As the year draws to a close, you may find yourself in a reflective mood. There’s plenty to take stock of as you look back on how 2023 went. There’s the quantitative stats — if your startup hit its revenue goals and if your team delivered on its quarterly numbers, how your team grew (or shrank), or personal metrics like how many books you read or miles you racked up on Strava.
But there are the fuzzier achievements to unpack — the things you got right, the mistakes you learned the most from, the relationships you deepened, and the “aha” moments you’re taking with you into the coming year.
It’s the nature of fast-moving startups that there’s not much space to stop and reflect. Of course, bits and pieces might be covered during annual performance reviews — but depending on your company calendar, those rituals might not line up neatly with the end of the year, and they also have a different (and narrower) lens.
Ultimately, a more holistic self-directed reflection exercise is well worth undertaking. Whether it’s how you spent your time, the morale of your team, the feedback you heard, or the direction of your career there are plenty of different yardsticks you can use to evaluate how you fared. And if you’re a resolution person, this can help you place the starting block for what you hope to achieve in the next 365.
To that end, we’ve combed the Review archives for our favorite questions and contemplative exercises that will help you embark on a wide-ranging retro to set yourself up for success in the new year.
WHAT PROJECT SHOULD I HAVE QUIT EARLIER?
Quitting isn’t exactly a popular topic in startup circles. Instead, we reach for softer euphemisms, like “pivoting,” “iterating,” or “going in a different direction.”
Annie Duke (a former pro poker player, bestselling author and First Round’s Special Partner in Decision Science) has made it her mission to rehabilitate the word, which has been given the Voldemort treatment. “Success comes from sticking to the stuff that’s working and quitting the rest. That’s why quitting is a skill you need to get good at.”
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.
As you look back on the past year, there are probably some projects that make you cringe a bit. Maybe they turned out to be complete failures, or they just took way longer than they should have. Whether it’s a new marketing experiment, a sales deal that just won’t close, a new direction with the product strategy, or a hire who isn’t working out, Duke doles out specific advice for reflecting on where things went awry this year and getting tactically better at quitting in 2024.
“There are all sorts of benchmarks that you can set for yourself of what you need to see happen within a quarter within two or three quarters. Those benchmarks become what I call kill criteria, literally criteria for killing a project or changing your mind or cutting your losses. If you miss them, it means you’re going to quit,” she says.
Here’s a simple formula for developing your kill criteria: “If by [date], I have/haven’t [reached a particular state], I’ll quit.”
You can apply this approach at every level of the company. Take this sales example: “Imagine that you are pursuing a sales lead that was generated through an RFP. It's six months later and you’ve lost the deal. Looking back, you realize there were early signals that you were not going to win. What were they?” says Duke. “Maybe you had a few meetings and they couldn't get a decision maker in the room. Maybe the RFP matched a competitor a little too closely. Maybe they just wanted to talk about pricing in the first meeting and didn’t even want a demo. They're probably trying just to use you as a stalking horse to beat somebody else down on price,” she says.
“When you’re actually in the situation it’s hard to see it. When you’re in the middle of a deal, you continue to pursue it and insist that you can still win. Assembling the criteria in advance can help you see if it’s not a deal that’s worth pursuing actively or bringing it further into the funnel. You can have different levels, like automatic kills or ones where you need to seek out further information before making a decision,” says Duke.
SHOULD I REVAMP ANY OF MY REGULAR MEETINGS?
For better or worse, you probably spent a big chunk of the past year in meetings. Be honest here — how many of these were actually effective, and how many could have just been an email (to borrow a popular lament)?
That’s not to completely bash meetings — a well-run meeting can be an incredibly effective tool for driving alignment and making quicker decisions. But this doesn’t happen by accident — great meetings are meticulously crafted.
“Executive meetings take up a big chunk of time and energy for everyone in the room. The last thing you need in the midst of all the other challenges of running and growing a business is for that meeting to become a bad recurring experience,” says Asana Head of Business and COO Anne Raimondi.
So rather than rolling into the new year with the same slate of meetings with the exact same structure, consider creating a short survey to send to folks:
When you leave the meeting, do you feel energized or do you feel drained?”
What’s your favorite part of the meeting?
What do you find most helpful?
What do you find least helpful or least productive?
If you could change one thing, what would you change?
Whether it’s coming up with crisper agendas and pre-reads, inviting in more cross-functional guest speakers, or firming up your approach to assigning deliverables and next steps, this simple survey can point you towards tangible steps that will move the needle.
And for your 1:1s with direct reports, try this idea from Mutiny CEO Jaleh Rezai for revamping your regular check-ins, dedicating one meeting a month to a higher altitude perspective.
Most of our time at a startup is spent zoomed in. Monthly reflection is when we zoom out.
Once a month, she asks each of her direct reports to reflect on the three things that went well the past month, and the three things that they want to improve. To encourage transparency, Rezai also shares her own 3x3 exercise. (Grab her template to try it out yourself.)
And crucially, the dialogue always ends on a buoyant note: What are you most hopeful about as you think about the next month?
HAVE I BEEN USING MY TIME WISELY?
When it comes to startups, it’s easy to feel incredibly busy. There’s no shortage of tasks to tackle, and not nearly enough time (or people) to take them on. The real challenge to being truly productive is focusing on the right things.
And there’s no truer test for if you’ve hit this mark by zeroing in on your calendar. Front’s founder and CEO Mathilde Collin recommends taking a step back to ask yourself the following questions:
Does your calendar actually reflect the priorities you’re orienting your team around every single week?
Is there an activity you aren’t spending enough time on?
Do you have the discipline and the built-in time to disconnect and step away?
To build this behavior in going forward, borrow her suggestion to make this calendar audit a weekly ritual. “I have a 15-minute ‘Review My Calendar’ slot every Friday afternoon. I revisit our quarterly goals and a few top-of-mind topics. I then look at my calendar for the upcoming week to make sure it matches up,” she says. “For example, if hiring is a big push, I need to spend about a third of my time interviewing executives. When I look at my calendar and it’s packed with product meetings or I only have one interview scheduled, then I know that I’m not doing enough to make progress, so I’ll add a sourcing session in.”
And if your whole week is completely booked up, that’s an important signal, too. Some projects (usually the most impactful ones) require deeper work, where you step back away from an endless slew of emails and pings, and dig into some of the thornier issues on your plate. Collin calls this her “stepping back time.” “It’s half a day each week where I allow myself only a notebook — no computer — to really concentrate on a key issue,” she says.
If you’re looking to more deeply audit how you actually spent your time, we suggest this detailed manual from Levels co-founder and CEO Sam Corcos. (He’s another huge proponent of using your calendar as a single source of truth, and he diligently blocks his time rather than relying on an aspirational to-do list.) Along with an exacting analysis of how he spends his time, he also shared a helpful (simplified) version of the spreadsheet that he uses, which you can make a copy and use for yourself. (Corcos notes that if you want to back-fill with your existing calendar data, you can go into Google Calendar and download all your historic calendar data as a CSV, then upload it to Google Sheets. If you haven’t been keeping a rigorous calendar to date, you’re better off starting fresh and keeping the spreadsheet up to date in 2024.)
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DO I KNOW WHAT’S MOST IMPORTANT TO MY BOSS IN THE UPCOMING YEAR? DOES MY TEAM?
You came up with a new project or initiative, pushed it across the finish line, and hit the targets you set. But it didn’t seem to make much waves across the org and instead seems to come and go with a whisper— what gives?
You may have misread what your boss cares about most — and focused your precious time and energy on a nice-to-have, rather than a hair-on-fire problem.
“The intersection of your success and your manager’s success is where magic happens, and where your opportunities for fulfilling impact lie,” says Julie Zhuo, co-founder of Sundial and former VP of Design at Facebook. But finding out what your manager cares about isn’t a one-and-done event at the start of a new quarter — it’s an ongoing exercise in alignment as the business shifts. And amidst the usual startup chaos, folks can lose sight of the bullseye.
Often people are so focused on solving their own problems, they don’t think about how their proposed solutions create more problems one level up. What are your boss’s problems and how can you solve them?
To get started with identifying this perfect overlap, try this simple idea from Davit Balagyozyan (software engineer at Stedi): “Write down every person you work with, their biggest need, and their most ideal ‘OMG this makes my life so much better!’ Now you have a list of your organization’s greatest needs and solutions. Now, decide if filling any of these needs aligns with you (Hint: If you’re excited about it, that’s usually the right mark)” he says.
This is of paramount importance for folks up and down the ladder. For those earlier in their career, it’s easy to default to looking for guidance from others on what you should be working on. Liz Fosslien (Head of Storytelling for Team Anywhere at Atlassian) encourages newer folks to make a habit to step back and ask yourself, “If I were running this company or team, what would I do? Where would I invest my time? What might I try that no one is currently working on?”
And for folks who are later in their career, managing their own teams, understanding what’s top of mind for higher-ups is essential to pointing the entire team in the right direction. Use these prompts as your guide:
Is our work making an impact on my boss’s most important issues?
How healthy and frequent is my communication with my boss?
Am I showing enough visibility of the work my team is producing to the right people?
Are we sharing our work at the highest level possible, at the earliest point possible and in a collaborative way?
Are we getting honest and frequent feedback on that work?
WHAT’S THE MOST IMPACTFUL PIECE OF FEEDBACK I GOT THIS YEAR? DID I GIVE CLEAR FEEDBACK AS A MANAGER?
A steady stream of feedback is essential to becoming someone who people are excited to work with — and it’s a career accelerant. On the flip side, not getting this intel is a silent career killer. You get passed over for new roles or special assignments without ever understanding why, never getting an opportunity to develop and prove you can do better.
There’s all sorts of advice out there centered around getting better at giving feedback to others, but rarely is it focused on attracting useful feedback about ourselves — even though it’s in our own best interest to do so.
So if there’s not a particular piece of high-impact feedback that stands out from the past year, consider how you might flip the script in 2024 and become a feedback magnet. Here’s some advice from Arise founder and CEO Shivani Berry to empower the folks around you to share more:
Narrow the question. 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.
Swap “feedback” for “advice.” “Feedback” is a loaded term. Not only do you tighten up when you ask for “feedback,” so does the feedback giver. Swapping it out for “advice” is more inviting and indicates you value your colleague’s counsel. Instead of saying “Can I have some feedback on what I could have done better?” say “Do you have any advice on how I can improve on X?” You’ll achieve your goal of receiving constructive feedback, but the experience will feel more comfortable for the feedback giver.
Get people invested. Start by sharing your improvement areas with your team and ask them in advance for feedback as they see you in action. This will help call their attention to it and de-risk their fears around giving you feedback. For example, say to your colleague: “In our next 1:1, I’d love feedback on how well we’ve been collaborating so far,” or “After my All-Hands presentation, can you please give me feedback on my communication skills?”
When you share more specifics around how you’d like to grow and then follow up to close the loop, folks will root for your success more — and celebrate in your wins alongside you.
And for folks in a management role, take stock of how often you’ve delivered transformational feedback to folks on your team — and whether you’ve been explicit enough that it cuts through the noise. “As a manager, it’s almost painful to say, ‘I have some direct feedback from you.’ It may seem pedantic or, at some level, contrived,” says Marcel Weekes, VP of Engineering at Figma. “Instead, we weave the feedback in among other things and now it’s watered down. It’s born from a place of trying to make people feel comfortable, but it has a very different effect — it makes people feel unsatisfied.”
It’s critical that we are very clear about positioning feedback as feedback. I want my direct reports to be able to leave the 1:1 and point to an exact sentence where they received feedback.
Even when we deliver positive, reinforcing feedback, we often leave out the specifics. “For example, if they nailed a sales call, instead of saying ‘Great job’ you can try something like, ‘Nice job on that call! I noticed that you built strong rapport with the client, made them feel heard, and diffused their concerns about the product.’ Now they have a better sense of what's working and what they can double down on in the future,” says Anita Hossain Choudhry, co-founder and CEO at The Grand.
HOW HAS MY JOB CHANGED?
The best (and sometimes the worst) thing about working at dynamic, fast-moving companies is that everything is always changing — the landscape, the product roadmap, what users want, your team, your manager. That means, what the company needs from you is always changing. But, because you are living it every day, it can be hard to detect even very material changes in your role and responsibilities over time.
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.
That’s why Brie Wolfson (who previously helped build Stripe Press and Figma for Education) recommends a semi-annual reflection exercise where you rewrite your own job description. It’s perhaps a bit unconventional, but it may peel back some unexpected insights.
Start with the main three components of a typical job description:
Overall description of the relationship between the role and the broader company and its goals (usually 1-2 paragraphs of prose)
List of responsibilities (usually bullets), and
Skills that are required to do a great job.
“I’ve found that 1 often remains relatively stable, 2 changes all the time, and 3 evolves steadily. Ideally, the responsibilities trend increasingly strategic and interesting to you over time and that 2 never outpaces 3,” says Wolfson.
Here’s a template you can use to construct your own JD:
“I would suggest that the first paragraph has a very memorable one-liner mission statement. Think about what you would want your manager to say if someone asked her, ‘what is $NAME working on these days?’ Why? Because they probably do! And, you should probably have some language that you can consistently use to talk about your role with others, says Wolfson.
And if you see meaningful changes from version to version, it’s probably a good idea to check in with your manager. Depending on how you are feeling about your role and responsibilities, you can use this to gut-check and guide a conversation on your areas of focus.
“Another thing I’ve been experimenting with is creating an aspirational job description for ~1-2 years out. This creates a clear, tangible articulation of where you want to go in the future. What you write doesn’t have to have any conception of your current skills or what the company needs. It’s all about you and where you want to go. You may find that this role exists, and that you can have it!” says Wolfson.
AM I READY TO MOVE ON?
As you look to the year ahead, many folks are gearing up for a job hunt, either due to layoffs, or stagnating in your current role.
For folks who are coming from the latter mindset, founder-turned-investor Ellen Chisa flags that a few different feelings might be popping up — nastiness, an unsettled stomach, FOMO, envy, or dread. Make sure these aren’t impatience in disguise, she cautions. Ask yourself these questions:
Am I not learning new things? Is that my fault or my company’s fault?
Do I disagree with how my co-workers are doing things? If yes, have I truly tried to change their minds?
Do I trust the leadership here?
Do I feel blocked, and if so, why do those roadblocks exist?
Have I given myself enough time to adjust? To learn? To find the right advocates/mentors/teachers/allies?
Is it just that the honeymoon has worn off and the real job has started?
When you start feeling unhappy in your work, you owe it to yourself to get specific about changes you could make for it to get better, and to develop your own innovative solutions and experiments to try. Before jumping ship, Liz Fosslien suggests three places to get started with leveling up your current role:
Find stretch job postings. “These are roles a couple of levels above where you currently are that excite you, and then look at the listed requirements. What skills would you need to build to be competitive? Which sound particularly fun to you? Then, bring your new list of growth opportunities to your next 1:1 with your manager or volunteer for projects that would offer you relevant experiences.”
Listen to those pangs of jealousy. Too often, we perform all kinds of mental gymnastics to convince ourselves we're not envious of someone else. Instead, try to pinpoint exactly what it is you covet, and then ask: Can I take classes to acquire that skill? Should I take on different kinds of projects?
Look into your network. Think about four people’s careers, then ask yourself: Whose career am I most envious of?” she says. “Break down their career path: What’s the first step you could take to bring yourself closer to what you envy?” When you’re struck with career envy, don’t push it down — observe it. What does that other person have that you wish you had? What steps can you take in that direction, to become a version of yourself that you’d be jealous of?
But if you run through these exercises and keep finding yourself looking for the exit door, it might in fact be time to move on. Molly Graham (a former exec at Google, Facebook, Quip and Lambda School), suggests starting with these four lists:
- Things I love doing
- Things I’m exceptional at
- Things I hate doing
- Things I’m bad at
“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.’ You have to know yourself well enough to turn those jobs down, even when someone offers you the super sexy role full of things you hate doing. It’s a role that will bring out the worst in you,” says Graham.
If you can’t immediately come up with items to fill each of these four lists, use these prompts as your guide which will, in turn, lead you to a more fulfilling next role:
What were my favorite things that I did this last quarter?
What moments or weeks did I feel at my best?
When did I feel like I could keep doing the same set of things over and over again and be happy?
When did I feel drained or depleted?
When did I feel bored?
At what moments did I feel like my worst self?
WRAPPING UP: LOOK TO MENTORS ALL AROUND YOU.
As you look to the year ahead, it may seem overwhelming to try to make tangible improvements in all these different areas. This is where you can lean on mentors — to encourage you, gently nudge you to be better, or point to an unexpected solution. But when folks talk about mentorship, they tend to sketch it out with a specific set of parameters. It’s a defined, 1:1 relationship between someone more senior and someone more junior. The mentor is the keeper of all sorts of wisdom — from functional expertise, to management advice, career trajectory, and everything in between.
Instead, consider that mentors come in all shapes and sizes, and they’re all around you. Identify the superpowers of the folks you work with (even more junior folks), and how you might best learn from them. Someone might be a remarkably productive person, with expert tracking docs that you admire. Another might run a sharp, effective meeting, or is a whiz with an analytics dashboard. Rather than looking to one single mentor who excels at all the different areas in which you’d like to grow, find bits and pieces from the folks you work with each day, both up and down the org chart.
So as you consider your own areas of self-improvement in 2024, try this simple framing from Raylene Yung’s career advice for engineers as your guide: How can I be as good at [X] as [this person]?