Last Friday (March 4, 2016), I had the opportunity to give a quick talk at the Mindtrust Leadership Development Program closing ceremony. I went through the program in 2009; speaking to the newly minted graduates was a highly rewarding way to close the loop. Since I really enjoyed giving the presentation, and got positive feedback afterward, I figured I would share it in written form with a wider audience. Hope you enjoy, and if you have any thoughts upon reading, would love to hear them!

One thing these fine people that introduced me didn’t tell you is that I really love swearing, mostly for emphasis, but a lot of times just for the sheer joy of it. Just love it! So, last night I’m thinking about this presentation, and I get this idea, and – this is a true story – I shoot Joe [one of the organizers] an email like “Joe, serious question, what do you think is the threshold of f-bombs that I can drop without getting kicked out of this ceremony?” I was just coming off a nap then, so once I fully woke up, I’m thinking Joe wouldn’t even reply… But being the stand-up guy that Joe is, he totally did! Thoughtful, completely balanced response. Essentially, Joe said “You do you, Masha!” So, in fairness to all, I promised I will keep it to 3 total f-bombs. Of course, knowing that I had such a small supply to work with, I did what anyone would do… I put them on the slides.

Anyway, I could stand up here and tell you my entire life story – like “Hey, I’m Masha, I’m doing a travel startup” – but that would be rather presumptuous about your interests, right? So, instead, I thought I would share 3 stories – 3 leadership lessons that I’ve learned, on a rough timeline from when I actually did the Mindtrust program, to, well, about 2 days ago.

First, let me take you back in the time to 2009. The setting is Mindtrust. We’re in that section where you determine your leadership style – authoritative, by influence, etc. And for the reflection part of the exercise I get paired up with this extraordinary dude – Sam, let’s call him – and he’s super-thoughtful, very kind, and has these great perspectives that are totally different from mine. Now, one interesting thing about Sam was that Sam was an introvert. Now, let me get a show of hands – when you guys did those round table discussions and at the end you had to present your table’s thinking to the larger Mindtrust group, how many of you had more than one person at the table volunteer to do the talking? Right, and that was the case in my class as well, because what are most of us that self-select into this program naturally good at? That’s right, talking. I mean I’m up here, right? So here I am, telling this guy about my leadership style, and waxing poetic about my feels on the subject, and finally I exhaust myself and run out of steam, and Sam just looks at me and goes, “Masha, through this exercise, I found out that I lead by influence. One thing I know about myself is that if someone else is talking, I let them do it. I think my biggest strength as a leader is that I just fucking listen.” That really stuck with me, because as an extrovert, I’m jumping in and out of conversations, I’m interrupting people, but the learning there was that just because someone isn’t talking, it’s not that they have nothing to say. In fact, their opinion could still be immensely valuable, and as a leader, you do yourself and your team a disservice if you don’t make sure to suss that out.

OK, lesson number 2. Fast forward to almost exactly two years ago, March 2014. You guys use Reddit? So the Reddit co-founder, Alexis Ohanian, was in town with his “Without Their Permission” book tour – good, quick read, I enjoyed it. I went to see his presentation with the sole goal of cornering the guy after he came off the stage to talk to him about Hipmunk – the flight planning startup he also co-founded. So Alexis does his spiel, highly entertaining, and then somewhere in the middle he tells a story about how they went to pitch Reddit to Yahoo News. He said that the guy they met with looked at their traffic numbers, and literally laughed them out of the office. Now, at the time, Alexis said it was pretty crushing, and that he used the guy’s rejection as motivation to make Reddit into what it is now – and, less than a year later, they sold Reddit to Conde Nast for approximately a bajillion dollars. And, I mean, what’s Yahoo News? So the guy clearly didn’t know what he was talking about, though it could equally have turned out the other way. The reason this story resonated so much with me is that I clearly used to worship smart. Growing up in an intellectual family, going into Computer Science, being surrounded by really really smart people – all reasons for me to put bright people on pedestals. Even with Postcard, I went through 2 technical co-founders, both absolutely savant-level smart… and entirely impossible to work with. So after doing this startup for more than 2 years now, I finally fully believe what Alexis said – nobody knows what the fuck they’re doing. You might think you know, or you might think that there are these crazy-smart Keymaker-type people out there that know, but literally – noone has any idea. All you can do is make an educated guess, and go for it. Which, by the way, brings me to my last point, which I just learned a couple of days ago…

In a startup, and in life, you have to make decisions all the time. Hopefully, most of the time, you have some data to base those decisions on, but there is no guarantee. And, I can definitely promise you there will literally _never_ be enough data for you to make any decision with 100% certainty. I consider myself a mostly rational person (which arguably is already a problem), so I tend to look for reasons to do something, as well as reasons not to do it. Sometimes, this is literally paralyzing. And in reality, the only wrong decision is the one you didn’t make. Because play this out: let’s say you have 2 potential ways you could solve a problem, and, with the limited data you have – which your data WILL be limited – it looks like there’s pretty much a 50/50 chance that either one can be right. Now, what can you do? You can try to wait for new data to come in to sway your thinking. This is my instinctual response, by the way. But that’s entirely out of your control. New data may come in, or it may not, meanwhile, you’ve stalled your group that you’re supposed to be leading because you are afraid. The only way you can take control of making sure that new data comes in is making the fucking decision. If you actually choose a path, you now a) at least have a hope of being right in 50% of the cases, versus the 100% wrong you were going to be if you had kept waiting, and b) you now damn well will collect new data that will allow you to assess whether that was the right thing to do or not.

So to recap, now that I’ve hit my f-bomb quota, these are the three lessons I learned over time that hopefully save you some of the missteps I made so you can make your own. 1, just listen, 2, nobody knows what they’re doing, and 3, make the decision. Thank you!