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The Hubris of It All

Early in my professional life, I took on a Web Developer role at a big media company. Back then, a welcome package from the company with its very familiar branding arrived at my doorstep. To some degree, I felt like I had “made it.” I felt like I knew so much about the working world (in truth: I was Jon Snow, I knew nothing – it was my 2nd real job out of college).

I remember deciding I was ready to give back and go back to my alma mater, the high school I attended, to do career day. They encouraged more recent graduates to attend since it was sometimes easier for the students to envision themselves in roles seeing someone that might be closer to their age.

Before the session, I remember talking to the administrators at the school and telling them about how “slides” are a thing of the past, especially for technologists. And the Jen of today thinks back on that and chuckles (as I work on 3 different presentations, all likely due in the next week).

In a lengthy career in technology, it seems like you live long enough to laugh at the hubris of your past self and develop the humility to know that you will often be wrong, but at least not catastrophically so.

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Cash Rules Every AI Around Me

I debated whether I should join the fray of technologists talking about AI but, as an elder millennial, I think there’s an angle to this story that isn’t really being discussed — and it has a lot to do with money. Or rather, the tenuous balance between innovation and profit.

Right now, everyone’s talking about how AI is our future and will deeply transform the way we live and work — this has already begun and I don’t think it’s far fetched to believe that we still don’t quite yet know the ways in which this will fully change us until we are living in the change. However, it’s also true that all the large operators in this space are desperately seeking profitability more than they are the lofty ideal of artificial general intelligence. And the need for a return on investment, especially with valuations reaching the trillions for some, will ultimately create winners and losers.

I think back to the early days of the internet — at least as I knew it. When I was an adolescent, a personal computer in our home and a subscription to America Online would routinely tie up the telephone line (before cellphones were ubiquitous). In that time is when I started learning how to code by seeing HTML side by side with the website I was creating. And it was incredibly accessible to get started; whether it was HyperMart, Geocities, or AngelFire, you could very easily spin up a website for free, no ads.

With age and hindsight being 20/20 and all, I now realize what was happening.

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How to Decide When to Get in the Weeds

I’ve been having trouble even starting to write about this topic because it’s such an interesting topic and something I’ve learned quite a bit about over the years — and continue to grow and learn about as I take on new teams!

As I’ve advanced in my career, I’ve gone from feeling like I need to learn every new technology or programming language (and getting overwhelmed and feeling inferior by the impossible feat) to realizing it’s impossible to know everything well. In the spirit of ruthless prioritization, I have to prioritize what it is I choose to know deeply (where I get in the weeds) and what I choose to only know at a surface level (usually relying on or deferring to the expertise of someone else who is in the weeds).

This approach to staying on the surface works really well when you can to defer to a colleague who you respect as an expert on their work (e.g. I understand we use XYZ technology but for any additional detail, talk to my colleague Jane in Engineering). And often times, a colleague will see this for what it is: trust that you will mind your own business because they’ve got their area under control!

It gets much more difficult when you need to do this with people who might report directly into you. Stay at surface and don’t know enough about their work? You seem out of touch (and isn’t it their job to “manage up” anyway?). Get in the weeds about everything they are working on? Now you are the dreaded micro-manager.

So how do you decide when to go deeper? There are tactics I’ve employed over the years that can help.

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Flavors of Agile

Many years into my career in software development, I was introduced to the concept of “agility” and specifically leveraging the “scrum” methodology. We were trained up over the course of a couple of days which included silly activities to prove a point like making paper boats. I learned about 2 week sprints, sprint ceremonies (like sprint planning, daily stand-up and retrospectives), and best practices around estimation.

At the time, I was on a very lean team responsible for operating a platform that was licensed to a competitor for what I understood was a large sum of money. Our product was important to the bottom-line so consistently delivering value was the name of the game. I enjoyed the structure that sprinting offered and the constant tangible value delivery to our customer appealed to the dopamine receptors in my brain that get excited when I check something off my “to do” list.

During that time, I also learned about the “agile manifesto” and that there was a real career path for people like me who enjoyed solving human-centered problems. And since then, I’ve worked with a number of different large enterprises that employ various flavors of agile.

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Unwritten Rules of Management: Managing Up

A while back, I worked for a leader whose management style I didn’t understand or appreciate until years later. I perceived his tactics as borderline micromanagement and I didn’t like the way he publicly challenged the team.

At the time, my direct manager gave me some tips for how to best manage the situation, especially given my future success at the company would depend on his blessing. In reflecting back on that time, I realize my manager had given me the gift of learning how to “manage up.”

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Unwritten Rules of Management: Air Cover

Recently I was discussing something fairly innocuous with a member of my team. Given there was a very small financial outlay for what I was planning, I mentioned I’d take it up with our manager just to confirm it’s not a big deal.

At that moment my direct report joked, “You can just do it and if anyone bristles, you can blame me.” I told him the first “rule” of being a decent manager is to not throw your team under the bus!

And this got me thinking that there are so many of these unwritten rules that I should share given it took me over 15 years of work experience to learn them!

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Transitioning from Peer to Manager

Early on in my career, I was given the opportunity for a promotion to lead the team I was on; this meant becoming senior to folks who had been my peers. While I was appreciative of the opportunity and others recognized my work ethic merited the offer, no one prepared me for the awkwardness of this transition. So. Very. Awkward.

Recently, I was approached by someone going through a similar transition and wanted some of my advice. I am sure I’m not the first to give this kind of advice and, obviously, your mileage may vary, but there are some basics that everyone going through this kind of thing should know.

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Gifting at Work: How Do You Handle the Holidays?

The holidays seem to be filled with societal pressures that push us toward consumerism. That said, there’s something really nice about receiving a gift, especially when it comes from a source you don’t usually expect: work!

There are some unspoken rules and general best practices to keep in mind to navigate this appropriately in most situations.

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What Do People Say When You Aren’t in the Room?

Recently, I was in a meeting where I mentioned that we’d need to recruit someone to help test. When I mentioned a particular colleague’s name, everyone’s faces lit up; she’d be the perfect person to help on this effort! This reminded me of something that is so simple but yet alludes many when it comes to work: if half the battle is showing up, the other half is how you show up.

But what exactly does that mean?

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Evaluating a Job Offer: How to Assess Culture Fit?

Recently, I was asked about how to assess the culture of a new organization before you join. As I mentioned in a prior post, it’s really hard to figure out whether you are joining a place where you’ll thrive and grow or if you are joining an organization with a toxic culture.

Here are some tips I use and recommend when assessing a potential company to work for.
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