Leadership Today: Using Coaching & Questions to Grow Your Business | Steph Korey | Skillshare

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Leadership Today: Using Coaching & Questions to Grow Your Business

teacher avatar Steph Korey, Co-Founder, Away Travel

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Taught by industry leaders & working professionals
Topics include illustration, design, photography, and more

Watch this class and thousands more

Get unlimited access to every class
Taught by industry leaders & working professionals
Topics include illustration, design, photography, and more

Lessons in This Class

    • 1.



    • 2.

      Leading as Coach


    • 3.

      Principle 1: Consistent Feedback


    • 4.

      Principle 2: Asking Questions


    • 5.

      Principle 3: Embracing Mistakes


    • 6.

      Final Thoughts


    • 7.

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About This Class

The secret to growing a successful company? It's all in how you lead your team.

Join Away CEO and co-founder, Steph Korey, for a 30-minute class focused on how the most successful, fastest-growing companies stem from building and coaching great teams. You'll learn the three key leadership principles Steph uses to shape and empower a team that's eager to take risks and get creative, fueling Away's stratospheric rise. From giving effective feedback, to embracing mistakes as a business advantage, Steph’s lessons are packed with actionable tips to start using right away. You'll learn how to:

  • Lead as a coach, not a judge
  • Give consistent and effective feedback
  • Embrace mistakes as a business advantage
  • Ask questions to empower strong decision-makers

Whether you're already leading a team or are an aspiring manager, after taking this class you'll see a new way to interact with and create effective teams. You'll have the tools you need to build a team that will truly care about your company, do amazing work, and grow your business in a meaningful way.


Meet Your Teacher

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Steph Korey

Co-Founder, Away Travel


Steph Korey is an entrepreneur, lifestyle innovator, and investor. In 2015 she founded Away, a $1.4 billion company focused on making travel a seamless experience. Away was named Fast Company’s “World’s Most Innovative Companies” twice and Steph herself was listed in Forbes “30 Under 30 list” for Retail and Ecommerce in 2016.


Steph graduated Brown University with a B.A. in International Relations and earned an MBA from Columbia Business School.


She has worked in product development, manufacturing, and fulfillment at Warby Parker and as a merchandising and supply chain consultant for Casper. Steph is committed to bolstering and empowering innovators from underrepresented backgrounds.

See full profile

Level: Beginner

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1. Introduction: Hi, I'm Steph Korey and I'm the Co-Founder and CEO of Away. Away is a little over two years old. We are a travel branch. We started with the perfect luggage and as a business right now we're expanding into the perfect version of everything you need to travel seamlessly. In this class, I'm going to walk you through a few of my favorite management and leadership principles and how I guide and lead our team. The three principles we're going to talk through today are giving regular and consistent feedback, asking lots of questions, and embracing mistakes as a business advantage. I think, more than anything, these three principles have led to a lot of the success and growth that we've seen in our company. They've been really consistent from day one and they are three things that we continue to double down on as we look towards the future. You're competing against companies that probably aren't as thoughtful about management and leadership and if you can be the most thoughtful company about these guiding principles, that can be the single biggest competitive advantage you have as a business. Throughout this class, I'll be giving you ideas and asking you questions that will help you be able to think about how to start implementing these principles today. I'd love to hear which one of these principles resonated the most with you. So feel free to upload a discussion topic to the project gallery, so we can all talk about it. Thanks for joining the class and let's get started. 2. Leading as Coach: We're going to be framing our discussion today on leadership as a coaching model instead of a judging model. When you're managing someone or you're a leader, if you treat your relationship with them like a judge, it can induce a lot of fear in what the person's working on because they feel like everything they deliver, everything they put out is going to be judged as either, "This is good. This is bad." If it's good, great, we move forward. If it's bad, you messed up and there's nothing we can do about it now. That judging model is like there's a final decision on everything you do can be really demotivating and does not facilitate a growth mindset at all. So, we really like to, at a way, facilitate a coaching model of leadership and management, where whatever it is that your team members putting out, whether it's good or whether it could use some refining and improvement, everything's just a jumping-off point to continue to learn, and grow, and expand your skills, and always get better. Even the good things can get better. So, we really like to take this coaching mindset of everything's a starting point, and then we're going to learn and grow and get better from here. When we talk about coaching, I think sports coaches are actually a really good analogy to this. Because if you think about what a sports coach is therefore, they're there to help their players get better and work together more seamlessly and as a team, operate more fluidly and give them the exercises and training they need as each individual person to keep being their very best and getting better and better. If you're coaching someone, you are helping guide them on, "Here's the goal or outcome we're hoping to get to. I know you're really smart and I know you're going to come up with a really thoughtful approach to getting there. If you need any help, come ask me questions, and I'm happy to chat with you. Otherwise, I trust you and have at it, and we can talk at the end." We take a coaching mentality to our team members from the day they start the company. For some people, if they're coming from a more judged leadership environment before Away, it can be a little bit jarring to them. Like, "Why is this person taking all this time to give me feedback on my work? Why is this person taking all this time to talk to me about what my goals are, and what I think my strengths are, and what I think my weaknesses are and how he can work on them together?" It can feel like a lot at first. But what we've seen over time is that as people get used to that style, they really appreciate it and they really see how it helps them grow and develop personally in their career. We've had some people at Away say that in the year they worked here, they think they've had 10 years worth of career growth and learning. So, when you have all of these individuals learning and growing at such a rapid pace, it really just elevates what the company can do and what the whole team can do together. Even though this coaching mentality takes more time, it's completely ROI positive for a business. It's time-intensive. You're investing that time, but the return you're getting on it from how the team is growing and how the team is working together is absolutely worth it. It's never been a question in my mind. So, with this coaching mentality, not only does it allow you to learn from the things that didn't go well, but it allows you to learn from the things that do go well also. Almost nothing we ever do goes as well as a cut out off. Even the most successful project in the world, there's always something that you could have done a little bit better. Instead of being like, "Great. The project was a success. I have nothing to learn. Pat on my back." If you have the mindset of, "It's great. The project was a success. Here's the one or two things that we could have done even a little bit better." That mentality really helps you have a competitive advantage as a business and always be improving even when the baseline you're improving from is already a really high bar. So, this kind of trust that we give people, it's not only for a autonomous work. We are a highly, highly collaborative environment at Away, there's so much teamwork. One of our core values is that we're in it together. Another one is that we're thoughtful. So, when we say we like to give our team members a lot of leeway to operate independently, it doesn't mean operate independently for independent work. It means operate independently from your manager on all the different types of work you're doing. A lot of which is collaborative projects and working together, but we want our managers to empower their people to collaborate and find teamwork methods that work for them without being under a microscope or without being micromanaged on how to do that. As long as we all have the same big picture vision and the same big picture and goal, we know we're all marching in the same direction. Everyone should march the way they see it best. As you can probably tell, I'm really passionate about coaching in this style of leadership. I'm excited to walk you through my three most important principles for executing on this. First stop, we're going to talk about consistent feedback. 3. Principle 1: Consistent Feedback: When I talk about consistent feedback, I quite literally mean just keeping an open dialogue all the time with the people you lead and manage on how things are going, and what they're doing well, and where the learning opportunities are. I think at some companies, you'll see feedback gets saved for like an annual review or a semi-annual review and then someone spends six months or 12 months operating in a way where on one day you're just going to give them a dump of information of, "By the way, here's all the things you haven't been doing well for the last six months." That's not a coaching mindset. That's not productive. And you missed a lot of opportunity for everyone there. So, at Away, we say, "If you spot an opportunity where someone on your team could have learnt something, or they did something really well and you want to continue to encourage that behavior, or there was something they could have done a little bit better, don't wait till the next tracking, don't wait till tomorrow. Just tell them. Just tell them right now." And when you keep it really consistent and keep it really real time, it takes the pressure off of feedback. It makes it not a scary thing, it makes it not a strange thing but just like this constant, open dialogue that's really healthy and really allows everyone to grow and learn every single day. A lot of the times when people are just getting started at Away, they do feel overwhelmed by this constant feedback. But ultimately we find that it does lead to higher retention especially for people who have that growth mindset and who can become comfortable with wanting to learn and grow. And the reason for that is, you just personally grow so much faster when you're getting regular feedback and coaching and guidance on how you can become better. So, people find they're elevating the type of work they do. They're taking on bigger projects, the type of sort of career growth even from like a promotion and leveling up perspective that another company might take years. At Away, it might take a few months or six months to get that several years of career progression because you're sort of on turbo speed of like learning, and growing, and iterating, and being more thoughtful, and understanding from an outside perspective what it is you could be always doing better. Everyone at Away has a weekly 30 minute check in with their manager. And the thought behind that was with that regular frequency, you really can break down the barrier of up to my manager and I have a trusting relationship about my career growth and my interests and where I'm going. So, we guide people in these one on one meetings that the first question is normally, "How are you doing? How are things going?" And because it's not a project status update, so in a project status update it can be like, "My projects haven't changed that much from a week ago, so I don't have that much to update you on. But how are things going? How can I be helpful? What are you hoping to learn? What parts of your job are you really excited about right now?" You can really uncover a lot about what motivates someone and where they're excited to grow and develop. And that relationship that you build through that of like, "I care about what you care about.", really builds that trust and results in team members who continue to evolve their role into something they're going to be really engaged with and really excited to jump out of bed every morning and learn, and grow, and add value to, and that mentality is a lot of what's allowed us to have our top people stay at the company, and keep learning, and keep growing, and keep adding more value to the business. The one on one check-ins aren't where we do real time feedback because while once a week may seem frequent, it's not frequent enough for that. So, what we got our managers to do is, if you spot anything you're team member has done in real time, whether it's really amazing or something that had an opportunity to be done even better or have some different principles applied to it. We encourage our managers don't wait, just tell them right then, tell them right in that moment, "Hey, I spotted something and I wanted to share my thoughts." And that way, it really takes the pressure off of, "I'm just getting this feedback all the time. So, it's not a big deal. It's just happening as things happen." And then, in the one on one check-in, what you can do is circle back on that and have a conversation of, "We both had time to digest this for a few days and I would just love to get your perspective on that feedback I gave you. And, was it helpful or do you think it applies to that type of situation in the future? Is there some way we can build on it to make it more useful?" And that way it's a really collaborative process. And you still have the opportunity to give that constant real time feedback in the moment but now you can use your check-in as an opportunity to continue to build that trust, and circle up on it, and build on it, and be really thoughtful. One thing we really guide our managers on is across the company, we should be starting with the presumption of positive intent. So, even if something didn't go that well, you have to assume that everyone was trying to have it go well. So, no one has malicious intent here and no one's trying to mess something up or trying to make a mistake, we're all trying to do a good job and learn and grow. So, that presumption of positive intent going into any feedback conversation is so important because it really puts everyone on the same team. Part of what we also try to encourage is, directness is really important but empathy is really important. So, if you're super, super direct but you're not showing empathy, it can really come off more like judging than coaching. Like, "Hey, here's what didn't go well here. Work on that for next time." That's judging, that's not coaching, because you don't have that empathy part of it and that's where things can go wrong. On the opposite side of the spectrum, if you aren't direct enough and you're so empathetic that you lose the message a little bit like, "Hey, I know you're working so hard on this and this was great, and this was great, and there was this like tiny thing that maybe could have been done slightly differently, but everything is amazing, and you did such a great job, and I'm so proud of you." That person is going to come out of the conversation having not learned anything. So, that was ineffective also, so you really want to have that right balance of empathy and caring but also directness where the person can come out of the conversation being like, "I totally get what was just communicated to me." So, if you're at a company that doesn't quite practice this regular constant feedback mentality, whether it's a small company that's just getting off the ground or whether you work at a really large company that just doesn't have this culture, you can still start implementing this. And what I recommend is, you don't want to just dive and do it without telling anyone what you're doing because that can feel really confusing, if it's really different from what people are used to in your own company. So, you really want to have an honest thoughtful conversation and say, "I want to build more trust and directness in our relationship. Here are the benefits that I think there are for you as a member of my team and how you'll be able to learn and grow as a result. And also for our whole team more broadly and how we'll be able to work together and the company more broadly beyond that." So, you really want to explain, "Here's why I think we should be doing this. Here's what I think the benefits are for you personally and more broadly. And here's what I think it's going to look like and I would love your feedback on if that's something you're interested in." That way you really start building trust in the relationship and you avoid it being jarring and coming out of nowhere. So, I hope after listening to this lesson that you took away some of the benefits of really giving constant and regular feedback, and next stop, we're going to talk about a related principle which is asking lots of questions. 4. Principle 2: Asking Questions: One of the most important things in our leadership and management at Away is the concept of asking a lot of questions. In a more traditional company, you might see situations where someone's manager is just saying, "Do this," or "Next time this happens, do that," and it's a lot of sentences that end in periods. At Away, we don't take that mentality at all. We like to end every sentence from a manager to a member of their team with a question mark. By turning it into a question, you make it a dialogue where, one, you get to get the expertise and input from your team member who frankly knows a lot more about what they're doing than you do. Two, you get to have everyone around the table have a lot of engagement and buy in over the things you're agreeing to do. No one likes to be told what to do. No one likes to be told what to do when they think it's the wrong thing to do. So, by really soliciting the feedback and input of everyone you're talking to, and making sure everyone agrees it's the best path forward, you end up with better decisions, and more buy in engagement from everyone around the table. One of our business's biggest competitive advantages is that, through asking a lot of questions, we really guide all of our team members at all levels to be thinking strategically. You don't see that at a lot of more traditional companies. Normally, you have maybe a strategy or an innovation department, and they're thinking strategically, or maybe a leadership team is thinking strategically, and everyone else is just taking directions that end in periods, and executing on them. Maybe they don't know why they're executing on them, or maybe they had an idea of a way to do it better and to actually be more strategic, but they don't even have a forum for voicing that. So, those businesses end up not being as successful because everyone isn't as empowered to think outside of the box, or speak up when they have a better idea. At Away, we really create competitive advantage by turning every single member of the team into both being strategic and being an executor. Every once in a while, I get an informational candidate that's reaching out to me and saying, "I want a job in strategy at Away," and I always tell them the same thing. There's not going to be a job in strategy at Away, everyone does strategy at Away. So, at a more traditional company, a lot of what you see is the more senior you get the more your job becomes all about making decisions, and we have turned that totally upside down. So, at Away, the more senior you get, the less decisions you make, the more you guide people into making decisions. By sort of disaggregating that power and that decision making power, you end up with better decisions because you have the experts on the ground making the decisions with your guidance of how to think through things, and because you're asking a lot of questions you're guiding them to the best decisions. From personal experience, I found a lot of situations where I have a little bit of a sense of what I think the right decision is going to be, but I'm never going to be the one to say it. So, I'll ask a lot of questions to try to guide the person into getting there. What ends up happening is, the answers to these questions lead us to a place that's a decision that's way better than the one I had been thinking initially because I didn't have all the info, and that type of question asking and having your team of people who you're leading and coaching and managing get the company to a way better decision than what their boss would have come up with, that's the success of this model. So, how do you actually put asking a lot of questions into practice? Every once in a while, a member of my team will come to me with a question. We have this option, we have that option, which one do you want to do? It's usually a newer member of the team if they're asking that because the people who have been around for a while know I'm not going to fall for that trap, and I'm not going to answer the question myself. Instead, I turn it around on them, and then say, "Which one do you think is the better option and why?" That sort of empowerment, turning the question around, or asking the other person questions, and allows them to if they're coming to me, it's maybe because they feel unsure. So, they'll say, "Well, I think option A is the better option, but I'm not totally sure," and then you just ask more questions. Why are you not sure? Is there additional information you would need to feel sure? What information is that? How can you get it? And all of these things under the question mark, and end up getting to a place where you're coaching the person into thinking through how do I make the best decision, what information do I need, and ultimately they know they're empowered to make the decision. I really try to avoid asking questions that are like yes or no questions or one word answer questions. A lot of my questions end with comma why. So, what do you think the pros and cons for this approach are and why? Or which direction do you think we should go and why? Because if you just say which direction do you think we should go in, the person might say, "that direction," and that could be the end of the conversation. So, the and why is how you really get the person to think more deeply and more strategically of why do I think this is the best interest of the business? What factors am I considering? What factors am I not considering? And that deeper thinking is how you get to the best decisions. One of the really important things to be mindful of in this tactic of ask a lot of questions is to be mindful of where the person is in their career and what types of questions they're prepared to answer. So, if you have someone on your team who's really entry level, this is their first job, you don't want to ask them questions of why is the strategy of your whole department what it is? They're probably not there yet. They're probably not going to be able to answer that question, and it can be disheartening. So, while you do want to ask questions that stretch people in their thinking, you want to make sure that the questions are still realistic for where they are in their learning process and their career development. Sometimes, you're going to end up in a situation where you're asking questions and the whole conversation is going totally off the rails, like it's going in the wrong direction, and there can be a temptation to just try to get it back on track by being like, "Okay, here is how we get back on track." But, I would encourage you to actually resist that temptation because I think you can still get there with questions. Your questions might need to become a little bit more obvious or a little bit more pointed. So, saying something along the lines of, "I don't know if we've been over this context yet. I feel like this context might be important for what we're talking about. Do you think it's important? And if so, how does that guide how we're thinking about this?" A lot of times in that situation, the person you're talking to will get to that realization of, "Yeah, wow that is important. We weren't thinking about it. Okay, that totally reframes the thinking here, and now here's where I think we should be going with this." For new members of the team, especially if they've come from organizations that have a really strong sense of hierarchy, where decisions are made at the top, we can sometimes get a sense early on that when they're asked questions, they feel a little unsure or a little uncertain, like, "Are they really looking for my genuine thoughts here. That's so weird. Maybe I should just try to guess what they want me to say and try to say that instead." You can tell when someone's doing that. So, back to the constant direct feedback as part of that conversation and the managers encouraged to just point blank say, "I don't want you to be guessing what I'm looking for here. I genuinely care what you think, and this conversation is really about what you think is best here." Our philosophy of leading with a lot of questions happens all day long on all channels. So, in my one on one check ins with people, I'm normally just asking questions. Even if we're in a Slack channel talking about a certain project or a certain topic, every once in a while, I'll get a question or someone's manager will get a question of what do you think of this? And the manager is almost always going to reply with, "What do you think of this? What do you think the pros are? What you can the cons are? What do you think the best direction to go in this and why?" So, it can be over Slack. It can be over email. It can be in person, but it's just really consistent that managers try to empower and encourage creative strategic thinking in the members of their team through asking a lot of questions. So, I hope you took away from this that asking questions is a really powerful tool for getting to the best decisions, and that as you grow in your career, you actually evolve into asking more questions and making fewer decisions yourself. Next, we're going to talk how embracing mistakes is a business advantage. 5. Principle 3: Embracing Mistakes: Next up we're going to talk about one of my favorite leadership principles which is embracing mistakes as a business advantage. At a more traditional company, mistakes are something to be avoided at all costs, and if you do make one, you better make sure no one finds out about it. I think part of the traditional company mindset and even to an extent human nature is that you avoid mistakes because you don't want to show any weakness, you don't want to show any failure, and if you have a 100 percent track record, maybe that helps your career and helps your promotion track. There is nothing negative to put in your performance review, and so there's all these sort of constructs that can lead people to feel like avoiding mistakes is the right way to go for their career. You're probably seeing this as a theme now but we've also turned that one upside down, and at Away we actually think if you're not making mistakes that's the problem. The reason making mistakes is so important is it means you are pushing yourself, you're getting outside your comfort zone, you're trying something new, you're taking a big risk, you're thinking outside the box, and when you do all of those things, you're never going to have 100 percent track record. Like if you're pushing yourself to that level, things will go wrong, you will make mistakes, and some things will fail. You might be asking yourself why is that something we would encourage? Why do we want people to make mistakes? It's a pretty simple answer. By swinging big, a lot of the time, you're going to have a big positive outcome and some of the times you're going to fail, but the benefit of those big positive outcomes totally outweigh the failures and make it totally worth it. But if all you do is play it safe, say you'll never make a mistake, you might have no mistakes but you have no big wins either. There are definitely different types of mistakes. So, the good mistakes which are the type we encourage are, I tried something new and I didn't really know that much about it, and here's what went wrong and here's how I learned from it. We actually really encourage people to share those learnings more broadly with their team or the whole company so that it's something we can all learn from, so that way the next time someone swings big, we're not making that exact same mistake again although maybe we're making a new different one. The types of mistakes we don't encourage are the ones we've already made. If we've already made that mistake, we should've taken the opportunity to learn from it so that as we swing big the next time, it's a new set of mistakes we're making and not the same ones over and over again. That goes back to why we encourage everyone to really share their mistakes and share the learnings with their team in the company. So, how do you actually start embracing mistakes as a company? In order to have the concept of embracing mistake's work company wide, it's so important that you give your managers the right guidance and training in how to handle mistakes and how to embrace them and learn and grow from them. So, part of what we do at Away is we think a lot about our guiding principles in terms of our core values. One of our core values is that we're iterative. What does iterative mean? It means we're going to keep trying new things all the time. We're going to keep learning from it, and it's okay that we keep learning, growing, shifting, everything we do. When we put that into practice, we encourage our managers that as soon as something goes wrong on your team, as soon as someone makes a mistake, this is not a moment to be a judge. This is a moment to be a coach and to coach them into how to being iterative. So, what have we learned from this mistake? What are we going to do differently next time? How are we going to put this into practice? And really guiding that iterative line of questioning is an important part of embracing mistakes and making it a true business advantage. One pattern we notice across the board at Away is people look up to leadership as an example of here's how I grow my career. Here are my role models who I should be trying to emulate. So, we think it's really important to show examples of our leadership being iterative or embracing their mistakes and learning from it and really sharing that more broadly across the team to set that example for everyone across the company of this is what leadership looks like here, it looks like making mistakes and being proud of that. Similar to our concept of constant feedback, learning from mistakes can happen in any channel or in any forum. So, sometimes it's something that gets discussed in flac in a channel of, hey guys I made a mistake and here's what I learned from it. Sometimes that can be a one on one conversation. If it's like a little bit more nuanced or everyone is still trying to figure out like, we know something went wrong here but what did we really learn from it. A lot of times that can start as an impersonal conversation to really dig into it and understand and it can happen in the one on one, and then a lot of times the recap gets written up and shared just to further that culture and environment of, I've been aware of my mistake proudly and I'm going to share it with all of you because now I've created an opportunity for everyone here to learn. 6. Final Thoughts: So you might be asking, some of these principles sound more up my alley than the other ones. Can I do some of them, but not all of them? I would actually say that all of them work together harmoniously. So, if you start giving a lot of direct and consistent feedback but you're not asking questions, then it can sound like you're ending all your sentences with a period and you're telling people what to do, and that feedback probably isn't going to be as well received. Or, if you're asking a lot of questions but you're not embracing mistakes, you can end up guiding your pupil to take some risks but then not making them feel comfortable when they don't do well and then will end up hiding their mistakes, or making the same ones over and over again because they didn't take the time to learn from it. So, I really think these three principles work in tandem and I would recommend if you're going to start doing one of them to start doing all three of them. So, if you're a part of a much bigger company but you're overseeing a smaller team within that company, I still think you can implement all of these principles within your team. I think the long term result hopefully in these situations and what's likely in these situations, is it works so well that it ends up growing your career and giving you new opportunities. Maybe at some point the pace at which it grows your career because you're implementing these things leads to you becoming the CEO of that company and then you can implement it for everyone. I think if you're switching to this type of mindset in an environment and with a team where they're not used to it, the first thing you want to do is just have an honest conversation with your team and say, "Here are some of the things that I think would help all of us be more successful, and grow as individuals, and grow as a team, and I want to get your feedback on it. What do you think of these?" So, you're a little bit starting with the questions there, but you're showing empathy and getting their feedback. I think you can articulate these things in a way where the framing will really help the person understand that this is in their best interest. Once you have genuine buy-in and the people on your team are interested in doing this that's when you dig a little bit more into, okay what's this going to look like? I'm going to write it down for you and we're all going to take a look at it, and chat through it, and iterate on if we think this is what makes sense for us. That way, if things get uncomfortable, you can really point back to that conversation and point back to everything you wrote down together to say, "We all agreed that this was going to be in all of our best interests, so let's keep giving it a try." I think if you embrace this in your own company and in your own culture, one of the biggest changes you'll see is really that all three of these things work together. If you're comfortable making mistakes, you're comfortable with direct feedback and constant feedback, you're comfortable with lots of questions and answering questions and being direct and getting to the bottom of things, and you're comfortable learning from everything you do. Really all these things work together just to create a much more transparent, and empathetic, and thoughtful, and collaborative, and growing culture at your company. If you have any questions definitely ask them in the discussion board and I'm excited to engage with you and chat through how you're implementing these principles in your own work and in your own life. Thanks so much for watching and good luck in developing your own team career and leadership style. 7. More Business Classes on Skillshare: