Latest / The Failure Gap / A Conversation With Linda Aiello, Chief People Officer, DraftKings

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A Conversation With Linda Aiello, Chief People Officer, DraftKings · The Failure Gap

• 0:00
  Welcome to the Failure Gap, the podcast where leaders get real about what it takes to move from agreement to alignment and turn strategy into action.
• 0:09
  I'm Julie Williamson, CEO of Kerakin's Group and author of the best-selling book Make How Matter.
• 0:16
  I started this podcast because I've seen the same pattern in boardrooms, leadership teams, and organizations of every size.
• 0:24
  Smart people agree on the strategy, the priorities, and the goals, but progress still stalls.
• 0:30
  The space between knowing what to do and aligning your team around how to do it together is what I call the failure gap.
• 0:38
  At Carrickens Group, our work is focused on helping leaders close the failure gap by making how matter.
• 0:46
  So alignment becomes more than agreement in the room.
• 0:49
  It becomes shared action across the organization.
• 0:53
  In each episode, I sit down with leaders from all sorts of organizations.
• 0:58
  To talk about the real stories behind transformation, the tough lessons, the hard decisions, and the breakthroughs that help them to move forward.
• 1:07
  Thank you for joining me today.
• 1:09
  Now let's close the failure gap.
• 1:11
  We talk with leaders about closing the space between agreement and alignment.
• 1:16
  We love talking with interesting people, and today we're joined by Linda Aiello.
• 1:20
  She's the Chief People Officer at DraftKings with a strong background in people and culture that spans high fashion, technology,
• 1:27
  and e commerce.
• 1:28
  Linda, welcome to the Failure Gap.
• 1:31
  Thank you so much.
• 1:31
  Thank you for having me here.
• 1:32
  I'm really excited to chat with you today.
• 1:35
  I think it's gonna be a great conversation.
• 1:37
  And I'd love to start it, Linda, by you just giving our listeners a bit about your background and your journey to leadership.
• 1:43
  How did you come to be the chief people officer at DraftKings?
• 1:46
  Sure.
• 1:48
  A long and winding road as it may have been.
• 1:51
  For for those who think that your undergraduate degree defines your entire career, I assure you that it does not, although it can help you along the way.
• 2:01
  My undergraduate degree was in musical theater and vocal performance.
• 2:05
  Okay.
• 2:05
  So I did not start out as an HR practitioner.
• 2:09
  I did not start out
• 2:11
  in business, although I will say that the skills that I gained from that chapter of my life have served me very well and will definitely serve me in this next iteration of work
• 2:19
  in this in this world where technology and people come together even more.
• 2:25
  But as you said, I spent a tremendous amount of time both in fashion, luxury goods, e-commerce, technology.
• 2:32
  And for me it was really interesting to have a career that went through several different industries.
• 2:39
  I think through that I was able to really gain a point of view and a different style and understanding different styles, different cultures.
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  and I started really more out on the fashion side and somewhat accidentally ended up in technology.
• 2:55
  And it's you you you never know what the moment is that will have you be seen somewhere to bring you into the next place.
• 3:02
  So, you know, when I was working for LVMH in Europe,
• 3:06
  I had an opportunity to interview with Uber, which was still in startup phase at the time.
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  And someone had heard about something that I was talking about during a case study in an executive development program.
• 3:17
  And was talking about dynamic pricing and how people could consider that in other in other industries.
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  And that was sort of my first foray into tech, which was a completely different world for me and absolutely fascinating.
• 3:30
  And it's sort of catapulted my career for sure.
• 3:34
  And you know, I I stayed sort of true to my fashion, my tech, with a little combination of the two in there.
• 3:41
  and when I had an opportunity to ha to talk to DraftKings, I was absolutely fascinated by this.
• 3:48
  First of all, it's it's legacy for me.
• 3:51
  my father worked in sports television and really created the future of what sports television was from sort of the late 70s until sort of 2010.
• 4:02
  And I had a chance to be part of that next chapter in what sports entertainment is, or more broadly, entertainment.
• 4:09
  And I I couldn't I couldn't help myself but to dive in here.
• 4:13
  And it's very interesting in terms of how different parts of my background take this through.
• 4:18
  But another important part of my journey was I spent about 10 years living and working abroad.
• 4:24
  It's the best thing I've ever done for my career.
• 4:27
  And also, you know, definitely had personal trade-offs that I made along the way.
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  wasn't always an easy landing.
• 4:33
  I moved country multiple times over the course of a decade, spending time in, you know, France, UK, the Netherlands, and Japan.
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  And you certainly learn a lot about yourself when you're seeing yourself through the eyes of other people's cultures.
• 4:46
  You certainly learn a lot about influencing styles and ways of doing business.
• 4:51
  So, you know, my journey my journey has landed me here.
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  I think oftentimes I I wondered, did I
• 4:59
  Was I intentional about the choices that got me here, or did I kind of let it happen?
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  And what I do realize is over time, you know, as humans, we're often thinking about what is the right decision and what is the wrong decision.
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  And I think we live in a world of abundance.
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  if we're as fortunate as we are, and you and I are in this moment today, that we're actually often choosing between two good things and choosing which one to leave behind.
• 5:23
  so I've chosen some things to leave behind, but it's also
• 5:27
  brought me to a place that it that I absolutely love today.
• 5:30
  What an awesome journey to have been on.
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  And thank you for for sharing some of those highlights.
• 5:34
  I love the idea of twists and turns along the way on your journey.
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  And, you know, not to be too on the nose about the similarities between where you are today, but Annie Duke talks about thinking in bets.
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  I don't know if you're familiar with her work, but you know, how do you think about business and the bets you want to place and each of those decisions that you make for your
• 5:54
  journey are it's placing a bet on where you go next.
• 5:57
  And some of them work out and some of them don't.
• 6:00
  Absolutely.
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  And like I've I've had some that haven't worked out where, you know, I I think oftentimes when you choose where you're going and when you're part of a team, it's it it's it's a
• 6:09
  relationship.
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  It's like matchmaking.
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  and sometimes you don't get it perfectly right and it doesn't mean that the people on the other that you're working with aren't exceptional.
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  It's just you're actually not right in that moment in time.
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  that group and you have to you actually have to take that moment and be self-aware and be able to say like I'm not actually to able to drive the outcome that this organization
• 6:30
  needs at this very moment and it's actually not serving that business for me to be the person in that seat.
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  And it's it's hard.
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  You know it it it it definitely definitely feels like a failure in the moment.
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  but you you sort of understand through the process what you should have looked at differently, what you should have understood differently going into that situation.
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  And also having the humility to know that as well as you can do it in some places and with some teams, you're probably not the you're probably not the player that they need at that
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  moment.
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  Yeah.
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  I really appreciate that connection also to it's like a relationship.
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  You can have two good people and they're just not meant to be together.
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  And you can have a great opportunity with a wonderful team or a good organization, but it's not right for you or for them at that moment.
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  So I think that's important for people to hold on to as they're navigating those twists and turns of of careers and building a career for themselves.
• 7:24
  For sure.
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  I do have to ask, I just want to click down one more click on your career path.
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  And know what was it like for a musical theater kid to show up in a business world like that first job where you were just like, this is corporate.
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  What was that moment?
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  you know, it's it's interesting because when you when you actually grow up in theater and performing, you are expected to show up and behave like a grown-up and have your stuff
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  together to know when your moment is, to be hidden when it is not your moment.
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  So there are there are actually some skills also.
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  I think that some of the performing skills and some of the resilience that was built through my experience there.
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  you know, I I learned to be
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  First, I I learned to crave feedback.
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  I I I liken this to you know my ballet classes.
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  when you get a correction in a ballet class, it's actually because the teacher believes that you're worth investing in, you are worth their time.
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  If you get no corrections, it's not because you're really good.
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  It's because they actually think that's not worth my time.
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  I'm gonna spend my time on this.
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  so it taught me to be hungry for that.
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  It taught me to to really want to build things as a team.
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  To be able to do something over and over again and try to get a little bit better at it or consistently deliver every single time.
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  And like I the most harsh feedback I've ever received in my life was absolutely, you know, in moments on stage and in rehearsal or post-a-show.
• 8:53
  And I think I I could never receive as personal or as harsh feedback in the business world as I could.
• 9:00
  But I I had a lot to learn.
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  and I was entering a world where you know people had absolutely prepared themselves and
• 9:07
  you know, for years, maybe through undergrad and business school, et cetera.
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  so there is a lot about listening and paying attention and understanding the cues and understanding in some sense, you know, the the part that you're that you're responsible
• 9:21
  for, the part that you're playing in this in this moment.
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  I also tease that oftentimes when we're presenting something at work or we're filming, people say to me, you're so natural.
• 9:32
  I'm like,
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  I'm not natural.
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  I worked really, really, really hard this for a long time.
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  But I did I did have to continue my my training in that capacity.
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  And I think as fast as the world is moving, especially now and as fast as things are changing, we do have to continually learn, continually adapt.
• 9:51
  and again, adapt to the environment around us, adapt to the cultures, adapt to the different players that are in that in that team at any given time.
• 9:59
  Yeah.
• 9:59
  You know, I really appreciate that point that call out that when people make something look easy, it's usually because they've worked really hard at it.
• 10:07
  And that you're bringing that whole experience of being in theater and how does that apply within the work environment?
• 10:14
  Because it's easy, I think, to assume that people are just naturals.
• 10:18
  But in fact, you know, there's a lot of work that goes behind making something look easy, isn't there?
• 10:23
  For sure.
• 10:24
  And I I mean, I see that in the people we hire and the executives.
• 10:27
  When you're looking for skills and talent, again, there are things that are honed over many, many years and a lot of again, a lot of failures, a lot of stumbles along the way.
• 10:37
  anyone who's an at you know, who's perceived as an expert in anything, and I see many of them around me at work every day or peers in the industry.
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  and they have also learned by failing and getting back up and doing it again.
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  And, you know, even
• 10:52
  my team, we actually had a conversation and there was frustration around a piece of technology that we were trying to launch and the first one was a little bit of crash and
• 11:00
  burn.
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  The second one was didn't work out the way we wanted it to, and we're kind of on our third iteration.
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  And they were really frustrated and feeling this deep sense of of failure and how are we ever going to make this happen?
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  And then our engineering team was talking to us about work that they had done on a product launch.
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  And, you know, they built four or five versions or some of something before it was
• 11:20
  precisely the right one because external market factors were changing or whatever that may be.
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  And then there was a sense of like, okay, as long as each of those iterations along the way, we're learning something, we're building better judgment.
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  and we're we're actually there there's something also about bonding as a team when you when you do try something, it doesn't work and you go back at it and like the level of
• 11:44
  satisfaction that you get when something finally does work or when you're finally expert at something is
• 11:50
  is is really sa it's it's just incredible for you know your your self-esteem and your your feeling and I think as adults we so want to be right.
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  We want to be good at something right off the bat.
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  Like, you know, we're in this moment where technology is changing how we work.
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  you know we were doing an AI hackathon a few weeks ago with my team and we spent 90 minutes on working in Claude Cowork.
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  And at the beginning of that call I had
• 12:18
  Or that session, excuse me, I had people who were really frustrated, like this is not gonna work and I don't have the right connectors and all that.
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  And at the end of 90 minutes had built something that was like not far off of production ready.
• 12:31
  but getting ourselves in that space to try something new and to be ready to do it.
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  And I I mean, I told them I was essentially asking them to sit down with an instrument they'd never played before and play a song by the time we got out of that room.
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  And people were not sure that could happen and were afraid to take that leap.
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  But
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  giving people a space where they could fail and iterate and do it in a in a sort of safe way and an engaging way.
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  it was it was amazing to watch how we can learn.
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  But yeah, you're you're you're not gonna be amazing at everything the first time out.
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  And really you shouldn't be, right?
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  Sometimes the hard work is what makes that deep satisfaction.
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  That's what that's what brings it on.
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  I had a and I had another guest who talked about failure.
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  He he tell tells his team that fail stands for first attempt in learning.
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  Yeah.
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  Yeah, you can deal with pride, right?
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  I I d it I've always remembered that though, first attempt in learning.
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  And you know, so often, by the way, we need to we need to be more comfortable with failure or we need to be willing to fail, or we need to fail fast.
• 13:34
  That is something that I hear leadership teams agree to a lot in my business, right?
• 13:39
  Like we're always talking with leaders who are like, we really need to get better at failure around here.
• 13:43
  Okay, well, that's pretty tough to align to.
• 13:46
  It's actually hard to bring to life.
• 13:48
  And some of the things that you were just sharing, I think are great elements to pull out around how do you get aligned to something like that?
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  And it's getting comfortable with you know, I love your
• 14:00
  challenge to your team of come in and you're not gonna know how to play this instrument but in ninety minutes I want you to play a song.
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  Doesn't have to be a concerto, but
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  Mary had a little lamb will do the trick.
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  Yeah.
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  Right.
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  Whatever it is.
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  Yeah.
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  But how do we get comfortable with learning?
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  And I do think as adults, you know, we talk about learning zone and performance zone.
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  And as adults, we're very comfortable in a performance zone.
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  And we have for whatever reason gotten to be uncomfortable with being in that learning zone.
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  But man, AI is gonna force everybody into a learning zone over if if it hasn't already, right?
• 14:36
  And so I appreciate that you brought that up with your team.
• 14:40
  I think there's a there's something about celebrating the joy of having learned because again we we haven't we haven't celebrated that as adults in in in a long like in a long
• 14:50
  time.
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  When you're young and you're in school and you know your first drawing that you do, it's it's not great probably.
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  And you take it home and your family is so excited about it or your mom hangs it up, et cetera.
• 15:01
  and you see how that progresses over time and and and you have that that joy of those, even those small incremental learnings.
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  And
• 15:10
  You know, as we're learning this next era, there's been a lot of talk in past years about like learning and the flow of work, et cetera.
• 15:18
  But we're legitimately going to have to take people, you're gonna have to stop what you're doing, learn a little bit differently, and then go back and apply it and then continue to
• 15:27
  learn.
• 15:27
  So just the style of how we have been operating and learning of working over the past, you know, probably two decades is is shifting.
• 15:36
  and sort of how do we how do we get comfortable doing that again?
• 15:39
  Yeah, I think that's a great question.
• 15:40
  And I think part of being able to get aligned to doing things together is being willing to give people the space to learn and to iterate and to take it in chunks and not expect them
• 15:51
  to go from zero to a hundred overnight, right?
• 15:54
  Like how do you give people that that learning space?
• 15:58
  And for you, when you think about your role as the head of people for an organization or people in culture and what that looks like, how do you think about
• 16:07
  encouraging your leaders to have the I'm gonna call it fortitude to give people the space to learn.
• 16:15
  There's so much of a drive for efficiency now.
• 16:18
  We're trying to do things so fast all the time.
• 16:21
  And learning sometimes is slow.
• 16:23
  Sometimes it takes time.
• 16:25
  For sure.
• 16:26
  And you know, it's it's interesting too because even when models are coming out from an AI standpoint, or you know, you suddenly have access to this tool and you you want that agent
• 16:38
  to operate perfectly the you know, the first time out of the gate.
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  And I talk to people also about the fact that like when you hire a new person, there's a ramp period and there is a period where you expect them to learn, et cetera.
• 16:53
  until they're operating like at full capacity.
• 16:58
  so also as we're working with tools, there's a piece about how you learn to work that with the tools and I'll talk about that in a second.
• 17:03
  But even as you're training models, it's not going to be perfect, you know, first day out of the gate.
• 17:08
  Your ramp time is probably going to be it it can it can actually be faster.
• 17:12
  The speed to ramp can be incredibly quick with a tool, even if you think about, you know, you're if if you're using Chat GPT or something,
• 17:20
  you know, what your responses were and how your interactions were when you first started versus two weeks later versus a month later and you're like, holy cow, I can't believe how
• 17:29
  much this tool had learned.
• 17:32
  but also you know it's it it's it's a little bit difficult to influence and say, actually you need your team to stop and slow down just just for a small bit to be able to help them
• 17:43
  leapfrog in these moments.
• 17:45
  So you know I tell my team often, and they laugh at me when I say it this way, but I say like kind of
• 17:50
  Go where you're wanted.
• 17:51
  So find that one leader or that one person who's willing to try it in this way and think about how they can then use this as a case and show the success of this and how then we
• 18:06
  can replicate that through the organization.
• 18:07
  And this starts to become a okay, actually that that worked there.
• 18:11
  So if someone's afraid to go first, there's someone who's gonna be willing to go.
• 18:15
  So find your person who's willing to go there.
• 18:18
  Like inside of DraftKings, we built something called the AI Academy.
• 18:21
  And there are, you know, there are elements that can be online.
• 18:25
  You understand kind of where you are in your journey.
• 18:29
  Then we do things that are in person.
• 18:30
  I mentioned the hackathon that I did with my team.
• 18:32
  We do that with other teams.
• 18:34
  We do live learning sessions.
• 18:37
  when we're sharing, it's not just like here's a best practice.
• 18:40
  We show something really, really briefly, but then we get people with hands on keyboards.
• 18:44
  But again, it doesn't have to be
• 18:46
  you know, a day out of work.
• 18:48
  It can be forty-five minutes that you're there.
• 18:51
  So like how do you actually make time in people's schedules?
• 18:55
  And like I I also recommend doing it where, you know, collectively there's one hour company wide because then everyone's not worried about, my gosh, I have to be on this
• 19:02
  other meeting and I can't do that because I have to be doing this.
• 19:06
  So like you actually have the permission to stop and to learn for 45 minutes.
• 19:15
  And then you start to see the impact of that.
• 19:18
  And right now, you know, we're we're training a workforce and we're reskilling a workforce in mass.
• 19:23
  You think you know collectively around intern programs or apprenticeship programs, where you're training a a group of people who are coming into the workforce, we're now doing
• 19:31
  that through an entire workforce.
• 19:34
  So we actually have to give consideration to that and to the time that it takes.
• 19:39
  But again, that like that s the ROI on that small bit of time is so meaningful.
• 19:44
  So yeah, find your example where you can prove that ROI and then and then start scaling that.
• 19:51
  I think there you know there were so many things in there, like my my head was exploding as you were talking.
• 19:55
  But I think I want to just go back to a couple of them.
• 19:58
  One is I I love the push to find someone who can get the ball rolling.
• 20:01
  When we think about aligning to a shared goal like learning and reskilling the workforce or embracing AI or whatever those big things are, they're easy in the abstract.
• 20:10
  But when it comes down to the details, you know, these some of the things that you called out there are so important.
• 20:16
  And one is
• 20:17
  Find that first starter who can build momentum and prove it out, right?
• 20:20
  Show that this works.
• 20:21
  I really like your idea around how do you how do you make it fit the space?
• 20:27
  So if you can't take everybody offline for a month and go to a training, whatever, how do you find those 45 minutes?
• 20:34
  How do you find those opportunities for people to do something self-paced, but where they can fit it into the the work and the time that they have so that it becomes a part of
• 20:43
  their day?
• 20:44
  And then I
• 20:45
  Really appreciate your push around doing it together.
• 20:48
  So this idea of even like a company-wide learning moment, right?
• 20:51
  So everybody's going to be taking this hour to learn something.
• 20:55
  Maybe not everybody learning the same thing, but this time is set aside for people to engage in the process of learning.
• 21:03
  That's really interesting to me because so often there is this idea that, well, learning is something I multitask, right?
• 21:11
  If I'm in another meeting, I'll pull it up and I'll kind of work my way through it.
• 21:15
  But if everybody is doing it together in a way that takes that pressure off, I think that you could see a really interesting return on investment with that.
• 21:24
  And those all speak to how do we get aligned around this big goal?
• 21:28
  And how do we move from just agreeing that we should have people who are better at this to really helping make people better at this.
• 21:37
  And this in there.
• 21:38
  No, I I think I think that's a I I I think you've extracted a lot of a lot of those points and I, you know, oftentimes finding like how do you find that person and what is the you
• 21:52
  know what what's in it for what's in it for them.
• 21:56
  And oftentimes I find when we're really connecting it to external customer.
• 22:02
  and at the end of the day, you know
• 22:04
  All businesses have a customer of sort.
• 22:06
  And you know, we are we are deeply focused on our customer.
• 22:10
  So it's pretty tough for my leader of the customer organization to say, like, no, I don't have time for that.
• 22:19
  And we're like, okay, this is the impact it's gonna have on the customer.
• 22:23
  so if we can start to just have a small focus there, so it's again finding that in that is deeply business connected and connected to the values of your organization.
• 22:34
  so again, the g you know, knocking on doors of who's interested in this is one thing, but like helping them understand how that's going to drive and improve their part of the
• 22:43
  organization, but also the customer experience that we're creating every single day.
• 22:48
  Yeah, and I'm reflecting back on your musical theater background, not to pick on it too much, but the idea that the audience, right?
• 22:54
  You're in service to the audience and you get immediate feedback from the audience, right?
• 22:58
  They you know if you've got them where they need to be.
• 23:01
  And I think in business, one of the interesting aspects of the customer focus is it's more difficult to get that instant feedback from the customer about is this something that's
• 23:13
  working for me or not?
• 23:14
  And you have to be really intentional and purposeful around that.
• 23:17
  I think that's another space where in our work we see a lot of agreement.
• 23:21
  Yes, we should focus on the customer.
• 23:23
  And yes, we want customer feedback, but there's a difficulty in aligning to that for a lot of reasons.
• 23:30
  You can imagine, right?
• 23:31
  Maybe we get feedback we don't like, or maybe we won't be able to interpret it properly, all sorts of reasons.
• 23:39
  But it sounds like one of the things that you're really focused on is how do we be true to that impact on the customer and knowing that what we're doing is going to
• 23:47
  improve the customer experience.
• 23:49
  Tell me a little bit about that and how what that looks like.
• 23:52
  Sure.
• 23:53
  well, one of the things we do that I think is fascinating.
• 23:56
  It's one of my favorite parts also.
• 23:58
  We just had a new higher immersion today.
• 24:00
  So it's when we have our our newest class this month of people beginning at DraftKings.
• 24:05
  And one of the things we offer is an immersion account.
• 24:09
  So we allow people to have a, let me dare I call it a sort of a a fake version of our account.
• 24:15
  So they have fake money in there and they're allowed to play with our product.
• 24:20
  so then what we're also doing a each person then is able to be a customer and understand what that experience is.
• 24:27
  And then when everyone is building and we're thinking they're thinking about, you know, what do we do next?
• 24:32
  How do we how do we approach this problem?
• 24:35
  They've actually had the experience as a customer and they can think about what through what lens they need to drive that.
• 24:42
  It's also how we figure out, hey, this works well, this is exciting, this is not exciting, this feels glitchy.
• 24:47
  You know, when I when I see this, this is hard to find, whatever, whatever that may be.
• 24:53
  and some really f you know, fun innovation that we've had of you know have come out of employees saying, like, hey, when I was doing this, I thought, what if we what if we tried
• 25:03
  X or what if we tried Y?
• 25:05
  So, you know, we're listening to tremendous data sets from external customer, and we're also
• 25:11
  you know, connecting it to the very work that every person's doing every single day because they're actually able to touch and experience what that is.
• 25:19
  And that that tends to be really powerful.
• 25:22
  and people are excited that we've internal competitions on it as well.
• 25:25
  You know, the people team will compete against the compliance team, etc.
• 25:31
  But it it's it's really it's it's really driven that.
• 25:34
  And when we also think about hackathons, people will come up with ideas that they've had over touching our own product and say, hey
• 25:41
  What if we can do this?
• 25:43
  And you know, there's only so many engineering hours or product hours that we have to do anything, but then we can do these like quick sprints and then have kind of a marathon
• 25:50
  that goes on after that out of this.
• 25:52
  Yeah, you you know, the expression you drink your own champagne, right?
• 25:56
  How do you make that possible?
• 25:58
  And I think that there are really creative opportunities for people to think about how to make that possible for their teams.
• 26:05
  Even in less consumer oriented kinds of businesses, I think something that sometimes gets in the way of alignment to the customer focus is really helping the team understand the
• 26:16
  customer experience.
• 26:17
  So I appreciate
• 26:19
  how intentional you're being about that and trying to create that environment where people can genuinely be a customer and see what that experience is all about.
• 26:27
  Yeah, and it's there, you I've I've worked in organ I've worked in the SAS, you know, or business to business, which it's it's a little it's a little tougher to to get there.
• 26:37
  But it's, you know, how do you organizations have the opportunity to find ways to get people in front of customers and listening to customers and understanding the pitch or the
• 26:47
  work that's being done by the sales teams, et cetera, and what feedback they're getting.
• 26:52
  So like how do how do people allow them
• 26:55
  either employees to immerse in that business regardless of what it is.
• 26:58
  And it may not be a consumer product.
• 27:00
  It may not be something you can touch.
• 27:02
  And there is an entry point in all spaces, I would argue.
• 27:07
  You you just have to be you have to be clever and creative about it.
• 27:10
  I agree with that completely.
• 27:12
  And I think that does get in the way of alignment sometimes is the call to action to be clever and creative and make the investment.
• 27:18
  If it's important enough to you, then you need to make the investment in it.
• 27:21
  Yeah.
• 27:22
  Yeah.
• 27:22
  I think when we think about an innovation is another space where we hear a lot, we need to be more innovative around here.
• 27:28
  We need to be more creative.
• 27:29
  We need to be leaning in.
• 27:31
  There's a lot of agreement.
• 27:32
  Nobody's going to disagree with that.
• 27:34
  But when it comes to aligning to it as a leadership team and making the investments and setting the priorities, things get
• 27:40
  pretty wobbly, pretty fast.
• 27:42
  And so I think what you're pointing out is you can be creative about how that looks and what the experience is for your teams to enable them to think in an innovative way or in a
• 27:52
  creative way about the product and how to continuously improve it.
• 27:56
  Right.
• 27:58
  The alignment, we have we've a l a lar we have a large leadership team and you know, there we have different parts of our business.
• 28:07
  So again, there's a limited amount of resources that can you know that can give or that can develop and we have to think about, you know, what are our priorities as an
• 28:17
  organization.
• 28:18
  And it doesn't mean that all parts of our business aren't important, but where are we going to push?
• 28:23
  What are we going to try to spike this moment?
• 28:26
  And when you're trying to get a large group of folks aligned, and I I actually I have a slide that I use and I talk about and I talk about alignment and consensus.
• 28:37
  And like we're not looking to walk out of the room with consensus, but we're looking to walk out with alignment.
• 28:45
  And you know, each person's version of what that might look like at the end can be slightly different, but as long as we're aligned on the overall
• 28:55
  goal, it's really important for us also then to be able to communicate clearly down through the organization.
• 29:01
  Otherwise you start to get chaos.
• 29:02
  And if you're looking for complete consensus, you know, I argue that you end up with a very vanilla version of something that can be really spiky and really interesting because
• 29:11
  you're trying to solve for every single person's isms and we all have them.
• 29:17
  And we want to do something again that's that's really
• 29:22
  unique and serves us.
• 29:23
  So again, you know, coming back to the customer and the focus on the customer is always really important.
• 29:28
  So we're aligned on that like eventual goal.
• 29:31
  We're aligned on what we're trying to achieve and you know how we get there.
• 29:35
  Each person may have done differently.
• 29:39
  But we're we're we're going to make that happen collectively.
• 29:43
  What in your experience do you think contributes to people staying in consensus or settling for consensus and not pushing through and getting to alignment?
• 29:54
  Yeah.
• 29:55
  there's there's a piece of it around being polite and being respectful and also being uncomfortable with debate.
• 30:05
  And one of the things I learned living abroad and working in a lot of different cultures, different cultures have different levels of comfort with debate and you know, sort of
• 30:18
  disagreement and being in that moment.
• 30:22
  and if you have a level of relationships or dare to say psychological safety, you you've given yourselves the opportunity to do that.
• 30:30
  we at DraftKings we also talk about radical candor.
• 30:35
  and I I I love the concept of radical candor and Kim Scott's work around this, and it it aligns very well with us culturally.
• 30:44
  But being kind is also being truthful and being thoughtful in and pushing one another.
• 30:51
  on those topics.
• 30:52
  And you know, I I worked for a French organization for a long time.
• 30:55
  And I think one of the things that they did best, and my colleagues told me it's something that's very natural from the culturally, is to debate topics.
• 31:03
  And when people were interviewing and they're like, how should I prep?
• 31:07
  So if someone asks you which one A or B, like it actually doesn't matter which one you choose in that moment.
• 31:12
  Choose one of them and have a case behind it because you're actually going to uncover so many other things in those moments.
• 31:18
  And you realize what you're trying to solve and you're able to kind of get to that spot.
• 31:23
  but so often, you know, we're we're not creating the space to challenge ideas or explore alternatives.
• 31:31
  we're not discussing the trade-offs openly.
• 31:33
  So we'll sort of agree to something in a room, potentially as, you know, adult adults in a corporate environment.
• 31:39
  And then, you know, you go off and you're like, Well, but you know.
• 31:43
  If X doesn't work or this is not there, this piece of tech is there, I don't have the budget, et cetera.
• 31:48
  You actually have to be really open about, you know, we're we're choosing this and we know these are our trade-offs.
• 31:54
  And coming back to like my my choice before, oftentimes you're okay, these are five different things that we can do that are all great ideas.
• 32:02
  We have the capacity to do three of them really well or two of them really well, which
• 32:09
  or three are we going to choose and which two or three are we going to actively choose to leave on the table and get comfortable on that.
• 32:18
  So there's a really important piece around relationships that you build that make all of this possible.
• 32:26
  and leaders also need to show that they're that they're open, that they're curious, that they're they welcome questions, they welcome changing their mind.
• 32:34
  You know, I I I work for an incredibly
• 32:38
  intelligent and future looking boss who's absolutely wonderful and he's he's brilliant.
• 32:45
  And you can start a conversation with him and he'll have a point of view.
• 32:49
  And if you do not feel like you have the safety, you would just go forward with what was said there.
• 32:53
  and you can have a great debate with him and if you're you know factually based in data and like you're able to shift.
• 33:02
  And his point of view can and will shift.
• 33:04
  But we end up coming up with
• 33:06
  like a much better solution because we've actually had that candid conversation.
• 33:10
  But we have our tr we have trust.
• 33:12
  We have a relationship that we've built together.
• 33:15
  and you know many times people want to go right right to action and right to the operationalization of something and are not thinking through the relationship pieces and
• 33:24
  the trust.
• 33:25
  you know I I I think most successful companies, funny enough, I think are truly built on relationship, not on process.
• 33:35
  And
• 33:35
  I know a lot of organizations feel that when it gets beyond a certain size and a certain scale, that it's impossible and that can't that can't work.
• 33:42
  I know I I I worked for a company at some point in time that was peaking over 80,000 people and was a company that was deeply run on relationship and was hugely successful.
• 33:52
  They were able to scale it, but there has to be an intentionality around there.
• 33:56
  And you're able to keep a a business spiky and energetic and growing even at that size when it it has the risk of turning into
• 34:05
  what someone once referred to as the blob.
• 34:08
  but that that relationship piece and that trust is is paramount to this being successful.
• 34:16
  I think, yeah, you're keying in on the idea that relationships and trust are foundational to have the conversations that you need to have in order to build alignment, to break out
• 34:25
  of consent consensus and just being polite.
• 34:27
  And we like to say ambiguity protects the status quo, right?
• 34:30
  So if you leave things ambiguous enough, then you don't have to change the status quo because it's just very comfortable.
• 34:37
  It's a very comfortable space.
• 34:38
  And you're talking about being visible and intentional about the trade-offs that you're making, the decisions that you're making, having clarity there.
• 34:45
  And I think these are all things that from Kerakan's perspective really fuel alignment because they they make things un unavoidable.
• 34:55
  You can't avoid the conversations that you need to have, whether they're debates or discussions or whatever that looks like.
• 35:02
  This inter I think it's really interesting though, the process versus relationships and that dynamic because so often people try to solve a relationship issue with a process,
• 35:11
  right?
• 35:12
  One hundred percent.
• 35:14
  And how often does that work?
• 35:17
  Yeah.
• 35:18
  Big goose egg on the board there, I'll tell you.
• 35:20
  I've I've seen it many times.
• 35:22
  And it's like we we will have this urge to go into you know, the this like we we want to go to action, and this bias to action.
• 35:35
  And you know, I I I talk to my team often, especially coming out of any form of survey, and they're like, Okay, well here's the action plan, but the bottom three that we're gonna
• 35:43
  do work on.
• 35:45
  and
• 35:46
  You actually have to step back and take the time and listen one step deeper.
• 35:50
  And I think even broadly with groups and trying to get them aligned, you have to listen before you diagnose and help the group understand different perspectives.
• 36:01
  We're each coming with a different expertise, a different set of knowledge, a different background, a different culture potentially.
• 36:08
  and you have to make sure that you're understanding that full scope.
• 36:13
  And that's
• 36:14
  You know, again, it feels time consuming in these moments where we just want to move quickly.
• 36:19
  We're so concerned about feeling like activity is happening.
• 36:23
  And it doesn't feel as satisfying if you don't see activity happening and you're checking some things off.
• 36:28
  one of the things that I did when I joined DraftKings, we have what we call the SLT, the senior leadership team.
• 36:36
  and you know, it's it's over 150 people.
• 36:38
  And
• 36:39
  In my first couple of months there, I had a 30 minute meeting with every single one of them.
• 36:45
  and I asked them, I asked them four questions each.
• 36:49
  And you know, one was like, What is the biggest improvement we've had in the last year?
• 36:53
  what creates friction when they're doing their job?
• 36:55
  What are they most proud of?
• 36:56
  And if they could ask the executive leadership team for any one thing, what would that be?
• 37:01
  And it just helped me understand through each of their lenses, it also helped me understand what not to stop and break.
• 37:08
  And sometimes when we're
• 37:09
  when we have this bias to action, we actually stop doing something that's really important to our customers, to our people, et cetera, because we actually haven't looked to the
• 37:19
  depth.
• 37:19
  So again, like on a survey from a customer or from an employee, something may score quite high and we think, okay, that's fine.
• 37:26
  We can leave it and something scores quite low.
• 37:27
  We've got to go after that.
• 37:29
  What you might find is the thing that scored low actually people didn't care about anyway.
• 37:33
  But that thing that scored a 4.7 out of five, that's the reason people love your brand or people love working for your company.
• 37:39
  And you need to, you know, protect that at all costs.
• 37:43
  And as we think through this next iteration of our business at DraftKings, a lot of companies are thinking about AI as an efficiency measure.
• 37:52
  again, I think I think about it as abundance and what it can create, but you know, as
• 37:57
  As we think about where we can create efficiency through tools, it's not enough for us to like keep a status quo on an NPS and you know, keep the same NPS and be able to do more.
• 38:08
  No, we have to push up that NPS at the same time as we're also becoming more efficient, because at the end of the day, that's the magic that our that our customers care about and
• 38:19
  that our people care about.
• 38:21
  Yeah, and they'll care more about that than a net promoter score any day.
• 38:24
  Yeah, yeah, yeah, yeah.
• 38:27
  If you were gonna give somebody some advice about if they're working with their team and they're trying to get them out of consensus and into alignment on something that they're
• 38:37
  working on, what would be the two or three things that you would tell them to focus on?
• 38:42
  We've talked about a few, getting kind of the the ball rolling, building momentum, enlisting people on some of the other
• 38:49
  Some of the other ground that we've covered today.
• 38:51
  But what comes to mind for you is kind of the top two or three that you would love to see see a leader really focus on if they're trying to move their team from consensus to
• 38:59
  alignment?
• 39:00
  Sure.
• 39:01
  say start with the why.
• 39:04
  So make sure you're really identifying the problem and the stakes.
• 39:08
  So you're really clear on that before you're debating solutions.
• 39:13
  I think that naming of trade-offs, I think the alignment gets really real when people understand what the organization is choosing to do and choosing not to do.
• 39:23
  And then, you know, when you're translating that decision into behavior.
• 39:29
  You have to build a cadence around it.
• 39:30
  It's not like it's not a one-time announcement.
• 39:32
  You have to continue to revisit that decision.
• 39:34
  You have to continue to measure progress on that and resolve the friction along that way and keep that narrative consistent.
• 39:41
  I think we're we're we get comfortable with like, okay, the the comm been sent, everyone knows.
• 39:47
  but how you know, how do we make sure that heartbeat keeps going and we keep
• 39:51
  you know, bringing it back to, okay, remember we had talked about that, this is why, and this is actually what we're doing on that.
• 39:57
  And even if you have to pivot along the way, again, that initial why that you've started with, that's still there.
• 40:02
  You may have had to shift how you're solving that problem along the way.
• 40:05
  Like external forces are changing at all times that you can't control, but you're still going after that why and reiterating that to people.
• 40:14
  And yeah, we're still solving the same thing.
• 40:16
  We've had to move 30 degrees to the left to do this instead.
• 40:20
  Yeah.
• 40:21
  Yeah, and you know what we like to say talk, don't tell.
• 40:24
  Sending out the comms is insufficient for leadership if you want to build alignment.
• 40:29
  It's really interesting, also in like in research that I've done, and I've I'm not alone in having discovered this, the most trusted source of information for people is actually
• 40:39
  their direct manager.
• 40:41
  And a lot of times when companies are trying to get people fully aligned on something, it's like, what is the corporate comm or what is the CEO saying?
• 40:49
  It is not enough to just have the ELT clear on what this is or how that work is connected or the senior leadership team.
• 40:55
  It's gotta be all the way through the organization.
• 40:58
  you know, to those frontline managers who are talking with their teams every day, to the people who are in front of the customers every single day to make sure again that that's
• 41:07
  that that's really clear.
• 41:09
  And you know, the number of times that that message has to be told or tied back to a piece of work.
• 41:16
  It's not one, it's not two, it's not three.
• 41:18
  Like so it's again that that drum beat has to keep going for people.
• 41:22
  Yeah, for sure.
• 41:24
  And maintaining the continuing to have the conversations is just so important.
• 41:28
  It's not a one and done.
• 41:29
  People need to hear it many times from from many people, including their direct manager.
• 41:33
  So I appreciate that push there.
• 41:34
  Yeah, Linda, this has been such a great conversation.
• 41:36
  I feel like I could talk to you for hours, but we don't have that.
• 41:40
  So we do have a final question that we ask everybody and it's a bit of a dream along with me question and
• 41:46
  If you were thinking about getting a group of people, any group, it could be your team, your family, your community, the company, the world, a group of people aligned to deliver
• 41:56
  something together, what would you like to see that be?
• 41:59
  Yeah.
• 42:00
  And this is this is where my my life and career come full circle.
• 42:05
  I would align people, I would align a city around making great arts education accessible to every child.
• 42:12
  So, you know, the arts teach empathy, confidence, creativity, collaboration, and the ability to see the world from someone else's perspective.
• 42:21
  And these are skills that are gonna matter even more and more in the future of work and in life.
• 42:28
  And I I s I sit on the board of the Huntington Theater.
• 42:31
  It's really very personal to me and I care so much.
• 42:35
  This has been a part of my success in my life.
• 42:39
  and I I want that to be a possibility for every child who's growing up now in a in a world that maybe feels so much about technology and a screen in front of you.
• 42:49
  So that's how you build a future ready workforce, but it it it starts it starts in a very different place.
• 42:55
  I I love that.
• 42:56
  I think that call to action to make the arts important and available and accessible to every child is a wonderful aspiration to try and get communities a around the world
• 43:07
  aligned to to bring that power to all of us as these children grow up and become parts of the parts of the business world and who knows where they go with that, right?
• 43:17
  Look at yourself.
• 43:17
  You went from being very comfortable on stage to being very comfortable as an executive.
• 43:22
  And that's an amazing journey.
• 43:24
  Thank you so much for sharing it with us today.
• 43:27
  Thank you so much.
• 43:28
  I've really appreciated this.
• 43:29
  Yeah, it's a pleasure.
• 43:30
  And it's been a great conversation for all of our listeners.
• 43:33
  I would just ask you to please like and comment and share this episode if you found it useful.
• 43:38
  And we will see you next time on the failure gap.