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5 Things You Need To Know To Successfully Manage a Team, With Keith Valory the CEO of Plex

If I could inspire any movement, I’d inspire corporations to figure out how to make charitable giving profitable. I believe it can be. In…


If I could inspire any movement, I’d inspire corporations to figure out how to make charitable giving profitable. I believe it can be. In the media space, it should be fairly easy. We’ve already seen that aligning artists, content creators, and big brands with causes that they care about helps everyone win: artists promote causes that are important to them, companies get the positive brand halo of doing something good, and the cause gets precious resources. I believe this can (and should) work in any industry. We’re still a small company, and we’ve made great progress in charitable giving every year, but I still want to figure out how to make giving more to charity better for the bottom line. There IS a way.

I had the pleasure of interviewing Keith Valory. Keith is CEO of Plex, the streaming media app that organizes your favorite content and streams it to all your devices. Keith and his team are working to provide consumers an easier way to discover, organize, and enjoy the content they love. Keith has nearly two decades of experience in executive and founding team positions spanning several industries. With a highly-customizable and easy-to-use interface, Plex boasts millions of users and is a Top 10 most-watched app with 4+ star ratings on all major OTT platforms.

Thank you so much for doing this with us! What is your “backstory”?

With a law degree and an MBA, I started my career as a corporate securities lawyer at a swanky Silicon Valley law firm in the late nineties working on IPOs, mergers and acquisitions, and venture capital financings. After a few short years, I realized I really wanted to help build companies and be more committed to a single mission — those start-ups were having all the fun! So I did the unthinkable (in those days), and left that cushy law firm to join the management team of a promising start-up called IronPort, which several years later sold to Cisco for almost a billion dollars. After a few years building the security business at Cisco, I helped start a cloud security company with a few of my IronPort friends that recently sold to VMWare. In 2013, I had the opportunity to work with some of my best friends and serve as the CEO of Plex — we’ve been having a blast ever since!

Can you share the funniest or most interesting story that happened to you since you began leading your company?

When we were raising our first round of venture capital financing at Plex, we were in the unusual (and enviable) position of being cash-flow positive and profitable. Wait, What? A little Series A start-up that was profitable? Nope, can’t be true. Anyway, a bunch of VCs loved this. A bunch of VCs couldn’t comprehend this. I remember one awesome meeting on Sand Hill Road when we got to the literal “money slide” where there were a number of green bars going up and to the right (I learned that in business school!) clearly labeled “profit.” Again, “profit.” So I was waxing philosophic about how we are going to rule the world while this very respected venture capitalist was staring intently at the slide (obviously not listening to … ahem … a brilliant word coming out of my mouth). When I finished there was a very awkward long silence. Then he asked, “Sooooo, what’s your burn rate?” Ummmm.

How do you synchronize large teams to effectively work together?

Whether you have a distributed team, like we do at Plex, or everyone under one roof, building a company with a great culture that works together effectively is challenging. As our remote organization continues to grow, we’ve learned a few things that have helped us build a talented, efficient, fun, and distributed team that we all love being part of.

Tools and dashboards that report priorities, check-ins, accomplishments, and milestones in real-time are invaluable and keep all of us accountable. We don’t have to punch a time card, and nobody has to look over our shoulder, but we still have near-perfect visibility into what everyone is doing. So people are free to balance their work and home life in the way that works best for them, and we trust them to get their job done without worrying that somthing might fall through the cracks.

We also use traditional systems and goal setting tools like Objectives and Key Results, often called OKRs and we have implemented a 360 degree review process that ensures everyone in the company, including myself, receive anonymous constructive criticism (and praise!) twice per year. If someone is consistently not pulling their weight, they can’t hide! But more importantly, when people are doing something special, it is recognized, recorded and replicated.

What is the top challenge when managing global teams in different geographical locations? Can you give an example or story?

While perhaps the most obvious answer, different time zones are certainly a challenge, though not impossible to work around. The inherent challenge is ensuring effective communication. We realized fairly quickly that we had to have a set of tools that could stand on its own in the absence of daily in-person interactions and meetings. We developed a simple, yet powerful dashboard that provides real time visibility for everyone in the company. It includes information like who is currently working on what team, company priorities, team priorities, project due dates, weekly status updates, etc. In addition, we use a number of great commercial productivity tools such as Slack for real-time communication, Github for code management, Hangouts and Zoom for video conferencing and Trello for project prioritization. Whether your team is distributed or local, it is so important to implement the right tools for clear communication, visibility and context setting. Having everyone sit in the same room won’t necessarily solve the communication challenge for you. In fact, I’ve been in a number of co-located teams where presence is taken for granted and leaders just assume everyone has the context they need to do their job the best they can — it takes work regardless of whether your team is distributed or co-located.

Even with the right tools in place, we’ve found that people actually work harder at communicating across the organization in a remote environment — they have to. Especially if you’re dealing with an international team that is communicating in a single language, you have to make extra effort to be clear and thoughtful in how you deliver messages and points. Just like it is often hard to convey the right tone in written communication, cultural nuances are easy to misunderstand and must be accounted for. So teams have to be more considerate as they work together — and that is a good thing!

There are benefits to a geographically distributed workforce too, not just challenges, which include opening your pool of potential candidates to anyone in the world, not just people that are able to commute to your “office” every day. Also, having people working across timezones ensures your company is always “on” and being productive around the clock. Lastly, having people in different locations helps to promote a more culturally sensitive product. This goes beyond having local language support, and includes things like being sensitive to linguistic nuances, user interface preferences, and customer use case priorities for different people around the world. It’s challenging to create cultural empathy for international customers if the vast majority of employees all live and work in the same place. Plus, having designers around the world means more perspectives and artistic talent from unique backgrounds, ultimately leading to a more beautiful, thoughtful, and impactful product.

What advice would you give to other CEOs or founders to help their employees to thrive?

Be kind. No act of kindness is ever wasted. When everyone on your team comes together, when they genuinely care about each other, and when they want each of their teammates (not just the company) to be successful, the end result is very, very powerful. Work gets done faster. The quality is higher. Morale is better. And, importantly, it is way more fun.

Most times when people quit their jobs they actually “quit their managers”. What are your thoughts on retaining talent today?

We’ve made kindness and helpfulness our two top hiring criteria. A friend in human resources once told me that she measures the health of an organization by how helpful its people are. I’ve still not found a better measure for either office or remote environments. If you really focus on hiring kind and helpful people, I guarantee that communication won’t be a problem — even if your tools and processes aren’t perfect — and you’ll have a very healthy organization. And a happy one.

Based on your personal experience, what are the “5 Things You Need To Know To Successfully Manage a Team”. (Please share a story or example for each, Ideally an example from your experience)

1. A manager must learn how to listen. I mean really listen. Have empathy for your team. So many young managers get wrapped up in the responsibility to lead and manage, that they forget to step back and let good people do good work. If you’ve hired good people, then listen to them. 95% of the time they SHOULD know better than you what the right answer is. If you’re always coming up with the answer, you’re holding it wrong.

2. A manager must learn how to have hard conversations. Everyone wants to be liked; even managers. And I actually believe it is good to be friends with your employees (many disagree with this). We spend so much time with each other. If we can’t truly care about each other, root for each other, pull for each other, then what’s the point? But at the end of the day, you’re the manager. It’s your job to manage and keep the team heading in the right direction. Often times that requires an uncomfortable conversation — humans are tricky. If you can’t effectively communicate in a hard conversation, an uncomfortable conversation, then you’re in the wrong job.

3. A manager must come to grips with their own strengths and weaknesses. You’ve heard the old adage: Only hire people that know more than you. That is not always literally true, but you should be looking for people who have strengths that you don’t so that the whole team is much stronger than you. An old boss of mine used to refer to this as his “Guns of Navarone.” Each one of his team members had a special skill (what we called “their brand”). Just like the movies touted the explosives expert, the comms guy, the weapons guru, he had his legal expert, his marketing genius, his sales savant etc. He had some of these talents himself, but he made sure that they were all far superior to him in their given field. If a CEO wants to be the smartest person in the room in their given area of expertise (maybe she was a VP of Sales, or CFO, or CMO), then she should quit and go back to that role.

4. A manager must learn to know when to cut their losses. This is true of any business decision from hiring mistakes to investment decisions. It isn’t always easy. It can wound one’s pride to admit they made a mistake, and so often we see leaders double down on mistakes to try and prove themselves right. Speaking from plenty of experience with making the wrong decision, the troops respect righting a wrong WAY more than doubling down on a wrong.

5. A manager must learn to inspire their people. This is a toughy for me. I’m not the guy who is going to get up and give a rousing speech that has the troops charging the hill with wooden rifles to win the battle. It’s not me. Even if I tried, it wouldn’t be authentic. A person who worked for me once told me, “Dude, you could stand to be a little more inspiring.” So I had to figure that out for me. I settled on uber-transparency. I’ve found that for me, being super open and honest with the team, communicating early and often, and never pulling punches (in a respectful way), resonates really well with my team. Is it inspiring? I dunno. You’d have to ask them. But I do know that I couldn’t ask much more of them — they absolutely kick ass!!!!

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

If I could inspire any movement, I’d inspire corporations to figure out how to make charitable giving profitable. I believe it can be. In the media space, it should be fairly easy. We’ve already seen that aligning artists, content creators, and big brands with causes that they care about helps everyone win: artists promote causes that are important to them, companies get the positive brand halo of doing something good, and the cause gets precious resources. I believe this can (and should) work in any industry. We’re still a small company, and we’ve made great progress in charitable giving every year, but I still want to figure out how to make giving more to charity better for the bottom line. There IS a way.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

Seriously, any famous quote on gratitude will do (there are so many!). I tell anyone who will listen (especially my kids) that the key to happiness is being grateful (and the key to not being happy is feeling entitled). Grateful people are better in every way. It is tough to look for when hiring, but I do my best.

Originally published at medium.com

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