{"id":1495,"date":"2019-01-25T23:31:36","date_gmt":"2019-01-25T23:31:36","guid":{"rendered":"https:\/\/knowyourteam.com\/blog\/?post_type=podcast&#038;p=1495"},"modified":"2025-04-21T15:11:36","modified_gmt":"2025-04-21T22:11:36","slug":"episode-17-interview-with-elena-valentine-ceo-of-skill-scout","status":"publish","type":"podcast","link":"https:\/\/canopy.is\/blog\/podcast\/episode-17-interview-with-elena-valentine-ceo-of-skill-scout\/","title":{"rendered":"Episode 17: Interview with Elena Valentine, CEO of Skill Scout"},"content":{"rendered":"\n<figure class=\"wp-block-embed is-type-video is-provider-youtube wp-block-embed-youtube wp-embed-aspect-16-9 wp-has-aspect-ratio\"><div class=\"wp-block-embed__wrapper\">\n<iframe width=\"1400\" height=\"788\" src=\"https:\/\/www.youtube.com\/embed\/815AhdTXqho?feature=oembed\" frameborder=\"0\" allow=\"accelerometer; autoplay; encrypted-media; gyroscope; picture-in-picture\" allowfullscreen><\/iframe>\n<\/div><\/figure>\n\n\n\n<h4 class=\"wp-block-heading\" id=\"h-with-a-focus-on-diversity-and-inclusion-the-ceo-of-a-chicago-based-media-company-focused-keeps-it-real-about-the-myths-and-struggles-of-leadership\">With a focus on diversity and inclusion, the CEO of a Chicago-based media company focused keeps it real about the myths and struggles of leadership.<\/h4>\n\n\n\n<hr class=\"wp-block-separator has-css-opacity is-style-wide\"\/>\n\n\n\n<p><strong>Claire<\/strong>: Hi everyone, I\u2019m\u00a0<a href=\"http:\/\/twitter.com\/cjlew23\" target=\"_blank\" rel=\"noreferrer noopener\">Claire Lew<\/a>\u00a0and I\u2019m the CEO of <a href=\"https:\/\/canopy.is\/?utm_source=blog&amp;utm_medium=post&amp;utm_campaign=heartbeat-podcast\">Canopy<\/a> (formerly Know Your Team\/Know Your Company)\u00a0and it is my honor today to introduce a very good friend of mine who is on the heartbeat, the one and only\u00a0<a href=\"https:\/\/twitter.com\/elena_valentine\" target=\"_blank\" rel=\"noreferrer noopener\">Elena Valentine<\/a>. She is the CEO and founder of\u00a0<a href=\"https:\/\/www.skillscout.com\/\" target=\"_blank\" rel=\"noreferrer noopener\">Skill Scout<\/a>, and she\u2019s actually based here in Chicago but we couldn\u2019t get together in person unfortunately, but her company is amazing if you don\u2019t already know about it. They\u2019re on a mission to bring storytelling into the workplace and have just worked with some amazing brands and companies as this media company to help folks better recruit for the jobs that they have.<\/p>\n\n\n\n<p>And so, the other reason for why I love Elena other than just being this badass CEO is that she is incredibly intentional about creating a more diverse and inclusive workforce, first and foremost starting with Skill Scout. They have primarily hired women and people of color and the way she looks at it is, if you care about diversity you\u2019ve got to walk the walk and so her company in many ways is a shining example of that.<\/p>\n\n\n\n<p>Just so excited to have you here today Elena.<\/p>\n\n\n\n<p><strong>Elena<\/strong>: Yes woo hoo!<\/p>\n\n\n\n<figure class=\"wp-block-image\"><img decoding=\"async\" src=\"https:\/\/blog.knowyourteam.com\/wp-content\/uploads\/2018\/12\/8be77-1b3oiihzjvpbtc8kvn-scdg.png\" alt=\"\"\/><\/figure>\n\n\n\n<p><strong>Claire<\/strong>: So Elena as you may know, I\u2019ve been asking this one question to all sorts of leaders over the past few months, and it is&nbsp;\u2026 You ready? It is: What\u2019s something you wish you would have learned earlier as a leader? It can also be more than one thing, if you want.<\/p>\n\n\n\n<p><strong>Elena<\/strong>: Yeah this is hilarious but literally I have been thinking about this, it\u2019s your receivables.<\/p>\n\n\n\n<p><strong>Claire<\/strong>: Oh.<\/p>\n\n\n\n<p><strong>Elena<\/strong>: You don\u2019t realize that when it comes to your cash flow, you have to keep really good track of your receivables to make sure you don\u2019t lose money. So that was certainly a big thing and one that we constantly go through even now to make sure that we can continue to do what we do, which I think, then gets me to the other one, which is the not so glamorous side of being an entrepreneur and leader.<\/p>\n\n\n\n<blockquote class=\"wp-block-quote is-layout-flow wp-block-quote-is-layout-flow\">\n<p>That it\u2019s about staying alive like a cockroach. And that\u2019s not glamorous and sexy whatsoever. But I think it\u2019s really all about, especially in the beginning, it\u2019s being able to survive another day and doing whatever, by any means possible to make that happen and sometimes that means that your business plans look really messy and it doesn\u2019t necessarily fit with the original intention.<\/p>\n<\/blockquote>\n\n\n\n<p>And it\u2019s being okay with the fact that things will not go as planned and that, at the end of the day, it\u2019s about continuing to move forward to survive, to build your business.<\/p>\n\n\n\n<p><strong>Claire<\/strong>: This is why I love you Elena. Keeping it real because I think there is this grand illusion around running your own company that oh, it\u2019s growth, you\u2019re killing it and I\u2019m not saying that you\u2019re not but you\u2019re bringing us back down to reality of building a business though is in many ways just about making it to the next day. It\u2019s about making sure you are making more money than you spend. It is about making sure you have enough receivables and in some mythology that we\u2019ve created, whether it\u2019s the media, whether it\u2019s all these ridiculous articles and books that we read around entrepreneurship or leadership, that gets lost.<\/p>\n\n\n\n<p><strong>Claire<\/strong>: Do you feel like before you became an entrepreneur and before you started your own company, you had bought into myth or did you know going into this journey as a leader that, all right, this is about surviving, this is gonna be part of the struggle? Were you aware?<\/p>\n\n\n\n<figure class=\"wp-block-image\"><img decoding=\"async\" src=\"https:\/\/blog.knowyourteam.com\/wp-content\/uploads\/2018\/12\/03157-1ryi9jvwf56r6j37nj-xapg.png\" alt=\"\"\/><\/figure>\n\n\n\n<p><strong>Elena<\/strong>: Yes and no. I\u2019ll be honest. And this is so hilarious and na\u00efve of me to think this way but when I got into this, I kinda came in thinking that there was only one way to build a business and that was to raise a lot of money and grow it to a point that you sow or you IPO, which is so stupid and na\u00efve to think considering that the majority of businesses in the world are boot strapped.<\/p>\n\n\n\n<p><strong>Claire<\/strong>: Yep.<\/p>\n\n\n\n<p><strong>Elena<\/strong>: And are small businesses.<\/p>\n\n\n\n<p><strong>Claire<\/strong>: Yep.<\/p>\n\n\n\n<p><strong>Elena<\/strong>: And are privately owned. But I think that was probably the most na\u00efve thing was I only really saw, kind of, one facet to building a business. I think for a long time I compared and contrasted what I saw out there to what our experience should be.<\/p>\n\n\n\n<blockquote class=\"wp-block-quote is-layout-flow wp-block-quote-is-layout-flow\">\n<p>It took a really long time to realize that I was comparing myself to elephants when I was really a giraffe and I needed to find other dope giraffes. And that took me probably up until the end of last year to really follow my true north and see that I\u2019m a giraffe, I\u2019m proud to be a giraffe and there are businesses that are incredible, that are run by giraffes.<\/p>\n<\/blockquote>\n\n\n\n<p><strong>Claire<\/strong>: Absolutely. There are so many dope giraffes and I love that you\u2019ve embraced the fact that you are a giraffe but here\u2019s the thing Elena, I really want to dig into this because I think you have hit on something that so many leaders struggle with, which is our desire to fulfill some sort of story arc that sometimes isn\u2019t even our own. Like you said, you used to only see one potential path to being a successful leader and running a successful business. And I think as leaders, we often think, oh yeah, there is only one type of successful leader and it looks like Steve Jobs or it looks like Elon Musk, or whoever that person in our minds is.<\/p>\n\n\n\n<p><strong>Claire<\/strong>: For you, speaking to other managers and leaders and CEO\u2019s who are watching this, what would you recommend to leaders who struggle with trying to fulfill that story or sort of please other people in that way? What\u2019s your advice? How have you copped with it? Especially at the end of last year like you said, you sort of came into your own on this..<\/p>\n\n\n\n<p><strong>Elena<\/strong>: It\u2019s not gonna make your payroll in two weeks.<\/p>\n\n\n\n<p><strong>Claire<\/strong>: Yeah.<\/p>\n\n\n\n<p><strong>Elena<\/strong>: Yeah. Honestly. It\u2019s not gonna make your payroll in two weeks. And I think that\u2019s what ended up coming down to it was I have to follow the path and I have to find leaders, kind of, building a similar business or type of business, really again, focused on kind of making it to that next month, those next two years. I think inevitably I am here to build a business to last, not to sell and once I realized and kind of knew that, that was my true north, it was circumventing everything else. Then I knew that there was a different story and that there were different leaders that I could aspire to be who were thriving, who were extremely successful in doing that.<\/p>\n\n\n\n<p><strong>Claire<\/strong>: Absolutely. Man, I\u2019m taking it all in because it\u2019s really refreshing to hear that clarity. I think a lot of leaders, myself included, have always wrestled with what is my true north?<\/p>\n\n\n\n<p>For example, especially when it comes to leadership style\u2026 You read that maybe leaders should be decisive and that leaders should be strong and have all the answers, but if that\u2019s not sort of your style, then how do you know what your true north is? Or here\u2019s the other thing, I work with some CEO\u2019s Elena and they go, \u201cClaire I\u2019ve been reading about all this stuff about being open hearted and listening and really emotionally in touch. I\u2019m just not really like that though as a leader. Do I change my personality?\u201d<\/p>\n\n\n\n<p>So talk to me about how do you find your true north and what advice might you have for leaders who are trying to do that? Should a leader sort of conform to what the books are saying, what they\u2019ve been reading and&nbsp;\u2026 I mean, how did you find that truth north for yourself? And your own sort of leadership style?<\/p>\n\n\n\n<p><strong>Elena<\/strong>: Yeah. So truth is, there\u2019s no one right way to be a leader, that\u2019s why there\u2019s thousands of books on it. And thousands of Bren\u00e9 Browns and Simon Sineks of the world, because there\u2019s not one right way to do it. I mean, I think that\u2019s the uniqueness of the human experience is that it\u2019s extremely multi-faceted. So that\u2019s one thing I would say. Now certainly there are narratives that are more popular than others&nbsp;.<\/p>\n\n\n\n<blockquote class=\"wp-block-quote is-layout-flow wp-block-quote-is-layout-flow\">\n<p>But I think when it\u2019s about finding your own true north as a leader, it\u2019s the idea that you are continuously learning and exposing yourself to all different kinds of styles. Even if you inherently know that, that\u2019s not the right one for you, to the very least know that it\u00a0exists.<\/p>\n<\/blockquote>\n\n\n\n<p>Because part of my business is service and building relationships, which means that on the other side of the table, if that\u2019s a client, if that\u2019s a potential employee, I\u2019m dealing with that specific kind of personality.<\/p>\n\n\n\n<p>And I in turn have to understand how I adjust and how I can elevate that relationship regardless if it\u2019s not exactly like my own, so that\u2019s one. But I will say I was very lucky, and I\u2019m sure in many ways like yourself, we\u2019ve all had our mentors and the kind of leaders that we aspire to be and I was super lucky to be professionally raised in the kind of innovation design, design thinking space. So my professional parents are Chris and Cira Conley who are the founders of&nbsp;<a href=\"https:\/\/www.linkedin.com\/company\/gravitytank\/\" target=\"_blank\" rel=\"noreferrer noopener\">gravitytank<\/a>&nbsp;now Salesforce, and they were kind of a main stay innovation design firm here in the city and that\u2019s the main exposure that Abby and I had of leaders, which were leaders who ate last, leaders who were empathetic first. And leaders who saw their biggest role as being servants to their organization and to the people who they worked with.<\/p>\n\n\n\n<figure class=\"wp-block-image\"><img decoding=\"async\" src=\"https:\/\/blog.knowyourteam.com\/wp-content\/uploads\/2018\/12\/33122-1kceljprokp9xzoc7eipd0w.png\" alt=\"\"\/><\/figure>\n\n\n\n<p>And so, as a result of that, I was working there and having these visions of the kind of leader I wanted to be. I wanted to be the female version of Chris Conley. And the way that he had taken me under his wing and allowed me to grow and allowed me thrive. It wasn\u2019t a lot of dictation, it was a lot of how would you solve this problem Elena? And giving me the space to fail, and to also present new ways to actually do it. There is a gift to being able to identify strengths of someone and helping them to leverage that.<\/p>\n\n\n\n<p>The other thing I really learned from him inherently as a result, again of being a design researcher, being someone who\u2019s always trying to put themselves in someone else\u2019s shoes, was always that, if someone fails, if one of my colleagues fails, if I failed under Chris Conley, the question always was, what did I do as a leader that set you up for failure? And what can I do as a leader to set you up for success? What barriers do I have to remove for you? What kind of structures of guidance do I need to put in place to make you successful?<\/p>\n\n\n\n<p>And when you do that, when you realize that, you start to open yourself up to actually having a true feedback conversation. So it doesn\u2019t just become around, hey Abby, Nicole, Colette, this is what you did wrong. It\u2019s to say, so I\u2019ve been able to reflect on this, and here\u2019s what I know I did wrong. Here\u2019s my CEO failure bow, of why I know this didn\u2019t look how it should have. And here\u2019s what I\u2019m going do to improve that. And so I open up all of those conversations when it comes to success and failures, of also making sure that I\u2019m opening myself up to reflect on what I could have done better, but also making comfortable for them to let me know what I could have been working on, in addition to their own reflections of what could have gone better in terms of them being able to bring something to the table.<\/p>\n\n\n\n<p><strong>Claire<\/strong>: Absolutely. No, I think you\u2019ve touched so much that\u2019s helpful for folks in terms of making sure&nbsp;\u2026 I love what you were saying first of all, of the awareness piece, right. Being aware of how you\u2019re coming across, right? Even it\u2019s not necessarily your style but what effect does that have on the client or the employee you\u2019re working with? I love your mention of mentors and how much that shapes where you draw inspiration from. I think all of us, hopefully, haven\u2019t just had the bad boss experience where we\u2019re like, \u201cOkay we don\u2019t wanna be that.\u201d Hopefully many of us have had the good leader experience and gotten to work with someone who we really admired, I know that\u2019s shaped some of my views as well. And then this last idea of wanting that feedback and being very open and saying, \u201cOkay, here\u2019s where I messed up. Here\u2019s where I just fell flat on my face. Tell me how I can be better,\u201d and how in those ways that can help shape your true north, your personal style of leadership, those three different pieces.<\/p>\n\n\n\n<p>That\u2019s brilliant Elena. I guess for new leaders and managers, we have a lot of folks who watch this who are newly promoted or a leader of a team for the very first time. What would you recommend for them to internalize&nbsp;\u2026 I mean, going back to the very first thing you talked about of surviving another day, what would you tell them to sort of internalize that ethos? Or is there anything more tactically or on a day to day basis for them to not get overwhelmed also by the process of feeling like leadership is&nbsp;\u2026 Yeah, it can be a grind and it can feel like you\u2019re just trying to survive and just get to the next day.<\/p>\n\n\n\n<p><strong>Elena<\/strong>: I mean, I think it\u2019s a reframe. I mean, obviously not everyday should feel like survival.<\/p>\n\n\n\n<p><strong>Claire<\/strong>: Yeah.<\/p>\n\n\n\n<figure class=\"wp-block-image\"><img decoding=\"async\" src=\"https:\/\/blog.knowyourteam.com\/wp-content\/uploads\/2018\/12\/ef598-1jyp2sdcdml_opkodl7oufg.png\" alt=\"\"\/><\/figure>\n\n\n\n<p><strong>Elena<\/strong>: But I will kind of harken back to another one of my great professional uncles, who we both mutually know, Josh Braun and whether it be a sale or whether it be leveraging your own team, your role as a manager or sales in general, is what can I do to help make you more awesome? And that could be about removing barriers, that could be about putting processes in place but I think that there\u2019s something really poignant about reframing to understand it on a personal level, be it for an external facing problem or an internal problem, what is it as a manger that I could do to help make you more awesome? So that I would say, is kind of&nbsp;\u2026 It\u2019s more of a key question and it\u2019s seeing that as a manager these are people and you have to look at them holistically and sometimes it isn\u2019t just a work tactical problem.<\/p>\n\n\n\n<blockquote class=\"wp-block-quote is-layout-flow wp-block-quote-is-layout-flow\">\n<p>There\u2019s something deeper than that and so I think part of it is not being afraid to go there because I think some of the best leaders who can go there can help to understand what are some of other just general and inherent motivations of that employee, to help support them or to know that they can feel comfortable saying, \u201cHey this is my kind of personal problem that I\u2019m\u00a0facing.\u201d<\/p>\n<\/blockquote>\n\n\n\n<p>And even to have that kind of cathartic experience with that hopefully, and knowing that you\u2019re listening, can dramatically help shift their work day that day, or what they\u2019re looking to accomplish. So I think that definitely reframing the how can I make you more awesome? Thinking about it more holistically. And a very simple question that I\u2019m always asking is, what can I do to make you successful in X?<\/p>\n\n\n\n<p>Can I be doing anything better? And it may not necessarily be personal, it literally will be&nbsp;\u2026 They\u2019ll just tell you, yes I\u2019d like to be able to carve from 11 to 11:30 every day to do this. And so, asking that simple question gets you very far.<\/p>\n\n\n\n<p><strong>Claire<\/strong>: That\u2019s amazing Elena, thank you so much. I\u2019m sure folks watching this are writing that question down, keeping it in mind. And in general, thank you so much for sharing all your wisdom on the things you wish you would have learned, on the things that have been helpful to you. This has been so fun.<\/p>\n\n\n\n<p><strong>Elena<\/strong>: Yes! Thank you Miss Claire Lew.<\/p>\n\n\n\n<p><strong>Claire<\/strong>: All right. See ya, thanks Elena.<\/p>\n\n\n\n<figure class=\"wp-block-image size-full\"><a href=\"http:\/\/knowyourteam.com\/?utm_source=blog&amp;utm_medium=banner&amp;utm_content=footer\"><img decoding=\"async\" width=\"2516\" height=\"944\" src=\"https:\/\/knowyourteam.com\/blog\/wp-content\/uploads\/2023\/02\/CleanShot-2023-02-09-at-19.36.32@2x.png\" alt=\"\" class=\"wp-image-7971\"\/><\/a><\/figure>\n\n\n\n<div class=\"newsletter-post-form-container\">\n  <h3>Never miss a post \u2013&nbsp;get our latest leadership insights, as they&#8217;re released&#8230;<\/h3>\n\n<iframe src=\"https:\/\/newsletter.canopy.is\/embed\" width=\"850\" height=\"150\" style=\"border:1px solid #EEE; background:white;\" frameborder=\"0\" scrolling=\"no\"><\/iframe>\n<\/div>\n<br\/>\n\n\n\n<p><\/p>\n","protected":false},"excerpt":{"rendered":"<p>With a focus on diversity and inclusion, the CEO of a Chicago-based media company focused keeps it real about the myths and struggles of leadership. Claire: Hi everyone, I\u2019m\u00a0Claire Lew\u00a0and I\u2019m the CEO of Canopy (formerly Know Your Team\/Know Your Company)\u00a0and it is my honor today to introduce a very good friend of mine who&hellip; <\/p>\n<p><a class=\"moretag\" href=\"https:\/\/canopy.is\/blog\/podcast\/episode-17-interview-with-elena-valentine-ceo-of-skill-scout\/\">Read the full article<\/a><\/p>\n","protected":false},"author":2,"featured_media":377,"menu_order":0,"comment_status":"open","ping_status":"closed","template":"","meta":{"episode_type":"audio","audio_file":"https:\/\/chtbl.com\/track\/D44D5\/https:\/\/knowyourteam.com\/blog\/wp-content\/uploads\/2019\/01\/KYT017.mp3","cover_image":"","cover_image_id":"","duration":"18:20","filesize":"16.78M","date_recorded":"28-03-2018","explicit":"","block":"","itunes_episode_number":"17","itunes_title":"Interview with Elena Valentine, CEO of Skill Scout","itunes_season_number":"","itunes_episode_type":"full","filesize_raw":"17596498"},"tags":[],"series":[3529],"episode_featured_image":"https:\/\/canopy.is\/blog\/wp-content\/uploads\/2018\/12\/8be77-1b3oiihzjvpbtc8kvn-scdg.png","episode_player_image":"https:\/\/canopy.is\/blog\/wp-content\/plugins\/seriously-simple-podcasting\/assets\/images\/no-album-art.png","download_link":"https:\/\/canopy.is\/blog\/podcast-download\/1495\/episode-17-interview-with-elena-valentine-ceo-of-skill-scout.mp3","player_link":"https:\/\/canopy.is\/blog\/podcast-player\/1495\/episode-17-interview-with-elena-valentine-ceo-of-skill-scout.mp3","audio_player":"<!--[if lt IE 9]><script>document.createElement('audio');<\/script><![endif]-->\n<audio class=\"wp-audio-shortcode\" id=\"audio-1495-1\" preload=\"none\" style=\"width: 100%;\" controls=\"controls\"><source type=\"audio\/mpeg\" src=\"https:\/\/canopy.is\/blog\/podcast-player\/1495\/episode-17-interview-with-elena-valentine-ceo-of-skill-scout.mp3?_=1\" \/><a href=\"https:\/\/canopy.is\/blog\/podcast-player\/1495\/episode-17-interview-with-elena-valentine-ceo-of-skill-scout.mp3\">https:\/\/canopy.is\/blog\/podcast-player\/1495\/episode-17-interview-with-elena-valentine-ceo-of-skill-scout.mp3<\/a><\/audio>","episode_data":{"playerMode":"dark","subscribeUrls":[],"rssFeedUrl":"https:\/\/canopy.is\/blog\/feed\/podcast\/the-heartbeat","embedCode":"<blockquote class=\"wp-embedded-content\" data-secret=\"Smcl154xUl\"><a href=\"https:\/\/canopy.is\/blog\/podcast\/episode-17-interview-with-elena-valentine-ceo-of-skill-scout\/\">Episode 17: Interview with Elena Valentine, CEO of Skill Scout<\/a><\/blockquote><iframe sandbox=\"allow-scripts\" security=\"restricted\" src=\"https:\/\/canopy.is\/blog\/podcast\/episode-17-interview-with-elena-valentine-ceo-of-skill-scout\/embed\/#?secret=Smcl154xUl\" width=\"500\" height=\"350\" title=\"&#8220;Episode 17: Interview with Elena Valentine, CEO of Skill Scout&#8221; &#8212; Canopy | Blog\" data-secret=\"Smcl154xUl\" frameborder=\"0\" marginwidth=\"0\" marginheight=\"0\" scrolling=\"no\" class=\"wp-embedded-content\"><\/iframe><script type=\"text\/javascript\">\n\/* <![CDATA[ *\/\n\/*! 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