One of our most popular posts last month was a Q&A with David Webster, the chief strategy officer in Microsoft's central marketing group, in which he explained what the company was thinking when it aired those head-scratching ads starring Bill Gates and Jerry Seinfeld.

As a follow-up, we've put together these excerpts from the rest of our conversation, starting with another burning question: What was the deal with Microsoft's decision to pull its sponsorship of a "Family Guy" special episode last year? Considering the show, shouldn't the company have anticipated that the content might be a little raunchy?

Continue reading for Webster's answer to those and other questions.

Q: Any lessons learned from the Family Guy experience?

Webster: I think, in general, we are, as a large company, surprisingly willing to experiment. We believe that if you're going to be relevant to consumers, you have to be willing to engage in the kinds of dialogues in the places where consumers are interested in having a conversation. I think the old world of purely running 30- and 60-second ads, and staying out of the other integrated brand approaches, ultimately isn't going to get the job done. It has its role, but I think we also need to be more of the moment, in the moment, borrowing cultural currency and associating ourselves with relevant experiences people want to have.

Now, that being said, when you adopt a principle where you're going to experiment and try some things out, you don't always know how every one of those things is going to turn out when you start going down that path. And you have to be willing to make some corrections and adjustments on the fly, in market, in a moment when you gain more information. We reserve the right to wake up smarter every day. In this case, I think that's probably the situation, as simply as you can put it. Things that sometimes look good on paper, and seem like there could be some good synergy in terms of audience, when you get closer to it and think about it, you're maybe not as comfortable with it.

Q: Right, I think the joke was, had Microsoft watched the Family Guy?

David Webster

Webster: Yes, I personally had. There were many different strains of comedy within Family Guy, and I think the difference between being in a Family Guy episode and advertising in a Family Guy episode, there are some nuances there. ... Frankly, we're going to continue to be willing to experiment, and try new things, and go new places, and that means sometimes at the 11th hour, we may still call an audible and say what looked good on paper doesn't seem like as good a fit at the scrimmage line. I think it's all part of being willing to engage in the moment and take some risks.

Q: How has Microsoft’s approach to marketing and advertising changed (more generally)?

Webster: The historical mode that we’d been in was “launch and leave.” Whenever we’d have a new product release, there would be a short burst of marketing, and then we’d go back to being dark. When you have some of your core flagship products actually only released every two or three years, that can leave you out of the public eye for extended periods of time. We really made the commitment that we were going to be doing sustained marketing for our core franchises and just be in the public dialogue with consumers on a far more regular basis.

Q: How does Microsoft build its overall corporate brand?

Webster: Ultimately, even though Bing and Windows and Office and Windows Phones and Xbox are very different products, they all come from Microsoft. Those products and the stories they tell should add up to something for the company. Our thought was, we’re already going to be spending significant amounts of money marketing our consumer brands, why don’t we build the Microsoft brand through those? Why don’t we have a point of view or a philosophy that’s inherent in all that work? That then starts to say something about the company itself that’s behind it. Starting with “I’m a PC” and that era, what you see is a commitment to using real people, to telling authentic stories, to trying to identify those real moments.

Q: One of the most interesting things about the “I’m a PC” campaign is that it was a martial arts move, using a line that Apple made popular. Was there internal debate about that, and how do you feel about the result?

Webster: We feel great about it. Any debate that we had was ended once we figured out how to do that storytelling in a way that was authentic to us, and wasn’t reactive. Obviously the line itself uses as a point of departure the statements that have been made. But in our case, we felt like owning that line, being proud of it, embracing it, not fighting it, bringing it to life with diversity. If somebody else is going to say there’s one guy who’s a PC, and he’s a nerd — even though he may be more amusing than the other guy — then we’re going to end up saying, no, there’s not just one guy who’s a PC, there’s a billion people who are PCs, and they are wildly interesting. The idea that PC owners don’t do anything interesting is obviously untrue. Effective advertising has to be built on something that’s true, or ultimately it’s just a creatively told myth.

Q: In the case of Windows 7, it doesn’t hurt when your product is seen as a major improvement over past versions.

Webster: That’s what all advertisers want, is a great product to stand up and talk about. You saw that carry forward again into the (Windows 7) “It Was My Idea” campaign. Those people are not actors, they’re just regular folks who had a point of view about how they thought Windows could do better, and sure enough, it ended up being reflected in the product. That notion that a billion users help us make the product better is factually correct, and it’s a story that is interesting for people to hear. So we really think we’ve hit upon a pretty good voice there for the Windows brand.

Q: For the upcoming Windows Phone 7 Series, is it safe to assume that your biggest opportunity is not iPhone, Palm or Android switchers, but people upgrading from standard mobile phones?

Webster: Yeah, I think if you look at the numbers involved, you have to conclude that. There are simply 10 times the number of feature-phone people headed to the smartphone category than there are people who are in the smartphone category. I think there will be people who do switch. But I think ultimately in terms of raw numbers, the number of people who have been outside of the category, looking in, dwarfs any of those other numbers.

Q: Microsoft is obviously big into digital advertising. What will happen to traditional TV and newspapers as part of your marketing mix?

Webster: Well, television is still phenomenally important. As much as we talk about the fragmentation of the television landscape, and DVRs (digital video recorders) and all these channels that are out there, people are watching more television now than at almost any other previous point in history. It’s more fragmented. In today’s marketplace, you’ve got to be in Hulu.com, you’ve got to be in web video locations, you’ve got to be on cable networks, you’ve got to be able to do branded integration into the television shows themselves. If you want to be DVR-proof, get yourself into the content. We’re spending more money on television than we ever have, we’re just trying to spend it in ways that give us the results that we’re looking for. Print is useful for specific kinds of audiences and specific kinds of messages.