6 Leadership Lessons From Reddit AMAs

Reddit can’t get out of its own way. Just when it seems like the controversy surrounding the bizarre ouster of CEO Ellen Pao was dying down, some new innuendo starts it up again. By this point, the conversation about the site’s abundance of tasteless (and beyond) subforums has been rebooted more times than the Spiderman franchise. But like most of the social media landscape, Reddit is a community with numerous and varied voices. Despite the well-earned scorn heaped on Reddit from more mainstream outlets, the community at large has often played host (via the crowdsourced mechanism at heart of one of its latest fiascoes) to a terrific cavalcade of interesting leaders and personalities. This was a cache, we decided, worthy of plundering.

**Special thanks to Brant Tedeschi of TopIAMA.com for compiling the linked Reddit AMAs into a more legible format!**

6 Leadership Lessons From Reddit AMAs

His answers may be short and, appropriately, sweet, but there are some noteworthy takeaways from Boxing Hall of Famer Sugar Ray Leonard’s AMA. Interestingly, the man with almost as many retirements as all-time classic fights claims to be totally at peace with the stop and start trajectory of his admittedly fabulous career. But it’s no surprise that a man who took 150 amateur fights before ever landing a payday would advocate hard work as the sole avenue to success.

Sugar Ray Leonard, Boxer

Q: What life lessons [has boxing] given you?
A: There are no shortcuts to success.

Q: If you could start you career over, with the knowledge you have now, is there anything you’d have done differently?
A: No, nothing at all. I feel that where I am today is a blessing.

Apparently not everyone at the zenith of their profession would agree with the Olympic Gold Medalist and World Champion on that last point. James Taylor, a 5-time Grammy winner and HOFer in his own right, bristles at the thought of missing out on yet another iconic song about friendship. Even given his incredible career, Taylor still sees opportunities he missed along the way.

James Taylor, Musician

Q: You’ve obviously been very successful and accomplished, but have you ever looked back over your career and wished you would’ve done something differently? i.e. do you have any major regrets?
A: Yeah, I’ve got one regret I can think of. Randy Newman asked me to sing the theme song for the first Toy Story film. And I couldn’t find the time to do it. Lyle Lovett did a great job.

But I wish it had been me.

That same specter of regret apparently looms in the mind of Sam Altman, a Reddit board member, appropriately enough, and President of startup finance organization Y Combinator. Prominent influencers like Altman know they must be conscious of the effect they have not only on the people and companies they choose to work with, but also on the ones they don’t.

Sam Altman, Investor

Q: Does it worry you that by rejecting thousands of startups each year from YC, you likely end up discouraging some good founders with good ideas from continuing to work on their companies? I realize you always tell rejected companies to keep at it, but is there more you could do to mitigate the real impact of rejection?
A: Yes. We are working on some new stuff, but honestly this is high on my list of worries.

Fellow Redditor CEO Steve Huffman, recently chimed in with his own AMA for obvious reasons and fielded a boatload of questions about recently deposed (and, some would say, scapegoat) CEO Ellen Pao. Huffman acknowledges that sometimes leaders are responsible for things they aren’t even really, well, responsible for. Certain things will always roll downhill, but as Huffman puts it, others flow up. That occasionally punitive structure is simply the price of admission for the people at the top.

Steve Huffman, Executive

Q: She can’t surely have been solely responsible for all the negatively perceived changes?
A: It’s hard to imagine she was, but responsibility flows up. I’m sure there will be times I’ve got to take it on the chin as well. Part of the gig.

Finally, Joseph Kim, a college student who escaped from North Korea’s isolationist regime at just 16 reminds us, among other things, how important perspective can be when our job is to relate to others. For most of us, the more we have, the more we take for granted…But as Kim’s story shows, sometimes the things we perceive as small can be very, very big to someone else.

Joseph Kim, Refugee

Q: I loved your video on TED!! Tears were shed…

What was the most surprising thing you’ve learned upon coming to America?
A: When I was in American Consulate in China, I saw a car in the building. And I remember going to see that car more and more every day. I was hoping to have that car one day. But then I came to America, I realized that the same type of branding car was used as a taxi, and that was really surprising, because I thought that was the best car ever in the world.

Conclusion

These themes of regret, self-awareness and responsibility are common threads in interviews of most any type, really, but they do seem particularly prominent in two-way discussions like AMAs and other Q&A structures that encourage a more casual (and less guarded) approach from the subject. As a result, the experience seems more educational and rewarding than a typical public relations handholding. Presentations like this are…dare we say it…fun.

You know, there may be a leadership lesson somewhere in there as well.





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