Practical Leadership Cast
Practical Leadership Cast
Guest Cast: Dana Ross on Recruiting, Leadership as a Trans Person, and Star Trek!
Forest interviews Dana Ross, a Senior Engineering Manager at Grindr, about her insights as a leader. We chat about how to successfully interview candidates. There is a discussion about how gender impacts empathy and leadership. During the gender discussion Forest mentions Abby Wambach and We Can Do Hard Things ( http://wecandohardthingspodcast.com/ ). When asked what a 10 out of 10 leader looks like Dana gave Lee Cockerell (former EVP of Disney Resorts https://www.leecockerell.com/ ) as an example. We also geek out for a bit about Star Trek.
Dana Recommends:
- Grindr is hiring and will be launching it's internship program shortly: https://www.grindr.com/careers/
You can learn more about Dana at her LinkedIn: https://www.linkedin.com/in/dana-rose-ross/
Dana suggests we interview Megha Bambra ( https://www.linkedin.com/in/meghadhall/ ) and Joel Keating ( https://www.linkedin.com/in/joel-keating-286a043/ ).
Music credits:
- The opening music is Like a Prism by Miyagisama .
- The closing song is Something About You by Marilyn Ford .
Thanks for listening. Please rate, subscribe, and share. Join the conversation in the Practical Leadership Cast Discord server: https://discord.gg/ewhPY6akRF
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In person, with somebody.
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My next question.
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What's your favorite interview question? And why?
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I wrap up every interview after we've gone through an hour together, talking about react talking about typescript, talking about Javascript, talking about projects.
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They've done in the past and times they haven't agreed with their manager, and then I just hit them with what is the proudest moment in your career.
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Totally open-ended question meant to bring us back to a human connection and also a chance to see what they value.
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Sometimes somebody will talk about a project where they had a difficult technical challenge that they had to deal with certain Api.
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They're working with a certain. Framework that doesn't do exactly what you needed to do.
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And they will discuss the brainstorming process and the problem solving process and how good it felt to finally reach a solution to that.
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Hmm!
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After hours or days, or weeks of work, or I have had people talk about projects that they built for hospitals, knowing that this application they wrote that on the surface didn't seem super impressive, was going to be saving the lives of children with cancer, even if it's just helping the receptionist make
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the appointment. It's contributing to a positive outcome for a sick child.
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I have seen people tell me about working. They have done, or the government's in terms of immigration, and people that they were bringing, you know, helping find a place in this country through the code that they wrote, and like I said, you get a good sense of what excites somebody about.
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Programming, a good sense of what motivated them in their previous role.
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And hopefully, you get sense of what they're gonna bring to the table when they're working for you as well.
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And I don't think there's a wrong answer other than you know.
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Sometimes people say I get a paycheck.
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Yeah.
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Which is still a valid answer. I've not going to disagree with that.
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But listen. We can take our labor anywhere if you have a job.
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Right.
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That's just a paycheck to you, I mean, that's perfectly valid. We live.
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In a capitalist economy, but I would hope that if you have a passion for what you do, our passion for helping people, that you find a role that makes you feel valued and welcome, and I hope you get to a point in your career where you have those kind of stories and you can rattle them off off the top of your head because
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they're continuing to inspire you every day.
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Awesome, Dana, what's the biggest lesson you've learned about leadership?
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This was a hard one for me as a leader. You are not judged by the work you do.
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Everyday you come in. You create documents, you schedule them meetings.
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You do this, that and the other thing you write Jira tickets, you write confluence stocks, you know.
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But you can have the most beautiful organized documentation but if it doesn't help a member of your team succeed, or someone outside your team succeed, it's not important.
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You can schedule all the meetings in the world, but they need to have a purpose and they need to help someone move forward.
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Otherwise you're just wasting your own time and the time of the other people you invited.
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You need to focus on the things that are gonna get people unblocked if they're struggling.
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That's gonna help them level up to be more productive members of the team.
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And you need to focus on things that are going to deliver results.
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And I had a matchager point out to me that once you're in a management or leadership role, it's not a 9 to 5 job anymore.
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Some days you may work 1 h, but if that 1 h moves the needle so much that your team is able to accomplish its goals.
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That's fine. Some days you may work the whole 24 h of the day.
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If there's something a disaster going on, and that's part of the job, too.
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And you are going to be judged by the output of your team.
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What they accomplished during that time, and what you were able to help them do, and how productive they can be.
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And that was really hard, because as a programmer, I was used to being judged by the all output of my work as an individual, the quality of the code I wrote the number of pull requests, I did number of bugs that were reported, and there's no such measurements when I go in for my performance
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review. Nobody is going to look at how many Jira tickets I created, how many new confluence stocks I created.
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They're going to look at. I had a product to ship to ship on time.
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I had a set of bugs to get through.
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How quickly were they at address!
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Hmm!
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Things, like app store ratings right. The overall impression we're making on our customers is very strongly implemented by the work that the team does every day.
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So if I can get stuff organized where they can just grab a ticket, work it, move to the next and get those bugs.
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Knocked out quickly and get our app store rating up.
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Then that is going to be a success for me personally, and the things I do on the day today don't necessarily reflect on me, and that would so hard for me.
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It really was.
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Yeah.
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What do you think? Got you over that hurdle?
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I would say it was working during the pandemic.
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And I'm sure a lot of us can relate to this.
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We found this in a situation where not only were we continuing to work, many of us, especially in the tech field, because we can work from home pretty easily if we have the equipment, but suddenly I had a 5 year old, I guess, 4 year olds, back then in under the same roof
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as May and my wife another adult doing her work, and you know I had to cook lunches, and I had to, you know.
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Make beds and all that stuff that I didn't necessarily have to do while I was working before, and the CEO of the team I was reporting to at the time said, You know to have everybody look, this is an unprecedented challenge for all of us.
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We know you're not going to be able to work a full 8 h a day.
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Yeah.
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So get that out of your head right away, and we are just going to do our best and you start realizing that a lot of the things that you filled your day with were almost busy work, and the show must go on right.
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You still need to deliver results. But you have less time to do it.
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You can eliminate a lot of the flop and just focus on what's gonna help people be productive.
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And especially when you're dealing with a challenge like a global pandemic.
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But any other team right? What's going to help people be productive?
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Yeah.
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Isn't always work related, either. It's giving them space to be full human beings to go to doctor appointments, to go to their kids, play to lay down when they're feeling sick, and yes, we have a certain bar of performance that people need to meet they need to show up to meetings to
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collaborate with other people, but we can be very flexible with them as well, and look at the output that they create.
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Who is your favorite leader to work for, and why?
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I would say Jeff gone for the former CEO of Grinder.
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And he was. This really was. He. Is this really friendly Guy?
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It was so amazing to hop on a meeting with the CEO and just have them be on the call.
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Genuinely caring about the people who report to him, and he remembered where people lived and what they had going on in their lives.
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He was always asking me about my cello or my kid, how the weather is in Boston, he remembered all that, and he built this rapport off with not just his direct reports, but everybody in the company we have about a 150 people.
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So it wasn't a huge company, right? He had lots of chances to meet people and talk to people, and once you have that report right?
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You know, this is a friendly person who? You know, cares about you as an individual, and supports you.
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It makes it much easier to have difficult conversations with somebody like that.
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Hmm!
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Whether it's you reporting less than optimal news, or if it's him having to, you know, give some tough feedback.
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Yeah.
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It's always easier when there's a history of not being a threatening figure in people's lives, and when you know, that's another human being there, I think so often people get wrapped up in their title and their position and forget that especially once you're at a level, like
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CEO. People don't really see you as a human being.
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They see you as your title. They see, as the person holds their job in their your job in their hands, and it's important to break down those barriers.
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It's important to humanize yourself to people. If you want honest feedback from them, and you want to be able to give them honest feedback and have it received, and to look this back to Jack, he was just wonderful from that standpoint.
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Everybody on the team respected him, and everybody on the team was willing to have frank discussions with them, and I thought it worked out.
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Wonderfully!
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So the inverse. Tell me about your least favorite leader, not who they are.
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But why weren't they a good match for you?
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I'm not going to name names, but earlier in my career I had a manager who, looking back, I really don't see him as much of a leader.
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We could tell. Every day he was under a ton of stress.
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He was in over his head as a manager, dealing with a very aging tech stack.
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Very modern demands from a real-time e-commerce website, and no budget for improvements.
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And he would yell at us over the tiniest things he exerted so much control over every process and everything interaction with our team and with other teams in the company and the thing I hated the most is he would walk into my cubicle and smack me in the back of the head
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as a way of saying how and hr told me. Oh, he's just being, you know, jocular.
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Yeah.
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It's nothing, you know. I didn't see it that way, and then I'd randomly find a new piece of computer hardware on my desk from them new video card new fans, something.
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And I realized later that that's very much like the behavior of an abusive partner.
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That's trying to make up for an interaction. And that is not how a leader should be behaving, and I certainly can relate to the stress he was under, and the demands being made of him by the Vice President.
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He reported to, but I think somebody who really embodies the concept of a leader should be taking better care of their team and having those difficult but frank discussions with their leadership to make sure they're aware of the challenges that they face and to guide them toward a an outcome that would reach the
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goal that they want to see, but with the resources that are available, and there's 3 variables, you can change when you're trying to to deliver our product or a project, you can change the deadline.
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You can always move that out. You can change the head, count, and you can change the scope, and when you present options to somebody in senior leadership, using those 3 basic you know points, I can hire 5 more engineers.
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We can deliver this 6 months late, or we can deliver 50%.
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Yeah.
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Now 50% later, it empowers them with the choice, and it makes them aware of the constraints you're under.
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And I think if he had been in a better place to have that kind of frank discussion, and if he.
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Okay, focused is frustration more on his senior leadership.
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And how he can affect change with them rather than passing on the frustration to the team.
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I think we would have been much more cohesive as a team and much more productive.
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Yeah.
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Yeah.
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But I realized, hindsight is 2020 and I'm looking at this as somebody who has 20 something.
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Years. Experience in the field and I don't know if he necessarily had even that much. You know.
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Experience under his belt at the time.
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Yeah.
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I'm gonna steal a page out of the believe.
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Okay.
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This is from an Hbr podcast so there's this concept of the the 10 question, the 10 rank question.
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And so the idea is, where do you rank yourself on a scale from one to 10 as as a leader and and better question is, What do you?
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What do you see as a 10 like what? What is a 10 liter, and like?
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What would you need to do to get from here to there?
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Oh, my goodness!
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This is an interesting one, because it almost reveals more about my ego, and how I see myself then, how I perform as a leader, and I think I would rank myself 7 or 8.
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I have one awards for my leadership, especially around high ranking.
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I receive constant praise from the people I report to, not to, you know.
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Struck by ego too much, but and my team, you know, has has given feedback to me.
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End to the Ctl that I'm a good leader.
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So it would be very easy for me to say, well, I'm definitely a 10, but there's always room to grow.
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Yeah.
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If I had to pick somebody who is a 10.
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This is my personal bias showing there is a leadership expert.
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I'm a big fan of Lee cockrow. Who is the former executive vice President of Walt Disney World resort, which meant, not only was he helping to run a theme park, but several hotels parking lots this that, and the other thing and he had how hundreds of thousands of people
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reporting to him, and when I hear him talk about the challenges he faced in keeping people motivated in keeping the unions happy and keeping the guests happy.
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I realize that managing a team of 7 people is certainly a challenge.
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Right.
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On the day today. But it's nothing on that scale, I think, for me to get to a place where I'm comfortable, calling myself.
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A 10, or even 9. I need that experience working with multiple tiers of managers and being in a situation where I'm not just the leader, you know, keeping a team motivated and working productively.
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I'm helping other people find that within themselves and get their own, their own direct reports, whether they're managers or individual contributors, or cast members, as they call them, at Disney.
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You know. How you motivate them, how you keep them engaged.
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How you communicate your values to them and get them to work aligned with your values.
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I think that's a much bigger challenge at scale, and when you're working in a role like that, especially for an organization like Walt Disney world, you're not just dealing with one little facet of the role right?
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I go in every day. I deal with programmers. I deal with web applications.
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It's pretty straightforward. He was dealing with janitorial staff construction cruise, housekeeping people working the gift shops all over the the park, you know.
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It's it's a very different set of challenges.
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Yeah.
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And so thank you for me to be comfortable, ranking myself any higher than that, I would need to see how I would perform under that kind of stress and that kind of challenge.
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And you said that you think you're 6 or 7.
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So like, let's say you're 7. What would you say?
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Got you from 6.5 to 7.
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Hmm!
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What got me from 6.5 to 7. Interestingly enough, was my gender transition.
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This is a very difficult thing for me to accept, but not surprising in the tech world.
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The, things that I used to get negative feedback on, as when I presented as a man, and when people accepted me as a man, things like empathizing with my team being very lax with time off requests and things like that, you know, focusing on the teams health and well-being
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giving people second chances when they screw up, using a pip as an opportunity to see somebody improve versus a way to fire them.
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Those are things. I got negative feedback on. When I was coming to work, as Dave Everyday, coming to work as Dana.
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Those are seen as superpowers, and I think the chance to put these principles into action of leading with empathy.
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Has kind of created a reinforcement. Look for me.
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It's given me opportunities to run my approach, to learn to add nuance to it.
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But I've come to realize by being able to lead with empathy and given space to do it and encouragement to do it, that being frank with people about their performance and their behavior at work is very much a form of empathy, and when you are so focused on 9 to 5 productivity measures
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tickets moving across the board. You know things like that.
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I think you lose sight of the humanity of the people working for you, and when my let's say my car isn't working right, I either fix it or take it to a mechanic who can fix it.
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And I think people tend to look at their direct reports like that.
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Hmm!
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They're not. They're people. And if you want to get results out of them, you have to take the time to do the work, to, not to fix them right, but to do the work and help them improve and work through whatever challenges they're facing.
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Thank you.
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Yeah. Sorry. That was a bit rambling.
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No, I love that.
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I've definitely gotten feedback from my children that I've improved as a parent since I transitioned I was a lot more angry.
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Which is, is different from what you were saying. But.
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But that's an experience I can really relate to.
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Yeah.
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I was grumpy. I was dealing with depression.
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I was not the best partner. Hi, Richard!
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Hmm!
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And yeah, almost every day. My kids, says, Mama, you are the best mom in the world, and that means a lot that I've been able to approach my work life and my home life with a whole new sense of piece and happiness, and the people around me have noticed and that is the most wonderful feeling
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and I know this isn't a gender podcast, or a Star
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Trek podcast but I hope people who are on the fence about, you know, pursuing a transition or exploring the gender possibilities available to them, take advantage of it.
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The journey was very valuable to me in getting to know myself and getting challenging how I define womanhood and challenging how I relate to the people around me.
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I would also say that before I went on hormone therapy, someone compared it to.
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When you get the new operating system on your phone and it re boots and everything just seems faster and better and smoother.
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I definitely had that experience as well. It just kinda changed how everything works.
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And again I found that piece. I found that happiness that helps me everyday.
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Yeah.
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There's!
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An old saying, I think that's from MIT, but I'm not sure that every computer program eventually gets so advanced that it has its own email program.
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Yeah.
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And so, perhaps, you know, every podcast eventually gets so advanced that it includes Gender and Star Trek.
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Yeah.
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I think that's really valuable, though. Again, if I can be frank, one of the reasons, I came on this podcast, and wanted to be part of it is because I listen to a lot of leadership podcasts and to be perfectly frank a lot of them are coming from older straight white men and
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they have very valuable insights, almost all of them.
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I'm not, you know, putting them down. But it is so important to have diverse voices in leadership not only to provide new viewpoints or people who are in leadership roles, but to prove to people from underrepresented groups that they can have a seat that table.
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I have had younger trans. Folks come to me, and almost treat me like royalty.
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Yeah.
00:44:20.130 --> 00:44:31.880
I'm 45 years old, whether it's somebody bringing my coffee at the cafe, or an intern or a new hire.
00:44:31.880 --> 00:44:39.900
There's almost this feeling of reference, and I talked to my therapist about that one day, and she said, Dana, I need you to realize you are everything they told you.
00:44:39.900 --> 00:44:41.290
They sorry Dana? I need you to realize you are everything they were told they could never be.
00:44:41.290 --> 00:44:50.620
Yeah.
00:44:50.620 --> 00:44:54.570
You've been married for 20 something years. You have a child, and you are in a senior leadership position on an upward trajectory.
00:44:54.570 --> 00:45:06.080
And now I can add, I own, a home.
00:45:06.080 --> 00:45:15.450
And it's important to be a role model. And I'm so glad that you're putting yourself out there like this and providing a new voice to people who need it.
00:45:15.450 --> 00:45:21.780
People of all walks of life, who maybe don't fit that mold of what we normally see from people in leadership positions.
00:45:21.780 --> 00:45:35.380
And it's important to have that forward and that representation representation really does matter.
00:45:35.380 --> 00:45:38.830
And I will be honest. I have listened to all the episodes you put out so far, and I've loved everyone of them because it is a different voice than I'm used to hearing coming from you know leadership.
00:45:38.830 --> 00:45:44.250
Podcasts, it's wonderful.
00:45:44.250 --> 00:45:52.930
Thank you. There's a podcast that I listen to, and I really love it.
00:45:52.930 --> 00:46:00.400
But it just at times makes my blood boil, because he was the the.
00:46:00.400 --> 00:46:01.950
Host was interviewing women's soccer Champion.
00:46:01.950 --> 00:46:06.060
Hmm!
00:46:06.060 --> 00:46:12.690
So she led the US Women's team to victory.
00:46:12.690 --> 00:46:12.870
2 or 3 times
00:46:12.870 --> 00:46:15.130
Meghan Rapina?
00:46:37.000 --> 00:46:38.190
Abby, Wombach.
00:46:38.190 --> 00:46:51.830
Okay.
00:46:51.830 --> 00:46:56.300
So Abby was being interviewed by, and she's very used to being on podcast because she's on a podcast with her wife and their sister. We can do hard things.
00:46:56.300 --> 00:47:17.230
It's a wonderful podcast. I think, but so she's she's being interviewed by this guy.
00:47:17.230 --> 00:47:30.040
And he's a leadership expert. And and she goes into all of this stuff about how hard it is to be in women's sports and like, how do you retire when you've you've come from women's sports and you get so much less money and he seemed to respect that and take that all
00:47:30.040 --> 00:47:38.220
in. But then he started talking about like asking questions about men's sports and about male athletes and I'm just like, did you hear anything?
00:47:38.220 --> 00:47:43.390
And she responded very politely, and she answered the questions, but like it just wanted me to.
00:47:43.390 --> 00:47:49.180
Made me wanna like go through the speakers and like slap some sense into him.
00:47:49.180 --> 00:47:51.360
Oh, absolutely!
00:47:57.960 --> 00:48:00.760
But absolutely. And yeah, there's this stereotype that Podcasters are always straight.
00:48:00.760 --> 00:48:00.900
White men. I don't know how accurate that is.
00:48:00.900 --> 00:48:03.910
Yeah.
00:48:03.910 --> 00:48:12.180
Yeah.
00:48:12.180 --> 00:48:16.880
These days. But yeah, we definitely need to seek out and encourage people to provide their own experiences and their own view on things.
00:48:16.880 --> 00:48:24.830
It's one reason I love Tiktok so much because it makes content.
00:48:24.830 --> 00:48:26.350
Creation as easy and as universal, as just opening an app on your phone and hitting record.
00:48:26.350 --> 00:48:29.320
Yeah.
00:48:29.320 --> 00:48:33.500
And there's something beautiful about that, and it doesn't need to be polished.
00:48:33.500 --> 00:48:35.100
Yeah.
00:48:35.100 --> 00:48:40.430
It doesn't need to be perfect. We need those voices.
00:48:40.430 --> 00:48:40.520
So, we're running a little low on time. I wanna know.
00:48:40.520 --> 00:48:42.520
Hmm!
00:48:42.520 --> 00:48:49.300
Is there anything you wanna plug?
00:48:49.300 --> 00:48:51.490
Okay.
00:48:51.490 --> 00:49:00.660
I would just like to plug Grinder itself for anybody looking for a new role.
00:49:00.660 --> 00:49:03.940
I don't have any personal projects that are close to fruition and the stuff I'm doing at work is kind of hush!
00:49:03.940 --> 00:49:12.740
Oh!
00:49:12.740 --> 00:49:18.840
Hush! Right now. But yeah, I know. Well, keep. Keep your eyes peeled for the next couple of months, but definitely Grinder is an amazing place to work.
00:49:18.840 --> 00:49:27.300
One of our company values is to be authentically quite, and we take that to heart.
00:49:27.300 --> 00:49:31.200
We are a sex-positive workplace without being a abusive harassment.
00:49:31.200 --> 00:49:43.800
Yeah.
00:49:43.800 --> 00:49:44.950
Film Workspace, and the way I like to describe it is, you know, we can have discussions about sexual things because sexual things go on using our app a lot of times.
00:49:44.950 --> 00:49:51.200
Right, right.
00:49:51.200 --> 00:50:03.900
Yeah.
00:50:03.900 --> 00:50:08.110
Yeah.
00:50:08.110 --> 00:50:12.900
But we don't direct any of that toward the people we work with, and I think there's a strong sense in maturity that the people who work here, and an understanding that we all have to come to work every day, and why make it a poor experience for anybody and we definitely build each other up we
00:50:12.900 --> 00:50:20.130
keep strong connections to the community. We keep strong connections to each other.
00:50:20.130 --> 00:50:28.400
Hmm!
00:50:28.400 --> 00:50:43.250
We have a amazing benefits, especially for trans folks. We provide money towards social transition for medication toward laser hair removal toward even search.
00:50:43.250 --> 00:51:02.640
It is a wonderfully inclusive environment in that respect, and we like to think we're raising the bar so that anytime somebody comes to us and does their work and becomes part of our corporate culture.
00:51:02.640 --> 00:51:06.380
And then, for one reason or another, leaves that they are going to expect that degree of respect, and that degree of encouragement, and that kind of reward for their work from every employer that they interact with for the rest of their career.
00:51:06.380 --> 00:51:18.900
And we are kicking off our internship program very soon.
00:51:18.900 --> 00:51:33.120
I have a meeting about it next week, and I love bringing interns in, so keep an eye on for our internship job listings. Anybody listening.
00:51:33.120 --> 00:51:43.140
Yeah.
00:51:43.140 --> 00:52:04.590
If you're interested, because again, I love ruining people at the beginning of their career, and setting this expectation of what their next role should be, and hopefully they will go out there and become the next generation of leaders and carry through with that kind of expectation for the teams that they lead that they will lead with
00:52:04.590 --> 00:52:13.850
empathy that they will value results over paperwork, that they will be authentic to whoever they are, no matter what walk of life they're from, and not constrain themselves to this narrow view of professionalism, that they will be fair to each other, all of that and that they will reward people, well.
00:52:13.850 --> 00:52:16.300
for the work that they do. And I, I definitely think it's a wonderful place to come to work everyday.
00:52:16.300 --> 00:52:25.140
I work with amazing people. Check out grinder.com slash careers.
00:52:25.140 --> 00:52:29.430
You can see information about the benefits we offer. The awards we've won, and the kind of things people are saying about working here.
00:52:29.430 --> 00:52:32.400
It's just phenomenal, and we're always hiring.
00:52:32.400 --> 00:52:35.400
So there's opportunities out there.
00:52:35.400 --> 00:52:36.630
And I'll include a link in the show notes.
00:52:36.630 --> 00:52:43.590
Please, please, do.
00:52:43.590 --> 00:52:50.160
Last question, who is one person I should absolutely interview?
00:52:50.160 --> 00:52:56.350
The Vice President. I reported to up until recently Mega Bombra.
00:52:56.350 --> 00:53:03.200
She left Grinder to pursue a a new opportunity.
00:53:03.200 --> 00:53:11.100
But she is phenomenal, and her and I clicked right away she's also a mother.
00:53:11.100 --> 00:53:16.400
She's been intact for forever. She still loves to roll up her sleeves and write code.
00:53:16.400 --> 00:53:40.700
And she very strongly believes in hiring the right people.
00:53:40.700 --> 00:53:45.650
Having fair hiring processes, and treating the people who work for you with empathy and encouragement, and just being a good person and a good leader, and we both have seen how well that pays off, and I think she would be a great person to bring in to provide her own experiences and stories, from her you
00:53:45.650 --> 00:53:51.900
know previous roles working with and founding Startup.
00:53:51.900 --> 00:53:54.250
I think she's just a wonderful person to talk to, and I miss her every single day.
00:53:54.250 --> 00:54:00.040
Hmm!
00:54:00.040 --> 00:54:03.780
Not that my current, you know. I currently report reports to Joel Keith Joel, if you're listening, Joel is amazing.
00:54:03.780 --> 00:54:07.630
Joel would be another person to bring on and talk to.
00:54:07.630 --> 00:54:11.300
Yeah, I really think Mega would be a great.
00:54:11.300 --> 00:54:14.340
Yeah.
00:54:14.340 --> 00:54:19.060
And again another woman voice which is very important in the leadership space.
00:54:19.060 --> 00:54:21.380
Awesome. Thank you so much, Dana. It's been great talking to you today.
00:54:21.380 --> 00:54:23.180
Yeah, and it has been wonderful to talk to you.
00:54:23.180 --> 00:54:25.400
Okay. Take care.
00:54:25.400 --> 00:54:26.400
You, too, have good one.