The role of a startup’s CEO is one which requires an insane
amount of multi-tasking and focus. One day you might be hammering out the
intricacies of your product or having a customer conversation to validate
product/market fit. Then the next you’re taking meetings with insurance
guys to make sure you have the right policies in place to protect your
business. Oh yeah, you’re also responsible for raising the capital needed
to grow and, more often than not, you’re doing some kind of sales too.
Balancing all these tasks is a skill that’s hard to quantify. Learning to manage the madness is, like many skills, one that is developed best by doing. This is one reason that investors like to back so-called serial entrepreneurs who have figured out some of the tricks of the trade.
After working with hundreds of entrepreneurs over the last six or seven years, here are two relatively simple thoughts on what makes a good startup CEO (these are just two, among many).
1. Great execs are usually uncommonly good at managing the little things. When I meet with a very early-stage entrepreneur who wants some help with their venture, I will often ask him or her to complete some sort of work. It may be to put together their slide deck or to forward the names of investors who they are targeting for their round. I do this not to be a jerk or to delay having to do work for the entrepreneur. Rather, I want to see how the entrepreneur works and how hungry they are to succeed. Shockingly, a great number of these folks will never get the deck back to me or it will be several weeks or months later. But the ones who come back on time or with additional execution beyond the bare minimum are the ones who I want to double down on and have the highest correlation to those who receive future funding.
2. While doing the little things is important, it is probably just as important, especially as you scale, to recognize little things for what they are. Little things. I know I sound like I’m talking out of both sides of my mouth here, but stay with me. Once you’ve started to grow your venture and have other people working for you, there’s going to be the never-ending slew of potential time sinks in your way. If you are hyper-focused in every detail of your venture, you’ll never effectively grow.
Here’s a real world example, straight from the banking world. If you are working with your trusty commercial bank and find that you’re calling every other week to ask why you’re not getting 20 extra basis points of interest on the $100k in your corporate account, this is probably not the best use of your time. $100k is a lot in a personal account but not a lot for most businesses and if 20 basis points of extra yield (in today’s, next to no-yield environment) is worth your time as CEO, this sends serious red flags about your ability to assess the real problems facing your company.
In summary, it’s important to do the little things well, to build credibility and get your venture off the ground. But as you scale, be careful not to get lost in the weeds. It seems paradoxical to suggest that one must both do little things well and not focus on the little things. Yet, it is precisely this quality (of learning to not dwell on the insignificant while also doing all things, even the little, excellently) which is a mark of a great startup leader. With both cases, it’s less about the little things themselves and more about what your management of the little things says about your overall ability to lead a successful venture.
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