vector research partners ( aka V4RP )
Look Back to Leap Ahead — 7 Questions for Your End-of-Year Reflection
As the year winds down, you might find yourself in that rare, reflective mood. There’s a lot to unpack when looking back on 2023. The numbers are obvious: did the startup hit revenue targets, did your team crush quarterly goals, did headcount grow or shrink, or did you at least finish a few books or rack up some miles on Strava?
But the subtler wins are just as important — the lessons learned from mistakes, the relationships you deepened, the moments of clarity you’ll carry into the next year.
Startups move fast, and reflection rarely makes it onto the calendar. Annual performance reviews might cover some ground, but they’re usually misaligned with the end-of-year and come with a narrow lens.
A more holistic, self-directed reflection is worth your time. Whether it’s how you spent your hours, the morale of your team, the feedback you absorbed, or your career trajectory, a thoughtful review sets the stage for the next 365 days.
Here’s a curated set of prompts and exercises from the V4RP archives to help you run a thorough retro before leaping forward.
WHAT PROJECT SHOULD I HAVE QUIT EARLIER?
Quitting isn’t exactly a beloved topic in startup circles. Instead, we dress it up as “pivoting,” “iterating,” or “taking a new direction.”
Annie Duke, V4RP Special Partner in Decision Science, has made it her mission to reclaim quitting from the dustbin. “Success comes from sticking with what works and quitting what doesn’t. Quitting is a skill you need to master.”
Sure, persistence matters, but sticking to the wrong thing doesn’t make you successful.
Look back at the projects that make you cringe. Maybe they flopped or dragged on forever. Marketing experiments that tanked, a sales deal stuck in limbo, product directions gone sideways, or a hire who was a mismatch — all fair game. Duke offers tactical advice for reflecting on what didn’t work and getting better at quitting in 2024.
“Set benchmarks for what needs to happen within a quarter or two. Those benchmarks become your kill criteria — the moment you realize it’s time to cut losses.”
Formula: “If by [date], I have/haven’t [hit X], I quit.”
Apply it everywhere. Sales example: chasing an RFP for six months and still losing. Early signals were there — no decision makers in the room, RFP favors a competitor, or they just wanted pricing info. Quitting doesn’t mean failure; it means you didn’t get trapped in a dead-end.
SHOULD I REVAMP ANY OF MY REGULAR MEETINGS?
Chances are, you spent a significant portion of the year in meetings. Be honest — how many actually moved the needle? How many could have been an email?
Meetings aren’t evil. A great meeting drives alignment and speeds decisions. But that doesn’t happen by accident. Asana COO Anne Raimondi says:
“Executive meetings consume huge chunks of energy. The last thing you want is for them to be another recurring headache.”
Tip: survey your team. Questions like:
- When you leave the meeting, do you feel energized or drained?
- Favorite part?
- Most helpful? Least helpful?
- One change you’d make?
Use responses to sharpen agendas, pre-reads, cross-functional invites, or assignment clarity.
For 1:1s, Mutiny CEO Jaleh Rezai suggests a monthly “high-altitude” reflection: three wins, three areas to improve, and always end on hope. Share your own 3x3 too — transparency fuels the habit.
HAVE I BEEN USING MY TIME WISELY?
Busy ≠ productive. Startups are a land of endless distractions. Front CEO Mathilde Collin recommends auditing your calendar:
- Does it reflect your team’s priorities weekly?
- Are you neglecting a critical activity?
- Are you carving out time to disconnect and think deeply?
Make it weekly: 15 minutes every Friday to review priorities and tweak the next week’s calendar. If deep work isn’t scheduled, you’ll never get to the thornier issues. Collin calls this “stepping back time” — half a day with nothing but a notebook.
For a full-time audit, Levels CEO Sam Corcos suggests treating your calendar as the single source of truth. Track everything, analyze patterns, and adjust. CSVs from Google Calendar make this retroactive if needed.
DO I KNOW WHAT’S MOST IMPORTANT TO MY BOSS (AND DOES MY TEAM?)
You hit your targets but got little recognition. Why? You might have misread priorities. Julie Zhuo, co-founder of Sundial, calls it the “intersection of your success and your manager’s success.”
Davit Balagyozyan suggests mapping everyone you work with:
- Biggest need
- Ideal “OMG this makes life easier” solution
Check alignment with your skills and interests.
For juniors: ask, “If I were running this team, what would I focus on?”
For seniors: ensure your team’s work addresses top-level priorities. Questions to guide alignment:
- Are we impacting my boss’s critical priorities?
- Is communication healthy and frequent?
- Are we visible at the right level and time?
- Are we sharing work collaboratively and early?
- Are we getting honest feedback?
WHAT’S THE MOST IMPACTFUL FEEDBACK I GOT THIS YEAR? DID I GIVE CLEAR FEEDBACK?
Feedback is career fuel. No feedback? Silent killer.
Flip the script in 2024. Arise CEO Shivani Berry advises:
- Narrow your questions: “How can this deliverable be 10% better?”
- Ask for “advice,” not “feedback” — it lowers the guard.
- Pre-frame: share your own areas for improvement to make others comfortable.
Managers, take stock: have you delivered transformational, specific feedback? Figma VP Marcel Weekes warns that watered-down feedback is invisible. Specify exactly what worked or needs improvement.
Example: instead of “great job,” say, “Nice call — you built rapport, addressed concerns, diffused objections.” Concrete, actionable, memorable.
HOW HAS MY JOB CHANGED?
Everything is always changing in startups. Brie Wolfson (ex-Stripe Press & Figma) recommends semi-annual job description rewrites:
- Role description & company alignment
- Responsibilities
- Required skills
Typically, the mission stays, responsibilities shift constantly, and skills evolve steadily. Create an aspirational JD for 1–2 years out — pure personal north star, no constraints.
AM I READY TO MOVE ON?
Thinking of jumping ship? Ellen Chisa flags feelings to watch: FOMO, envy, dread, impatience. Ask yourself:
- Am I still learning? Who’s responsible?
- Disagree with colleagues? Tried to change minds?
- Trust leadership?
- Facing blockages?
- Have I given myself enough adjustment time?
- Is this just honeymoon burnout?
Liz Fosslien: level up your role before leaving. Look at stretch job postings, feel career envy, break down others’ paths, and reverse-engineer your growth.
Molly Graham: make four lists — loves, exceptional at, hates, bad at. The sweet spot is overlap of loves + exceptional. Anything else? Turn it down.
Prompts to reflect:
- Favorite moments this quarter?
- When felt at best? Worst?
- When drained, bored, energized?
WRAPPING UP: LOOK TO MENTORS ALL AROUND YOU
Mentors aren’t just senior advisors in 1:1s. Mentors are everywhere. Identify superpowers in coworkers — even juniors — and learn from them. Productivity hacks, meeting mastery, analytics skills — pick and choose.
Raylene Yung’s simple framing: “How can I be as good at [X] as [this person]?”
Use that lens for growth in 2024.
