How to Play the Talent Game

Colleen Aylward recruits talent for some of the hottest Internet companies around. If you want to win the best people, she says, you’ve got to understand the new rules of dotcom hiring.

You’re sitting in a conference room, waiting for a much-anticipated job interview at an Internet startup, when a hiring manager walks in, dumps a box of Legos on the table, and says that you have five minutes to “build something.” Wait a second, you think to yourself. I’m looking to become the head of marketing at this company, not land a guest spot on Sesame Street.


Welcome to the ever-changing dotcom talent game. “Internet companies no longer have time for hours-long, let’s-get-to-know-you interviews,” declares Colleen Aylward, who plays the new game better than almost anyone else. “They certainly don’t have the luxury of hiring the ‘nicest’ people with the toothiest smiles, and then training them. Companies — especially startups — need people who are creative, who can turn on a dime, and who can use their street smarts to solve real-world problems.”

That’s a good description of Aylward herself. Aylward, 46, is the founder of Devon James Associates Inc., a fast-growing recruiting firm based in Seattle. She’s played the talent game for some of the best-known Internet companies in the Pacific Northwest, including, Avenue A Inc., eCharge Corp., Inc.,, and Visio Corp. In a game where the rules keep changing, she says, victory goes to companies with the most commitment and the most clever tactics.

In August 1999, for example, Mike Leo, cofounder and vice president of strategic development at Avenue A, an Internet-marketing company, told Aylward that he needed new employees at positions across the board — engineers, marketers, sales-people, advertising specialists — and that he needed them immediately. So she organized a pub crawl for potential recruits. Aylward, who is pencil-thin, with a head of red hair to match her fiery personality, ushered a posse of 100 Avenue A employees, dressed in matching T-shirts, through a collection of Seattle bars and nightspots. The idea behind the crawl? To use this attractive group of highly motivated employees to spread the word about the company and to convince other people to join. In the days following the pub crawl, hundreds of resumes flooded Aylward’s recruiting war room — and resulted in about 35 hires.


Aylward recently let Fast Company tag along as she raced through Seattle’s streets in her red Alfa Romeo (which doubles as her office), stopping only to coach companies and job candidates on how to play the new talent game. Here are her rules for success.

How do you help startups wage the battle to find talent?

What talent shortage? I’m deluged with resumes. There are plenty of talented workers out there. It’s just that great people already have great jobs. The burden is on companies — both startups and established organizations — to become more rigorous and more creative about finding the talented people that they need, and convincing those people to join, even if they’ve never thought about leaving their company.


Everyone has a price. I can pull just about anybody from one company and put them into another. You simply have to understand how the environment has changed.

What’s changed?

I think of the competition for talented workers as more of a game than of a battle. Both sides have become more jaded, more savvy, more open about their intentions. Most startups don’t really care how people get to the company or about their development once they’re in the door. They care whether people will work themselves to the bone in order to move their enterprise forward. They’re not looking for lifelong employees. Meanwhile, job candidates have become much more astute about how the game works. These days, people stay with a company for two or three years, and then they’re ready to consider something new. By the time they’re in their mid-thirties, they’re interviewing with their third or fourth startup. They come to a company’s bargaining table with incredible sophistication about that company’s venture backers, its market, and its prospects for an IPO.


A few years ago, candidates who were talking to officials at, say, would feel smart if they asked how many stock options they’d get. Now, the typical questions being asked are: Who are you looking at for your third round of financing? What’s the insider price today? What’s your strategy for going public? These are the kinds of questions that you hear being asked by a marketing person making $50,000 a year.

Are startup veterans different from those who are new to the game?

There are at least two different generations of job candidates today. There are people whom I placed years ago at or Visio, who are now at their third or fourth startup. They may be in their mid-thirties, but they’re not considered youngsters anymore. They’re incredibly street-smart.


People in that veteran generation are looking for management stability. They want to see solid funding sources — Benchmark Capital as the venture capitalist, Goldman Sachs as the investment banker. They actually care about job titles — they want a title that pushes them ahead on their career path. And they still want a lot of stock. But now they don’t want to take a big cut in pay.

Then there’s a younger generation — those people who are coming out of college. They’re not as willing as veterans are to work 18-hour days for what could be a financial crapshoot. At the same time, they do expect to hit it big. KPMG did a poll of college seniors about their work expectations. Fully 74% of those students said that they expect to become millionaires.

This is the kind of world in which startups operate. It’s no wonder that CEOs and HR people have so many headaches!


So how do you maneuver in this new world?

The first thing that you do is take a lesson from the restaurant industry. Your job is not only to create a sound, solid company. It’s to create a work environment that people want to be a part of — to make your company a fun, fresh, hip place to be. There’s not just one right way to build a work environment — but you do have to have an environment that job candidates will find compelling.

Also, now more than ever, you’ve got to have some marquee names associated with your company — either on your board or in senior-management positions. With so many startups making so many claims about their prospects, one way that candidates cut through clutter is to focus on people with genuine track records of accomplishment: Successful people tend to attract other successful people.


The third big-ticket item for this new generation is “wingspan.” People want job titles and work roles that are open-ended enough to let them do all kinds of different things. They want to spread their wings. We just lost a candidate for head of HR at a promising startup. The candidate chose instead to sign up with a high-risk Internet incubator. Why? The incubator job had incredible wingspan: “Come work for us, and you’ll get to work with a dozen small companies, learn their technology, and help them recruit.” This candidate knows that the other job is a crapshoot. But if that company makes it, not only will everybody in town know her (and notoriety’s a big thing too), but she’ll be at the nexus of a dozen companies and she’ll have all kinds of opportunities to grow. It’s hard to argue with that kind of wingspan.

What kinds of questions and techniques won’t work?

What won’t work anymore are questions like “How many manhole covers are there in Seattle?” What won’t work are obnoxious, aggressive, confrontational interviews, like those that Microsoft has perfected. The only company that can still get away with that approach is, well, Microsoft.


People have a low tolerance for those tactics nowadays. Those interviews make people testy. Job candidates have already been through similar hoops with other companies, earlier in their careers. It will be harder to attract talented people if part of your evaluation process is to make them uncomfortable, because they can simply walk across the street to a company that won’t make them uncomfortable.

Of course, you still have to figure out what makes job candidates tick, how they solve problems. Are they the kinds of people — in terms of personal attributes and values — who tend to flourish at your company? For an answer to this question, old-fashioned “situationals” are back in vogue. Companies are judging candidates on how well they handle real-life scenarios, as opposed to brainteasers.

But let’s get real for a moment. You can ask all the interview questions you want and probe for the values and attributes that you think are important. But when it comes right down to it, you want to know four basic things from candidates, in terms of experience: How have they helped their companies to increase revenue? How have they helped them to decrease costs? What kinds of problems have they solved, and how have they solved them? How creative are they? If you can get accurate answers to those four questions, you’ve done a good job of evaluating candidates.


People still invoke the mantra, “Hire for attitude, train for skill.” What kinds of attitudes should startups be looking for in candidates?

A few years ago, the important thing was for candidates to demonstrate that they were “can-do” types — that they had limitless energy and that they would get a job done, no matter the cost or the consequences. That was the kind of attitude every company wanted in a candidate.

These days, companies are more hungry for candidates with wisdom — with the quiet confidence that they only get if they’ve been through a war. Companies want people who are “old” before their time. People who are wiser for having been beaten up in previous startups. People with street smarts, those who can turn on a dime when the situations calls for change, who are open-minded enough to listen to someone else’s opinion and recognize that opinion as a good idea. Raw energy and blind commitment just don’t count for as much as they used to.


There’s another attribute that distinguishes people who succeed in the startup environment from those who don’t: self-awareness. If you don’t understand your strengths and your weaknesses, if you think that you’re better than you really are, then you’re fried. Working in a startup can be a humbling experience. When you’re under fire during every minute of every day, it’s awfully hard to hide. Everybody can see what you are and can smell what you’re made of. So, if you don’t know what you need help with, and you’re too cocky to ask someone about what you need help with, you’re going to pay a price.

What do you tell people at big, established companies who decide to enter the dotcom fray?

I tell them that I’m sure they’re very excited about the Internet and about the technology behind it, as well as about the business culture that goes along with it — because they certainly wouldn’t be dumb enough to make a major career move based on greed. My advice to anyone who wants to join a startup simply to cash in on the gold rush is to open an Ameritrade account instead. Day-trading is the same kind of crapshoot — without the chaos.


People who want to jump from a 20-year career with an established company to an Internet environment had better ask themselves some tough questions: Do they really want to live a startup life? Do their families know what they’re getting into? Are they eager to be in an environment where almost all of the perks they’ve gotten used to — doting secretaries, car services — simply do not exist anymore?

I wouldn’t be surprised if we begin to see a talent migration from dotcoms back to big companies — people who signed up with a startup, didn’t make millions, and now see big companies as more stable and more humane environments. Big companies should put scale models of the Statue of Liberty outside their offices: “Give me your tired, your poor, your huddled masses, yearning to breathe free.” That might be all it takes to win back some of the people those companies lost a few years ago.

Anna Muoio ( is a senior writer for Fast Company. Contact Colleen Aylward by email (, or visit Devon James Associates Inc. on the Web (


Sidebar: Ten Questions

Colleen Aylward, Web recruiter extraordinaire, has created all kinds of tactics to attract and to evaluate talent. And she’s heard just about every interview question ever asked. Here are 10 questions that she believes will always get you the information that you need.

  1. Take me through a time when you took a product or a project from start to launch.
  2. Describe the way that you work under tight deadlines.
  3. Describe how you work under tough managers.
  4. What is your definition of working too hard?
  5. Persuade me to move to your city.
  6. How do you manage stress?
  7. What kinds of opportunities have you created for yourself in your current position?
  8. In a team environment, are you a motivator, a player, a leader, or an enthusiast?
  9. In the past three years, what part of your professional skill set have you improved the most?
  10. If you were a new employee, what would you do to gain respect from peers in 30, 60, or 90 days?