Following up on my post about tools I learned to use in 2017, I wanted to also touch on some of the soft skills and lessons that I have been learning over the course of the year too. I believe that being a well-rounded investor [person] is way more about the soft skills than the actual technical part of the job. Below are some of the lessons that I have been digesting over the past calendar year. None of them are rocket science and some may not even be particularly insightful, but they have been hammered home to me nonetheless.

Lessons learned

  • RTFM - Read the [Freaking] Manual

    It seems like no matter how many times I learn this lesson, I need to be reminded of it on a continual basis. When I need information on how something works, go to the source. The formulas in the excel sheet, the language in the legal docs, the raw data used in the analysis; whatever the original source may be. Especially on something where there is complexity or lack of clarity in a group of people. Takeaway: go straight to the source.

  • The right person makes all the difference

    When you have the wrong person in a role at a startup, everything seems harder than it should be. And startups are hard enough without that. In many cases at many companies, I have witnessed a dramatic shift when the right person fills a role. Suddenly so many things that seemed painful or complicated are less painful, even if there is underlying complexity. Takeaway: you can’t settle when it comes to finding the right people.

  • Don’t kick the can

    This is another lesson I have been slow to learn and the awareness has built over time. My observation is that nothing good ever comes of waiting too long to make the hard decision–we all have a human tendency to delay the things we dread. In his book The Hard Thing About Hard Things, Ben Horowitz had a great line, something to the effect of, “if you’re going to eat sh*t don’t nibble.” He nailed it. If it’s time to do the hard thing, do it. No half-measures. No kicking the can down the road. Takeaway: resist the urge to delay a hard thing purely because it’s hard.

  • Pick up the phone

    When I was younger, my tendency was to do as many things as possible over email or text. I like having the history and documentation at my fingertips should I need it later. Over time, I have shifted many things away from email, in particular, things that have any emotional content or sensitivity. Too many things are missing from the medium–depth of tone, emotion, etc.–and it’s far to easy to have something misconstrued. Maybe I need to apologize or take responsibility for something, maybe I am delivering bad news, maybe I am asking for feedback on something. Sometimes I will even call people to let them know about an email coming later. I can think of many times I have regretted using an email to deliver a message, but not a single time I regretting telling someone on call. Takeaway: phone > email for emotionally-charged things.

  • Asking the right questions

    I will probably end up writing about this one separately because there’s so much to it. I have been thinking a lot about how I ask questions when meeting with a company. On its face, this sounds so easy, but there is so much nuance to it. It’s easy to ‘lead the witness.’ It’s easy to drag out the question in an effort to show off some domain expertise. It’s easy to ask questions that will focus on a risk or problem, when I should be asking questions that explore what’s possible. Takeaway: the questions I ask are a reflection of my posture toward the company.

As with the tools I have been learning, I’m not claiming mastery of any of these. I suspect I will continue to be reminded of these lessons for many years to come!