I’ve asked many people a version of the question – “what makes a person successful in this role”, and the answers are pretty standard. Recently however, I asked this question of someone who was to become a mentor, and he gave an answer that was both concise and comprehensive:
Be humble. Be aggressive. Be proactive. Be precise.
As I’ve begun executing by these principals, I have been able to trace every single error or failure on my part to a violation of one of these pillars.
Humility – This has, admittedly, not always been a strength of mine, but the more I learn and pay attention, the more I think about how wise Plato’s Socrates was when, in The Apology, he said:
For my part, as I went away, I reasoned with regard to myself: “I am wiser than this human being. For probably neither of us knows anything noble and good, but he supposes he knows something when he does not know, while I, just as I do not know, do not even suppose that I do. I am likely to be a little bit wiser than he in this very thing: that whatever I do not know, I do not even suppose I know.”
Most people I know are and should be proud of their accomplishments – but it those who have accomplished great things and who continue to believe that there is so much else out there to learn that impress me the most. As hubris and arrogance become part of someone’s persona, the absolute value of their contributions as a leader and/or contributor diminish. People can, of course, get away with this lack of humility, but that does not mask the fact that it is a net negative in the aggregate over the long run; pride and confidence are important (I would argue critical) traits, but when unchecked by humility, they lead to a lack of awareness and limit the ceiling of one’s success.
Aggressiveness – This is something that I had always considered a strength, but by raising the bar and treating tasks as absolutely critical, I can now see that I was not properly calibrated for what it takes to aggressively execute in a startup environment.
An example:
12pm. We have a mission critical legal document that needs to be proofed and executed by 9am tomorrow to secure financing (though we don’t technically need to send out until 1pm). I send an email to the lawyer with a note that this is super important and needs to be done by midnight (9 hours early!).
2pm – He responds saying that he will get to it ASAP.
7pm – I follow-up via email just to be sure we are on track (he said we were good, so I’m really being extra diligent on this one).
11pm – I follow-up again via email, a little worried, but I built out that awesome cushion, so shouldn’t be a big deal.
1am – He responds via email – day was crazy and wasn’t able to get to it; will get someone on it first thing in the morning.
1:05am – I thank him via email and say by 8am is fine.
7:30am – I email him with a message of urgency.
9am – Miss deadline. I fucked up.
This is just one example, but it’s one I lived through, and when that deadline hits, there is only one person responsible here – me. At each point on the timeline, I made a critical error in aggressively ensuring that we met our goal. Phone calls are generally more effective than emails, and to make sure that a lawyer (with many clients) has this top of mind, I need to be all over this. If he can’t promise delivery, he needs to find someone else at his firm to bang it out; if he can’t, there are plenty of law firms out there, and I’m likely no more than a 2nd degree LinkedIn connection away from most. It doesn’t matter that I prioritized the ask or that I built in wiggle room ahead of the deadline or that I pinged him five times letting him know we need this. If anything, it shows that I was aware of the importance of the issue, but still failed to find a way to make it happen because email is easier, and I didn’t have his number, and that 9am deadline was a little arbitrary anyways, and he said it would be all set, and “I did my job”. My job was to get the document executed, thus I did not do my job.
Being aggressive doesn’t mean being a jerk, but you can bet if some other MBA intern called up the lawyer at 1pm with a critical ask and ensured delivery with an explicit set of asks and deadlines, that was getting done ahead of my nice emails sent at socially acceptable intervals.
Pairing humility with aggressiveness is generally a recipe for success.
Pro-activeness – a little more generic, but important to both a company and to personal growth. Thinking strategically while executing on the ground level can be difficult, but the benefits of looking ahead, both for disasters to avoid and for opportunities to exploit, can be a game changer. When you have downtime, refresh yourself with a context switch and find a place to add value; maybe it’s a customer in the pipeline where you have the right inroads, maybe it’s a potential advisor that you could catch up with for 15 minutes to give an update, maybe it’s looking at the calendar for a meeting that could use extra prep work. Don’t wait for someone to tell you what your next task is; find a task that excites you, and do it.
I often hear people complain about stagnation in their role. In a startup environment, if you feel this way, you’re probably right. And it’s probably your fault. I’ve found that there is a lot of correlation between being proactive and being aggressive – but I think the difference is worth calling out.
Precision – While the other three pillars are more character/personality based, this is one that stands a bit on it’s own – delivering good work through attention to detail and precise execution.
This doesn’t need a lot of expounding, but I do think that being aware of the process through which you deliver your most precise work is important. Some people work better when procrastinating, while others needs to plan well in advance; some like to work alone and finish a project in one go, while others prefer to iterate and get feedback along the way from others. Regardless, precision is one thing that you absolutely cannot succeed without (especially when you are in more junior positions where granular analysis is so critical).
I recently helped conduct an interview, where each of the other three boxes was checked with ease, and it looked like we had a deal. When an exercise (sent as a baseline test for competency) was turned in that fell short of the level of precision expected, the process was stopped dead in its tracks. Non starter.
This isn’t a scientific analysis; others will have opinions on the nuances of the above, and on the weighted importance of each. For me, I make a concerted effort to align my work with these four pillars, and by tying my failures back to each of them, I have tangibly improved my execution.
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