Offense or Defense by Jessie Young Poonam Garg

Automatic Summary

Offensive and Defensive Leadership: How to Balance Your Approach

Welcome to our session today about the interesting balance between offense and defense in leadership, featuring our dynamic expert, Jessica Young. As a leading figure at Uber, focusing on grocery and retail delivery, Jessica shares her experiences and insights gained from an exciting career journey. In addition to her professional achievements, she boasts a multitude of varied interests ranging from being a yoga teacher and amateur surfer, to philosophy, wine tasting, and much more.

Curiosity and Continuous Learning

Jessica runs us through her personal journey shedding light on the importance of being insatiably curious and a hungry consumer of learning and life. In her view, the journey towards achieving your career and personal goals isn't straight-line but rather a constant adventure. Manifesting this, Jessica highlights how she is always a student in different aspects, exploring different interests like learning Italian, joining book clubs, maintaining physical activity and dreaming of what could be.

Strategic Leadership Approach: Offense and Defense

The idea of offensive and defensive strategy in leadership stirs a lot of thoughts and questions. Jessica emphasizes the importance of designing a strategy as a leader who is either playing an offensive or a defensive game. In this context, Jessica provides perspective on what playing defensively means; taking actions based on positions that one seeks to defend, either for oneself or business. On the other hand, playing offensively is more about what you aspire to, and less about what you seek to defend.

Enhancing your Leadership Skills

  1. Mindfulness: This is the first and fundamental skill according to Jessica. Mindfulness in yourself is to know how you are turning up and whether your goals are rooted in outputs or inputs. It's about focusing on input metrics, not just output metrics.
  2. Authentic Leadership: Jessica defines authentic leadership as the intersection of trust and vulnerability. It's about owning your mistakes and being clear on what you choose to excel in, and what trade-offs you are ready to make.
  3. Being advocative: This involves leaning in further and claiming your power at inflection points in your career. Jessica stresses that there is nothing lost in asking for what you believe you deserve with clear metrics to back it up.

Managing Defensive Team Members

Jessica acknowledges the challenge of dealing with defensive team members. It comes down to aligning your behaviors with that person's interests and what they are defending. By understanding their KPIs and what motivates them, you can position change in a way that aligns with their interests.

Conclusion

Jessica encourages the audience to envision their ideal selves and align their behaviors towards that goal, all the time emphasizing that the outputs will take care of themselves if they focus on their behaviors and remain authentically themselves. The takeaway is learning to balance offense and defense in your approach to leadership, asking for what you believe you deserve, and remaining mindful of your actions.


Video Transcription

Welcome to the session and uh I welcome here Jessica Young. We are driving the session called offensive defense.And uh and I would like Jessica to introduce yourself first before we go for it,

Jessica. Thank you so much, Priam. Um We've obviously had the pleasure to chat a few times before this conversation. Uh For those who I've not met before, I'm an Aussie in New York who is leading new business lines at Uber, currently focusing on grocery and retail delivery. I really love my job because I really love solving difficult problems in pine environment. I'm um I'm also a yoga teacher, an amateur surfer and a lover of coffee and of red wine in terms of vocation. I'm a student of philosophy. I was a lawyer in my early career working in corruption and advocacy in a PAC. I'm a former management consultant, turned finance leader and I have a host of failed and flourishing start-up experience as both a founder and an advisor.

OK, thank you, Jessica. So when uh as Jessica mentioned, like we already touched base and I was so inspired with her story of offense and defense and I would like to share with you all. And by asking a few of the questions with Jessica, probably uh if anyone has a question, you guys can put a, a question on Q and A I will take your question in between with the session. So let's learn from Jessica, how his her, how's her journey looks like? So my first question, Jessica is what makes you

Yeah, it's a good one. I would say I'm a, I'm insatiably curious and a hungry consumer of learning and of life. Here are five ways that, that manifests. Um I'm always a student at the moment. I'm learning Italian with my husband and I'm just completed my sommelier course. So hopefully I passed. Um Secondly, I really always have a book in hand. I actually started a book club when I first moved to New York and I love to write fiction myself. Um I usually read a few at once that complement each other at the moment. I'm reading, we begin at the end and the period repair manual. Um In the third thing is that I never need reminding to move. I was a runner when I was younger. Uh And my husband was an Australian water polo player. So we move every day. Um Before I'm always dreaming of what could be. I'm usually incubating an idea at the moment. Um My co-founder Jules and I are working on an idea on how to better empower new carers with their baby essentials. And the final thing is that I'm always up for an adventure. I'm usually planning a trip or an adventure somewhere with my best friend. My husband. This year, we set the goal to climb as many peaks as we can uh metaphorically, but also literally. And next week I'm going to Norway to climb some peaks there.

Oh, that sounds great. It soon, soon. It, it seems like it, you have a couple of fantastic journeys coming up right now. My next question is like, because we have a 13 minutes. So I would like to go with real good questions. So I would like to learn from you too and definitely the audience would like to learn from you. So would you mind to share as a strategy we should be playing as a leader? Uh the role of offensive or defensive?

Yeah, it's a really good question and maybe a bo it's just taking a step back for those who are listening in terms of the context that we've had about what we think that means. And I think if you could walk away with one thing from this session, what we'd really hope that the, the key takeaway is, is how to design a strategy as a leader who is either playing an offensive or a defensive game. So what does that mean? Well, uh the defensive game is one where the actions that you take are based on positions that you seek to defend either for yourself or for your business in protecting against your downside risk. And your offensive game is less about what you seek to defend, but more about what you aspire to. And, uh, and about how you optimize for upside. There are times when both are required. Um, but I think overwhelmingly one of the really interesting conversations beam that we've had is that as women a lot of the time, uh, particularly in a, if you, if you feel a little underrepresented in your uh in your workplace, you're often playing a defensive game in that you are seeking to justify your right to be there or your work or the ideal that the idea that you must be perfect or ideal in some way.

And if you are able to take a step back from that and instead of being motivated by that, which you stand to lose, think about that, which you stand to gain that can lead to some really powerful impacts.

Sounds right. So, is there any skills that we would like, we need to have it before we play this game or we strategize this thing?

Hm. Yeah, it's a, it's another good question. I would say the, the first and most fundamental skill is uh is that of mindfulness, which is simple but not easy um mindfulness in yourself to know how it is that you're turning up and whether your goals are rooted in ah outputs or in inputs. So, I'll give you an example, you know, an output metric maybe to grow your top line by X percent or to achieve a X million run rate. But the input metric for your business, maybe something much more fundamental about the way that you engage and interact and harness your customers and understand the true life of a customer. An output metric as an individual or as a leader may be that you seek a certain uh promotion or um or you know, salary or output of some sort. But the input may be actually that you want to be the most empowering leader that you can be or you want to be brought to the edge of possible problem solving.

And if you start to solve for your inputs, what you'll start to find is that you are solving for that which you can control for rather than that, which is controlled by others. And when you reclaim that power, I believe that that's actually where you start to have the greatest impact. So I would say the first skill or tool is the mindfulness to check yourself on whether you are motivated by that, which is performance based and outcome based. And instead think about where you can reframe your approaches to reclaim your power in terms of what you give out.

OK. Uh Another uh So my question now goes back to here is like, so what is actual definition of in your language, effective authentic leadership? In that case, what it looks like.

Yeah, I think um to borrow a principle from Brene Brown, I think authentic leadership really is the intersection of trust and vulnerability. And I used to once think that um that the former was a predicate of the latter. And now I realize that both are essential and I think that is true, both as an individual as a leader of a team and as a business, you need to build that with your customers. Um just as you need to build it within yourself, just as you need to build it with your team. Uh And so what that means is owning your mistakes failing fast and um and, and really being clear on what it is that you are choosing to be excellent in um and potentially what you are choosing to be bad at and making those trade offs.

So what best advice would you give to us, our audience, like if they are in the middle of the journey, right? And they would like to go for, they would like to, you know, get into the ahead of their leadership journey. So how should they play in this role?

Yeah, I think um when I reflect on a career journey, it's very interesting because often what gets you to a certain point in your career right now or what got you here is not what's going to get you there. And so the question is at what inflection points. Do you need to lean in further? Do you need to claim your power or do you need to become an advocate for yourself? And sometimes that can feel like you need to become, um, something more of an offensive player in your career and that you need to find your voice a little more. What I would say is that there is nothing ever to be lost from asking for what you think you deserve with the clear metrics to back that up. I'll give you some very practical examples. If you know that the role that you want in two roles, time requires a certain set of competencies. And you believe that you're not getting the exposure of those competencies in your current role. It is your responsibility to advocate for yourself to make sure that you are building those and nobody will be that advocate unless it is you first.

And so you should feel entirely within your power to again focus on the input metric of building those competencies, whether that is saying to your manager, hey, at this next T presentation, I'd really like to present XYZ slides because I want to practice my exposure or my communication to that audience.

And you will find that nearly nine times out of 10 when you start to claim the inputs and then you wear your results as your outputs, you will, you will start to make the traction that you seek.

Mhm And then can you show me where we can play, you know, at the leadership level, the defensive aspect, do you see like we should play? Uh because as you explain, like, where we can play that offensive, being an advocate about ourselves, right? Where we don't know the skill sets and we would like to uh empowered uh and uh have to have that skills within ourselves. But where should we play as a defensive role? Because sometimes we, we unknowingly and knowingly we oversteps into the people toll, right? So for example, I really don't know the language and the skills that I'm looking for. But I would like to acquire that. I had my conversation with my manager and he said like, OK, looks good. But at the same time within uh maybe your peer might be also looking for that. But and he ordered and the somehow manager forget from his head, like your leaders, forget from the other head like your boss. And he said to you, yes, but you took the work of the other one who would like to do the same thing. So how would you approach it being a defensive? And that mm

Yeah, I think fundamentally there is a time and a place for uh defending your boundaries and for managing against your, your downside and for choosing not to take risks sometimes and sometimes choosing to hold caution and hold tone just as that is true in business dynamics, you know, at the moment we're looking at a macroeconomic rotation from to 15 years of hyper growth and certainly in the start up world and in the VC world, we're looking at a rotation from growth to profitability and we're starting to look at companies taking more defensive stands about how to manage for their downside risk.

So fundamentally, as a, as a leader, you owe it to yourself to question where your actions are more about preserving a status quo in yourself or an unachievable ideal that you think you need to be, particularly this idea of, you know, protecting against being perfect or not being willing to make a mistake at work or in front of your team or to misstep.

Um because that might actually be fundamentally holding you back from the very thing that you're seeking to achieve. And I have a dear friend who is actually presenting during this conference as well. Her name is Brooke Taylor. If you can find one of her sessions, she's fantastic and she talks about the idea of the success wound as something that success becomes a position to defend rather than something to aspire to. And so what I would say is that there are certainly times when you want to tread carefully. Not every, not every day is a sprint and not every day is the time for a big risk and to jump off the side of the mountain. But also I think every day is the opportunity for you to really question where your growth is coming from and how you control your growth. You know, it's a service you can do to yourself and to your team is to moderate and limit yourself based on trying to protect against an ideal of perfection rather than playing the offensive game of being willing to fail, but optimizing for growth and for your inputs.

So what should you mean, what should you give to our audience as a key takeaway with that, with that narrative? Like we should balance out offense or defense or should we pick our battle? What do you, what do you want to want to give our audience a key to get away on that? I think,

think about your ideal self and what, and, and really close your eyes and envisage who she is as a, as a leader, as a mentor, as a change maker. And then think not about what it is that she does, but think about who she is and what her behaviors are and then make everything that you do. Now in the present a way of optimizing or aligning your behaviors to who she is and know that then the outputs will take care of themselves. And so again, they say it is simple but not easy, be really clear on what being authentic to you, you means and be really clear on what the behaviors are that will make you the most powerful version of yourself and when you are mindful and can check yourself on that so that you are optimizing for your behaviors rather than your outputs.

I think you'll start to see really meaningful change in your career and the way that you command change

now, I will leave two minutes for our audience. If they have a question to ask to you, feel, feel free to post the questions, guys, I'm looking in the Q and A board if you guys have any questions with Jessica.

OK?

So Jessica as no one is asking, let me ask last question. So since playing this role of an offense and defense, OK, there is a one question came up. Let me, let me entertain that. How do you navigate other team members that may be defensive? That's a very good question. I was coming back, I was coming into the same question. Honestly, Jenny.

Yeah, it's really, it's really challenging and I would say that in a really cross functional org and depending on where you, where you sit, particularly if you work in a, in a product or a DEV world and you are interacting with different kinds of stakeholders. I imagine you come up against this a lot. And again, I think it's coming back to one assuming positive intention, but to try to think about what positions that it is that are, that is motivating someone, what are their Krs um or their key results that they are trying to defend against and then how can you align your behaviors and the actions that they need to take around those behaviors?

Sometimes I'll be so deliberate about that when I know that I have a challenging or very defensive stakeholder to even ride it out before I go in knowing exactly what it is that I think they're going to need to be optimizing for or defending against so that I can make sure that I can position the change that needs to happen in a way that is aligned with their interests.

OK? And looks like we are end of the session. Thank you, Jessica and thank you for entire participants who join our session and looking forward to more sessions to join.

Yeah. Thank you so much. I really appreciate it. Yeah. Enjoy this conference.