I’ve been in the workforce for a while now.

During a meetup in London with the data team at Automattic, for my turn at a flash talk I gave a Brief Unabridged Resume, writing out my full professional timeline on post-it notes laid out on the wall of an AirBNB in Westminster. It took about forty minutes and wiped out the sticky notes!

I’ve only had two jobs since then (things have calmed down some for me, professionally!) but I do still look back and sometimes wish I could take things I’ve learned and beam them back into my younger self’s brain.

(Not that my younger self would listen!)

There’s a way of re-framing embarrassment and shame about your behavior and decorum during your early days, which goes something like, “If you look back and are embarrassed by what you did, or said, that means you’ve learned from it, and you won’t make that same mistake again.”

This has been a helpful mental model for looking back on things that clearly did not go well – but when I think about advice to my younger self, I am thinking more about how things could have gone much better, not necessarily eliminating regret. What are the things I’d suggest, that would have had the highest leverage?

(Or, as this exercise implies, what I today would expect to have the highest leverage – maybe in another 13 years I’ll write another series about how my advice to my younger self was all wrong!)

The first high leverage bit of advice here, for me, as a younger professional, would be, ask more questions.

Now, folks who have worked with me, or who have followed this blog (#,#) might find this a little confusing – I’ve always been a bit of a question-asker, definitely a talk-to-thinker, but I have often let fear and concern about how others perceived me, to shape what I was and was not up to explore in conversation.

Now, this isn’t to say, that a good professional, a good Product person, is tactless and without consideration as to how their questions or behavior is perceived – that’s very important in fact. I mean more, and perhaps this is only really clear to any person in retrospect, that we must know ourselves, and try to move forward driven with intention rather than be driven by our background, upbringing or personal history.

(What a sentence! Might be getting outside my lane a bit here)

I grew up in a pretty classic rural setting in late-20th century America – when folks hear New York they picture the skyscrapers of Manhattan, but there’s a lot more to the state. Westernville, NY is just over a four hour drive from the city, and I have a lot to be grateful for, having it as a hometown. One piece of it, though, was a real sense of anxiety around asking questions, especially in a professional setting.

Upon reflection, much of my professional success has come only after learning to ask good questions, and to set my own fear of being seen as silly or uninformed aside. It helped me to look at my workplace with a greater sense of humility, too, when I was able to start to feel safe expressing things I didn’t know, or didn’t feel I really understood well.

In a healthy professional culture, folks will be game to explore and explain. All human endeavors are more complicated than you think – there’s a whole well studied psychological Effect about how bad our brains are at understanding the complexity of things we don’t know much about. It’s almost always good to ask more questions – about the products that you use, about how different teams work together, about other folks’ understanding of a complicated situation.

A professional workplace is one where folks engage with questions thoughtfully and in good faith – especially given that to ask a question can be indicative of a possible mis-alignment somewhere else in the organization or architecture, and someone saying, “Wait, can you explain that a little more?” isn’t because they weren’t listening – but because they’re digging for deeper problems.

Especially for internal or platform PMs, you must get good at this – understanding the bare-metal Capital-T truth of how things work and get done at your organization is a huge factor in your ability to steer toward your organization’s goals (and your personal goals!)

(There is of course the situation where, there is no Capital-T Truth to be found, which is a situation for a whole different post)

Note that sometimes this means product or technical questions like, “Can you explain to me how these services interact? How do we get data from here to there?” as well as, “Can you help me understand how your team, Frances’ team, and Jean’s teams work together? Who is responsible for what?” – these can both be serious areas of confusion, uncertainty, and friction within a firm, especially when the answers are different from person to person!

It isn’t so unusual for folks who have been in the workforce for a while to have seen the ugly side of the Dunning Kroger Effect – it feels like every software engineer and data analyst has a story about a colleague confidently displaying a shocking lack of interest or understanding of their area or way of working – “And then Product said, can we just add a column for ARPU?” – “Can we squeeze in an Okta integration this sprint?”

When we are able to come to the table representing (rather than misplaced confidence!) a curiosity to learn more and the will to overcome our own fear and anxiety, we build better relationships, better organizations, and in the end, better products.

• General