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I love being a manager and I love talking about management. It’s similar to the topic of leadership, but in my mind management is almost synonymous with mentorship. One of the great pleasures of running Wine Library and VaynerMedia has been the opportunity it has given me to show people how to be better managers. We all probably have our own opinions of what makes a good manager, but in this one man’s point of view it’s the ability to reverse-engineer every person that works for you and put him or her in a position to succeed at the task for which they’ve been hired. That’s what I try to do for the people who report to me, and that’s what I expect the people who report to me to do for the people who report to them.

In less than four years, VaynerMedia grew from thirty to more than five hundred employees. And in all that time, we had only one person in the HR department—me. That’s how much my employees matter to me. Every company lies about how much they care about their customers, and how much they care about their employees. It’s such an easy thing to say, but it’s really hard to put in the work that proves it.

From the very beginning, when AJ and I were just starting VaynerMedia, we made a few key decisions and set standards that we swore would be upheld no matter what. We did this because we had seen too many companies become breeding grounds for unhappiness, places where uninspired, unappreciated minds went to wither. For that reason, my employees’ happiness is paramount, to the degree that I tell my clients up front that I care about my employees first, their customers second, and them last. Interestingly, I’ve never lost business because of it, maybe because my track record speaks for itself. Clearly, putting my employees above everything else hasn’t hurt my business. It could only help yours.

The quality of management in any venture is, like its cousin leadership, one of the core determinants of whether a business will succeed or fail. You want the people working with you to want to be there, to feel challenged, appreciated, and valued. People always respect and like the manager who’s thinking ahead and guiding them to places they’d never thought of, but they love and admire when that manager stays with them until 2 A.M. working that deck or stocking the shelves. Is this you? A disproportionate number of the readers of this book are managers or will be someday. In fact, the day you launched an entrepreneurial venture you became a manager.

One of the reasons I was excited to write this book was that I knew it would allow me to freely explore some of the topics about which I’m passionate and that have made The #AskGaryVee Show so much fun for me. Management is at the top of that list.

imageWhere is the best place to hire employees?

I’m at a sweet stage in my career where I’ve become a known personality and my company has made its reputation, so people are coming to us. But don’t let anyone tell you it’s tough to find good people. It’s actually really easy. It’s only hard for people unwilling to do the work.

You can break this down in a few easy steps.

1.Go to Twitter Search and start looking for the people who are talking about what you do for a living. Search the terms that would line up with the responsibilities inherent in the kind of job you’re trying to fill. If you need a Web designer, find people who mention website design, or graphic design, “landing page optimization,” or any other term that might indicate they’re talking about or interested in the kind of work you need done.

2.Find the most promising candidates, click on their profiles, click on their home page, click on their portfolio, and see which ones look like they have talent.

3.Email them and find out if they’re interested in looking for a new position. Most will probably say no, but maybe one will say yes, and the other three would probably give you referrals.

4.Interview five people and hire one.

There. It might take you as little as eight hours. Eight hours of hard work, to be sure, but far less than the days and weeks it might take you if you go the traditional hiring route and wait for the right résumé or LinkedIn inquiry to land in your inbox. And yes, someone did try this approach and met with success, so I know it can work.

imageWhat role does internal culture play in a company’s success?

A starring one. Building a strong internal culture is one of the best ways to ensure success for your company. Sales matter, profits matter, customer relationships matter, but every one of those pieces of your business—in fact, every piece of your business—is affected by the culture. Culture is a product of people, and when people aren’t happy and instead are constantly thinking of a way to get out, their work will reflect it. Wouldn’t it make sense, then, to make your culture a priority? And given that people shape culture, wouldn’t it make sense to keep it at the forefront of your mind every time you hire?

Because that’s how you build a strong internal culture—you hire one. And you don’t make hiring or firing a financial decision; you make it an emotional one. Just because you suddenly have the budget to hire someone new doesn’t mean you should. Just because someone isn’t performing the way you expect doesn’t mean you show him or her the door right away. You have to think about how every hiring and firing will affect the collective community before taking action.

Hiring and firing should be emotional decisions because you’re dealing with people, not contracts. We’re all told to think “business is business,” which is generally interpreted as a mandate to remove our emotions out of our decision making so that we can arrive at the most objectively and financially profitable end. Well, I disagree. Business is business when it comes to financial or contractual negotiations, but not when it comes to deciding what happens to the human beings who make your business run. Besides, there are financial consequences when you treat an individual’s job prospects as a financial return on investment; they’re just harder to see because they don’t show up right away on the balance sheet. They’re there, though, coloring the unmade profits, the missed opportunities, the lost innovation and enthusiasm that results from the low loyalty and morale that pervades companies where people don’t come first.

That doesn’t mean you can’t fire people who aren’t performing, of course. It just requires that you take more time to think through other alternatives. For example, let’s say you’re unhappy with someone who is extremely popular at your company because they’ve got great people skills. How much will everyone else suffer if you let him or her go? Is it possible they’re just not in the right position, and that maybe putting them in a different department would solve your problem, increase and improve their work, and keep everyone happy?

Maybe you really need to let this person go. Could you help them find another position outside the company over the span of sixty days, rather than cutting them loose in one day? It’ll cost you a lot more money, but it will salvage just as much in the form of an intact, vibrant company culture. And at some level it’s just a great thing to do.

Never underestimate the power of great culture. You want outstanding results and sales and projects and awards and accolades, and you know you need great teams, great leaders, and hard work to get them. Well, how many great teams have you ever encountered that are made up of tired, resentful people? How many great leaders hate what they do? How many unhappy people are willing to give their jobs everything they’ve got? Not many. A great company is grounded in great culture, and great culture begins and ends with whom you hire, and how they leave.

imageWhat’s your best time management tip?

Hire an assistant and make him or her the czar of your time. If that’s not possible, use technology apps and programs like proworkflow.com, Evernote, Calendly, Asana, timetrade.com, and even the Apple Watch.

Make time management your religion. Learn to say no to the things that keep you out of the clouds and dirt.

imageWhat do you look for when hiring creatives?

Good creatives love their art, but great creatives who work in business love to use their art to sell. In other words, they aren’t held up by romantic notions of artistic integrity. A creative who wants to work effectively and happily at an agency shouldn’t care more about the craft and winning awards than the agenda. So that’s the kind of person I’m looking for—someone with tons of creative talent who wants to make fantastic art, yet who understands that we’re in the business of selling stuff and gets a thrill out of that, too. If we don’t move product, or raise awareness for the cause, or inspire people to donate, or click, or buy, we haven’t fulfilled our obligation to our client.


Benjamin Israel Lazarus

imageDo you drug-test your employees? Why or why not?

We don’t.

There is no real overwhelming reason for it. It just doesn’t seem needed or appropriate, or something I have any real emotion about. I don’t have any huge stance on drug culture. It just hasn’t come up.





imageWhen running a company or providing marketing services for a VaynerMedia client, how do you segment out sales, marketing, and business development? All three disciplines overlap so much, and the waters can get really muddy when one or more of those areas are clearly lacking and the others are strong.

They all work together. Being good at marketing is different from being good at sales, but a good marketing campaign can lead to massive sales. By that same token, business development is just a gateway drug to sales. Now, when all three are working in harmony, you’re obviously cruising. A great example of that would be SalesForce. They’ve invested heavily in salespeople, they market themselves excellently for a B2B SAAS business, and they execute on business development through events like nobody else.

But not everybody is SalesForce, and that’s okay. Take a look at HubSpot, which is one of my investments. Maybe not as strong with sales early on, but they crushed it on biz dev and marketing and had a highly successful IPO as of this writing.

I would argue that a business’s strengths and weaknesses will always be somewhat uneven depending on the composition of its DNA, culture, and people. What it comes down to is recognizing if one of those three areas—sales, marketing, or biz dev—is bringing you down as a collective, and addressing the problem through hiring, training, re-orging, or some other solution. The good news is that unlike a car, where the failure of one cog can cause the whole system to break down, I have found that when one branch of a client’s company or my own businesses isn’t working, it doesn’t necessarily drag down the entire organization.

The truth is that all three of them lead to the same finish line, so if you have one that is overindexing, it’s possible that you can ride it home. Obviously, I’d love for you to be great at all three, but don’t get too worried if one is lagging behind the other two. This all speaks back to my core tenet of betting on your strengths and not your weaknesses. I’m much more interested in you doubling down on the two things you’re good at instead of the one where you’re behind.

imageWhen transitioning to a new project management role, how do you maintain high standards with your team while still keeping projects on time and on budget?

Use your ears more than your mouth. Take the time to understand everything that’s going on in your department, and listen before trying to take control. If you see a problem, let your team explain to you what they think is the problem, and then instead of coming up with a solution, guide them to coming up with it themselves. That may require you pitching in, but you’re not above getting your hands dirty, are you? Become known as the person who “gets it” and you’ll always have all the information you need to make the important calls because people won’t be afraid to come to you for help. Creating an open, trusting, compassionate environment where everyone knows what you expect will save everyone a ton of time and help you achieve your objectives.

As your team continues to grow, hire other great listeners. The best listeners who know how to calibrate all the data and act on it will be the winners. No one ever solved a problem alone.

imageHow do you prioritize which project to execute first?

I take care of the biggest fires where I get the biggest upside if I put them out quickly, like calming a new client or handling an employee disagreement. I focus on those immediate concerns while making sure the company vision is still clear and that everything I do will eventually help me build the company and team I want, which will ladder me up to buying the Jets. You know, clouds and dirt. And I don’t worry about anything else in the middle.

imageHow can agencies make staff meetings more productive?

By cutting them in half.

Now, how are you supposed to do that when you’re also supposed to be giving your employees room to talk, spending time with them, being compassionate, and all those other touchy-feely bits of advice I tend to offer?

You just do.

I swear to you it works. Estimate how much time you think you will need to cover your agenda, and then halve it.

If you give people a ten-pound bag, they are going to fill it with ten pounds of crap. If you give them a fifteen-pound bag, it’s the same—fifteen pounds of crap. They will never overfill or underfill the bag. When I schedule an hour meeting with my team, we’ll banter a bit and talk about a few other things we didn’t plan on talking about, but we will fit everything we need into the hour. If I cut that same meeting to thirty minutes, we’ll still accomplish everything that needs to be done, hands down. And we’ll have saved thirty minutes, which is really what this is all about, right? Our time is valuable. When you’re hustling like I do—and which I’d like to think you do—every minute, every second counts.

When everyone knows they’re going to lose your attention as soon as the allotted fifteen or thirty minutes are up, they prepare. No one’s shuffling around papers, no one shares irrelevant anecdotes, no one talks around the point, and no one is winging it. People have spent their time before the meeting getting their information straight, pulling their papers together, and tightening their message because they know if they don’t, they won’t get a second chance.

All that friendly touchy-feely stuff I believe in? I do it, but I do it fast. Heck, I do that as I’m walking into the meeting. But the minute my butt hits my seat, everyone had better be ready to go. I’m positive that if there is any one answer that could probably benefit every single person reading this book, it’s this one.

imageWhat’s one question you ask in interviews?

There is one question I only raise if an interview is gaining momentum and I feel like I may have found a good fit for my team. It’s not just a question I love to ask, it’s one I need to ask. In fact, at some level it’s the only one I really care about.

“Where do you want your career to go?”

I spend most of my interviews trying to get people comfortable enough to answer that question truthfully should I decide I want to ask it. I don’t care if the answer is you want to be the CEO of VaynerMedia, or you just want to move a couple of levels up and have great work-life balance. I don’t even care if you want to come work for me for two years, suck up all my IP, and then go somewhere to start your own agency. I really don’t. Truly. Whatever your agenda is, I’m fine with it. I just want to know what it is, so I can help us get there. You and me.

See, I’m a creature of contradictions. I welcome chaos and love to take advantage of trends and have built a business that serves as a port for companies swimming in a constantly undulating sea, but man, I hate change at the personal level. I want to keep people in my ecosystem for as long as possible, because once I like working with you, I want to work with you forever. And I know the best way to keep you close is to deliver on what you want, so the faster I can get that insight the better.

By giving people opportunities and helping them achieve what they want, I keep my relationships with my employees positive and open. Such a positive environment not only makes it hard for people to leave, it ensures I always know what’s going on. This allows me to execute quicker, and together we can do amazing work faster.

I hire a lot of young people, so I know change is inevitable. People fall in love, they decide to start families, and their lives and interests evolve. And that’s the way it should be. But by keeping the communication funnel open and clear, I have a better chance of finding a way to help my best talent achieve all their dreams while still working with me. And I want to start from day one, five minutes in.

imageWhat would you do if all six hundred employees quit VaynerMedia?

Well, first I’d be an idiot if I didn’t step back and wonder what the hell just happened. Then I would spend a lot of time going to each of the employees and apologizing to them because obviously something went very wrong. But then I’d have to take a positive approach. I’d have to decide how I wanted to take advantage of everything I’ve learned for the last six years. I’m an emotional guy, but I would work really hard not to react with a knee-jerk “I’ll show them!” and just go out and rebuild. I’d be tempted because I’d want to show I could do it, but I think I have enough self-control to refrain from letting my emotions get the best of me. So in deciding whether to rebuild or walk away, I’d have to consider what would be the best use of my time, the decision that would get me back on track, because I’m forty years old now and want to buy the Jets. But make no mistake, if I chose not to rebuild it wouldn’t be because I couldn’t do it. It would be because I chose not to.

imageIs the lack of chairs in your office a part of instilling the hustle in your employees?

No, but I wish I had thought of it. Limiting chairs to create a competitive culture? That’s brilliant! Someone else should totally do it.

I actually have no hard-core tactics for instilling competitiveness. I just breed it because I’m competitive as sh@t, and I think people know that to keep up they’re going to have to get hungry. After all, as I’ve said, everything stems from the top. I think it is important for everyone reading this book to understand their DNA and how they like to roll, allow their companies to ride that wave, and not push against it.

What makes me happy is that as competitive as we are, I’ve heard a lot of people say that VaynerMedia is one of the first places they’ve worked where people want to compete with the quality of their work, not at the expense of others. That tells me we’re creating great culture and great work.

imageWhen hiring for a team, is it better to bring in specialists or someone who can wear multiple hats?

You can certainly benefit from both, of course. It’s always good to strike a balance within a company. And since I believe everyone should exploit their strengths, it’s important for leaders and CEOs to hire people with complementary skills.

But if you have to choose, go for the jack-of-all-trades.

And if you want to enhance your marketability and value, become one.

Many would argue that by trying to be good at many things, you’ll never master anything. Bullsh@t. If you work hard at trying to be good at many things, you’ll get good at many things. And taking that attitude will force you to say yes to new challenges more often. You might be really good at something now, but why not find out what else you can dominate? Because I know it’s not just one thing. We’re all better than that.

Be open to adapting and evolving your skill set as your life progresses. I get so bothered when I hear people say they don’t have to learn anything new because they’ve become so good at the thing they do. It’s such a limited mind-set. And it’s dangerous, too, because you never know when you’ll need to tap into a new skill. There’s nothing like a layoff to make you regret you didn’t pick up that extra knowledge or experience. Expand your arsenal. It’ll allow you to always prove your agility and your ability to offer value wherever you go. It’s never too late to get better. Start moving. NOW!

imageWhen faced with two equally qualified candidates for one position, how do you choose?

Two thoughts came to mind when I read this question.

1.I don’t think there’s such a thing as two people who are literally equally qualified for the same job. Someone always has a slight edge. It may not be enough to make that much of a difference, but you can use that to help you make the call. Or go with your gut. That usually works, too.

2.If you like them both that much, consider hiring them both. I’m a big fan of hiring ahead of my growth. I would never unduly burden my payroll because I wouldn’t want to lay anyone off, but I anticipate. Always look ahead at what your needs are going to be, not just the ones you have now. If you’ve got two candidates who can each bring you that much value, a creative solution may be in order.

imageWhat three values do you hold highest in life?

I have more than three, but these are the three that I look for in a new hire.


I want to work with people who believe in paying things forward and doing good for others, but I want to know that they don’t do so expecting immediate gratification. Because there is no immediate gratification when it comes to business. You can do amazing things, and get nothing back for a good long while. That’s a really tough pill for some people to swallow. But I want to work with people who have the patience to keep going even when they haven’t seen immediate results, people who appreciate that success takes time. I’ve seen how a lack of patience can keep people from achieving their greatest aspirations, and I want to work with those who will.

Word is bond

I’ve said this goes down as the greatest lesson my dad ever taught me. I want everyone at VaynerMedia to believe it, too. When you make a commitment, no matter what, you stick to it. The best part? Every time you live up to this credo, you add one more person to your list of people who may deliver for you in the future.


I hire for this one because I know it’s what makes a great leader. I need to know that my managers are going to listen to their teams and work with them, not drive them, especially when problems arise. I want to hire people who look for solutions, not someone to blame. I want them to assume the best of people. It’s pretty rare for people to fail because they wanted to, so it’s up to a good manager to figure out what happened and then offer the support so it doesn’t happen again.


I like people who don’t take anything for granted. It makes for a really motivated worker, and generally a nice person to work with.

imageWhen you work on projects with clients, how much is done online, for example via Skype, and how much in person?

I can’t speak for anyone else, but I predominantly like to work through email and meeting face-to-face. I get a charge out of other people’s energy, so face-to-face meetings are always more productive for me. Plus they allow me to get to know my client better and build a stronger relationship, and you know how much I value that. I hardly ever use the phone, though I am trying to push more clients into using text, and I am using Skype and Google+ more and more lately and seeing real value in it.

imageIf you were the owner of the Jets how would you turn around the team and make us a Super Bowl contender?

I could have put this answer in the sports chapter, but I think my answer shows what kind of manager I am in general.

As obsessed as I am with the Jets (and enjoyed my time working with them during the years they were a client) there are still things about the team unknown to me. So I’d first run an audit so that I knew what I was dealing with.

My first order of business after that would be to mandate that every two years, we draft a quarterback in the first two rounds of the NFL draft until we had our guy. We’d bring a guy in, give him twenty-four months so he got two seasons, and then if it wasn’t the right fit, whether he played a snap or not I’d draft another guy, and two years later another, until I had one, because the quarterback is the linchpin of the team.

I’d also work on PR. I might do a weekly live-stream show so the fans could pound me with their anger. But guess what? I’d pound them right back. Different, right? I think I could get away with it because I am one of them, and most likely an even bigger fan than they are.

I’d execute some fun marketing ideas like sending a Jets jersey on the sixth birthday of every kid living in the New York–New Jersey area. I’d do inappropriate things like get into it with the media because I think they’re out of their collective mind with the way they are handling the Jets in this city (a dangerous idea, I know, but I would do it with respect). I’d watch the games from the stands (and then probably get reprimanded by the NFL for cursing).

That’s the kind of owner I’d be: methodical, obsessive, creative, combative, passionate, loyal, un-PC, and loving every minute of it.

imageWould you support Vayner employees who wrote their own books and curated their own content streams and personal brands?

I not only would, I already have. Ask Jason Donnelly. He left VaynerMedia to go write a book, and when he was done he came back. I bought copies and gave it to people throughout the office.

I didn’t do that to be nice. You can’t say you care about helping people succeed and then suppress them when they actually do. And you can’t be afraid that someone else will trump you. That’s one advantage to having a big ego—when you think you’re the greatest of all time, you’re not ever worried anyone else will surpass you, so there’s no reason to hold them back. I have no reason to fear anyone else’s talent or keep them down. If they wind up being better than me, so be it. I believe in capitalism, meritocracy, and fairness, and that’s what it should look like.

imageHow do you push your team beyond their best?

There’s a right way to do it and a wrong way. The wrong way is to crack the whip and compensate for the brutal work conditions by paying people well. The right way in this one man’s point of view is to appeal to their sense of guilt. (I’m not joking.)

I’ve already talked about what it takes to be a great manager, such as listening, getting to know your team’s ambitions, and being supportive in all their endeavors, even if they don’t necessarily benefit you. Now, you want to do that so incredibly well, and instill such a sense of family and loyalty, that your team would do almost anything rather than let you down. Relationships are a two-way street, but when you’re the boss, and you go in about 51 percent of the way, your team will go above and beyond to give you that 49 percent back. I know it’s true because I’ve seen it work at both of my own companies.

I didn’t take home more than $30K for the first five years I worked at Wine Library so that I’d have the money to call people’s bluffs. You’re telling me you could really crush it if I hired some more staff? Great, here you go. Now show me. Were my feelings hurt when things didn’t work out as promised? Yes, but that didn’t stop me from giving people what they asked for when I could. That worked as a huge motivator, because then everyone else on the team saw their friends getting what they wanted, and they’d work hard to get what they wanted, too. It made for a very happy place to work.

A good boss is doing his employees a favor when he or she pushes a team beyond their limits, because otherwise they’d never know what they were capable of. But you have to make them believe they can do it before they actually do it. If you want people to overdeliver, you’d better overdeliver for them, too.



Founder of IMScalable.com

imageHow do you hold your employees accountable, aka actually do work and get results? I mean it’s not like you can send them to their room, and firing them still leaves you with no work done.

There are a lot of ways that I do this and that we’ve done in the companies I’ve run.

1.Company culture. If you’re able to build an environment where people really enjoy the work they’re doing, believe in the mission at hand, and (most important) really love their coworkers, you probably won’t encounter these circumstances in the first place. I’m often shocked to see employees at VaynerMedia who are more afraid to fail their coworkers than anything else. The best results come when employees feel like their responsibility is toward their teammates more than a charismatic boss, or a client, or even their own pride.

2.I think you do fire. If you’re in the mind-set that firing someone will leave you with no one to do the job, then you’re in big trouble. If you honestly believe you can’t hire someone else to do the job, maybe you need to look at yourself more than anything else.

3.Finally, I really do think it comes down to communication. Many organizations don’t actually do a good job at communicating that there is a problem in the first place, so that is on you. Sometimes all it takes is an honest conversation with that person to ask them what actually motivates them. Once the problem is agreed upon by both parties (and make sure it is!), you need to figure out what makes that person tick. You might find that a couple of extra weeks of vacation makes that person dramatically more productive within forty-eight weeks instead of fifty weeks.

At the end of the day, helping your employees get the work done has as much to do with you listening as it does with you talking.

imageThe dress code at VaynerMedia is clearly casual. Do you think dress affects professionalism or performance?

Dress doesn’t impact performance or professionalism. I work with people who execute incredibly well every day, and I think they’d do that even if they came to work in their bathing suits. I think the people who disagree with me will lose because they are holding on to a tradition that is cracking as the world evolves. I want to use this book to help you recognize the subtle and not-so-subtle changes occurring in our society and how they impact the business world. Anyone who doesn’t yet hear the sound of modern business dress codes changing, and quickly, is being tone deaf.

imageWhat are your thoughts on employing friends?

Working with friends is the best, and it works if you practice a meritocracy.

A lot of managers will probably disagree with me. They’ll say it can ruin a friendship, and that nepotism is inevitable and lowers people’s motivation to work hard. To that I say, seriously? If you’re in charge of hiring and running the company, are you really going to let that happen? Give yourself a little credit, whydoncha?

Rather than being a risk, there’s a huge benefit to hiring a friend with just as much experience as a stranger. I hired my best childhood friend, Brandon, to work at Wine Library because I knew he was awesome from our baseball card days and I trusted and loved him. When my brother, AJ, and I started VaynerMedia, we hired a handful of AJ’s friends from college and high school to get the ball rolling because we knew that these particular individuals would bring a certain energy to the company and establish a fun, awesome, hardworking, passionate, and competitive culture right off the bat. After them, we hired a few more people to round out the organization, and continued to hire as we needed.

Fast-forward, and those initial employees are now working in very different places within the organization. But as we’ve grown, they’ve been key in establishing and communicating our culture throughout the company—just as AJ and I knew they would.

The key to hiring friends successfully is simple: Be ready to enforce a meritocracy. Sometimes it can be hard to divorce yourself from your friendship and evaluate people solely on their work performance, but it is possible. I’ve had to fire friends. You hire friends because you think you know what you’re getting, but sometimes the new environment opens your eyes to parts of them you didn’t know about before. That can suck. But if you can be professional, the firing won’t be as horrible as you might think. After all, if you’ve been doing your job right, it won’t come as a shock. You’ll have worked with them for a long time to try to improve performance or fix a problem, and even had a “last warning” talk in which you also ask “How do I help you?” By the time the firing comes, you’ll probably both be relieved. And great friends know that you don’t want to hurt them.

imageOnce you recognize your weaknesses, should you keep working on improving them or delegate?

I don’t know the full answer. I had to work on getting better about being clearer with negative feedback because I led with so much honey that people didn’t realize they were being told they needed to improve their performance. I needed to be more direct, and I’ve worked on strengthening that skill because I thought it was important. I wouldn’t say I’m particularly scary, but I’m no longer a pushover, either.

Try applying the 80/20 rule, also known as Pareto’s law. It’s probably a good idea to spend 80 percent of your time on your strengths (though I really wouldn’t mind 95/5 because I just believe so strongly in betting on one’s strengths) and 20 percent on shoring up your weaknesses. We all have them. If you’re not sure which one needs your attention most, ask the people who work for you, whom you work with, and your closest friends what they think. It means you have to roll with humility, but you can’t fix a problem if you don’t know it exists.

imageDo you have any tips on delegation?

Sure. Once you accept that 99.9 percent of the things you deal with every day don’t matter as much as you think, it’s a lot easier to let other people do them. Good leaders know when to let go, and they let go of a lot because they’re in the clouds and dirt.

Some people don’t delegate because they’re positive no one can do as good a job as they can. That may be true, but not every job needs your level of perfection anyway. You’ve got to know when good enough is enough. Let the bright, interesting people you hired do their jobs and make yours easier. It takes humility to accept you’re not as unique or indispensable as you think, but it’s also freeing.







imageWhat are some of the key challenges facing freelancers today, and what tools can they use to overcome them?

I think the biggest challenge that most freelancers have is that while they are great at their individual specialty (design, consulting, video, etc.), they don’t actually know how to run a business. The difference between having expertise in an individual skill and being a business operator is huge, and at the end of the day being a freelancer means you’re running your own, one-person business.

A freelancer’s biggest asset is time, so any tools or software that can help to save time is going to be huge. I mean it applies to me, too. I don’t like doing the billing, following up on invoices, or managing our P&L. None of that stuff is fun for me, and it’s going to be even less fun for a freelance designer. The output is the fun part. The reason so many professionals don’t freelance is that they want to do their thing, but when they start getting into the goop and the gop of billing, insurance, and all the other stuff that comes with running a business, they check out. You should be looking for any and every tool that helps you save time with those tasks.

The other thing that might be helpful would be to find a business mentor, or even take business classes. Learn everything you possibly can about business management so that you can worry less about the side stuff, and spend more time on the fun stuff.

imageI need to hire an office assistant, but though sales are great I don’t have the capital to hire anyone. Got any creative ideas?

Use your social capital. Most people think money is the best compensation, but there is somebody out there who needs experience or visibility more than money. That’s how DRock first started working here. He asked if he could do a video for free, he did a great job, and we formed a relationship, which led to a full-time gig. Without him, I may not have ever done the show, let alone written this book.

There are many ways to barter your services. Announce on Craigslist and social media what money you can offer, and then add all your services free for a year. Make a video that shows why you’re a great person to work with. Offer your stuff, your services, your time, or your name. Make a deal where you pay out very little in the beginning of a project but your assistant gets a sweet percentage of the final payout. Leave no rock unturned.

Whatever you do, however, make sure you can deliver on whatever promise you make.

imageThey say you should hire slow and fire quick. How many chances do you give your staff?

There’s nothing worse than firing someone. I’m not usually the one who does it here anymore, but when I was I’d spend a month figuring out how to make myself feel better about it. We’re not in the one-, two-, or three-strike policy here at VaynerMedia. We actually have enormous continuity, and I think part of that is thanks to the firing policy. People see that we try to handle things with empathy and grace. Also, no firing ever comes as a surprise. We work hard with people to try to help them achieve what they wanted to do when they came on board, or to help them find a better fit within the company. I think word of that effort gets around, and it makes people feel good about working here.

I don’t think what’s most important is to fire fast, but to fire well. It’s better in the long run for everyone—you’re free to find a better fit, and the employee is free to go succeed somewhere else. But if you don’t have the EQ to do it well—to make it feel like a liberation and not like a punishment—find someone who does. If I hadn’t had it when I worked at Wine Library, I swear I would have asked my mom to do it. She could make you see how death by firing squad could be reason to celebrate.

imageHow do you motivate teams of remote workers without a payment incentive? So far positivity and hustle are not producing results.

Take the blame, and then start communicating better. If there are people on your team who are not performing to their best abilities, that’s on you. But it’s a relatively easy problem to solve. Arrange for a meeting and then tell them they’re not executing at the level you were hoping for. Then ask, What can I do to help you? And then start helping.

imageWhat does it take to work at VaynerMedia?

It all depends on what job you want, of course. The more interesting question is, What does it take to win?

The losing players at the VaynerMedia game tend to disappear within the first year or year and a half because they’re not playing the long game. They’re either solely motivated by money, or they have the audacity to think they’re better than they are. I like bravado and confidence, but you’d better have the goods to back it up. Admittedly, on occasion VaynerMedia has missed that talent and the employee had no choice but to leave. I hate it when that happens, but even I know we can’t always win.

What about the winners? They tend to have all the qualities we’ve discussed before: empathy, self-awareness, respect for others, amazing work ethic, and patience. They’re not only good communicators; they advocate for themselves in a constructive way (hey, I know we’re not perfect). It takes hard work and smarts to succeed here, but what trumps all of it is heart. Skills can be taught; heart just is. If you’ve got it, I’m interested in working with you.

imageWhat key factors should a Millennial-owned branding company look for when hiring other Millennials as it quickly scales?

Why are you intent on hiring Millennials? Lou Pearlman was a middle-aged blimp marketer before he put together two of the biggest boy bands of the nineties, the Backstreet Boys and NSYNC. He wasn’t a thirteen-year-old girl, but he knew how to market to them. I am not a Millennial, but I know how to market to Millennials better than many, including Millennials. Just because you’re twenty-four doesn’t mean you know how to sell sh@t, even to a twenty-four-year-old.

The questions you need to ask Millennials are the same ones you’d ask anyone. Do you know how to market to this age group? Do you understand their behavior? Do you know how to create content that will also create the sale?

imageWhere would you start building a digital team in a traditional (TV/print) agency?

Traditional agencies that sell print, direct mail, outdoor media, or PR are all shifting to digital because that’s where the dollars and storytelling are going. This isn’t difficult. Hire seven people skilled in digital social, bring them into your department, and work with your CEO to integrate this new thing. VaynerMedia often starts new divisions, from live events to video production. We have to integrate them into the business and we do it by bringing in people with the right skill set. Now, how does that practice get molded into the org? I’m often hands off for the first three to six months, but then I get my hands dirtier. Leading is knowing when to step in or step back. It’s just about deciding when to do it.

imageWhen do you shift from hiring a freelancer to hiring someone full-time?

You should transition a freelancer to a full-time employee the moment you fall in love with that person’s work and personality and know they are going to bring tremendous thunder to your business and your workday . . .

Or . . .

When you need to because your business is growing or your client is producing more stuff and why would you look for someone new when you have someone you trust and like who knows the brand right there with you . . .

Or . . .

When the freelancer falls in love with your business and keeps pushing you to let him or her join your team. It may not be a practical move to take on a hire, but do what you can to reward that passion and invest in the relationship for the long-term stickiness and ROI it will afford you.

imageIs terminating the bottom 10 percent still a good idea? Even on a team of all-stars, someone has to be last.

This is a legendary mantra that Jack Welch introduced to the business world, and this answer came straight from the horse’s mouth when he appeared on the show:

If you believe that the best team wins and that business is a game, you have to field the best players. So you have to be aware of who are your top 20, middle 70, and bottom 10. Make your top 20 feel 6’4”. If they’re already 6’5”, make them feel 6’8”. You let them know you think they’re that good. Tell the middle 70 you want them to strive to be like the top 20. Tell your players at the bottom of the rankings why they’re there and give them a chance to fix what’s wrong. If they can’t, let them go. But always love them as much on the way out as you did when you let them in.

I asked Jack whether this advice would be true for people who only had 500 employees, not 400,000 like he did when he ran GE. He said it would be even more important. Then I pointed out that a lot of people who watch my show have maybe five employees. And he acknowledged that that would be very difficult, because now you’re looking at the people who got you started. But you have to do it.

Suzy Welch, Jack’s wife and writing partner, who was also on the show, pointed out that there is no perfect team. There is always someone who is performing better than someone else. Instead of bemoaning the fact that you have to let go of the bottom 10 percent, celebrate everything you’re doing to nurture the top 20 percent.

imageAs a business grows, what is the best solution for documenting policy, procedure, and process so all are on the same page?

There is no business on earth that won because it had a supertight handbook. Maybe a behemoth like GE should have something in place, but that’s what their lawyers are there for. A company of only five hundred or so employees shouldn’t have to document every little thing. As Suzy Welch said, work on building your values and culture. Make sure everyone knows the mission of the company, where they’re going, and why. Hold on to your entrepreneurial spirit for as long as you can.

imageHow can efficiency and creativity better work together?

Jack Welch also pointed out on the show that to get creatives to be efficient you have to get creative. That means hiring creative people. You want everyone in your company, no matter whether they’re on the account, client, or creative side, to be thinking of better ways to do what they’re doing. I think one way to do that is to put your players in a position to succeed. So long as the work that gets produced is quality, I don’t really care how you get it done. I’ve tried to get people to work within my version of efficiency, and I find that it’s just better to let people do things their way. I may not like that you need to retreat to a private Zen garden, but if I like your output, why should I care? Prima donna creatives can be irritating, but if their ROI is awesome, it’s worth it. A supremely efficient creative who lacks the magic is not.

One thing Jack, Suzy, and I were all in agreement about when we heard this question is that it’s an awful thing to elevate the innovators in a company above everyone else. Don’t put them on an altar and tell everyone else to just put their heads down and get to work. Don’t let anyone’s mind go to waste. Encourage everyone to be an innovator. At VaynerMedia we expect our creatives to be practical, and our account strategists to be creative. It works, creating an energizing sense of mutual respect.

imageMy business is completely digital. How important are real-life meetings?

The number of online tools at our disposal makes it extremely easy to allow people to work from home, or to facilitate conversations and transactions with people working across town, across the country, or on the other side of the world. But even if your company is entirely digital, you should not eliminate in-person meetings.

Why? Because human beings make decisions, not machines.

Digital should be seen as the gateway to a human interaction, but not as a replacement for it. You just can’t get the same nuance or establish the same context via conference call or Google+ as you can in person. That isn’t to say emotion can’t be conveyed digitally; I get plenty emotional on Twitter and more and more on Instagram. But those exchanges don’t have the same energy as an in-person one does. And it’s important to keep fine-tuning your ability to read a room and people’s body language. It’s a tremendous skill that doesn’t just make you a better boss or employee; it makes you a better person.

So whether you need to talk to an employee, client, or your boss, create opportunities to meet in person sometimes, especially if it’s been a while or you have something important to discuss. Keep doing that until the robots take over. When that happens, we can reevaluate.

imageHow do I keep my old employees from hazing my new employees?

Be the parent. Tell them to stop or you’ll fire them.

I had a similar problem at Wine Library. My staff wasn’t hazing anyone per se, but they were making immediate judgment calls on new hires. Within two days, if they had decided a new person sucked, they froze that person out or made their life hard. My ultimate solution was to sit down one by one with my entire staff and tell them that if they didn’t work with me to fix the problem and become part of the solution, they would be gone. And you know what? I had to fire a few people. It happens.

imageHow much of your staff’s time is spent on you as opposed to other projects?

If you mean the staff that helps with my content production and the business development around it, then that entire team is part of “Brand Gary” team. Some were already working within VaynerMedia and were plucked out of the machine, and others were hired specifically for the team. I didn’t need this many people when I was producing Wine Library TV, but now that I have so much more scale I can produce more content outside the show, and I need help to do that. This is what a production team for one person looks like. I believe the future for people with sizable audiences is less about having a PR person and more about building a modern production company around that person.

imageHow do you handle it when people miss their deadlines?

It all depends on what I expect from you. If you’re a person who is usually a hard-core executor who’s extremely reliable and I rely on you to be that all the time, I’m going to be pissed. If you’re kind of disorganized and a little weird, and I never quite know what’s going on but somehow you always make magic happen, I probably didn’t ever believe you’d make your deadline and had planned accordingly. Bottom line, the level at which I or anyone else should get upset at a missed deadline will probably change depending on our expectations. If you know what someone usually brings to the table and they “miss,” you have to wonder whose fault that is. Is it possible you put them in a situation where they weren’t working to their strengths? It’s great to challenge your strong players but you need to be fair. Put players in positions to succeed and when you put them in a spot that is challenging, make sure you remain empathetic. Above all, be fair.

imageHow do you diplomatically tell the boss he’s f*ing it up?

I think any boss worth his or her salt will be pumped if you’re brave enough to respectfully point out where you disagree, and I think it can be a win-win situation. If the boss agrees with your feedback, you’ve won points. If he or she doesn’t and starts disrespecting you, then you know you work for a dipsh@t and need to look for another job. For that reason, there’s no risk in giving critical feedback, especially if you don’t love your job. It’s a good way for people to audit their bosses and gauge whether it’s wise to put their career in their bosses’ hands and follow his or her leadership. I have massive respect for the people who are comfortable telling me they disagree with me. The key is to make sure you remain gracious and respectful while still expressing passion and holding true to your point of view. And of course you should go in with a good sense of who your boss is. My direct reports know they can get away with a lot more with me than they could with many of the bosses in my own companies that are below me. Know your judge.

imageWhen trying to get your point across to meet a goal, do you prefer to be abrasive or compassionate, and why?

I’m constantly adjusting to my clients, start-ups, employees, and investors in real time. Compassion, empathy, competitiveness, warmth, straight disrespect—every situation calls for a different brew. I have neither a favorite move nor tactic. Sometimes I’ll try six months of compassion and then karate-chop people to the mat because clearly that isn’t working. Managing is a never-ending 365-day test-and-learn. You don’t want to get into the habit of using one move over and over. It’s kind of like medicine; if you use it too often, it stops working as well.

imageWhat are your suggestions when you have to work with external partners to get the job done, but they don’t share your hustle?

You mean like the rest of the world? Ha! If you work for an agency or a client service business, you’re stuck. You have to play well in the sandbox. It can be hard for people in the trenches when I insist they be nice to a partner that’s dropping the ball. But I don’t think we gain much from calling people out on their idiocy. I think our work speaks for itself and that the truth is undefeated.

Here’s a challenge: When you’re having trouble with a partner, don’t get aggressive or nasty. Win them over with kindness. Go for a drink together if you can. Build a real relationship and you may just find that they know they stink because their company stinks. When you can find some common ground and a way to align yourselves it can take some of the venom out of the situation and make you feel less resentful.

Communicate with your team. Communicate with your partners. Communicate with your clients. Communicate, communicate, communicate.

imageIf you have a business that is growing fast, is it more important to perfect the system or to focus on adding more people to the team?

Why can’t you do both? It takes hustle, but that’s the only way to get huge victories. I worked very hard on the system at VaynerMedia while hiring people and trading them up and building the team. Integrate the team from 9 A.M. to 5 P.M., and then spend 5 P.M. to 2 A.M. perfecting the system. Go all the “hell in” now or you will miss your moment. Extract all the value you can out of your day while you still can, especially if you’re young. That’s what I’m doing as I approach my fortieth birthday. My fund, The #AskGaryVee Show, VaynerMedia, family life, my health . . . I’m pushing it all harder than ever because I know that when I’m forty-two I may not be able to do it as much. Squeeze everything you can out of the time you have right now.

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