Category: Career

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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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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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When to Say Goodbye: Do You Need to Stay 2 Years at Every Job?

A former colleague reached out to me earlier this year with a situation. She found herself in a position at a company that didn’t quite measure up to her expectations in terms of work/life balance and culture. It’s really hard to assess these things upfront and especially difficult for folks early in their careers with less ability / means to be choosy when job hunting.

Her question for me was: do I really need to stay at this position for 2 years to make this look good on my resume? Or can I start looking for a new position now?

My response to this question is nuanced because life isn’t quite so black and white.
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What Homeownership Taught me about Technical Debt

In 2018, my husband and I embarked on buying our first home. We purchased an older home (built in the 1920’s as far as we know) and it was in pretty decent shape. We knew there were some cosmetic things that could be updated (we dreamed of adding a new kitchen and finishing the attic) and that we’d tackle them over time.

What we didn’t realize was the tremendous iceberg beneath the surface: the water line to the house was lead and needed to be replaced for health reasons because at the time, we were planning to start a family; the gutters needed to be fixed because the holes led to puddles that froze over and became ice skating rinks in unfortunate places (like our front door); the home had zero insulation and would need some blown in because otherwise we’d be paying for more natural gas than we really need. I could go on and on. You get the idea.

And you might be wondering, so what does this have to do with digital products?

It is very similar to the concept of “technical debt.”
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Ownership Mindset

In the past, I’ve heard folks say that a Product Manager is the CEO of their product. This kind of thinking creates a strange founder-like mental model where folks feel work will simply fall apart without them so they can’t take a vacation. You can also sub Product Manager for any other ‘Lead’ role within a digital product team (think Lead Engineer, Product Owner, etc).

In short, this line of thinking is not sustainable.

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