Photo by Dplanet::.

If you’ve been freelancing for awhile, you may have come to the financial crossroads of Mom and Pop versus larger companies. I think it’s far easier to make money with big clients who wield big budgets, who understand the creative process and the importance of marketing and advertising.

In 2004, after a decade of copywriting in ad agencies, I took my first position inside the marketing department of a large corporation. Suddenly I was across the aisle. For three years I interviewed dozens of freelancers and small agencies for projects in print, Web, and broadcast. I learned firsthand what worked and what failed during the interview process from the corporate perspective.

This experience has served me well. I developed a playbook of do’s and don’ts that has been tested and honed for my style in the freelance arena with Fortune 500s. If you’re courting corporate clients, here are 10 tips to consider during the interview process to land your next big gig.

1. Cover the basics, and your tattoo. Maybe you won an ADDY last year or your photos don the covers of Vogue Magazine. Then by all means, wear flip flops, use a Trapper Keeper for your portfolio, and whine about your horrible morning. Otherwise, please err on the side of professionalism and keep in mind, (a) this is marketing, where packaging matters, and (b) I work in a mauve cubicle on an old PC, so your grunge T-shirt might not be so cool in my starchy environment. The basics of interviewing are so often neglected by busy freelancers: Be courteous, on time, well heeled, prepared, upbeat. Desperation is your death knell. Try for confident and slightly nonchalant. The basics won’t garner many kudos, but without them you risk certain failure.

2. Prep work and industry IQ matter. It gets easier for successful freelancers to wing it. But don’t be so overconfident that you neglect some simple research, and don’t wear Nikes into the meeting with ADIDAS. Do you know anything about my company? Did you study me a little online? Do you know the name of my VP in case she stops by? You don’t need to get carried away preparing FBI files on my admin assistant. But 15 minutes of prep work on the company Web site can make a huge difference. Show me that you’ve done some homework, that you’re interested in the project. On the other hand, don’t pretend you understand my job or my industry because you did an ad once for a similar company in a different market.

3. Wear one special little hat. I know as an experienced freelance writer or designer, you can write or design whatever we throw at you. But the interview process isn’t the time to prove it. In corporate culture, I want to hire focused, niche professionals. The last thing I want to hear: “I’m a brand, PR, lifestyle, direct mail, technical writer, and I do some design, too.” Once you’re inside and we’re working together, then you can sell me on your full range of capabilities. Choose a path based on your research and stick to it, even if it means losing this project for future work.

4. We’re suckers for sincerity. I’m not impressed by the appearance of slick-looking, fast-talking, business savvy freelancers (unless that’s just naturally your style). We have plenty of folks just like that in the company who play corporate politics. I’d prefer to hear: “I have a helpful mentor. I started as a coffee boy in my Mom’s company.” This will land you the gig faster than trying to sound like a high-powered executive. This works just as effectively in New York City as it does on Maui. Many corporate professionals have an ear for a kind of “truth” on what it takes to be successful and they will respond favorably when they hear it.

5. Repeat after me: “No, thank you.” This is so difficult for so many freelancers and small agencies. It’s imperative for the long-term health of your freelance business and our relationship that you set boundaries around time and money. It starts during the interview. Often, I completely buried freelancers with too much work and tight deadlines. When they couldn’t deliver, I never worked with them again. If you don’t do spec work, don’t do it. If you need three weeks, don’t say yes to two. If you plan to farm out some of the work, tell me so, and tell me how you’ll manage it. If you do say yes, you better deliver and you better assume, no matter how many disclaimers you share, that you have just set a precedent. As I am pressured by my company and the marketplace, I will expect you to repeat this feat regularly.

6. Sell yourself, not your portfolio. Often, I watched a freelancer share too much information and go down in flames in a situation where I was already sold on hiring them for the job. Don’t withhold important tidbits — maybe some namedropping helps — but don’t keep selling me on your experience either. Don’t launch into your portfolio in robot-like fashion. Try for a casual conversation about the fish tank on my windowsill. If I start sharing details about the project, introducing people on my team, or asking you about your upcoming schedule, take these as excellent signs that I’m already sold. Often, I don’t even need to see your work. I’ve already seen enough online or I trust the referral I received. Maybe I just want to know that you can represent our department well in meetings and that you’re not a smelly psycho.

7. I want to be Super Hercules. I’m in a corporate environment where I have to attend multiple meetings and provide updates to a dozen VPs. I want to be the hero. I want to boast and to receive kudos that I found an awesome freelance resource for our project. Your work will reflect on my work. Can you help me look good? Can you supply added value? At a basic level, can you remove the pressure of worry from my busy schedule? Can you show me how easy you are to work with? On a higher level, can you work upstream, from the tactical delivery to strategic development? Do you understand the big picture of campaign development? A word of caution here: don’t be didactic. Don’t assume that I don’t understand the creative process.

8. Ask Qs and listen like you care. I can’t tell you how many times I trapped freelancers into chatting nervously and sharing too much information until they dramatically reduced prices or lost the gig. How did I do it? I just sat quietly, stone-faced, seemingly unimpressed. Ask me about my brand guidelines. Tell me you’ll get started studying the brand right away. Show me that you can think strategically. When experience matters, there are two things that will attract my attention from your portfolio: big name accounts or big name agencies where you worked. Short of that, I’m more interested in knowing that you can listen and respond thoughtfully. I want to know that you “get it.”

9. Showcase your best 4 to 6 samples. I hope that your samples showoff your stellar capabilities. Each page should be like a hook of anticipation. I’ve interviewed enough people to categorize you within seconds. Even if my assessment is wrong, you’re not going to change my mind in the time we have together. If you’re a graphic designer, for instance, I’m thinking: Art Director, Designer, or Production. Keep your portfolio short and simple. You should already know that I wanted to see print ads versus direct mail pieces. And please, don’t assume you know what I want to see in terms of creative approach. If I’m a financial company, for instance, showing a bank sample to showcase familiarity with the industry is great. But I might be looking for someone who can pump life into our stodgy creative, so I’d prefer to see the skydiving ad you created.

10. Empathize with corporate speed. “Hurry up and wait” is the corporate mantra. During the interview, set reasonable boundaries, then smile and nod. I’m already managing a creative team who complain about parking spots and bad hair days. I want freelancers who are easy to work with and who understand corporate culture. In a big company, there are often too many people involved, too many departments, and suddenly, my VP can kill or accelerate a project. The ideas rise up and are just as quickly brushed aside. Let me know that you understand the corporate reality. It will go a long way to help build our long term relationship.

Ultimately, how you conduct yourself in the interview should connect with your style. Many of your decisions can be determined by how you landed in my office, whether by referral, multiple sales calls, or answering an online job post. Finally, leave with a reason to contact me. Send me a thank you note. Put me on your mailing list. Stay in touch.

Corporate America awaits. Good luck.

Jeffrey Selin is a writer in Portland, Ore., and the director of Writers’ Dojo.