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I've worked as a senior leader at Microsoft, Meta, and OpenAI, and ran my own startup. Many people consult me over email and LinkedIn. Instead of answering them privately, one person at a time, I wanted those answers to benefit everyone… so I launched this: a public archive of anonymized answers, open to everyone.

Majestic Cheetah asked

answered Sep 11

Hey Philip, your experience is impressive, and thanks for putting in the effort to share your thoughts.

I find myself in a bit of a career dilemma and would really appreciate your perspective.

I genuinely enjoy systems, coding, engineering, math, and solving technical problems. What I’ve struggled with is the corporate environment around engineering — deadlines, organizational politics, people management, and sometimes spending more energy navigating the organization than actually building things.

I also came to financial literacy relatively late in life, but over the years I've become much more interested in investing, capital allocation, and thinking about businesses from an investment perspective. Through saving and investing consistently, I've reached a point where my family has a solid financial foundation and I don't feel much financial pressure to start to work immediately at all cost.

Earlier in my career, I was quite focused on titles and career progression. I eventually reached a fairly senior engineering position at a large tech company, but I was working in an area where I didn't have as much depth or passion as I would have liked. I was eventually laid off after about a year.

I then joined a smaller startup, but that experience also didn't work out and I left after only a few months. With the current job market being difficult, I'm increasingly concerned that these short recent experiences may make my resume harder to position.

At the same time, I'm genuinely excited about data and AI and would love to spend the next few years working in this area. I'm even willing to optimize for learning, technical depth, and long-term opportunity rather than maximizing near-term compensation.

The confusing part is that, looking further ahead, I increasingly wonder whether my natural strengths may actually be closer to capital allocation / investing / evaluating businesses than being a career engineer. I still believe I have a lot to contribute technically, though, and I don't want to walk away from engineering prematurely simply because I've had a couple of difficult experiences.

At the same time, I am bullish to the AI trend and willing to join one of the AI labs both for more financial security and personal learning and fulfillment.
How would you suggest me position myself? What career advice would you give for me? Should I just focus on preparing interviews and trying to get into those companies and also finding a matching team?

Philip's answer

Recent experiences, especially with being laid off, can understandably affect self-confidence. It's completely understandable you're hesitant about re-entering the interview cycle and seeking another employer in the tech space.

You have several potentially great choices before you, but there will be unresolvable ambiguity as to how to move forward. A few thoughts:

  • How much do you want to explore or lean into your interest in capital allocation as a potential full time job? For instance, would a stint at a VC be of interest? Or even an EIR at a VC, which gives you a chance to interact weekly with the capital allocators while exploring your own projects?

  • Are there companies outside of the main labs that are also interesting to you? I ask simply because getting into the main labs is incredibly competitive, such that I'd recommend backup plans for even the most qualified people. If you're interested in AI, there's hardly a major tech company which doesn't have significant investments, or at least teams which focus on AI (whether that's fine-tuning models or building their own).

My guess, given only what you've communicated, is that you might enjoy a stint at a VC quite a lot. During my time as an EIR at Madrona, I was able to sit in on the weekly partner meetings where investments were discussed, but also meet with a bunch of founders and research my own startup ideas. If you were to do the same, you might find you enjoy the partner role, or perhaps find an operational role you love.

Calm Pebble asked

answered Sep 9

How do I break the IC5 > IC6 boundary ?

I have been an IC5 for almost 2.5 years in Meta. Same org. And been feeling that I have been stuck at this level.
I was first in a team where I had the opportunity (only 1 IC6 in the team as compared to the regular 2 in other teams), but didn't have scope. Managers and mentors would kept saying "create scope" but there were not a big enough problem that already an IC6 was not working on.
Then I got re-orged into another team (same org), that has a lot of scope, but there are 2 IC5s already ahead of me in this team who have been in here longer than me, and much closer to 6.

I keep thinking the quote "what got me here won't get me there" and that I need to change strategy, but can't figure out how. It seems to me the best way to 6 is "influence in the org", but Meta seems much more top-down than before nowadays, so it seems people who get the opportunities on these top-down projects are the ones already having influence, so its hard to create own scope now.

There is also the feeling that Meta probably might not be the best place for growth anymore. Friends at smaller Big Techs (like Snap and Pinterest) have started getting Staff and are now working towards Principal and seems to me that maybe Meta is just really becoming too beaurocratic to grow at, so maybe leaving might be the best option (even though that might mean taking a comp hit for a long term growth).

Philip's answer

Setting expectations first:

  • I wouldn't be surprised if more than half of all engineers never get to IC6 in their entire 40-year career. There's a reason IC5 is considered a "career level" at most major companies.

  • That said, 2.5 years from IC5 → IC6 is reasonably spritely, all things considered.

I don't know you personally so can't have an informed opinion about whether your appraisal of yourself (and the rush implied in your question) is reasonable given your talents and abilities, but I wanted to surface those expectations explicitly.

Managers and mentors would kept saying "create scope" but there were not a big enough problem that already an IC6 was not working on.

Is that the case? That you had multiple managers and mentors advising you to "create scope" where it was impossible? I'm trying to get a better sense the accuracy of your perception of what's blocking you from growth. If you have multiple managers and mentors advising you to do something that is impossible, you arguably have many terrible managers and mentors... or perhaps another parsimonious explanation is that they see a path where you don't.

It seems to me the best way to 6 is "influence in the org", but Meta seems much more top-down than before nowadays, so it seems people who get the opportunities on these top-down projects are the ones already having influence, so its hard to create own scope now.

I don't think this can be true. What you're saying implies that no one at Meta will grow from IC5 to IC6 because of some structural change in the company. I'm willing to bet this can't be true. There have got to be hundreds of people going from IC5 → IC6 at Meta in any given year. Perhaps especially at its current size, since large companies often succumb to grade inflation.

I fundamentally question the claim that Snap and Pinterest are faster places to grow, and that you're stuck in IC5 simply because you're at the wrong company. There are of course situations in rapid-growth companies (e.g. early Facebook) where people are given opportunities to learn much more quickly than at stagnant companies... but Snap and Pinterest aren't those fast-growth companies abounding in opportunities.

Your entire question and tone externalizes the cause of your stasis. Knowing only what you've told me, the error bars on my judgment are huge: but I'd hazard a guess that externalization might be the root explanation of why you're not growing. Everything you'd said is about how the situation isn't right for you: the team's not right, the mentors and managers are giving advice that's impossible to implement, friends are growing faster simply because they're at other companies. You haven't mentioned a single thing you'd like to grow in yourself to earn the IC6.

If I were a betting man, I'd likely guess that your best path to growth is to solicit feedback and introspect about the true blockers to your continued growth. If a single person is promoted from IC5 → IC6 within Meta, you should ask yourself how you could have been that person. And the answers need to be something within your agency; otherwise, you're just externalizing blame, and you may well find yourself growing much more slowly than your talents theoretically make possible.

Serene Narwhal asked

answered Sep 3

With AI agents now able to iterate on their own code, test through the UI, and debug against logs, what would you value most in a senior SWE today, and what would you stop valuing?

Philip's answer

Raw code output is no longer as differentiating (though I bet the best senior engineers can still output more production-quality code because of characteristics below). And in a funny way, I wonder whether the ability to communicate clearly & persuasively across functions might be diminishing in importance as more companies can be built out of just 2-5 people.

"Instincts," for lack of a better word, feel even more important. For instance, I often get a sense even before checking the code for ways in which AI would likely have made mistakes. Or the sense of how to factor a larger codebase such that the code is componentized in a way that minimizes dependencies.

The latter is something the AI is obviously getting better at with each revision, so I wonder how long it remains a differentiator for a great senior engineer. Overall, that's perhaps the biggest theme of my current take: that it's unclear to me how much longer the average senior engineer will have an advantage over AI.

Eager Cheetah asked

answered Aug 30

Hi Philip,

About a year ago, my family and I moved to a new city because my husband was asked to relocate for a new job. Around the same time, we also welcomed our toddler, so I made the decision to step away from my tech career and dedicate my time to my family and the move.

Now that it has been about a year, I’m ready and excited to return to the tech industry. However, getting back into the job market has been much harder than I expected, especially as a mom returning after a career break.

I’m not sure how best to address the one-year gap on my resume. I’ve applied to many positions, practiced extensively for interviews, and reached out to people for referrals, but I’m still not getting phone screens or interviews. At this point, I’m wondering if the career gap is making it difficult for recruiters to consider my applications.

Honestly, I’m at a stage where I’m not sure how to navigate this or what I should be doing differently. I’d really appreciate any advice or perspective you might have on how I can position myself and successfully make this transition back into tech.

Thank you so much for taking the time to read this.

Philip's answer

I'm so sorry to hear you've had such a hard time getting back into the workforce.

This is an especially hard time to rejoin. The past year or so has been the first time in my professional life where I have a few friends, each with 20+ years of experience, each looking for jobs for over 9 months without landing one. Each of them has had plenty of FAANG experience, so I don't think it's just about their qualifications.

Although it's impossible to know, my intuition is that what you're experiencing isn't because you've had a gap in your employment (especially in your case, where you've been on parental leave, which is totally understandable). At least in all the times I've hired people personally (and I've interviewed over a thousand people), I've never considered gaps in employment problematic unless it felt related to poor performance. What I can't speak to is whether modern hiring/filtering tools might take gaps into account... but even there, I tend to doubt it. I suspect what you're experiencing is, for better or worse, a reflection of how hard it is in general to get a job in the current market.

My advice:

  • You've not become a worse employee. A gap for parental leave is completely healthy and admirable.

  • While awaiting callbacks and interviews, build with the latest AI tools and get very good at the latest approaches. Read up on new developments. Try things yourself. You have a huge edge right now that others in jobs don't have, which is the freedom to explore whatever technology you want. Use this to your advantage.

  • In a tight job market, employers start biasing toward false negatives. Not being called back or not passing interviews isn't an indictment on you. Keep the faith and be prepared to take many shots at goal before something sticks.

You can do this. My sincere hope is that you land something great soon.

Hidden Tiger asked

answered Aug 29

Hi Philip, first, thanks for sharing your wisdom on your here, and on your podcast appearances and substack articles. I learned a lot from them.

I'm curious how you reason about when to stay in a role. For context, I joined Meta 2 years ago as an M1, and had pretty good success growing my team and launching a new 0-1 that was taking off. I was getting EE ratings, trending GE for this half (but then took parental so N/A) and getting funding for 6 new headcount (all e6+7).

Then the great flattening hits, and suddenly I'm an IC6 again.

I'm actually not too worried about delivering as IC6, but I can't help feel a bit dejected. Like all the progress I made towards my goal (eng dir, one day), over 2 years of work, went out the window.

My leadership (skip) is trying to reassure me that isn't the case, that I'll get to E7 soon, etc etc... but it feels hard to accept, and to trust. Even if I get it, is it likely I can convert to M2 later in this new flattened world? What does M2 even mean when M2 and M1 are now basically peers (16 reports)?

I also have a strong offer to go be an EM elsewhere (outside of meta). I really like the people and the technology here, but I can't help feeling that the timing or team fit maybe just isn't right for my long term goal.

What would you do? Stay? Leave? Aim to boomerang? I'd appreciate any thoughts. Thanks.

Philip's answer

Deciding what to do here depends a lot on the outcome you want. For instance:

  • Is your goal to become a director at Meta? A director at any major company? A director anywhere?

  • Why is being a director the goal? Would you feel just as good as an IC8, compensated the same? What if you could get paid more being an M1/M2 elsewhere?

Although I've had several Meta coworkers go from IC8 straight into a directorship, those situations tended to happen only in cases when they had equivalent management scope in a prior job. So it feels not impossible, but unlikely, that you'd go IC6 → IC7 → D1.

Given that's the case, a big question is how you continue to learn and grow your ability to manage larger teams and/or more senior people. You mentioned an offer with a different company; what are your options for switching within Meta itself? Sometimes when switching within an existing company, you have the advantage of already having positive social capital as well as understanding how best to work within a culture. If you had an opportunity to manage a set of people as an M1 elsewhere in Meta, you'd likely start with an advantage over switching elsewhere. (This is said without knowing more context around your other offer).

From the way you describe it, I don't myself automatically think of what's happened to you as "all the progress... over 2 years of work, went out the window." You had two years' of experiences learning how to be a great M1. That's definitely progress.

Which brings me to a final point: remember that your level is a delayed external metric of your internal capabilities, if everything's working correctly. What's most important is growing those internal capabilities. Going from M1 → M2 isn't half as important as learning the skills to act at an M2 scope. Benjamin Graham (the investor) used to say, "In the short run, the market is a voting machine. In the long run, it's a weighing machine." Optimize for your intrinsic value, your ability to do larger scope work and manage larger scope teams. Sometimes, that'll mean being thrown into the deep end of managing something you're barely competent at in order to learn the skills before drowning. At other times, it's about finding opportunities to hone those skills so that when the right role arises, you're the obvious choice for the job.

Look for opportunities to do the latter, whether that's inside Meta or elsewhere. Always work with and for the best people you can, and focus on emulating and practicing the skills which will make you a slam-dunk candidate for the job you want. Don't let external measurements and metrics drive that decision.

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