Revisiting self-awareness in technology businesses

posted by Jeff | Sunday, September 20, 2020, 11:00 PM | comments: 0

I was shooting the shit today with a former co-worker about the ups and downs of technology businesses, entrepreneurship and trying to be a parent in the midst of all that stuff. I think that one of the reasons that we still connect is that, aside from having awesome wives, we have a non-trivial appreciation and empathy for the business side of what we do. Neither one of us started our professional lives writing code, and maybe that's why empathy for the other side of the hall is strong. Also, we've both been in various stages of making money from our endeavors outside the service to a full-time employer.

A lot of what we talked about today had to do with the world of sales and marketing, areas we're not exactly experts in, but deeply understand that they can be difficult to work in. I totally get this... I turned POP Forums into a product earlier this year, but as soon as I started my new job, in the midst of a pandemic, that was it. I did not endeavor to market or sell it the way that I intended to, in part because of the time commitment I couldn't make, but also because I wasn't sure how to effectively go about it. I mean, I have ideas, but mentally I don't think I could find the time to act on them, let alone the confidence to implement those ideas (or spend money on them).

This brought me full circle back to the topic that I've talked about for years. Self-awareness has a huge component in success. I've written about it probably a dozen times over the last decade. The best leaders know what they don't know, and engage with the people who do. Business growth, and sometimes survival, only occurs for the leaders who are brutally self-aware. I've had a front-row seat to this so many times now. It's not that growth is the only reason to be in business, certainly, but I've seen so many instances where leaders didn't know how to go about it.

In fact, I've seen what I thought was self-awareness many times, but it was all hubris and talk. My first view of this was in the first job I ever had in a public company. For whatever reason, I got invited to all the things at Penton Media, which at the time was one of two or three companies that owned the business-to-business magazine and tradeshow space. I was an inexperienced 26-year-old, but I "got" the Internet, and maybe that's why I found myself in the board room a few times. So in late 2000, I was part of a big off-site meeting that lasted two days, where the company would embrace the Internet future and evolve. I was skeptical of this room full of old-school white media guys, but believed they were figuring it out and were in fact self-aware.

You can guess where it went from there. The company experienced epic failure, which is why I left it that next summer (and went to another B2B startup media company, which was a pretty horrible idea). The company was even de-listed from the NYSE. Since then, I've seen failures, stalls and stagnation at various technology companies, but also some success stories. What has been different between the two outcomes?

If I had to nail it down, I would say that it's experience. Founders, first-timers, idea people... they're good at creating something from nothing, but I'm surprised at how infrequently they really understand the limits of their capability. But many of those leaders do understand the limits, and they without fail team up with people who do have experience. Self-awareness isn't enough... these leaders need to be self-aware enough to augment their gaps in experience with the wisdom and scars to fill the spaces. They can think beyond product-market fit, starter technology and brute-force sales strategy. They can turn the "why" of a company into action and success by working with and empowering people who can do what they can not. It's magic and deeply satisfying when you see it, and can be a part of it.

I've tried very hard in various scopes of enterprise to operate like this, with varying degrees of success. For my personal hobby business, I've brought people in to do sales for me a few times, back when that sort of thing didn't involve Google, and I've contracted with designers and even a developer once. If I ever want PF to be a business, I probably need to do that again. In my day job, I feel like I'm in a great environment now where self-awareness and experience is high, and I do not take that for granted.

As I am presumably just past the middle of my career, I'm very reflective about the experience part of the equation. When I was starting out, I truly believed that success was just about trying as hard as possible or being persistent. That was probably a little naive, and I wish someone would have told me that experience isn't something you learn, it's something that you have to live. It's not strictly an issue of time, mind you, because we've all known people who have all-star experience at a young age, and veterans who seem not to have learned anything. There's an aspect of self-awareness I never considered, knowing whether or not the experience that you're getting is actually valuable. I know I've had some "lost years."

Not sure where I'm going with this, I just felt like I had to write it down. Self-awareness is just the start. What you do with it makes a difference.


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