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“I think continuous learning and personal development is the key to feeling happy at any job.” with Chris McCarthy and Chaya Weiner

Changing something as significant as workforce culture can seem too big for one person. However, any change really does have to start with one person to ignite a spark and create a movement. As I mentioned, I think continuous learning and personal development is the key to feeling happy at any job. It is our […]

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Changing something as significant as workforce culture can seem too big for one person. However, any change really does have to start with one person to ignite a spark and create a movement. As I mentioned, I think continuous learning and personal development is the key to feeling happy at any job. It is our personal responsibility to be proactive about bettering ourselves, learning new skills, and pushing ourselves beyond our comfort zone. Challenging ourselves may seem counterintuitive to our own happiness, but boredom leads to unhappiness. We need to take initiative and identify skills we are interested in, request access to tools to acquire that talent, and then enjoy the satisfaction and joy that comes with accomplishing a new skill.

As a part of my series about about how leaders can create a “fantastic work culture”, I had the pleasure of interviewing Chris McCarthy, CEO of Degreed, a San Francisco-based startup that created the world’s first career long skill building platform. Prior to becoming CEO, Chris was the Chief Operating Officer of Degreed for five years. He specializes in strategy execution and has served in various roles at Chegg, Zinch and The Palladium Group throughout his career. Chris earned his MBA at the Harvard Business School, where he studied strategy and entrepreneurial management. He also holds a Bachelor’s Degree in Management, summa cum laude from Northeastern University.


Thank you so much for doing this with us! Can you tell us a story about what brought you to this specific career path?

I am lucky enough to figure out what I was good at and what interested me early on in life. I have been entrepreneurial for as long as I can remember, even starting a business in high school that still exists today. But my passion for education and learning started when I went to college to study entrepreneurship and was the first freshman in the schools history to win the entrepreneurship award. But the school wouldn’t let me adjust my class schedule to spend time building that business. I looked at the student debt I was accumulating and realized how broken education was. So I dropped out of college, took two years to get some real world business experience and travel. Then I decided the best way for me to keep learning was to go into strategy consulting and learn about lots of different industries and companies…sort of boot camp for a business career. Except no firm would hire me because I didn’t have a degree! It was one of those surreal moments. I had all these skills and unique experiences to offer, but the demand side of the job market was forcing me to go back and take on a life crippling amount of debt just to pass a toll gate. So I went back to a great school (Northeastern) that let me piece together my degree through night classes, day classes, testing out of basic things, work experience, transfer credit etc. I ended up finishing on time despite the two years off and got hired as a strategy consultant and had a great pre-mba career. If Degreed existed back then, I would have been better able to showcase my skills and move through my career faster. That experience plus the insane student debt crisis in this country led me to join a startup called Zinch after business school. Zinch helped kids get into college and pay for it and our motto was “I am more than a test score.” It was acquired by Chegg after 2 years and I ran that business at Chegg for 3 years. Through my 5 years there I learned more from people like Anne Dwane and Dan Rosensweig than at any period in my life. Anne specifically taught me what it meant to be a leader, and how that was different than being a star performer or being a manager. The chance to work for Anne was really a modern day apprenticeship and it positioned me to do what I do at Degreed. It’s also where I met David Blake, co-founder of Degreed. And the rest is history.

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

It’s been a pretty wild ride across the board, hard to pick just one! But last year the Founder and CEO (Eric Duffy) of the only other company in our space we viewed as a real competitor (Pathgather) approached us about possibly bringing our companies together to run faster together after the massive opportunity in front of us. So we set a meeting with a small group of folks, and snuck him in the back door at our office and up to a conference room. It was a fascinating start because we both weren’t sure how we felt about it, we had been battling for 4 years head to head, and didn’t know each other well. Pretty quickly we got to the question of “what are you optimizing for? If there is alignment, the rest is just details.” We both had exactly the same answer of 1) the mission 2) our clients 3) our team. Nothing in there was about money, title, etc and we had tight alignment on the mission. From there I think it was like 45 days before we closed the merger and 70 days before these two intensely competitive companies were in the same Slack channels and working together on projects and clients. Just a fascinating couple of months and a testament to Eric, the team he built, and the power mission aligned organizations.

Are you working on any exciting projects now? How do you think that will help people?

The business world is rapidly changing and companies are struggling to keep up. In the past, a career meant getting a job at a company, working your way through the ranks, and retiring with a nest egg after 30-some-odd years.

Work looks a little different today. Careers can be longer by 30 to 40 years, tenures are shorter, and skills stay relevant for less time. Based on LinkedIn’s 2017 Workplace Learning Report, the average skill has a shelf life of five years. Our goal is to make sure no one, and I truly mean no one, in today’s workforce becomes irrelevant after a mere 5 years in the workforce, due to a lack of new skills.

We are constantly working with the most innovative companies such as Airbnb, Boeing, Unilever and others, to future-proof their business by up-skilling their most valuable assets: their employees. People want to learn informally, in the same ways that they already are: picking up news from social media, online sources, and podcasts. We’ve created a platform that mimics the user experience of these socially-enable sites, allowing people to learn anything, from any source, from anywhere, while allowing businesses and teams to share content, and track and measure learning — literally giving people new skills in a very digestible format.

Recently we announced a very exciting project: a partnership with Harvard Business Publishing which pairs content from Harvard Business School and Harvard Business Publishing with Degreed’s informal learning platform. This partnership brings the learnings of Harvard Business School right to your phone or computer, allowing you to use Degreed’s seamless technology to learn wherever you want.

This has the potential to change lives. It gives employees the confidence to learn new skills which leads to greater job security, bigger promotions, job opportunities, or simply just deeper self-esteem. It used to be that people got a four year degree and that was the end of their learning. Now people can be as adaptable as the changing business landscape, constantly learning new technologies, skills, and staying relevant and in-demand.

Ok, lets jump to the main part of our interview. According to this study cited in Forbes, more than half of the US workforce is unhappy. Why do you think that number is so high?

In a work culture where some companies are offering free breakfast, lunch and dinner, and break rooms look more like a preschool playground than a traditional office space, it’s easy to get sucked into thinking that a great work culture is one that offers the most fun and free stuff.

Let’s be honest; a job, at some point or another, is going to feel like work. No amount of slides or soft-serve machines are going to mask the fact the a company hired you to get work done. Once the excitement of all the extra stuff wears off, at the end of the day what makes people really happy is feeling like they are a needed, contributing member to important or interesting work.

A successful work culture that provides lasting contentment is one that betters their employees and keeps them engaged through continuous learning and skills building. And quite honestly that all starts with who you let on the bus for teammates. That’s an area we have put an incredible focus on..managing the raw inputs to culture, people.

Based on your experience or research, how do you think an unhappy workforce will impact a) company productivity b) company profitability c) and employee health and wellbeing?

An unhappy workforce is an unmotivated workforce, and leads to high turnover. A company culture of learning creates an engaging environment and can prevent employees from feeling bored or stagnant at an organization, which may lead to longer employment and happier employees. Learning and development is worth the investment into your people, and maximizes performance — and therefore profitability — while at the company.

Can you share 5 things that managers and executives should be doing to improve their company work culture? Can you give a personal story or example for each?

  1. Start with purpose. At Degreed, everything we do is in support of the mission. We’ve created one of the most mission aligned companies I’ve ever seen. Sometimes this comes into conflict with operational alignment or business priorities. And we have to make hard decisions. But having a guiding north star is essential. Essential to the company and to attracting the type of world class, dedicated team that we have here. Star performers want purpose from their work. Stars always have options, job offers, high opportunity costs. Making an impact while at the same time building a giant company is a rarer situation and we have to do both to truly succeed here.
  2. There is a great Muhammad Ali quote “It isn’t the mountains ahead to climb that wear you out, its the pebble in your shoe.” Its a great leadership and management lesson. I keep pushing my team to be pebble-kickers, to remove the pebbles from the shoes of the team we are climbing the mountain with. The challenge is that pebbles are often hard to find and non-obvious. To better understand where they are, I always ask employees 2 questions when they have 1:1 time with me. 1) If you had one thing that would help you do your job better, faster, easier, what would that be? 2) if you were me, where would you pay more attention or spend more time. The answers are fascinating and often seem trivial to an executive. One finance employee told me they wanted an older version of excel because it was faster to build financial models in. That may seem silly to most of us, but if your job was spent building models in excel, and you were losing 20% productivity every day, it wears you out.
  3. Create an engaging learning environment. By creating systematic approaches to identifying, measuring, and developing emerging skills, innovative companies are building a learning culture that attracts and engages next-generation talent. We conducted a study a couple of years ago asking workers if they had $1,000 in a new benefit what would they want their employer to spend it on. “Help me learn a new skill” came in first over everything including 401k, food or travel stipends etc.
  4. Focus on skills for the future and take your teams with you. Sixty-four percent of CEOs feel they must upskill or reskill 25 percent of their workforce over the next five years for their companies to stay relevant. With that in mind, the most successful employees in today’s workforce will be those who focus on building skills for the future — using whatever resources are available. These employees will feel more integrated into the company and more invested in its future, and therefore more content.
  5. No matter what, get out of your bubble. Do skip level 1:1s. As the business grows, its harder and harder for a CEO to stay close to what’s happening day to day. Monthly I have dedicated time to do 1:1s with the directs of my directs. It allows me to build personal relationships one layer deeper in the org, get feedback on my directs and also drive alignment in our next level of leadership. It is incredibly useful and I wish I had time for more.

It’s very nice to suggest ideas, but it seems like we have to “change the culture regarding work culture”. What can we do as a society to make a broader change in the US workforces work culture?

Changing something as significant as workforce culture can seem too big for one person. However, any change really does have to start with one person to ignite a spark and create a movement. As I mentioned, I think continuous learning and personal development is the key to feeling happy at any job. It is our personal responsibility to be proactive about bettering ourselves, learning new skills, and pushing ourselves beyond our comfort zone. Challenging ourselves may seem counterintuitive to our own happiness, but boredom leads to unhappiness. We need to take initiative and identify skills we are interested in, request access to tools to acquire that talent, and then enjoy the satisfaction and joy that comes with accomplishing a new skill.

How would you describe your leadership or management style? Can you give us a few examples?

Whenever I interview executives I ask the same set of questions. Imagine everyone in your current company (or team) was out at a happy hour and was given an anonymous poll to rank everyone in the company based on who they would blindly follow to the next company or career opportunity. Where would you rank? If you are #50, why not higher. If you are #1–5, why would people follow you? Would they follow you here? What do you wish you did differently at that company that would have made you higher or lower?

The point of the question is to understand how this executive is perceived as a leader and why. It’s also a guideline I try to operate by. I am proud of where I would rank to that question and it starts by treating everyone the same way and fairly. By being approachable and transparent regardless of who you are talking to. But it’s also not a popularity contest. The best leaders instill the confidence and swagger in the rest of the team that we can and will execute on what we set out to do. No one follows someone they think will lose. We operate more like a sports team at Degreed. I recruit the best talent and teammates I can possibly put on the field, try to get the most out of each of them, but more importantly get them to work well as an aligned team so we can execute. And when that alignment is off, or people are stuck, move as quickly as possible to remove those barriers and get back on track.

You also need to pick your spots as a leader. When you have great talent you can’t micromanage everything, otherwise there is no reason to have great talent. The old Bill Parcells analogy is appropriate. If you want someone to cook dinner, you should let them shop for the groceries. In return for that autonomy I expect that when I do push hard on something, the team gives me the latitude and faith that its the right decision. CEOs have more context than anyone and that context helps make good decisions. Your job as a CEO is to let your team play, but steer clear of icebergs and solve problems when they come up. Problem solving in 15 minute increments is a good chunk of the job and as you move from finance to sales to product to marketing to HR you often aren’t the functional expert in the room. It’s not your job to provide deep functional expertise and force a decision. Trust your team for that or get new players. Your job is to bring the greater good company/mission perspective, a structured decision process free of bias, and consistent principles to the problem. More often than not, this leads to empowered execs who work well together and steady execution. And if you need to break a tie, then to it quickly and don’t look back.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I mentioned her above, but its Anne Dwane. 5 years later I still realize examples of when she covered for me, or put me in a position to succeed, or taught me something that I didn’t realize at the time. I try to model a lot of my mentorship of more junior people after Anne. One specific example is how she would use a portion of our early 1:1s to share different situations and issues that would pop up across the business. Some of them were brutal, would cause a loss of sleep and completely changed my interpretation of what was a “big problem.” Early I I wondered why Anne would bring me into these problems. Only later did I realize its because she was calibrating my stomach and ability to process the often impossible situations that come from building a company. 4 years ago Dave Blake (Co-Founder of Degreed) and I were sitting in an empty office, late at night, dealing with one of the scariest problems of Degreed’s history. I had slept in the office on an inflatable bed for most of that week. Dave looked at me and said “Can you imagine if we were first time entrepreneurs how this would feel. The walls and ceiling would be closing in on us.” We laughed a bit, and got back to work solving the problem. But most importantly, the rest of the company never knew anything was wrong because they didn’t sense it in us. And the problem got solved and that was it. But there is zero chance I would have been equipped to lead the company through that if it happened before my experiences working with Anne and others.

I should also call out Dave Blake here as well. He says he’s an education reformer first and entrepreneur by necessity, but he’s wrong. He’s one of the most powerfully motivating leaders I’ve ever met. I only hope one day, everyone else gets to understand how much Dave did to make this work. He simply put himself last and willed Degreed to work. It will be a case study some day.

How have you used your success to bring goodness to the world?

I’ve now built two companies that had a major social impact. You don’t get many opportunities to build a giant business that also does major social good. When Degreed is at full scale, the megaphone it has to change the lives of people globally could never be matched by what I would do personally. Degreed is that vehicle for goodness to the world. We will create a 100 year company that enables millions of people to become lifelong learners, build their skills and unlock opportunities all throughout their careers. And I hope that is career defining for all of us.

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

“Opportunity is missed by most people because it is dressed in overalls and looks like work” — Thomas Edison, but first said to me by my Father Brian McCarthy who I am incredibly close with.

My father was always an incredibly hard worker. I ran a landscaping business in high school. To this day he tells a story of waking up early in the morning to go to work and it was pouring rain and dark. I was already sitting at the kitchen table reading the paper drinking coffee. My father asked what I was doing and I said getting ready for work. He pointed out that it was a hurricane out and I guess I responded that we had plastic bags for our boots. I don’t remember the interaction, but he tells it with such pride 25 years later.

The point is, most people have no idea what it takes to build a successful company, sports team, etc. There are no silver bullets and no easy answers, just hard work over a million little interactions. Most people lack the competitive stamina required to win over the long run. People are more concerned with how their LinkedIn profiles look and when they will be a VP. The ones who win are the ones who are willing to compete and grind over a sustained period. Line of code by line of code, client by client, event by event, hire by hire. At Degreed, we hire for intensely competitive people who want to win each of those million little interactions and want to coach and push others to win them as well. Every meeting, every pitch, every decision. Over time, that adds up to winning. But its dressed in overalls and looks a lot like work. Don’t let anyone tell you anything different regardless of what their LinkedIn profile says.

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. 🙂

My precocious 7 year old tells people “My Dad builds companies and makes jobs for people”. There is also some part of that were he tells people that not even Amazon can beat Daddy’s company. Which is adorable, and only comes from his being upset about Toys R Us going out of business! But I tell him if I could do it all over again I would have applied myself to curing cancer, something that has deeply affected my family. So now he says that he is going to cure cancer when he grows up and I would bet on him. I hope by being a great Dad I will have a big influence on the world. But for now, I would love for some of our best and brightest to solve the student debt crisis in this country. I’ll stay off of my soap box, but I 100% believe that bubble breaking will be worse than the housing crisis. The cost of college in the US is ruining the next 3 generations of leaders. Most of them will never get a chance to be featured in Buzzfeed because they will be crippled with debt you can’t even get out from in bankruptcy. If I didn’t get a scholarship to business school I would have ended up back in a job that allowed me to service that debt and never would have even had the chance to do what I do now.

No matter how hard I try, I can’t even get my own extended family to avoid massive student loans. Maybe I’ll tackle it when I’m done at Degreed, but for now, I would love for someone to step up and solve the problem so we can enable the next generation of entrepreneurs to build lasting and impactful companies. And then Buzzfeed can write about their leadership styles and influence years from now.

Thank you for these fantastic insights. We wish you continued success!

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