Look Back to Leap Ahead: Questions for Your End of Year Reflection

And just like that, we’re just a week-and-change from 2024. Looking back on this past year, things were nothing if not eventful. There were maligned rebrands (but can you really call it a rebrand if everyone still uses the old name?), CEO ousters (and reinstatements), an AI mega-surge and all sorts of notable moments in between.

Even in startup circles, where things have always been tumultuous and at a breakneck pace, it seems like these days news happens faster, quarterly plans change on a dime, and the old adage of “building the plane while you fly it” has never rang truer.

Amidst a rapid stream of emails, meetings and Slack pings, crucial moments to pause and reflect probably won’t come to you organically. Instead, you’ve got to carve them out with intention. And what better time than as we turn the calendar to a brand-new year?

It can be easy to skip over this sort of hand-wavy exercise and just forge ahead into 2024, ready to take on whatever gets thrown your way. But there’s plenty of value in taking stock of the past year — of the tangible numbers that your team hit and the ones they didn’t, but also in some of the fuzzier, more nuanced aspects of how we show up at work. Excavating your team’s health, understanding how your own job has shifted, or unpacking some of the more surprising bits of feedback you received isn’t the sort of work that can be squeezed in between meetings.

To help you get over the blank-page problem, we assembled seven of our favorite questions and contemplative exercises for you to leverage in your own year-end retrospective. We hope they’re helpful frameworks to lean on as you look to 2024 with a fresh set of lessons in your back pocket. Here’s a quick preview at a few of the prompts:

• What project should I have quit earlier? "It's true that in order to be successful at something, you have to stick to it — but that doesn't necessarily mean that sticking to something makes you successful,” says bestselling author Annie Duke.

• How has my job changed this year? "Your job shifting is like aging — hard to detect on the day-to-day scale, easy to detect on the decade scale, and fuzzy-ish in between," says former Stripe & Figma marketing leader Brie Wolfson.

• Do I know what’s most important to my boss next year? “The intersection of your success and your manager’s success is where magic happens, and where your opportunities for fulfilling impact lie,” says founder Julie Zhuo.

• What’s the most impactful piece of feedback I got this year? “Instead of asking vague questions like, ‘Do you have any feedback for me?’ or ‘How can I improve?’ ask specific questions to unearth truly constructive feedback. ‘How can this deliverable be 10% better?’ or ‘Was I saying ‘like’ too much in that meeting?’ are much more likely to elicit specific areas of improvement,” says leadership coach Shivani Berry.

• Am I ready to move on? “The best version of your career is finding jobs that are in the Venn diagram between what you love doing and what you’re exceptional at. This may sound obvious, but oftentimes as you get more senior, the Venn diagram is often ‘things I’m exceptional at’ overlapping with ‘things I hate doing,’” says veteran tech exec Molly Graham.

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