How Ben Casnocha Is Changing The Future Of Work For Millennials

“CEOs and executives always say, ‘We’re one big happy family.’ The last time I checked, in a real family, you cannot just layoff your annoying brother if you get into an argument at the dinner table.”

The future of work is changing radically and Ben Casnocha wants to make sure that it’s for the better. He is the co-author of The Alliance: Managing Talent In The Networked Age and The Start-up of You with LinkedIn founder Reid Hoffman. Heleo’s head of video, Michael Kovnat, spoke with Ben about his path to entrepreneurship and what millennials get wrong in the workplace.
This conversation has been edited and condensed. To watch the full video, click below.

Michael Kovnat: You once wrote about how you put out a question to your network about what their biggest regrets were. What inspired that question?

Ben Casnocha: When I turned 18, I emailed everybody I knew who’s older than me and asked, “What’s one thing you regret not doing when you were 18?” I didn’t really know what I’d get in response.

Their replies came back and to my shock, there was a consistent theme throughout the advice, which is that people really regretted not traveling when they were younger. I traveled somewhere in the States, grew up in the Bay Area but I never left the country. It just wasn’t something we did as a family.

I posted a message on my blog saying, “Hey, I never left the States, I’d like to see the world. Who wants to host me in their home in exchange for a potentially interesting conversation?” It helped me travel around Ireland and France and China and Chile and India — all around the world — staying at the homes of people who read my blog. They took me into their homes and they introduced me to their culture. It was a totally life changing year for me. I loved understanding how arbitrary so many of my customs were in America, just how arbitrary so many of my default assumptions were.

There are so many layers to the experience. When I first traveled, it was just the sheer wonder of diversity. But over the years, what I’ve learned is, there’s something much deeper happening when you have sustained engagement with something. I continue to try to build a life that’s substantially global both for cultural intellectual reasons, but also for economic reasons. I think there’s tremendous opportunity around the world.

“People think entrepreneurs are these geniuses who conceive an idea and then put their head down and work for ten years until they change the world. For most great companies — Starbucks, Pixar, almost any tech company — the initial idea and what the company ultimately became are quite different.”

Michael: How did you get started as an entrepreneur?

Ben: Initially, it was classic entrepreneurship in the way we typically think of it, which is starting companies. But over time, I’ve learned that you can manifest that spirit and energy in all sorts of different ways. You don’t have to be technically starting a company to be an entrepreneur.

Reid Hoffman and I wrote a book called The Start-Up of You in which we argue that certainly people who start companies are entrepreneurs but you could be a doctor, a lawyer, a video producer, a journalist — anyone embracing the entrepreneurial mindset and skill set.

The beginner’s mindset is one that has a huge emphasis on learning and development and growth. That’s the ultimate entrepreneurial trade I think, that they never stop learning, they’re always iterating, always trying to fix bugs in themselves and in their products. So there’s a mindset that’s quite universal and there’s also a set of skills that entrepreneurs employ when creating businesses that we think anybody can deploy in their career, in their work, no matter the sort of work that they do.

Michael: Can you give me an example?

Ben: When you start a company, you tend to have an initial vision but then once you get going, you realize the competition’s different, the market’s different, customer needs are slightly different. So you have to evolve and change your business idea to meet the market needs. It’s a great myth, actually, of entrepreneurship; people think that entrepreneurs are these geniuses who conceive an idea and then put their head down and work for ten years until they change the world.

For most great companies — be it Starbucks, Pixar, almost any tech company in the Valley today — the initial idea and what the company ultimately became are quite different. The process by which an entrepreneur adapts their business is systematic and intentional and we think that process and that mentality can be applied at any number of other career contexts.

If you look at successful people like Sheryl Sandberg, the current COO of Facebook, people think she must have had a life plan that she articulated after college and then spent 30 years pursuing it. In fact, she’s had to pivot and adapt and collect feedback and reinvent herself over and over again. Adaptation is a core strategy that all of us need to employ as we try to build a new competitive career.

“I try to reject naïve truisms like, ‘Be vulnerable in the workplace.’ If you’re going into a meeting with your boss and you’re feeling really confused about your career, it’s not always wise to go be vulnerable in that moment.”

Michael: One of the trickiest parts of getting feedback is having the skill of knowing when the path you’re on is not working. Do you have advice on figuring out when to pivot?

Ben: I once wrote a post about the skills you have to unlearn from school. People often say schools prepare you for the real world but they also impart certain values and habits that you actually have to actively unlearn.

In school, you do an assignment, you get an A by someone who’s qualified to give you that A and you get these grades consistently so you know exactly how you’re doing. In the real world, you can spend years of your life on a path and not really know whether you’re succeeding and only wake up a decade later and say, “Oh my God, I’ve been doing it all wrong.”

What we always talk about in The Start-up of You is how you can use the people you know to get insight on what you should do. We call that process network intelligence. People often talk of network as something that you use to find a job but you should be using your network for a whole range of day-to-day decisions in your life.

Michael: I think a lot of us have a hard time doing that because you have to be vulnerable to do that.

Ben: One of the things I always try to reject are these sexy-sounding, but actually naïve truisms like, “be vulnerable in the workplace.” Sometimes that’s good, sometimes it’s not. We have to be realistic about that. If you’re going into a meeting with your boss or your manager and you’re feeling really confused about your career, you’re not sure if this is the right job for you, it’s not always wise to go be vulnerable in that moment.

You have to be strategic in a sense about when to be vulnerable. So much of this self-help world is overly simplistic about that. “There’s no such thing as a dumb question” is partly true, but you don’t want to ask the dumb question in a meeting where you’re trying to make a positive impression.

There are a lot of cliches around workplace success in general, all sorts of bad advice. And while there are always kernels of truth in the advice, we want to be sophisticated about how we process it and realistic about how to apply it in the real world.

Michael: Do you think people are accepting of the need to give advice? Sometimes I resist asking for advice because I don’t want to impose. At the same time, I do try to be thoughtful when people ask me for advice.

Ben: I think people tend to ask for advice less than they should. The biggest mistake I see people make when they ask for career advice or life advice is they employ what I call “blue sky questions,” which are utterly vague. Far better to narrow the conversation. It’s something that the person can work with. For example, present options like, “I’m thinking of these three paths. How do you interpret the pros and cons of each path?”

Even if you’re not quite sure that there are three paths, the compare and contrast exercise is easier for someone to engage in. Of course it depends. If you’re talking to your hired executive coach, certainly get into all the nuance. If you’re taking a busy person out to lunch and have limited time, you’ve got to be a little more crisp in the framing of the issue. It’s great to have a friend who can spend three hours with you and help think through all the issues, but you’d better hope that that relationship is solid before you ask for a three hour deep dive session on your life.

“CEOs and executives always say, ‘We’re one big happy family.’ The last time I checked, in a real family, you cannot just layoff your annoying brother if you get into an argument at the dinner table.”

Michael: Tell me about your latest book with Reid Hoffman, The Alliance: Managing Talent In The Networked Age.

Ben: We decided to do a follow-up book [to The Startup of You] around how an individual can thrive at a large organization, but also from the manager perspective, “How do you attract and effectively manage an [entrepreneurial] employee?”

If you’re an employee and you want to take a risk on a job, you want to adapt yourself. You want to build your network. You want to develop a personal brand. It’s helpful if the company and your manager embrace those instincts. We argue in The Alliance that it’s imperative for a company to embrace those instincts because it’s entrepreneurial employees that develop the next big idea for your organization. If you want to take a risk in the company, you need employees who can take risks.

This idea that you land an entry-level job at a company like GE or IBM and then work your way up the totem pole for the rest of your career, and the company guarantees job security to the employee, is no longer affordable in this much more competitive economy.

Both sides, employees and companies, need to develop a new relationship where the company looks at the employee and says, “Okay, if you help make our company more adaptive, more innovative,” which is the ultimate imperative today, “We will help transform your career, long term.” The employee says in turn, “I won’t be here my whole life. If you help transform my career, I will help transform the company.”

It’s a relationship characterized by that sort of mutual investment and mutual benefit.

Michael:  Right, there’s been a paternalistic sense that the company will be a parent to you. You also talked about how this notion of the company as a family can be deceptive.

Ben: It’s very deceptive. CEOs and executives always have to say, “We’re one big happy family.” The last time I checked, in a real family, you cannot just layoff your annoying brother if you get into an argument at the dinner table. A company is more like a professional sports team. People show up and if they add value, they stay. If they don’t, or get bored, they leave.

It can still be very high trust, and a fantastic experience. But it’s premised on mutual performance, mutual ethical commitment.

I think it’s important for employees to also be thoughtful about how you articulate your own career aspirations to your manager to the company. A lot of millennial employees say, “I can see myself working at this company for a couple of years” and a lot of managers hear that and think, “Disloyal.” The phrase that we’ve coined that we use with companies is “Tour of duty.” If you’re an employee, you should complete an honorable tour of duty at a company and put in a meaningful amount of time to complete real work to have significant accomplishments. Just  be transparent about how long that mission might take.

Michael: Are you actively looking for companies to sign on to this mindset? How do you know if this idea is gaining traction?

Ben: This is the way that a lot of Silicon Valley companies have been managing the talent relationship for the last 10-15 years. It’s a highly liquid labor market, with very talented people moving around a lot, and it’s the framework that we think works here. In the last couple of years, we’ve been working with dozens of organizations around the world helping their managers and leaders engage with employees in this way.

And it’s working. There’s a lot of cynicism in corporate America today. Studies show employees today have record lows in terms of level of trust in their managers. Many managers, especially when asked about millennials, are at their lowest point regarding whether they can trust their employees to complete key projects.

The relationship has really disintegrated. I think a lot of companies are looking for a different path forward. They know the family model doesn’t work. But they also know that treating your employees like free agents, embracing what Jack Welsh once called one-day contracts in which you just fire somebody the moment they stop adding value, that doesn’t lead to real relationships either. It has to be some middle ground and so we’re trying to offer a third path, trying to coach and train managers and employees alike on how to build that relationship.

In the end, why I’m passionate about it is that most people spend most of their life at work and so if you can improve the quality of the relationship they have with their manager, or just improve the level of trust they have with their company, I think that’s probably the highest impact way to increase happiness around the world.