I rarely submit questions for Google's Matt Cutts, but I did submit one and he actually answered it in a video.
The question was, Matt - what are your regrets related to web spam. I specifically asked "Was there a key moment in your spam fighting career where you made a mistake that you regret, related to spam?"
Matt said he regrets two things, maybe more, but he listed two things:
(1) Not acting faster on paid links that pass PageRank.
(2) Making the wrong decision early on about content farms.
Here is the video where he digs into each one:
I also summarized it in detail at Search Engine Land, so if you do not want to watch the video, you can read my summary there.
Here is the transcript of the video:
0:00: today we have a fun webmaster question from Barry Schwartz in New York
0:04: barry asks with their key moment in your spam fighting career
0:09: where you made a mistake that you regret related to spare him so he's not just
0:13: talking about choices order over anything like that
0:16: I can think about least two mistakes other than a half million related to
0:20: stand hopefully in Upper
0:22: I remember hmmm talking to a very well-known SEO
0:27: and a search conference in San Jose no
0:30: probably seven years ago give or take
0:33: and and then issues that you know what
0:36: paid links are just to prove wonders to cook their two common there's no way
0:40: that you guys will be able to
0:41: crack down on them and enforced and come up with good algorithms or or take
0:45: manual action disorder
0:46: put the genie back in the bottle as he put it and a and that was when I
0:50: realized that made a mistake and that we had allowed
0:53: paid link that has been trying to go a little bit too poor
0:56: and become a little bit too common when and so in the early days over out yet
1:00: 2005-2006
1:02: you'd see Google cracking down a lot more aggressively in taking a pretty
1:06: hard liner rhetoric about feelings the past Adrian
1:09: at this point most people know that Google disapproves amid
1:14: probably violates like the Federal Trade Commission's guidelines all those sorts
1:17: of things
1:18: we have now released a targeted we take spam reports about it
1:21: and so for the most part people realize that's not a good idea
1:25: if they do that they might base the consequences and so for the most part
1:29: people try to steer clear appealing to the past a drink at this point but we
1:33: probably waited too long before we started to take a strong stand
1:37: on that particular issue hmmm another mistake that I remember
1:41: is on there was a Gruber content farms
1:45: and a and we were getting to internal complaints where people said look
1:50: this website or that website is really bad it's it's just
1:54: poor quality stuff on a legal it's been our low quality
1:57: but it's a really were pleaser experience and I had been to one
2:01: particular page along the sides because
2:03: one point my my toilet was running and I was like okay how you diagnose the
2:08: toilet was running
2:09: and I had gotten a good insert from that particular page
2:13: and I think I might have over generalized a little bit been like no no
2:16: there's not a great bonding
2:17: quality content onto the sides because look here with this one-page the Hope
2:21: Solo
2:22: the diagnostic why does your toilet run and how do you think that all that sort
2:25: of stuff
2:26: and the mistake that I made was judging from that one in it do and not do in
2:30: larger-scale samples are listening to the feedback or
2:33: you know looking at more pages on the site and so I think it took us a little
2:36: bit longer
2:38: to realize that some of these lower quality sides are content farms or
2:41: whatever you want to call them
2:43: we're sorta mass creating pages rather than really solving users needs with
2:48: with fantastic content so I think Tom as a result we did wake up to that we
2:53: started working on it
2:53: months before really became wide scale in terms of complaints
2:57: %uh but we probably could have been working on it even earlier mom
3:01: regardless you know we're always looking for good feedback we're always looking
3:04: for where we missing when we need to do to make our web
3:07: result better-quality and a and so anytime we roll something out
3:11: there's always the question up could you have bought have some way to
3:15: to stop that were to take better action or or more clever algorithm
3:19: and could you have done it sooner and so on you know
3:22: you like Google does a lot a great work and that's very rewarding than we feel
3:26: like okay we have
3:28: cool you know heard are bird
3:31: working hours with many people work and you at the same time you always wonder
3:35: could you be doing something better
3:36: could you belinda cleaner way to do it a more elegant way to do it something with
3:40: higher precision
3:41: I recall and that's okay you know it it's healthy for us to be asking
3:44: ourselves then
3:45: so great question those are coupled he moments like to remember where
3:49: like we made a mistake by not paying attention to a particular topic soon
3:54: book that helps