Parenting = Coaching = Managing with Penny Williams

Penny Williams, VP of Marketing at EnGen, talks with Jordan about the parallels between parenting, coaching, and managing a team.
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Show notes

VP of Marketing at EnGen, Penny Williams, believes her role as a mom, among other things, is to prepare her nine-year-old daughter for the workforce.

How does she do that? She has one definitive rule: participate in a team sport each year.

She explains the reason why to dad, coach, and founder and CEO of Greaser Consulting, Jordan Greaser.

Sure, it’s healthy. Sure, it promotes resilience. But Williams has another reason. Listen in as these two parents relate raising kids to managing a team.

Jordan  00:00

Hi, everyone, this is Jordan, the owner and CEO of Greaser Consulting. We’ve got with us, today, Penny Williams. She was formally in marketing at Outreach, and that’s where our paths cross. But today, she’s doing a lot of great work at a company that’s working on equipping refugees for the workplace. You hear a little bit about that in the podcast. But today’s topic is, is actually around parenting and leading a team and, and just, you know, how do you push people down this path that like knowing their gifts or capabilities, where they should end up, but also balancing that with like their own autonomy, right? But teetering on that line between equipping and pushing in that direction versus, versus just sort of cultivating and guiding somebody. Penny is always fantastic to chat with; you’re going to hear about some of the things going on with her and her nine-year-old daughter; I think you’re going to enjoy today’s episode. And with that, we’re going to kick over into it. Have fun.

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Jordan  01:22

Hi, everyone, this is Jordan, and I’ve got Penny with me today. Penny, why don’t you go ahead and introduce yourself?

Penny  01:28

Hi, everybody. Thanks, Jordan. Penny Williams, I used to work with Jordan back in the day. So it’s really, really fun to reconnect, living in Seattle still, you know, moved around the country. And that has really informed my, my background and working at advertising agencies and then on the client side in marketing, and I’ve been in tech for over 10 years now, kind of, you know, you, you live in Seattle, and you walk out your front door, and you trip on a tech company. So that’s what we do around here. So and then I have the, the, when I’m not doing that, I have a nine-year-old daughter and husband in the in the burbs.

Jordan  02:09

In the burbs? Well, Penny, you, you said you used to work with me; I think we, I would have qualified, at that specific season of being like the young punk, who was just a pain in the rear. So to say that you worked with me is probably pretty polite. Like it’s probably more like you dealt with me for a span of time. I think it’s probably more accurate.

Penny  02:33

Well, Jordan, I think we were about 3,000 miles apart. So I think there was a buffer or filter there. I think we were, yeah.

Jordan  02:43

Yeah, thank goodness. Ah, thank goodness there was a buffer.

Penny  02:48

That was fun. No, you were fantastic. That was fun.

Jordan  02:49

Yeah, we did. We had a, we had a great time. And I know this isn’t really the topic of today. But I just think this is so amazing. So before we even get into things, Penny, could you tell people right now, like what your company does, that you’re working at today?

Penny  03:09

Yeah, you know, I would love to, I work for a company called EnGen. And while it’s a newer company, we spun out of a 10-year-old company called Voxy. About a year ago, year and a half ago, we spun out of it. And it is this brainchild of our brilliant, brilliant founder, Dr. Katie Brown. We work with immigrants and refugees to give them the career English, I always say that career English that they need to upskill and provide them with what we refer to as economic mobility. And so that is really just boots on the ground, being able to get a better job, get those promotions, be able to integrate and to have, meet your social goals of being able to help your children with their homework. These immigrants and refugees come in here and meet, Jordan, I know you know this from your past life. But the lot of them come in with their income incredibly credentialed in their home countries; these are doctors who are driving taxi cabs, or these are entrepreneurs from their own countries who come in here and, and share their, their knowledge, their skills, their passions here in this country. And we are so lucky to have that. And that’s what makes this country so, so interesting. So we help them with their career English to help them meet their career and social, social goals.

Jordan  04:38

Well, I know the, the commentary there is like the capability but what they’re allowed to do can be so dramatically different. And I remember being in a refugee camp in northern Iraq, and this is my own ignorance coming out is I’m thinking oh, like, these are people that were suffering and struggling and they ran away. And then I meet all these folks. And they’re doctors, they’re lawyers, they’re dentists. And they’re sitting there in the refugee camp because they’re country’s at war. And the thing that was really difficult about that is like, you know, these are people that are highly educated, very talented, because, but because they had the status of refugee in the country; I was in northern Iraq there, and we’re talking about Syrians here, that they were in, they were unable, or they were sort of passed over, by the local community as like, well, these are these like, lower class refugees, right? As opposed to like, actually, they’re probably smarter than you are, like, the probably more talented than you are, and you’re over there, like passing these people off as nothing. And I just remember how painful that was just watching some of these people that are just really talented, you know, treated like they’re less just because of like, their country’s having an issue. And this one isn’t, right? So yeah, I’m 100% in there with you, which this is going to be the most interesting segue I may have ever made. But talk about like, capability, but also opportunity, right? Of like, where you’re talking about, you have a nine-year-old daughter today. And the premise of this whole conversation is like what you tell your daughter, which we know what a good mom, that’s worked 10 years in tech, and you’ve seen the high sort of side of things, but now you’ve seen this, like, sort of refugee side of things, right? So you’re, you’re blending some worlds and you’re helping people get up and running. Talk to me a little bit about, like the discussion that you’ve started having with your daughter at nine years old about like, the workplace, like, what, what’s out there for her, like how you navigate some of the… Have you started into any of those conversations?

Penny  06:51

So I have always felt that my job as a parent, at the core, at the core is to prepare her for the workforce. That is how I think of it; everything that she does, I’ve talked to her school about it as well. And they, they are starting to think in a lot of those same, same lines. And I don’t mean in the skills that they’re, they’re teaching them in coding and in languages and what have you. But one requirement I have for my daughter and have since she was, started school, so at five is… she must be, she knows this rule really, really well. She must play one team sport a year. So Jordan, do you know, you know why? Or does that? Have you heard that before?

Jordan  07:42

The big thing I mean, I’ve got two daughters. I’ve got two sons and two daughters. And the big thing I think about is resilience. That would be my, my two cents of watching my kids work really hard and then sometimes fail. And then how do you, how do you build resilience to keep going? But that would be, it’d be the first thing that comes to my mind. But you tell me your hypothesis here.

Penny  08:09

So for me, I think that’s great. Of course, there’s so many things, so many directions that that can go but for me, it, we all work in teams; we’re all driving toward one goal at work, whether it’s a project or in building this company, like an Outreach or like EnGen, where I am now. Right now I’m at the same size company as when Outreach when I started there, about 20 people. So we’re all coming in, and we’re all working toward this one goal. And the other pieces of that Jordan is that sometimes you’re the leader, and sometimes you’re assisting. So, you, whatever those plays are, that you, whatever strategies or whatever you’ve determined whatever is the plan is sometimes you’re in the lead, sometimes you’re assisting so that you could all meet that goal; you’re keeping score along the way, checking in at you know, at the quarters, but it’s all that teamwork. And then for me that also builds into another note I have is the, the relationships. I learned that from a very, very dear family friend who is in her, she says 77 now, but youngest 77-year-old you’ll ever meet

Jordan  09:27

77 years young.

Penny  09:30

Yes, she is insane. And she used to be this executive when, and she’s African American. When women worked, you know she, she had to just the words of wisdom coming from this, from this gal. But she is all about those relationships. And for her, it came up from living and growing up in Hawaii. And so she, you’re on an island, you know everybody; it’s all about relationships, and so she’s carried that on onto into her work world. And that’s another really, really important one that feeds into that idea of teamwork. Working together and those relationships that you build. We are often… women are often, I heard this from somebody years ago, and it just really jumped out at me. And I say a lot of this Jordan as a, as a mom of a girl, too. So that’s where you’ll hear a lot of my kind of my bias. And when I, when I talk about what I do, how I teach her, and or my, my opinions, my guidance for her is often women tend to interact very transactionally. And I think that’s just part of being multitaskers. Trying to do so much at home being that default parent at home while also having your career and you just you’ve got so much going on, we end up being very transactional in our, in our interactions. And so I really want to teach her that about those relationships.

Jordan  11:01

So let’s lean into the whole sports side of things just a little bit. Because when you get into sports, you’re right. Like, you might be the leader, you might be the assistant. But then you also have like the role player, right? And so the reason I bring that up is I’ll see some, some kids and we’re talking purely sports here, okay? I’ll see some kids that like, like, they’re, they’re gonna be a role player on the team, but then their parents won’t let them accept that, right? Because like, “Hey, you got to be the leader, you got to be number one, you got to be up there.” And so that’s one of the things for me, as a dad, that I’ve tried to like, I’ve tried to comprehend of like, when am I pushing my kid that like, “Well, no, you should try to Excel; you should try to maybe be the best.” But then over here, like, “Well, actually, it’s okay though, if you’re like, you’re the defender,” right? Like, you’re not going to play offense; you’re playing defense. And that’s like, that’s a good job too; like, it’s just as important. It just looks a little different. So when you get in there, and you’re working with your daughter in this team environment, are you one of those parents on the side that are like, “put her in. She needs to be number one, let’s get rolling.”? Or are you like, “oh, okay,” like you’re willing to accept the role position?

Penny  12:18

I am really, very much in the role position camp. And that is really, again, you know, though I, she’s nine, how old are your kids?

Jordan  12:30

My oldest is 6. I’ve got 0, 2, 4 and 6. It’s been wild, Penny.

Penny  12:41

I can imagine. So I’m not sure if… I can only speak to this age group right now. But I really believe that every position, just like at work, Jordan, every position has its, has its role. And they’re all important; if they’re not important, then it’s got to go. So I think that that’s, that is something that I, at larger companies, I’ve really kind of struggled with that; at startups, we all have a role. We do sort of bleed into other, other and that, that’s part of our job is we have to find those, those gray areas; we have those gray areas until we figure out how to how to work them. But I think you do that on the, on the soccer field, too, is you’ve got to have coverage. And how do you, you know, you’re not bound necessarily directly to this spot, or this little perimeter, but you’ve kind of got to move too and flex with the team and, and see what else is going on. So that’s that’s how I think of it. What do you think?

Jordan  13:46

Well, what do I think about it, so I’m coaching my oldest son and my daughter; right now they’re on the same team. And what, the thing I’m working through as the coach is like, there are some good players that maybe are a little better, and maybe a little worse, you know, whatever. But week to week, my kids are different. So I have a week where they’ll come in, and they’ll be super aggressive, and they’ll be trying to get in with the ball. And then the next week, maybe there’s a big kid on the other team and they just get kind of scared and sheepish and like they’re sort of drawn back. And so, you know, for me, it’s it’s been a little less like, what role do you play and, and also just trying to, like, work through consistency with them, right? Of like, like whether the player’s big or the player’s small, like play your game, right? And maybe that’s the role you’re talking about, but like, you need to play your game. And listen, they’re six and four, so it’s not a too complicated conversation. But you know, as the dad sitting over there, like, I want you to be aggressive, but you’re sort of shy today. So like, I don’t want to drive you too hard, but at the same time, like play your game, you know, which it… The thing that I find that’s really amazing about some of this is that a lot of like this parenting stuff, and I’m gonna have somebody that’s listening to this, and they’re gonna be like, “Oh, well, now it makes sense why you talk to me this way.” But like, it’ll translate over to the workplace, too. You know what I mean? It’s like, well, these are like little mini versions of like you as an adult. So like that stuff’s still in you; it just looks a little different. And so when you think about that, do you think about raising your daughter and you’re helping her through all these life things? Like, do you find yourself constantly teetering between like work mode and home mode, as you’re talking with her or you’re in talking with your, your direct reports?

Penny  15:42

Coworkers: treat them all the same. They… So absolutely, that is, I think that I always thought it was interesting because I had kids late, and so or had her late, when I was older, and saw the people who were, who are parents and saw how they would juggle. And I thought it was interesting, and like, I’m not sure that’s for me, that’s, that’s, that’s a lot of, that’s a lot of work, I’m just gonna stay and stay in my lane and just work really hard. But when my daughter was born, and then as she’s grown, as she’s gotten older, the… I am 100% with you, Jordan, because I want to see that success, where I see it, or where it translates for me is where I want to see success for them. So I want to see success from my direct reports. And I have, the… more… sometimes I think a clearer vision of what I think they should be doing, or what should be next in their career. So the same way you are for your kids, and you’re looking steps ahead, because you have that experience and that, I don’t know if it’s wisdom, or just it’s just sheer experience, and I do the same for my direct reports in having an idea of where they should be, where I think they should be. And I you know, so far, you know, folks have been really open to that idea. But, and then how to how to get them there and how to support them on that, I… that’s how I think the crossover between parenting and management happens is in looking out, using your experience and helping to guide them to the next thing or their bigger goals.

Jordan  17:29

How do you, like, incorporate or allow failure? And again, this could be kids, and this could be direct reports. And I touched on resilience earlier. But there’s, there’s like places where my kids get and then there’s places where, like even people I’m working with, they get to this place where like, you might not be ready for that yet. But at the same time, like I’m not sure how to get you ready until I put you in a situation that where you might not make it. And that’s it’s just a little bit of a different… I remember a coach telling me one time a long time ago, saying he doesn’t like to put kids in situations where they could fail, like he tries to get them ready so that they’re just gonna like, they’re gonna naturally get into that next place. And part of my struggle as a parent and a manager is like, I love that mentality of like, let’s put you in a position where you can win. But then there’s also certain times where like, I’m not sure you’re gonna develop unless we just kind of push you out there. And obviously dealing with adults and, and dealing with a nine-year-old daughter, you know, it’s a little different when things don’t go as planned. But do you, do you like prescribe to that “let’s allow you to fail” mentality? Or are you like this old coach of mine that like I’m only going to put you in an environment that you can win?

Penny  18:47

In the padded room or in the safe, in the safe, in a safe cushioning? That the parent would the safe, I know my daughter is not in the safe, safe suit. So for, so I think that you, you put them in positions where they are challenged. And then, but you know what, Jordan, I think you be there to pick them up. So you’d be there to be on the other side of that. And you’re alongside… I’m probably that parent who’s like running alongside the field. And then, but if they trip and what have you, I’m going to be there to help pick them up and help lift up their spirits on the other side and say “cool, all right, well, what do we learn? You know, brush it off, and let’s, let’s go.” That’s where I am. How about you?

Jordan  19:35

Oh, I’m the I’m more of the sink or swim dad. Like, like, let’s let’s throw you in the deep end and see what happens. But that’s, I still, I still remember playing baseball peewee baseball and being in fifth grade. I was the pitcher. And my dad was the coach, and he went to go to the bathroom or something when I was pitching. This kid hit a line drive right into my shin, and I was on the mound, just like crying because my shin hurt. My dad came back, had no idea what happened. He came back, looked at me, then looked at everybody. “So what happened?” They told him what happened. He said, “Get in the dugout; you’ll be fine.” And I was like, “what? Like, I’m over here crying here, and you’re telling me just like, I’ll be fine.” But, and he’s a good dad, he can nurture sometimes. But I’ll tell you, I’m a little bit of a product of that mentality of like, “Come on, move on. Like, there’s no reason why and about it. Come on.” What’s that famous, “there’s no crying in baseball”?

Penny  20:35

No crying in baseball, but I do want to set up my, my folks who I manage as well to absolutely go out there and try things. I probably do it potentially, in… I don’t know, I don’t put them out into something that I think is super high risk. That’s probably, that’s probably the best way to describe it. But I definitely put some like my SDRs right now. I’ve got one who I’ve been lobbying internally to to get him moved up to a closing, to, to an AE role. So we’ve got him on target, hopefully for later this year, moving over. And he didn’t know exactly where he wanted to be. He’s 23 years old. He is an exceptional SDR, wants to be an entrepreneur; he just has run with this, like it’s his own business. Fantastic. But humble enough to keep on learning and just really, really, really strong. So I, he didn’t know what he wanted; he wanted, you know what he wanted to do, Jordan was he wanted to be an SDR manager. That was what, because he enjoys, he enjoys the role. And he wants to coach others. So I get that because he’s become, you know, an expert in it. I get it; he loves that he has a lot of confidence around it, because he’s good at it. I’m pushing him to being an AE, because he wants to own his own company; he went to school for entrepreneurship. He wants to, at some point, run his own company. I said our best and I learned this at Outreach from Manny, you know, your best salesperson has to be your CEO, you know, in those early, early days, when you’re starting out. So I said to him, “if that’s what you want to do, I need, you need to, then I think your next step is as a closer, as an AE”. And so I am moving him in that direction. And we are putting him in with, while he’s doing his SDR job, he’s also moving to close, moving through stages; he’s just on his first one right now of a deal, of a very small deal. And that and that’s what kind of and there’s some inbounds that are coming in. So they’re, they’re already high interest, lower-hanging fruit, probably, you know, much more likelihood to close, build up his, just, rigor on process, and answering, you know, objection handling and kind of what the processes are, and get and get them to close. So and then, you know, throughout the year, we’ll get him on to bigger and bigger things to deal with bigger and bigger challenges kind of kind of again, goes back to the kids; as they get older, and the problems get bigger. It’s the same idea. Anyway, that’s what I was…

Jordan  23:14

I want to touch on something you said right there. Because earlier you were saying, you know, I’m gonna, I’m gonna like sort of help them get to where I think they need to be. And then you’re saying here that like, he was saying, “I want to be an SDR manager,” but you’re saying “no, I know, you ultimately want to be a business owner. So let’s go this path.”

Penny  23:32

Like my daughter was, you know, kids, when they’re when she was like three or four years old, you know, wanted to drive the, the ambulance, or she wanted to drive, you know, the fire truck or the whatever it was; I forgot what it was now… is it sometimes it’s garbage truck because that looks like fun. You’re playing in this big thing and moving levers. And my, our family friend said, “as long as you own the company, sure, go ahead. You can play that all day long.” And so with, with this gentleman, though, this SDR I was referring to, I think… this is my opinion, and I have told him I will support him whichever way he wants. We’re too small right now, for him to have anybody to manage any SDRs; there’s only a couple of them. So it’s not going to be a huge opportunity yet. You know, hopefully in the future, it will be, but right now No. So you kind of weigh that too is what’s, what’s your opportunity right now? He could go somewhere, learn another company, another company’s processes and go be an SDR manager at a very large company if he wanted to. But he is… And so when you say that when initially when you ask that question, what I was hearing is for me, I think he’s looking very short-term versus long-term. And as a 23-year-old, I’m trying to you know, I gave him my opinion and I said, here look, and we had many conversations about it was not a one time thing. I said, “this is my opinion, I will support you in whatever you want to do. But I think if this is your ultimate goal, this is where you should be headed, or this is this is how that’s this will benefit you most in the long run versus that short term good feeling of being a subject matter expert.” What do you think?

Jordan  25:23

Well, Penny, I, I gotta go sideways on here for a second just because you mentioned garbage truck. About, about three weeks ago, we were in our office, and one of the ladies came in the office. She was like, “I just saw the coolest thing in the world.” And we’re like, “what did you see?” Her name is Leah. We’re like, “Leah, what did you see?” She’s like, “I was driving by,” and she’s like “a garbage truck pulled, pulled up beside me.” And she goes, “there was a woman driver. And then there were two ladies on the back doing the garbage.” And she’s like, “I put my window down. I was yelling you all are BA, blah, blah, blah” and she said, she was just freaked with it later. Like 10 minutes later, what do you know, that same garbage truck went right by our office that she ran out again. And everyone’s clapping and yelling. She’s like, “that’s a coolest thing in the world. You know, girl power, you know?” But anyway, you talked about the girl who wants to drive the garbage truck; I can connect her with a certain certain crew of women from Pennsylvania. Yeah. Future, future garbage ladies of America. But the thing that this woman was saying was like, “Hey,” she’s like, “I can’t even tell you if I’ve ever seen a woman garbage person before.” Like, I haven’t either, right? Like, I’ve never seen it. She’s like, so I’m not saying it’s a glamorous job. But she’s like, it was just cool to see representation. Right? That like here are these ladies doing a job that like, maybe you don’t want to do but they’re out there making it happen for their families. So she was pumped.

Penny  26:53

I agree with her. I think that’s fantastic. There’s some girl power happening in there, I don’t care what you’re doing.

Jordan  26:58

Hey, good old Central PA blazing the trail for progressive thinking. Right?

Penny  27:04

I love it. Yes. I love it. I love it. So anyway, so that’s, that’s yes, exactly. That’s where, that’s where I’m, that’s where I’m headed with it. Yeah, she could do whatever she wants. Maybe those ladies are like vying to like buy the company. Jordan, you know?

Jordan  27:19

Listen, they could be. I mean, I didn’t want to mess with them. They seem like they knew what they were doing. They know a lot more than I do. I can’t drive that truck. So anyway. Hey, with that said, we’re coming right up on time. Penny, any last, whether it’s parenting or director, any last sage advice you want to give everybody?

Penny  27:39

You know what I can’t, I can’t close this out with just some of the regular good reminders about treating people with respect. You know, being nice, being nice to folks, you know, building relationships, all the you know, Golden Rule. My, my, my daughter and her buddy are all about the Golden Rule, and they fight over the nuances of it. “Hey, you’re not following the Golden Rule.” But, you know, work, whether call it at work or on parenting, it all applies. So I think there’s just so many, so many of so much overlap that, uh, we could you know, we could keep on going, Jordan, so I guess we’ll close it out there for today.

Jordan  28:25

Oh, Penny, thanks for coming on. And for everybody listening, we appreciate you tuning in. And we look forward to having you next time. See ya.


Hot dog. That was a great episode. Thanks for listening. If you want to learn more about Greaser Consulting or any information you heard on today’s episode, visit us online at Be sure to click the Follow button and the bell icon to be notified on the latest here at RevOps Therapy. Thanks and see you real soon.

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