The IC’s Guide to Driving Career Conversations — 25 Tips for Purposeful Career Planning
People & Culture

The IC’s Guide to Driving Career Conversations — 25 Tips for Purposeful Career Planning

Top startup leaders and operators share a tactical manual with 25 tips for direct reports to take charge of career conversations with their managers.

There’s a reason that “Where do you see yourself in five years?” is one of the most frequently-cited interview questions — career planning is expected to be top-of-mind for folks, particularly when approaching a new job opportunity. But in reality, many often take a much more haphazard approach to plotting the points along their career roadmap. See if the following symptoms sound familiar: Maybe it’s the feeling of dreading performance review season and leaving your self-evaluation to the last minute. Perhaps you’re racking your brain to come up with a cogent response when your manager asks how they can support your career development. Or you’re starting to look for a new job and struggling to take stock of what you want — and don’t want — in your next role. Or perhaps career planning was something you did when you were first entering the workforce, with a long-shelved 5, 10, and 20-year plan.

One of the biggest signals that career planning has been on the backburner is delegating most (if not all) of the heavy lifting to your manager by default— trusting them to highlight your strengths, surface opportunities across the org to flex those muscles and deliver a steady stream of feedback. But folks looking to take ownership of their own career should take the driver’s, not the passenger’s seat.

And that requires shifting your perspective, particularly at high-growth startups where career ladders are constantly shuffling (if they even exist in the first place), managers are lacking in training, and career conversations are too short-term, just check the box — or worse, don’t even happen at all.

While there’s an abundance of advice out there for how managers can hold better career conversations with their reports, ideas for folks looking to drive their own career, wherever they are on the ladder, often falls short. With that in mind, we spent the past few weeks reaching out to some of the sharpest leaders and operators we know for their take on this question:

What is your best piece of advice for driving your own career?

What follows is a list of can’t-miss frameworks, tips and tactical ideas from folks all over the org chart, with experience at fast-growing startups, as well as the more established tech giants. Their advice includes tips for approaching performance reviews with purpose, teaming up with your manager, and looking to cross-functional partners for the greatest needs of the business. This isn’t meant to be the definitive guide to copy/paste all 25 tips into your own playbook — some ideas may resonate with you, others may not quite fit. You’ll also notice that a few of these tips may contradict each other or take alternate approaches to the same problem — that’s by design.

Looking years in the future feels like staring up at a mountain where the summit is hidden by fog — you don’t know exactly what it looks like, or the particular route you’ll take to get to the top. Our goal with this guide is not to give you the exact map to the summit, but to give you the tools to craft your own map, and to continue tinkering with it along your journey. We’ve broken this mega-list down into six categories (and you’ll notice we kept the driving theme going). Use the outline on the left to navigate to each section. Let’s dive in.


1. Start with these four lists.

We’ve turned to Molly Graham many times here on The Review for her knack for delivering spot-on startup advice, whether it’s the charge to “give away your legos” or the mandate to “make friends with the monster chewing on your leg.” Across her management career at Google, Facebook, Quip, and Lambda School, she’s honed her signature advice for her direct reports.

“I always tell people in their 20s that they should use the first 10 years of their work experience to build four lists. Though some of these might sound the same, as you get to know yourself better, you realize they are distinct but overlapping,” says Graham.

  • Things I love doing
  • Things I am 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.

But this isn’t a one-time list you make only in the early innings of your career. Every work experience you have — every project, every role — can add more data to the lists. During your performance reviews, take some time to reflect backward, using these questions as your guide:

  • 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?

Next, bring these lists to your manager. “If you have a great manager, they should want to help you add to these lists and apply the lessons moving forward in shaping your work. What projects can you take on next that let you do more of what you love and find energizing? What does the company need that overlaps with the things you are exceptional at? A great manager can help you use your time at the company to get to know yourself better and help the company grow by using your strengths,” says Graham.

2. Swap out your lenses and track progress monthly.

“People who are earlier in their career often say they want professional development, but they don’t actually know what their career goals are. This can become a mental block that stops you from driving your career journey — but it doesn’t have to be,” says Nick Hurlburt, Director of Engineering at Tech Matters. His advice? “If you don’t have long-term goals, pick shorter-term ones. It’s normal to not know what you want 10-20 years from now, but there’s a good chance that if you achieve your goals for the next 1-2 years, you’ll be in a better place to tackle the next set of short-term goals, then the next. Those shorter-term goals compound to build a career you’ll be proud of,” says Hurlburt.

He sketches out a few places to start. “A perfectly valid default for a short-term goal is to develop the skills needed to get one notch higher in your organization’s leveling structure. Or you can look to someone you admire who’s a little ahead of you, identify what they do well, and work on closing that gap in your own skill set,” he says.

Especially earlier in your career, any move forward will build the latticework on which your future goals will rest.
John Cline, co-founder and CTO of ShelfLife

John Cline, co-founder and CTO of ShelfLife, has also leveraged shorter-term goals within the 2-5 year timeframes. “Next, I line up how my current role fits into that roadmap and what areas I need to work on. I then present that plan to my manager to get their perspective on how I’m envisioning my role, and ask for their help on how we can take the next steps. Sometimes that means working on a new skill, or getting a new project, or getting clear feedback on how I could be approaching my role differently,” he says.

This next step is critical: “Once my manager and I are on the same page about the next steps, I’ll set a goal for what I want to improve in the next six months and set calendar alerts to follow up every month to get feedback on how I’m making progress,” says Cline.

3. Alleviate the pressure of perfect.

Andrea Spillmann-Gajek, Head of Customer Success and Strategic Partnerships at SV Academy, also sees far too many folks get bogged down in the need to have it all figured out. “Careers are not linear. Don’t worry if you don’t know the end goal 10 years from now. And let go of the idea that there’s one ‘right’ or ‘perfect’ path for you. There are lots of interesting paths to follow — and I bet none of them are ‘perfect’ for you,” she says. Her book recommendation for carving out a nonlinear path is “Designing Your Life” by Bill Burnett and Dave Evans.

And while there are no perfect paths, that doesn’t mean you should settle. “If you’re not happy in your current role, spend time thinking about why that is. Is it what the work is, who you’re doing it with, the structure or load of the work, etc.? Don’t just ‘suck it up’ or ‘pay a debt’ now to make it better later. Focus on what makes you happy, not what you think others will like, admire, approve of, or think of as success," says Spillmann-Gajek.

If you follow other people’s paths, you’ll never truly arrive.

4. Leap away from “Career Frogger.”

While Russ Laraway agrees that there’s no “perfect” job, setting your sights on a distant dream job can put your next steps into clearer focus. “I know from experience with over 1,000 people that formulating the long-term vision is hard for many, and may even seem impossible. Nonetheless, it must be done. Here’s why: You want to grow and develop, and your manager very likely believes it’s their job to help you grow. The problem is that neither of you has answered the most important next question, which is: ‘Grow into what?” he says. “This question can only be answered by doing the hard work of articulating your long-term vision — not your arbitrability-articulated ‘five-year-plan,’ but instead your dream job — the vision you have for yourself at the pinnacle of your career, when you are happy, challenged, and not longing for more.” For more here, check out his conversation prompts for managers he’s previously published on The Review as well as his upcoming book, “When They Win, You Win: Being a Great Manager is Simpler Than You Think.”

He also pulls from an unexpected arcade reference.  “If you don’t articulate your career vision, then your future job decisions are all likely to be untethered,” says Laraway.

Don’t be the main character of Career Frogger — jumping from open space to open space, dodging proverbial trucks, going nowhere special.

Liz Fosslien, Head of Content at Humu, also strongly advises folks to avoid leapfrogging. “A lot of people will encourage you to try a bunch of things to figure out what makes you come alive — and that’s good advice, but only to a point. Once you’ve found a group of people you like working with and work that you find generally interesting, I think it’s valuable to commit for a while and turn down new opportunities (unless, of course, you stumble upon something really amazing)” she says. “If you’re constantly hopping around, you’re less likely to build real expertise, learn how to see long-term strategic projects through, and develop deep, lasting relationships,” she says.

5. Look for sparks of inspiration — and envy.

Feeling stuck? Try scrolling LinkedIn — even if you’re not looking for a new role just yet. “Find stretch job postings (for 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,” says Fosslien.

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?


6. Start a brag doc.

Aaron Pelz, Engineering Manager at Pinwheel, suggests rooting yourself in the accomplishments you’re proud of thus far. “Keep a brag doc and reread it every so often. It reminds you of what you’ve already done, which focuses your attention on how you want to grow. It also reminds you if you keep taking on projects that fit squarely within your comfort zone, thus nudging you to seek opportunities to flex different skills,” he says.

7. Look at both sides of the coin.

Nikhyl Singhal, VP of Product, Facebook

“The hardest skills to develop are the ones that are tucked behind your superpowers,” says Nikhyl Singhal, VP of Product at Facebook. “Let’s say you’re a terrific collaborator — you might struggle to hold people accountable. Or you’re exceptionally principled and data-driven — you might struggle to innovate where faith and naivety are essential.” His advice? “Work with your manager and your peers to understand your top strengths, but take the additional step to assess where they might be holding you back or require tuning. When you connect strengths and development together, it’s a huge career unlock,” says Singhal.

Your superpowers can get you far, but they can also cast a shadow over the skills you need to become a great leader.

Howard Ekundayo, Director of Engineering at Netflix, also encourages folks not to rest too comfortably within their zone of genius. “A prior manager shared some advice that redefined how I look to progress in my career: ‘Who you’ve been to get to your current level is likely not who you’ll need to be to reach the next level.’ Often we limit our areas of growth and professional goals to the historical context of our career. As one seeks to move to the next level, you need to recalibrate based on gaps, opportunities and business needs. Those who quickly and strategically respond to these moments with a growth mindset position themselves as critical leaders that are needed most,” he says.

8. Make it a weekly exercise.

Jimena Sanchez Gallego, Associate of Strategic Operations, Flatiron Health

Staring down performance review season is often an intimidating (and overwhelming) exercise — attempting to summarize a quarter or six months’ worth of work into a tidy narrative. To reduce the burden, Jimena Sanchez Gallego, Associate of Strategic Operations at Flatiron Health, captures data and reflects often. “I have an hour-long block on my calendar every Friday to review the work I’ve done that week and spend the time capturing the skills on the professional ladder that were reflected in that work. I also capture lessons learned and things that I would do differently next time,” she says. “This has been incredibly helpful for my professional development chats, because it allows my manager and me to point back to specific moments when I did something well, and those where I could have done better. As we come upon performance reviews, it’s much easier to think through my evaluation because I already have examples mapped out to the specific competencies and skills I’m expected to display in my role.”


9. Focus on the right zone.

Matt Wallaert, Head of Behavioral Science at frog, finds these conversations often go awry when direct reports are looking to directly emulate their managers. “Often, we are strangers to ourselves. So when you ask a manager about emulating their success, what they give back is often a posthoc rationalization synthesized from their own experience (with all the biases attached). Ultimately, just like they did, you're going to learn by doing,” he says. “So rather than trying to get advice, try to get opportunities. Keep career advancement conversations focused on your ‘zone of proximal development’ — the things you aren't yet ready to do completely on your own but can do with the assistance of others. What opportunities can they set you up with and guide you through? Where do you perceive your ZPD? Where do they?”

And if you’re not totally sure, don’t completely hand over the steering wheel, says Davit Balagyozyan, Software Engineer at Stedi. “Don’t let a manager ‘decide’ for you if you’re undecided. If you have a career direction (i.e. an engineer may want to become a PM), then you need to either push for it, push back, or be transparent that you are undecided. It's okay to be undecided but if you are sending mixed signals, a manager will try to ‘decide’ your next step for you,” he says. His book recommendations for the undecideds include “Principles” by Ray Dalio and “Skin in the Game” by Nassim Nicholas Taleb.

Aaron Pelz also suggests putting on your reading glasses. “Read blogs from folks in the industry you respect and you can apply their ideas to your daily work. For me, that’s Will Larson’s blog, which is a treasure trove of engineering management stories and advice,” he says. (For a taste of Larson’s advice, check out his Review article on sizing and assessing teams.)

10. Explore the ladder.

“If your role has a career ladder with explicit performance expectations built into each level, ask your manager to go through each dimension of the ladder at the current and next levels and discuss specifically where your gaps are. Then work on a plan to grow in those areas and fill the gaps. Document that discussion and repeat every few months with the notes from the last one as a reference to discuss the progress you've made,” says Josh Haimson, Director of Product Management at Flatiron Health.

“If your role doesn't have a career ladder with explicit performance expectations per level, ask your manager to help define them for you. Bonus points for offering to help build the ladder since it can help take work off of your manager's plate while helping you learn in detail how the people in your company think about career progression and performance expectations for your role,” he says.

11. Prioritize honesty and transparency.

“Never be afraid to ask for what you need and want. Most managers welcome the opportunity to have an honest, transparent conversation with you when it comes to your aspirations and desires. I've learned to frame these conversations in a way that illustrates the benefits to both parties. What will provide me the best opportunity to learn, grow, and evolve and what will provide the organization the most impact to the bottom line? In that regard, it's a win-win. Be able to back up your asks with data, specific examples, and testimonials from business partners and even customers. And make sure you listen to and take to heart, constructive feedback. Feedback is the greatest gift you can get,” says Kim Courvoisier, Director of Content and Customer Marketing at Lob.


12. Look to the folks you interact with the least.

Julie Froelich, Head of Product Design, Perpay

Julie Froelich, Head of Product Design at Perpay, shares an important reminder: “You don’t know what you don’t know, and that’s what will hinder your growth — so go explore! For me, growth has come through a diversity of experiences. I’ve asked to help form partnerships with other experts in entirely different divisions of the business, which grew the relationships and skill-sets in my career,” she says.

Froelich shares an example from her own career: “I noticed we didn’t partner much with customer service, in part because my manager and myself didn’t know much about that side of the business. I asked if I could be the liaison and find some overlapping projects we could tackle cross-functionally. Just to start off, I started running a recurring status meeting to open up conversations with that side of the business, and a beautiful partnership was formed,” she says.

But don’t just stick with new projects out of obligation. “Be self-aware and recognize when you don’t have passion for the project, and do a graceful handoff. New things can be hard, but they shouldn’t be painful. Move on quickly and use that time to discover new things that better align with what you enjoy,” says Froelich.

13. Take a three-phased approach.

For Pedro Tanaka, Engineering Manager at Google, owning your own career means focusing on being value-oriented to stakeholders. “My personal approach consists of three main phases: Survey, Confirm, Act,” he says.

  • Survey: “In the survey phase, I explore and define the boundaries of my own role. I identify areas of opportunity where perhaps there are no clear owners or projects — but I see value to be gained from executing on them.”
  • Confirm: “In the confirm phase, I focus on enlightening decision-makers and stakeholders of the value of my proposal, with the goal of gathering consensus and building momentum.”
  • Act: “Once I achieve critical support, I then act on the proposal while also regularly surveying the landscape to adapt to any changes in the environment.”

Davit Balagyozyan similarly starts with a simple list: “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.

14. Bring an ownership mentality.

“Think like an owner. Especially earlier in your career, it's easy to default to looking to others for guidance on what you should be working on,” says Liz Fosslien.

Make it a habit to take a 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?”
Cristina Cordova, Angel Investor and Advisor

Cristina Cordova, former Head of Platform and Partnerships at Notion, points to an example from her own career. “In my time at Stripe, I let my manager know that I wanted more of a GM-like role where I could manage people across different functions. At the time, Stripe was run very functionally and he let me know this wasn't possible. But I kept pushing for this, and eventually, the organization was growing and the timing was right to hire the very first people in these kinds of roles at the company. Knowing what you want is critical, communicating that in a persistent but respectful way can ensure you're top of mind for when the opportunity comes along,” she says.

15. Take an informational interview.

Informational interviews can get a bit of a bad rap — but Rick Chen, Head of Public Relations for Blind, believes they’re massively underutilized. “Seek opportunities for information interviews — it’s not just for people earlier in their careers or job seekers. It’s always helpful to learn more about what your preferred company, industry or role is like from those that are sitting in that seat,” he says.

If you cringe at the thought of sending a cold email, try this tactic instead. “A new Director of Public Relations joined the company I was working at, and I sent a short personalized note and was direct with my ask: ‘Welcome to [Company]! Do you have 20 minutes to chat this week or next as you’re getting up to speed? I’ve been here for two years and can walk you through the company, people and product. I’d also love to learn more about PR from you, as I’ve worked in political communications in the past, but never at a PR agency or in-house as you have,” says Chen. “That conversation eventually helped me transition industries and disciplines early in my career.”

16. Step in for a cross-functional win-win.

Randhir Vieira, SVP of Product Management, Omada Health

“Plant seeds throughout the year with your manager about the skills you’re trying to acquire that are outside of your immediate role,” says Randhir Vieira, SVP of Product Management at Omada Health. “Restate these at your regular performance reviews, but also when someone on the team or in the organization leaves, which may be a win-win for you and your manager. If you know the company may be considering a reorganization, offer your skills to be considered. Change can be hard, but it’s also often the best way to grow in your current company,” he says.

Cristina Cordova also strongly recommends proactively searching for these opportunities. “I've found that projects or opportunities that have been most helpful to me in my career have been ones that have given me exposure to people who are outside of my usual day-to-day work/function. This has been both because it allowed me to build a reputation for myself outside of my specific organization and it gave me more exposure to other functions I'd like to explore for my own professional development. It's also common to see that promotion within an organization requires work that has cross-org impact, which these kinds of projects can help with.”

17. Embrace negotiations.

Trish Leung, Senior Director, Head of Monetization and Pricing Strategy at Pantheon Platform, finds that far too often, folks focus their next steps squarely within their own department, rather than widening the aperture. “Knowing what you want is more than half the battle. Figure out the role(s) you'd like to try and map the skills you need to get there. Learn from your cross-functional teams where the gaps are in the company. With that in hand, you're ready to map the skills you want to grow and the areas that need attention. Any good manager will want to see you, the team and the company grow,she says.

And if you’re looking to take on an opportunity, whether it’s a new project or a new role, get comfortable with making your case. “At the end of the day, this is a negotiation. You are negotiating for the right to take on new challenges and potentially a promotion and/or raise. Thus, come prepared to present why you are the right person to do what's been proposed. Hopefully, you regularly showcase your accomplishments and have others help sing your praises. Lastly, don't be afraid of negotiating. It’s a word that can bring out a lot of anxiety for folks, but negotiations are simply discussions to achieve outcomes,” says Leung.


18. Zoom out beyond the “issue of the week.”

“One of the first steps that many people miss is making sure that you have regular growth conversations on the calendar. These should be separate from any usual 1:1s with your manager (pro tip: name the meeting accordingly). While the cadence can vary, these meetings should be explicitly for the purpose of talking about career growth,” says Ting-Ting Zhou, Product Manager of Meta.

Don’t let your manager or yourself hijack the conversation for the latest issues of the week — be selfish and focus the time.

Cristina Cordova also recommends separating these wide-ranging conversations from regular 1:1s. “While some managers will proactively schedule career conversations with their reports, not all do. When I’ve worked with busy managers, it’s difficult to spend much time on this in regular 1:1s, so setting aside time for it once per quarter can be helpful and allow your manager time to prepare as well,” she says.

19. Put pen to paper.

“In prep for a 1:1, I always spend some time reflecting on myself in relationship to my performance, the team, and my personal and professional goals. From there I like to write things down. Even if I end up tossing the paper in the trash, the exercise of putting pen to paper helps me to track my thoughts in an important way. I end up writing down where I am, where I want to be, then solutions to getting there,” says Collin Butler, Community Growth Representative at Alma.

“Whether they're small challenges like building in some productive daily habits or larger ones such as issues pacing to goal – I write them down. Then I filter out what's notable, worth discussing, or something I'd like support or feedback on versus what's not. At this point, I have a few bullets that are worth some time in a meeting and actionable for both my manager and myself,” he says.

Ting-Ting Zhou also suggests keeping a running doc to reflect on every career conversation with your manager. “You can jot down your goals, gaps, where you need support, what you want to learn, what you accomplished, etc. Keep yourself and your manager accountable to having these conversations and using this doc as an accountability measure,” she says.

20. Write up your own promotion.

Anjuan Simmons, Engineering Coach, Help Scout

“One tool that's often overlooked in driving your career is using the performance process at your current job. Most companies have annual reviews where performance reviews are compiled and used to determine who is ready for promotion. Don't wait for that review period to drive your promotion. Find out the critical success factors your supervisor will need to see in order to support your promotion,” says Anjuan Simons, Engineering Coach at Help Scout. “Start filling out your promotion document now and list how you're meeting the expectations for the next level. That's right, you should be the person who writes every word in your promotion document. Then, review it with your boss regularly — at least monthly. Even if you're many months away from promotion, you should make this a regular part of your conversations with your supervisor.”

By having an ongoing discussion about your fitness for promotion, you'll organically create a compelling case for your advancement. Don't leave such a vital part of your career to the last minute.

21. Help your manager help you.

Greg Ratner, co-founder and CTO of, encourages folks to take requests one level deeper. “Coming to the meeting with a very specific outcome that you want to drive is supremely helpful. Your manager can't read your mind. So saying something like, ‘I want to lead a large project’ is made even better if you know of a specific project coming down the pike and raise your hand for it. The more specific and actionable the better. Make it easy for your manager to help you,” he says.

And when your manager is underwater, tailor your asks accordingly. “Your manager might be too busy to directly help you with skill-building, but connecting you with a more senior IC in your org can make it much easier for them to help you,” says Cristina Cordova.


22. Use this framework for spotting opportunities.

“While there are many great managers out there, the unfortunate truth is that for a variety of reasons, a team member's professional development is often not top of mind for their managers. This often leads to them sharing guidance that may be incomplete, suffer from recency bias, or not be as thoughtful as desired. The ultimate goal here is to identify opportunities — be they for personal growth, company growth, or ideally both — and address them with your manager's full support,” says Sean Twersky, VP of Operations at Sprig. With that goal in mind, here’s how he would advise his younger self:

  • Identify: “What are my actual goals? Is it learning skills? Is it being top of my class? Is it a promotion?”
  • Preview: “Let your manager know your ask for feedback is coming. During a 1:1, share your goal(s) and ask for some focused time to discuss, e.g., ‘I'm really focused on continuing to grow here. Can we use next week's 1:1 or find some dedicated time to hear your thoughts on my current performance and what I can do to continue to advance?’ This places your development top of mind, giving them an opportunity to prepare.”
  • Engage: “Try to come to the conversation from a place of curiosity. It's natural to be defensive about almost anything that's not perfect. When opportunities are shared, ask for suggestions on how to improve. For example, if you receive feedback regarding poor presentation skills, you can ask ‘Is there anyone whom you think does this really well that I learn from?’”
  • Follow-up: “Maybe you put everything into an action plan that you share with your manager, or maybe it's a few bullets on a list you resolve to come back to. Whatever you and your manager's preferred method, ask about progress, e.g., ‘I've really been working on the feedback you provided regarding getting the whole room involved in group meetings. I think I've been able to make some progress over the last few weeks, but it would be great to get your perspective.’”

23. Create a user manual.

“Don't assume that your manager knows how you personally like to receive feedback — everyone is different. Creating a ‘user manual’ of when (in the moment vs. later), how (verbal vs. written), and why feedback is important to you (‘I want to be better at X, Y, Z’) is a great way to set expectations and avoid miscommunication,” says Jimena Sanchez-Gallego. “A mistake I often made earlier in my career was to respond to constructive feedback in the moment it was delivered. I have since learned that it's better to thank the person for their feedback (whether you agree or disagree), take time to absorb and reflect on it, and schedule a follow-up conversation to dig deeper into the areas you understand and the areas you'd like more clarity on.”

24. Use the right words to ask for weekly feedback.

Some managers and teammates will feel more comfortable giving feedback than others. To nudge them towards more versus less feedback, open up the opportunity over and over. “Ask your manager for feedback every week in your 1:1. Sometimes they won't have something meaningful to say, but it will nudge them to be thinking about giving you meaningful feedback more regularly,” says Aaron Pelz.

Monty Fowler, Senior Manager of Revenue Enablement at Lob, leans on one favorite phrase: “Every formal 1:1 or review conversation with your manager should include the following: ‘Please tell me one thing I should stop doing, one thing I should keep doing, and one thing I should start doing to help me progress in my career.’”

The conclusion of any particular project is a natural opening for reflection. “The best way to move forward in your career is to learn, and the easiest way to learn is to do it in the flow of your work. After you finish a project or task, ask your manager and teammates, ‘What one thing could I improve?’” says Liz Fosslien. Word choice is critical here. “When you ask, ‘Is there anything I could improve?’ it's very easy for people to simply say, ‘Nope.’ But by using the phrase ‘one thing’ you're much more likely to get a piece of specific and actionable feedback.”

25. Check your ego.

Michelle Valentine, co-founder and CEO, Anrok

Broaching career conversations — particularly when talking about promotions — can feel tense. Michelle Valentine, co-founder and CEO of Anrok, suggests framing these career goals as questions to solicit feedback. "A classic framing is: ‘These are the things I'm thinking about career-wise and I wanted to get your thoughts on what I can do to move in that direction.’ By presenting your goals this way, you can get buy-in from managers and have them be a thought-partner in the process. Too often ICs set the tone for a combative negotiation when a soft power approach can unlock more opportunities," she says.

Davit Balagyozyanalso sees these conversations go awry when ego makes its way to the table. “When you inadvertently say something to the effect of, ‘I hear your advice, but I don't want to follow in your footsteps so I am not going to follow your advice,’ that's the wrong tactic. Avoid bringing either your ego or your manager's ego into the conversation by writing down your talking points and preparing. Don’t wing it.’ Even if you don’t want to follow your manager’s exact career path, they could have valuable advice,” he says.