards the middle of that, that you’re talking about. And you touched on it a little bit: fellows that don’t speak up.
Andrea: Hmm!
Bryan: As leaders, if we can’t pull that out of them and get their input, we lose so much. And those that are constantly shining, you know, they just love to hear themselves speak. We get more than enough of them, and we need to quiet them down. A and so if we can have this community of conversation (I guess that’s the way to say it), we’ll get greater feedback from all sides. And we’ll get greater quality out of it.
Andrea: Yes.
Bryan: And so it’s really knowing when to shine and when to shut up, that kind of thing.
Andrea: Absolutely.
Bryan: Yeah.
Andrea: Humility and courage, humility and courage. And this is the deal. Improv is such a beautiful way to help people practice that skill because it doesn’t feel sharp. It feels sharp to tell someone “We’re hearing too much from you.” You don’t want to dim the people that are passionate, that are contributing. You don’t want to take the wind out of their sales.
Bryan: Yup.
Andrea: But you do want to make sure that they’re giving everybody room to shine. And the people that are maybe reluctant to speak up, boy, I have learned from watching other Improv coaches, because for the longest time I just loved Improv and I wasn’t teaching it in this way. I just loved it and I started this company by accident because I never shut up about how great it was. (Laughter) They started asking me to come to their offices. (Laughter)
But I watched other Improv leaders, meaning owners of theaters, or people who had been doing it forever coming into non-comedian settings to try to teach it, and then call shy people out and be like “You need to participate!”, and then watch these people wilt in front of them.
Bryan: Yes.
Andrea: So here is an art to how you do this. And you don’t want to make your people that struggle to speak up, you don’t want to shame them. So there is a way to do it. And I feel that this system I’ve created does a good job of helping people tap into their courage, helping them to tap into their humility at the right moment.
Bryan: And something you said reminded me of what I was thinking of. I try to drive into my kids—and we have eight million kids!—that if you’re thinking of yourself you’re not doing things right. So if I’m scared I’m thinking of myself and what others will think of me. If I’m thinking of myself I’m narcissistic because I’m trying to just get everybody to think like me. Whereas, if we can have that humility and that active listening, that curiosity, that respecting of others, that really comes from thinking of others.
Andrea: Mm-hmm.
Bryan: Because as soon as you’re thinking of yourself, I’m not listening; I’m not watching you. I’m not doing anything that I need to do to have a good conversation. So the sooner that we can look and focus in on that other person, this stuff accidentally starts to happen on a natural basis.
Andrea: Yeah.
Bryan: So if we can be intentional about focusing on the other person, and then leverage in some of these tactics of Improv, then that’s going to give us the human relationship skills to be able to do this. That’s kind of at the core of all of this. Is that kind of on the right track?
Andrea: Yes; you’re absolutely right. And this is the reason why Servant Leadership is such a great guide for this. And so earlier you were talking about how often leaders and managers tend to lead by title. I think that’s what you said.
Bryan: Right.
Andrea: And use power. “Do what I want you to do or you’re going to get fired!” And they don’t really necessarily say those words. But the entire attitude, the entire vibe that everyone is receiving is “Don’t tell me what you think. Tell me that I’m right.” (Laughter) “Do what I’m asking you to do.”
And I call that collaboration theater. I’m pretending because I broke out a white board and some post-its. But I pretty much know what needs to happen right now. This is what’s going to happen to do it, you know?
Bryan: Right.
Andrea: And so the opposite of that is servant leadership. And there are a couple books I could recommend on that. I saw on your prompts that one of the things was what guides and things you recommend. And I of course have resources as well. I have created quite a lot of free content on my YouTube channel. But there are two books: The Servant by James C. Hunter, and The Servant Leader by Ken Jennings and John Stalwart that really speak to what you just said.
And it’s everything that I believe in and teach. But it’s also just a free market that is proven to keep well-intentioned leaders from behaving in this title first, it’s my way or the highway, this enthusiasm murdering way of leading a company.
Bryan: So conversation and feedback isn’t hey, tell me all the great things that I’ve done. That’s not the feedback that we should be giving?
Andrea: No; that’s not the method that I recommend. (Laughter)
Bryan: Well, okay. So I think that’s just a ton of foundations. So let’s take the specific of what the topic is here. How do we take that from a customer success to a sales perspective, right? Because when we’re on sales we’re trying to do everything to win the day. And there’s a lot of pressure here, right? So taking that, how do we do that #1, customer facing, but then #2, so we don’t over-promise and crush the customer success team? So two different sides: the external customer and the internal customer. So how do we take all of this and put it in that context, please?
Andrea: Yes. So I’ve seen people handle this in a variety of ways. I can pull up the foundation answer from what we’ve covered so far. It starts with honoring your theme partner, and also that frequent communication, because I’ve worked at companies before where the sales team has its own department. And it’s completely separate from everybody else. There is very little relationship between the two departments. And there is very little incidental conversation, or the ability to just quickly be like “Hey, thank you, customer, for asking that question. Why don’t I put you on hold for one quick second? Joe, does this seem like a feasible thing?”
There isn’t any ability for that because it’s worlds apart, you know? So I think part of it is physical proximity.
I also had the pleasure of working for a company where they had teams between sales and customer facing. And so it’s like they sell products or do new company initiatives sort of like in pods, where you have someone from sales, a couple people from development, a couple people who are doing customer support working together. That way there’s just so much more trust. And there is also so much more understanding of what goes into it.
So part of it is when we can cross-educate so that sales has a little bit more understanding of what goes into this from a development perspective. But the other part of it is that we are each other’s yin and yang. Just like I was saying the last time we talked, some of the things I have loved a lot about some of the sales people in my life is their innovative, sky-is-the-limit spirit, and their genuine belief I n the capability of their developers to build the moon. (Laughter)
Bryan: Because we don’t know how hard it is. (Laughter)
Andrea: Sure. And so part of it is this gift orientation. You know, let’s not imbue our theme partners with the worst possible characteristics. I know what it feels like, having worked in sales and having worked with customer facing rules.
You just make the worst assumptions about this person. They’re only chasing a commission. Why think that? Why choose that story instead of the story that says that this person is an optimist that believes we are capable of so much. And this person has given me the gift of hearing what the market is asking for right now. You know, those are really important pieces of information.
I am offering an understanding of what technical capabilities are right now. I am offering the perspective of what is all on the table, and what our technical band width is to do new things. And so that’s valuable as well. But we don’t need to think the worst possible things about each other. But just like you said earlier, that comes down to trust.
Bryan: I was just going to say that there’s a lot of cognitive bias that comes into that, because if I think that you’re all about commission, then I’m not going to give you the benefit of the doubt. I’m not going to trust you and I’m going to think the worst of you. And now I have these lenses on that’s your commission breath. Or you’re a killjoy on the other side, or whatever negative stereotype that we throw out there, and that ruins the whole entire idea here—the scene, if you will—from doing this.
Andrea: Yes.
Bryan: Whether from the customer external or internal. So yes, absolutely.
Andrea: I have seen and personally heard, and to be perfect honest, participated in the name-calling and the distrust across this divide. You know, the development, the people that are in charge of fulfilling whatever has been sold, they’re the sticks-in-the-mud. The people that are selling, they’re the commission chasers. You know, they are not tied down to reality at all.
The most logistical answer to solving this problem is truly to give people more opportunities to have relationships with each other. Give them more opportunities to communicate. Put them in closer proximity. Allow them to collaborate in so many areas so that they see each other as a whole person and not just as a job title. But they also understand more about what each other’s hard work load is, their responsibilities. Help them understand each other better, you know?
Bryan: Yeah.
Andrea: Yes. Go ahead.
Bryan: I was just going to say that right now you can’t get into proximity. So it doesn’t necessarily mean the proximity of space, but proximity of communication. Like you said, these pods, getting to understand one another. And the curious thing is (and I’ve been taking notes down here), that whenever you talked about the trust, there’s transparency. We have an episode coming up in a couple weeks from now with a guy by the name of Todd Caponi, and he talks about transparency. And forgive me, Todd; I can’t think of the name of your book; I feel like such a jerk. But it’s a great book; I’ve got it up on my Audible right now. But having that courage to speak trust, having the courage to be transparent, and whenever we don’t think that we have that capability to say, “Hey, listen! Let me just be up front with you. I don’t think we can do that. Is that going to be a show stopper?”
“Yeah, we really need that.”
Well now I can go back to my customer success or my development team and say, “Hey, this is a show stopper if we don’t do this. This is where we are. Can we do this, or do we need to offload this?”
Because here’s the deal. A lot of this, especially since you were talking about technology on the Sass model where certain software is a service, that renewal is everything. That’s where the money is made. That’s how your company is profitable. And if we don’t say no, and we should never have won that deal to begin with, not only are we not going to get the renewal, but now the reputation is going to get tarnished. And whenever we do have the capability now they’re not going to listen to us because we already lied to them.
So there’s so much at stake here by doing what you said—having the courage to speak out; humility with curiosity—having this presence of mindfulness in collaboration with the whole, entire team. So there’s a perfect alignment there.
Andrea: Absolutely. And even with that we opened up talking about the why, understanding the why of your company, you know. And so you should be able to deliver on what your why is. It’s the shiny objects that seem tangential.
Bryan: Yes.
Andrea: That are close, but not exactly why you’re here. You know, that is something that I have struggled with a lot. That may have been the number one thing I’ve struggled with as a business owner. It’s that my heart is in a lot of places. And with these things that we’re talking about Improv applies to so many different things.
And so boy, is it difficult for me to stay focused on like this is what I care about; this is the way I do good in the world. It’s by helping people create cultures that honor everyone. You know, this is my way. I teach people how to be peace-building conspirators at work. At work I teach them the skills that they need to literally build a beautiful peaceful world in every area of their lives. This is how I do good.
It’s easy, though, to get distracted with, “Oh, you know what? I’m a foster adopt mom.” And there’s this whole group of foster adopt moms that is trying to figure out how to start businesses. Maybe I should do an online class for them. No! Maybe that’s a great idea ten years from now.
Bryan: Yeah.
Andrea: Don’t get distracted with that right now Do you think I built that bad program? Yes. Was it a huge failure because I didn’t have the band width to do it right? Yes. (Laughter) You have to focus on this. When you’re a small business owner you are sales and fulfillment, so you have this war within yourself. And it’s so critical.
What is your why? Don’t get distracted selling extra stuff because you can justify it in your brain in some way. Focus. It is safe to keep it simple. It is safe to say no. It is safe to focus because that is how you can deliver the most value.
Bryan: Yes. Gino Wickman has a good line. He wrote the book Traction. And he says, “Less people die of starvation than they do of indigestion,” because we get enamored with the shiny thing and we get off on these tangents instead of staying on our why and our purpose and getting the foundation all down. You know, that’s really sound advice.
Okay, so good stuff. Hopefully everyone got some good tactical, practical advice here, how we can take all of this that we’ve talked about. But really, if you want to boil it down to the most simplistic, have good conversations. Be transparent. Respect the other person with whom you’re speaking, actively listening, being creative and problem solving together, because we can problem solve together a lot easier than in an antagonistic kind of world in which we’re unfortunately living right now. So really, really good stuff.
All right. So as we’re winding down here, oh my gosh! These podcasts are fairly long. So hopefully you as the listening audience are getting as much out of this as I’ve been. Time always just flies so quickly.
Give us this real quick—I think you just did!—you know, the biggest business challenge that you’ve seen. Has it been that shiny object, chasing other things? What’s been—
Andrea: To me that’s been my biggest challenge. It’s the need to stay focused, especially as a small business owner. You cost yourself time and money by getting distracted And so you need to focus on the why. People will often reach out to me. “Hey, I could really use some coaching for public speaking. I’m trying to do more online videos like you do. Could you help me with this thing?”
And I’m so tempted to do it because Improv absolutely does help with that. But that’s not why I’m here; that’s not me doing my work. That’s the distraction, you know.
So yes, I’m having to stay focused on this is why I’m here. I’ve got to stay on this path.
Bryan: Have you figured out any tactics or tricks or hacks for us?
Andrea: For how to do that? Yeah. So one thing that I do is that I have a bunch of white boards; I’m big into white boarding. But my why, the thing that I’m staying focused on, I write with a sharpie on the white board, so that even as I am drag erasing other stuff and figuring out what my week is this week, I’ve got the why, the anchoring thing that is my true north, is sharpies. Don’t get distracted.
Bryan: Nice. I like the tie into the true north.
Andrea: I’ve also invested in business coaching. I mean, that’s another thing. Don’t be afraid to invest in getting the help that you need to get your head on straight, you know. And that’s the one thing that I’ve done.
Bryan: Yet it’s a curious point, right?, because we’re in the weeds. And for whatever reason we can’t see it and somebody else sees it plain as day. “Did you see this?”
“No.” So that’s absolutely some good advice there. Okay, now how about a business hack for talent, sales or scale? I mean, do you have any suggestion of how we can use this—your expertise—whether it’s for talent, saling or scaling the business?
Andrea: Yes. So I think mine mainly has to do with scale. And so it’s right in the time line of my business. Forward together. Don’t let yourself think that if you’re a slightly smaller business right now, for example, it’s easy to think, “I’m too small to worry about culture right now.”
No, you’re not. Now is the perfect time to be thinking about what kind of leader do I want to be? Maybe I only have five, ten, twenty employees right now. But if you have aspirations to really scale, now is the time to think about what kind of culture you want to have. What kind of leader do I want to be? Because it’s a lot easier to pivot right now. If you need to course correct now it’s going to be a lot easier to do that than when you’re the size of the VA where I’ve worked before. And the most miniscule change goes through about twenty tiers of leadership to do one small thing.
And you know, I know that’s a really drastic example, but the point remains. You’re agile now. Now is a great time to think about culture and who you want to be, especially because when you’re very clear about your culture expectations that is how you will hold yourself and others accountable, having those very clear tent poles laid out right now.
Bryan: Yeah. And I think that’s sound advice, because if you don’t lay out the culture you’re going to get the wrong people on your team.
Andrea: Mm-hmm.
Bryan: And you’ll fail nevertheless. So culture is critical from the get-go. So I think that’s really sage advice, so I like that.
How about resources? Are there any books that you would recommend—podcasts, guides, anything that you would suggest?
Andrea: So many books I would recommend. Of the books I have I mentioned two books earlier: The Servant by James C. Hunter, and The Serving Leader by Ken Jennings and John Stalwart. (I almost switched their first and last names.) So those are two great books if you[‘re interested in servant leadership.
Dare to Lead by Berne Brown, my future friend, (laughter), has not been preached enough. I think I own all of her books. I love her very much and she just gives fantastic advice.
But also I really recommend that if this conversation isn’t resonating with people, and you’re like “Great! I have these foundations; this is really important to me. I really want more tactical advice on the accountability part. What do I do if I’m super on board, but my co-founder isn’t? Or there’s one person at my company,” like that one person I was telling you about before. Everyone’s always like “It’s Todd’s fault,” whatever. (Laughter)
Bryan: Todd!
Andrea: All of these people, fractious employees, are difficult people to coach. I have a free Web&R.

That offers some of these very tactical evidence-based things. I was sharing my background with them.
Bryan: Yes.
Andrea: Like how people make lasting changes. And we’re really getting into behavior modification coaching. If you’re trying to figure out how to do that it’s a free Web&R.

And you can get some very tactical advice about how to handle those coaching conversations.
Bryan: Is that on demand, or—
Andrea: Yes. I was thinking about HBO, and I was like no. But if you know someone at HBO, I’m really happy to put something up there. (Laughter)
Bryan: Got it. Oh, that’s perfect! All right, so what does the future hold? I mean, with all this craziness going on what do you see from the circles that you’re talking to? What’s going to come down the pike that if we’re not expecting is going to bite us right on the back side?
Andrea: I mean, if you’re not expecting what I’m about to say by now you’re probably already going to get bitten. (Laughter) But I think what the future holds is brave leaders. I think that what the future holds is brave HR teams, brave team members. And what that means is that the conversations that feel the scariest to have right now, about racial justice in particular, about gender equality, these conversations that feel like “I just want it to be fixed! In my heart I’m the kind of a person that’s like yeah, I don’t want that stuff to be happening. So I’m not a part of the problem, right?”
I think what’s going to happen in the future is that hiding behind general niceness is not going to be enough. It never has been enough. But I think what’s going to happen is that the leaders that are most reluctant to really be brave and talk about this stuff, even if, (especially if, not even if), especially if you’ve got listeners that are working at the smallest companies that are mostly or all white people, or mostly or all white dudes, and they’re like “Oh, I don’t know what to do about it,” those companies are going to fail. I do not believe that the future holds all white small entrepreneurial groups like the ones that I was coming through on a start-up weekend back in my tech start-up days. I don’t think that’s how it’s going to work anymore.
I think consumers are a lot more conscious about working with customers that are embracing these incredibly important ideas. But I also think that it’s going to get harder and harder. The longer that companies wait to course correct, the longer that companies wait to get brace and have these conversations and do better, the harder it’s going to be for someone to come in at the company and be willing to take that risk.
As a woman I know that it would be really difficult for me if in five years the company is like “Can you come in and help us have this conversation?”
I’m going to be like “Why are we having this conversation right now? Why did it take you so long to get brave?” So I think that right now I think that’s where the future is headed.
Bryan: Yes, so courage and bravery. And I also think of humility on the listening side, too.
Andrea: Mm-hmm.
Bryan: because everyone is talking over each other. So I’d agree with that wholeheartedly. All right. So Andrea, who should reach out to you? How should they do it, and why should they reach out to you?
Andrea: Yeah. So the who would be leaders or HR. You’re not the owner of the company, but you’re the leader of the HR team. They’re usually the best folks to have a conversation with me.
And if you’re in a situation where you’re desperate for continuity. Your heart is there; your leadership team is already there. But you’re like “We are not consistent across all departments. We’ve got departments that are consistently reporting these problems of culture. People are not respectful. They’re not upholding our culture vision, our brand promise. We’ve got people that are not consistently delivering as leaders, and we’re not really sure what to do about it.”
That is where I live all day. And so if you’ve got that type of a problem, and you are desperate to get some continuity in your culture, please reach out to me. That is who I love to help—caring, empathetic leaders solve. And the how of reaching out to me is that you can reach out to me through my website, or directly email me; that’s fine. I can provide you my contact information.
But also that Web&R that I offered, that free Web&R at

That’s a great place to get started and kind of get a sense of if this feels like a good fit to you. And then there’s a contact form on that page as well if you want to reach out.
I’m really into giving you something that’s valuable right at the beginning, to see if that feels like a good fit. And then I also make sure that we hit the ground running in our work together.
Bryan: Nice. Give to get; love it. Well hey, I really appreciate it, Andrea. This has been a lot of fun. And I was not expecting it to be this jam packed with good content. I thought it was going to be a lot of fun, but this is a lot of fun and a ton of good content. So—
Andrea: People expect Improv to be mostly fart jokes. (Laughter) And they’re pleasantly surprised. Whoa, there’s real substance here!
Bryan: Yeah, right. Yeah, perfect! So we’ll get running here. So I can’t thank you enough. Hey, this is Bryan Whittington with this episode of The Talent, Sales and Scale Show. Be empathetic. Start listening. Oh my gosh, get after it; have some fun already! Hey, thanks, everyone. See you.

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