Today we’re sitting down with Amy Young, Outpace coach and founder of Redefine Possibility, to dive deep into specific, actionable guidance on how to manage high performing teams.

From leading teams as a vice president at CBS, a partner lead at Google, and launching your own coaching practice. In your experience, you’ve directly managed many teams and navigated through some tricky leadership challenges.

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So, we'd love to get started just with an overview of your story — just sharing how this incredible journey you’ve been on in your career has unfolded. And then we will dig into the specific tips and strategies you have for how to manage high performing teams.

Amy: Sure. Well, thank you for asking and thank you for having me on. It's been a wild ride. I started my first 15 years of my career in media. I worked at CBS Television in a variety of roles from an assistant in their local television stations unit, to then growing their set top box video-on-demand product and RET retransmission consent business, which at the time I left, was projected to be over two and a half billion dollars.

Being able to grow a business from zero to that was a completely phenomenal experience and wild ride, and it was not just me. I obviously worked with an amazing team and led a phenomenal team to do so, but about that time after building that business, I got the itch to do something new.

So, I moved over to the ad space where I was involved in really bridging the gap between traditional and digital ad, and that's when Google approached me and asked if I would come over to work for them, leading a team tied to their largest partnerships with media companies and to help them not only grow those partnerships, but also really get more involved in the traditional television space and had the amazing opportunity to do that for two years before burning out if I'm being completely honest. In making the change, and leading a team, and being global and doing all the things, I just decided to take a step back for both my health and the longevity of my career and my relationship with my family. I had always been very interested in personal development and decided that it was about that time that I wanted to become a certified coach. I had worked with a coach previously in my career and found it so beneficial. I remember thinking at that time “There's something here.” It kind of planted that seed inside of me that I helped so many clients try and listen to and find that I decided to scratch that itch and see if there was anything there.

That was about five years ago when I became certified. I left Google to start my business, and so now I'm here trying to help other executives and leaders try to avoid that same path to burnout and help them create a career that matters to them, that enables them to have some longevity.

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Just the depth and richness of your experience is so helpful, in terms of having the empathy and that connection with people that you coach because you've been there. You've been through that. In that journey, what have you noticed is the most effective when it comes to team management and being a really effective leader?

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Yeah, it's a great question because it's an area that I love to watch and study because in my experience, I have [had] the opportunity to work at a very traditional company like CBS Television where it [was a] company that had been built since the early 1900s and grew but still was very old school right then going to a company like Google where it was just much more progressive. The culture there was just very different, and in looking back and evaluating both of those experiences, when I think about the best leaders that I learned from and those who have challenges that I learned from, it still boils down to a few common facts, and honestly, those skills, [with] communication being the top one. The ability to communicate with some level of transparency to all levels, whether it's your team members, whether it's to your senior executives or your stakeholders, is extremely important and is a skill that any effective leader that I've seen, they're able to harness that and use their communication skills to their advantage. Connection, the ability to build connection with the team, to almost create that why. As a leader, we really, really have to be that person to foster that connectivity with each individual and why they're there and how what they do adds to the larger picture.

And then the last thing, honestly, is humility. When I think about some of my leadership or the leaders that I've learned from, it is the ability to come to the table and say “Hey, I don't know everything, but here's what I do know,” or “Hey, we missed the mark on that deliverable or that project, and here's what I come to the table owning, and so here's what I need you to come to the table, and now we're all going to figure this out together.” So, the combination of that communication, the connectivity, and the humility is really that recipe for success when I think about what I've seen [from] effective leaders, no matter the scale or the type of culture that the company exists within, that enables them to have success. 

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When you've witnessed that or when you have embodied that yourself, are there some specific examples you can share, like instances or times that stand out to you that can make those three aspects of effective leadership and team management a little bit more concrete?

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Sure. So, the best example that I have of this is when I was in business development at CBS, we were working on a negotiation with a major satellite provider, and it was the first time in CBS history where we pulled our signals from the satellite provider, so no one could watch. The CBS channels that we owned; we pulled the signals. No one could watch because we couldn't reach a deal [for the] first time in the history of the company. So, the team that I led was responsible for the marketing campaign around that entire pull of the content and really behind the scenes, orchestrating all of the data sharing and knowledge, and really architecting the strategy behind why we were doing and what we were doing. My team was responsible for emails from the CEO out to all of the stations, down to everyone on the engineering side as to what we were doing, when we were doing it, and how we were doing it.

What I learned in that time: Everyone having access to the same information, so that could speak to that communication. Everyone having access to the most up to date information based in data at the same time, so there was no catch up involved. It was “Okay, here's the communication at the same time,” so everyone's dealing from a level playing field. Then, it was me also separately communicating with all the stakeholders, so that they knew “Hey, here's how your individual fits into this larger picture,” so that we all felt like we were rowing in the same direction in this campaign. That was that connectivity piece. “Station, I understand you're losing ad revenue right now, but here's what we're hearing from the viewers, and here's what's at stake here. This is why it's really important that even though you're feeling this pain point right now, this is what it's going to add.” Then, also from a humility perspective, being able to come to the table and say “Listen, this is really hard. I know that we are working around the clock, and I know that this is super hard.” This turns into a good story for us because at the end we were able to come to a deal that really worked and was advantageous for us. It was a paradigm shifting deal at the time, and it showed the value of our content.

In the end, we all felt really good about what we did and the way that we performed, but had those three elements not been in place, it would've been a much more disjointed effort that many people would've felt much more pain through, versus in the end, we all felt like a team no matter what role we played. That accomplished something, and it enabled us all to feel really proud, and it's something that we could all look back on and still talk about. 

I think it also speaks to the fact that many leaders that I coach, we need to expand our definition of our team and who we lead. We are leaders, not just to our individual teams, but for instance, in that example, yeah, I was leading without a lot of direct influence, right? There were a lot of stakeholders at the table there that did not roll up to me that I had to build trust with.

So often, when we're thinking about the challenges in front of us, it's not just looking at our team myopically to think “Okay, how is this going to affect us?” But it's expanding our vision to think about what are all of the people involved in my daily life that this could affect or this one decision that I have, or the decision that I make, how this is going to affect the people around me? That gives us a much wider view to understand how we can create so much more impact than just looking at our insular team. 

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Are there certain strategies, tactics, or mindsets people should be adopting to shift from being a good manager to generally more effective leader?

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This is one that I wish someone had told me early on. I remember the very first person that I managed, and thankfully I'm still in touch with her. She doesn't work in my space anymore, but we still talk a lot, and I wish someone had explained to me that we are not just born managers. We become, and so we actually need to get into the mindset of always being a student and a learner. Every single person we meet, we have an opportunity to be both a student and a teacher too. So, when we think about how to be a good manager, how we can be a good leader, we have to constantly be willing to learn. I often try to push clients more when we're talking about whether it's their first time in leadership or whether maybe they're in a scaling company, and so they're about to embark upon just a new level of leadership and what that means. We need to start looking at who's been there before, who can I learn from, how can I invest in myself? How can I possibly be a student of management and leadership rather than just thinking I should? This should come naturally. So many leaders give themselves a hard time for not performing, or not performing how they think they should perform, or not just getting it, when really experience and leadership comes through learning.

So, I think we need to shift our mindset, in general, around leadership to think about it more in terms of an investment and an education opportunity rather than something that should just come naturally. It's also sometimes difficult to think that way because in many cases someone is promoted into manager, right? So, it feels like, “Okay, I should know all these things. I should be good at this because clearly, I got promoted,” or “Clearly, I'm being recognized for this.” Then, when there is something that they're not sure about, or there's a struggle, it's harder. It can be harder to ask for help because you're like “Wait, I got promoted, I'm supposed [to be] really good at this, what's going on?” and then the imposter syndrome kicks in, and it just becomes a vicious cycle, potentially. I find that senior executives, also, aren't always as forthcoming as they could be around the fact that they've had to learn this too.

If you think about some of your early leadership examples, and you look at some of the senior leaders in your company, and to your point about imposter syndrome, you kind of give yourself a hard time thinking “Well, gosh, they're so strong, right? Look at how they're able to weather adversity. They just seem to know these things.” And so, you don't think about the amount of trial and effort, and you don't talk about the amount of trial and effort that they've had to go through, probably, to get to that point where they are. I think having more of these open conversations, and this is what I love about reading memoirs [from] CEOs and leaders is that you just get to learn about the adversity that they face and what they learned from it, so that hopefully you can learn from their mistakes and maybe help build a higher performing team earlier on and make some of those decisions that they wish they had made.

I didn't even know what executive coaching was. I didn't know that all these leaders had a secret weapon and all the support that they had to become as effective as they were when I was early in my career. Even the first time I became a manager, I was like “Wow, why does this person just seem to be so composed, so confident?” and the amount of work that can happen behind the scenes is so rarely shared and discussed. Plenty of leaders that you see on CNBC and CNN, they had media  training. Oftentimes companies will invest tons of money in their senior executives, but it's just like plastic surgery. You don't talk about it because it’s just like “No, I just woke up like this. No, I'm not aging.” It's kind of a similar thing with leadership, and it's one of the reasons why I love what you're doing at Outpace because you're democratizing this access to coaching in a way where it just becomes natural to have support.

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I don't have to wait until a certain point. I can ask for it. I can get the help that I need now, so that I can lead a healthier organization going forward so that five years from now it doesn't become “Oh, we should have done this five years ago.” As part of that, when you've been working with senior management or other executive teams, are there other secrets or important things that people should know and consider in showing up as a leader and working with executives?

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Yes, one of the biggest learnings that I had that changed my trajectory in companies as a leader that I wish more leaders who were on the precipice of executive leadership paid more attention to and knew was really doing the deep work to understand what was important for the senior team.

So, for instance, when I worked at public companies. I started listening to the quarterly earnings.  When I started reading the 10-Ks, when I really started paying attention to if my CEO, or my COO, or my executive team was speaking at any sort of major conference, that I could get the transcript to understanding what was going on in the marketplace around us, in addition to what was top of mind for my senior leaders, and the major investment points where we were both succeeding and where we were struggling, iIt enabled me to have perspective and have filters put on. Anytime I proposed action or  prepared communication to the executive team, it o equiped me with knowledge so that I was able to build and propose new business models and ideas to the team in a way that spoke to directly what their needs were, so it wasn't about me and what I thought. It was about my knowledge of what the company needed, and where we were hurting, and it enabled me to connect to what the company was doing in a way that helped me both help the company and grow my career. 

For any leader who is just in that place where they want to grow, they're getting access to senior leaders. They're in that pivotal growth area. You must do the research to know what's important to your senior leadership, so that you are not wasting their time, so that you're crafting communication that just hits and that establishes you as a leader that knows what you're talking about and can obviously grow within the company as well. So, do take that time to listen and do the research. 

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That's such great advice. At face value, it can seem so obvious, yet in the day-to-day, it's easy to get caught up in the meetings, the work, and not make time to do these really important, higher level strategy things and taking the time to pause, reflect, and really try to synthesize all those insights that you might be gathering from a quarterly earnings report. Were there some ways in which you practiced accountability in leadership? Or how did you incorporate that into your life?

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Well, I put them on the calendar, and I created them as non-negotiables because once I started to see the effect that it was having on my career, the fact that I was able to sit in meetings and impart knowledge or come from a place that was knowledgeable, people just automatically started looking to me as a thought leader within the company.

The more that connection is starting to be, the more that you understand how important it is to create and guard that time. But that is honestly the other thing that dovetails with what I find most leaders aren't doing for themselves these days, which is investing in themselves and creating the time to do so. Often in my coaching sessions with leaders, it's about them going from fire drill to fire. They have pressure from the tops down. They have pressure from the bottoms up, and there's stakeholders on the side, and they are just trying to serve everyone at the same time. And so what falls by the wayside, of course, is any time for them to focus on their own development, whether it's development in themselves as a person, development in themselves, and development in their career, or just time to do research and time for deep strategic thinking. Those are the first things that tend to fall off the calendar when really those are some of the absolute most important things that leaders can need to protect because those are the things that not only elevate their career, but that gives them the energy to keep pouring into their [work].

I would love to see a future [where] companies are helping leaders protect that strategic thinking time, protect that personal investment time because the more energized leaders we have in the corporation, the more ripple effects that's going to create because then their teams are able to react to that energy and then can build wonderful products themselves and have the energy to then give back to the team, as well.

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Absolutely. This kind of touches upon the next question, which is that it sounds like that is one of the most common mistakes that managers and leaders make when it comes to managing teams when they're in that position and you do have so much pressure. What's been effective for you and what has been effective in what you've seen other leaders do? Do you decide, “Okay, I can ignore this for now and focus on me and my development for the time being”? Or how do you prioritize and make those decisions?

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One [mistake I’ve noticed leaders make] is believing that they have to wait to make these investments in themselves. So often, I see early leaders or people who even wouldn't call themselves a leader but have the aspiration to be one, thinking, “Well, I'm just going to put my head down and do the work, do the work, do the work, and then either someone will acknowledge me or then it'll be time for me to actually invest in myself.”

And investment can look so many different ways, I would argue. Having fun is an investment. Being creative is an investment. Thankfully, we're getting to a time of consciousness in the business world where we see the power in creativity. It's not just about punching in and punching out. Digital revolution has given us access to be able to work at different times, in different places, right? The whole definition of work is changing. What an amazing time to be part of the workforce in general.

I see we're still kind of trying to fit ourselves in this mold of the old way of working. Really, we have the ability and the agency now to really rewrite the way that we think and the way we approach work. So the biggest piece of advice I would have for someone who's maybe wondering how to invest in themselves or what to think about? Obviously coaching is a big one for I'm a firm believer in having the support system of a coach or a wonderful company like Outpace to work with, but start getting curious about yourself. Start thinking about, “What do I really like doing? What are those times in my work where I'm in the flow? What [are] flow moments? What [do] those flow states look like for me and what am I doing at that time? What are the skills that I'm using? Where do I like working? Do I like working out of an office? Do I like being a nomad? How am I programmed as a person?” 

You set yourself up for success using all of that knowledge that you want to unearth about yourself. Then it's about looking at your circumstances around you: that you've built the company that you work for, that you'll lead the part of [the team] that you're with today. What else can I do here to help me operate at my absolute highest level? We have not been curious enough about ourselves in the way that we work to build a life around that, because that is what enables us for longevity in our careers. When I think about burnout, when I think about the symptoms that I see amongst a lot of high performers, it is about not taking that breath and not taking that time to just take a momentary intentional pause for reflection so that we can make sure that we are still aligned with the things that we enjoy, with who we are, with where we're going. And that could be both personally and professionally. But if we don't do that, we get to this point where we pick our heads up, we go, “Wait a minute, how did I get here? Am I happy? I don't know.” So the more that we can get into a groove of taking that intentional time for ourselves much earlier on and with a much more regular cadence and creating and protecting that time, that's the biggest investment point that I see and that's my hope for future leaders, is that we just start to learn that, and that seriously is a skill. 

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That needs to be said 10,000 times over to those who have just begun leading a team. Effective leadership truly starts with yourself. Speaking of, what are a few key behaviors or characteristics of really effective leaders that you've observed over the course of your career and the people that you've coached? 

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Again, it all honestly comes back to communication because I think what leaders really [need] to do to be effective leaders, [is] to harness and grasp the concept that you are the filter. You truly are the filter between the information that's coming to you from the top down, that you then need to pass on to your team in a way that still motivates them to come to work to understand how they're a part of that bigger picture.

But then when you think about it from the bottom up as well, you are then the filter to the information that gets passed on to that senior executive team and to those leaders. So from a gatekeeper perspective, you are actually one of the most important assets to a company because you are sitting in that critical point of protecting the knowledge flow amongst all levels of the companies.

So being able to communicate, being able to be that filter and to communicate with intention and to know where you fit is a part of that whole story of the organization. And what they're trying to accomplish in that mission is absolutely critical to your ability to thrive as a leader in any corporation.

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It is so challenging, I think, for people to really take a step outside of their own goals and perspective, to really see that bigger picture and understand exactly how they fit in amongst the overall organization. And doing things like reading articles about the trends or understanding the C-level perspective helps you fit yourself in the picture more effectively than just staying in your silo and your team.

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One of the things that we haven't touched on yet is the concept of trust. Because also the greatest leaders that I have ever worked with or under or have studied have all had the skills to enable a culture of trust within their organization. When I say trust, it is about helping your team feel, seen, heard and valued. Those are the core elements to building a high performing team.

I mentioned that negotiation [at CBS]. We were working all hours of the day, sometimes in a conference room eating junk food at 2 a.m. just to stay awake. We hadn't seen our families in way too long. But we all had established such trust amongst each other and we all knew what we were working towards so that it enabled us to have the energy to keep going and do what we were building. We could look at the person in the foxhole to our left and we could look at the person in the foxhole to our right and say, “You know what? I know you have my back. We're in this together.” And that was what really enabled us to come out with the results that we did.

So as a leader, you want to look at: Is my team seeing each other? Are they hearing each other? How are we in those micro moments of every day showing that we value each other? Because when the rubber meets the road and things get tough, as they most often will, what sets teams apart is when you've done that work to communicate and create the trust within a team so that when it does get tough, you're looking to your left and your right and saying, “You know what, I am in a good place and we are going to come out of this stronger than ever.” Rather than having a team that wants to bail on you. That is what I've seen to be the major difference factor in teams that have grown together and teams that have cracked apart. 

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Thanks, Amy. That is just such an important observation and also feels like it's a great parallel for marriage. Are there any other final thoughts or strategies you'd like to share with us? 

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Really trust yourself. We talked about trust amongst a team, and you really need to get back to basics to build trust with yourself, to understand that at any given time, you are doing the best you can, [with] all of the knowledge that you have. So leaders also in this time need to give themselves a little bit of grace.

I think back to everything that's even gone on this week in November, when we're taping this interview right now, the election cycle, the announcements of mass layoffs at so many different companies not only this week, but that have been happening for the last few quarters. It's a really, really interesting time to be looking at companies that you would have considered stable right now, having to go through a new layer of metamorphosis.

So we all need to just take a step back and reevaluate where we are in our careers, who we're becoming, become comfortable with ourselves, really just get back in tune with who we are, and know that at the end of the day, we're all trying our best, right? Give ourselves that grace to stay in tune with ourselves, our skills and what we want. Reinvest in yourselves that you can come out of any situation much more strongly than you went into it. 

If you're interested in up-leveling yourself as a manager, check out Amy's Outpace Guided Program: Managing a High Performance Team.

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