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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.

From the Archives asked

answered Jun 1, 2018

I have a couple of questions regarding learning to be better at speaking. I noticed that throughout the seminar, you were really good at keeping everyone’s attention and expressed your thoughts without hesitation or fillers (like, um, etc)

I’m on the quieter side, and like you, am an introvert. Sometimes I get really nervous when people directly ask me a question and I can’t respond to the best of my ability. I like to weigh the pros and cons of everything before I make a decision. Also, due to this, I feel that people often question my abilities, and when I do speak, people don’t listen and/or brush my comments away, or respond to me rudely.

I hope to one day move into management but am worried that this will cause me to not be able to reach my goals. I’m also stereotyped to be the “quiet Asian girl” and am not sure how to break out of that. I’m not sure how I can change these habits and become someone that people can trust, respect, and listen to. When I was younger, I would prove that I could do things better/faster than others but as I get older, I am surrounded by people who are similarly smart and successful and find this harder to achieve.

If you have any advice about this, it would mean so much to me!

Philip's answer

I completely empathize with the feeling that there can be a large gap between what you're capable of expressing (e.g. what's on your mind) vs. what people perceive from you if you speak tentatively or without confidence. I'm honestly not sure what has helped me most through the years. I still stutter, and for the longest time (all the way through my early twenties) this stopped me from expressing myself in many situations. For me, one of the biggest changes was deciding that I'd speak even if I stuttered, and just let people deal with it. In fact, at times I'd first tell people that I stutter, which removed a huge part of the anxiety for me (and consequently led to less stuttering too, which was an unintended but appreciated side effect). I think sometimes telling people that you're a bit nervous about speaking up might lead to a similar effect, especially if you are doing a larger presentation. But that's just speculation on my end; everyone's experience will be different around this.

At the highest level of abstraction, though I'm not sure what helped me through the years, confidence in a way begets confidence. So it builds on itself. This is why I recommend people seek opportunities to speak more, and to force themselves to try difficult things when it comes to speaking. It snowballs after a while, and you may find that your similarly increases. The whole dynamic of the difficulty of responding real-time is also something that I experience; it's especially true that introverts have real difficulty when put on the spot and asked to make a dynamic decision, or to speak before they're ready. My interactions with others have improved over time as I've practiced this; some of it, for me at least, is to be willing to speak even before your mind is made up, when the circumstances require it, but qualifying what you say appropriately. So, for instance, I'll sometimes tell people, "Having only thought about this for 10 seconds, my initial reaction is [blah blah]. But I might feel differently after reflecting on this later." In this way, I'm able to participate when the need arises without feeling like I've overcommitted to a perspective that I might not hold long-term.

Don't let this stop you from reaching your goals, whether it's to manage teams or to do anything else that requires a lot of communication. You can definitely do it — many, many introverts do. (Have you, btw, read Quiet, by Susan Cain? If not, I'd recommend doing so; it's very good when it comes to encouraging introverts not to get stopped by these things, and giving some practical advice as to how to advance). Practice makes this easier over time; and also, in the long term, competence does show through. If you'd like to practice in a focused way, one avenue is to join your local Toastmasters group. Many engineers who've worked with me have joined such groups and benefited a bunch from a safe environment away from work where they can practice these skills.

I wish you all the best. You'll do great! If you ever have any questions in the future, just reach out.

From the Archives asked

answered May 21, 2018

I'm interested in focusing on product management as my career progresses. Since I'll be starting my career as a software engineer, what is the best way to transition into a product management position early on?

Philip's answer

Transitioning from a software engineer to a PM is much easier than the other way around. In fact, the other way around is rarely done, because the requisite skills to move into software development are arguably harder to pick up on the job, whereas good PM skills aren't difficult to learn along the way, especially for someone who's already interested.

I can only speak for larger companies, like Microsoft and Facebook, but I'd say in larger companies that there are a few easy times in a career to transition, and a few hard times. In general, early in career is an easy time to transfer. This is because most entry-level people are primarily learning their profession anyway, and so if you were to switch, you'd be treated like everyone else who's new to PM. Once you get to a middle "journeyman" level (like L63-64 at Microsoft, or E5 at Facebook), it actually can become harder to switch. This is because your peers at that level are all quite good at the PM skillset, and you'd be compared with them when judged for performance. Not impossible to do, but harder. Funny enough, later in your career, at the Principal or Partner level of these firms, things can once again get easier (to switch from dev to PM); the reason there is that at those levels, many of the skills between those functions are once again shared. People at those levels tend to spend much of their day communicating, leading, and planning. Thus engineering and PM jobs can actually look pretty similar later in career.

I encourage people to switch within the first few years of their career, or perhaps 10-15 years in. It's between years 3-10 that it's probably harder. Not impossible, but harder.

I hope that helps!

From the Archives asked

answered May 11, 2016

I'm got a different job in the government and We're relocating to AZ. One of the benefits the Gov't will help me sell my house. The only responsibility I have to list my house and find a buyer. After that the Gov't will take over and pay for the agents commission and closing.

I owe $230K, it hasn't officially appraised but I talked to 3 realtors and the ball park value of my house is about $200K.

So basically I have to come to the table $30K to sell my house.

Option 1: Quick death write the check for $30K, that's third of my savings. But I can finally walk away for this house, and my dad said its tax deductible.

Option 2: slow death, rent the house. My mortgage is $1900, the average rent is $1600. With the 10% rental manager charges, out of pocket every month is $350. (My interest rate is 5.75% I can't refi bc it's a CDA loan. They require me to live in the house to refi and we've moved bc of work.) the lost is also tax deductible.

I've been going back and forth with what to do. I was thinking with option 2, in ten years, maybe the value will go up and I'm chipping away at that principal and I finally break even and if I do sell it, I'd came out of pocket $35K just to break even.

Two other factors. Sally is in grad school and we're trying to pay out of pocket so slow death favors our savings. Second factor, she also owns a house, we'll break even either selling it or renting it.

I don't like the idea of renting two houses in [state] and most likely buy a third in [another state]. I think we can manage to rent one. She'll make good money after she graduates and my earnings will increase about 25% in 3-5 years but with 2 rentals and a mortgage that's lot of potential for financial pit falls.

What would you do?

Philip's answer

Fascinating financial situation. Before I give advice, I'd like to caveat it by saying that I'm (of course) not a financial professional, and that all financial advice, from anyone, should be taken with a grain of salt. I'm always really happy to tell you what I'd do in the same situation -- but that doesn't guarantee that things will work out. ;)

Remember when selling your house that, in addition to the market price, you'll typically be paying sales tax for any house sale. Typically selling a home involves fixing some parts of it (after inspections turn up issues), etc. All I'm really saying here is that you should expect the total out-of-pocket cost to be higher than $30k.

Rental will likely cost you more than you think. A 10% commission on $1600/mo is $160/month, which means you'll get rental income of $1440 a month. Compared with your mortgage, that's -$460 out of pocket every month. But remember there are real-estate taxes you'll be paying (which, as an example, appears to be 1.1% of the property value per year in a place like your county, which works out to $2200 a year, or $183/mo). Then there's landlord's insurance, which might be $1000 a year, or perhaps less. So you might be looking more at around $700 out of pocket every month. And that ignores any repairs you might have to do (remember: those are real costs. A furnace repair, easily $1-3k, works out to nearly $200/mo spread across a year!

Assuming $700 out of pocket a month, you'd be paying $8400 a year to keep the house as a rental. If you assume your house stays exactly the same price over the next few years, you'd essentially be doing "the wrong thing" if you rented out the house for over 4 years (when your out-of-pocket will exceed the $30k of selling it now).

And here's the question: how much might a house go up in value? This totally depends on where the house is. In general, the US housing market has gone up, on average, by 4% a year over the past few decades. (Remember : this is only an average. Places like Detroit have gone through the floor. Places like SF have gone through the roof. Your results may vary.) But assuming 4% growth, you'd be "making" $8k on appreciation of the house per year. Basically just about break-even with your fee of renting it out. And remember, if you need to pay commission yourself when selling later, you'd need 4 years' worth of appreciation just to pay the $35k of commission.

And here's the other complicating thing: Sally owns another house in [state] as well. That's putting a LOT of your real-estate investment in one place. In my opinion, that's way too much counting on one area of the country growing in value, especially when you don't own those houses out of "extra" money that you don't mind losing.

Here's one way to think about your current situation: pretend you only have Sally's house, and the house you'll buy in [state]. Pretend you don't own the $200k house in [state]. Now I come up to you, and I propose one of two options that you can choose from:

1. Pay me $30k right now, and I'll leave you alone. End of discussion.

2. Borrow $200k from me right now, which you're forced to invest in a stock that, on average, has made 4% per year for the past few decades, but has also fluctuated a lot up or down in any given year. When you borrow this money from me, I will charge you 4% per year. Some years, I'll charge you 5-6% -- but never less than 4%. When you finally sell this stock, I will charge you $30k commission.

Your current decision is essentially the same as this. The 5-6% borrowing rate, in certain years, simulates some repairs you'd need to do on your house. You can basically make this current decision as if you don't own the house we're currently talking about.

Does that make your choice any clearer? For some people it, it will. For others, it doesn't make a difference.

To me, it's down to a few things:

- Cash flow. Do you need the $30k now, and would rather pay the $30k later?

- Risk tolerance. Can you stomach the possibility that your house could further lose value? Would that matter to you? This risk is taken on the hopes that the house actually appreciates in value. And there's a (small, but real) chance it might appreciate a ton.

If it were me, I'd sell right away. Here are my reasons.

- People often expect houses to only go up. But they can go down too. If your house loses another $20k, and then, for whatever financial reason, you're forced to sell, it'd be even more painful.

- The rental earnings (well, actually, the rental loss) is just about break-even with the expected average housing price rise over the next, say, decade. That's a long time to hold a $200k investment only to break even.

- You already have another house in [state]. This is probably a key point for me.

Here's the deal: you have to ask yourself why you wouldn't sell right away right now. If it's because you think you might make good money on the investment, remember that you already have another house in [state] -- if housing prices really go up dramatically, you'll at least make whatever that house makes without doubling down on yet another [state] house.

But remember: if you sell this house now, and prices go up 20% in the next two years (highly unlikely - but I'm just saying), you have to be very comfortable with the fact that you sold it in order to reduce your personal risk and exposure. People forget that the housing market has had years where people lost 20%+ as well -- and in your case, that could be an additional $40k loss.

Let me know what you think. I'd personally sell.

From the Archives asked

answered Apr 1, 2016

hey philip, i just read your post from Feb about receiving the worst review of your career. i'm really sorry and a little shocked to see that. i'm curious, if you're willing to share, what you think really happened? it sounds kind of like an arbitrary punch in the face the way you described it. it makes me wonder what's really going on here at FB behind all the fancy meals and shiny hoodies.

Philip's answer

Hey! I'm glad you asked for more context, because I think context here is really important.

Ultimately, I think my review was fair. I disagree with parts of it, but I truly do accept its outcome. And it didn't feel at all arbitrary. Smart people, myself included, legitimately disagreed.

I had two jobs last half: I was supposed to split my time between managing the London Friend Sharing team and running the site. I rated myself Meets Some on the Friend Sharing side (which is two notches below Meets All); I rated myself Exceeded on the site leading. My managers agreed with both -- so, at the highest level of abstraction, we're actually all completely on the same page.

Where we differed was this: I felt that I had to turn more attention to the site because the site needed it. My managers felt like I turned too much attention to the site, and that I could have let some of those site things go. Put it this way: what if I had instead just met expectations on the site? Could it have enabled me to also meet expectations on leading my team? I believe I could have. Where we differ in opinion is that I felt my managers put me in a position where I had to pivot more towards the site, whereas they don't see it that way. After much discussion with them, I think it comes down to just a plain and simple misunderstanding: I felt I was focused on the right things; they were worried about what I wasn't focusing on. My scope is so broad that people trust me to go months without intervention (literally); so this sort of divergence can happen.

On a meta level, I also completely own that I should not have been surprised by the outcome -- that is, that as a senior leader, I should very quickly detect these sorts of misalignments and correct them. So on that level, I also completely own the result.

I love my previous manager (Rushabh). In fact, I'd gladly work with him again. He is one of the most genuine people -- and very people-centered. Throughout this process, and even afterwards, I still completely trust him and would love a chance to work with him again.

On an even higher meta level, for context, I think FB's got one of the best review systems I've seen, even when comparing notes with many managers who've joined us from startups and large companies. No system is without significant flaws; but the FB system, from my experience both as an IC and a manager, is fairly good. I continue to have faith in the system as well.

And, random context here, I also believe around 2 years ago, when I was promoted, I was the highest level engineer promotion that had ever happened outside of Menlo Park. So I'm definitely not looking a gift horse in the mouth. I can't accept the supremely good without also enduring what's difficult. My review last half was difficult - but I accept and understand the results.

Does that help? Happy to chat more.

From the Archives asked

answered Sep 20, 2014

Sally (my wife) is going back to grad school. the tution cost about $80K. she has a college loan that only covers half the tution and the interest is at 6.7% that start upon disbursement.

we have about $100K in saving. we're looking to buy a house after she graduates in 2 yrs. we are currently living with my parents.

also we have 2 townhouses in baltimore that are under water but we have tenants. Sally makes a lil money and i pay $150 more a month.

so our options are:

1. pay for Sally's school using our savings. less debt but will take a chuck from our down payment.

2. do the college loan $40K at 6.7%

3. take out the $40K on my retirement plan. its a 2.3% and i pay back the interest to myself.

the other $40K for tuition i should be able to pay out of pocket b/c we dont have that much expense living with my parents.

im leaning towards option 3. it sucks taking money out of compound interest gain but its the lesser evil IMO.

what do u think?

Philip's answer

It's an interesting question you're asking. No obvious answer. But here are the things to think about.

You should look at your net assets and liabilities, as a whole, in your life when making decisions. In other words, don't think about these decisions separately -- think holistically, then make the right decision taking into account every last thing.

Example: let's say you have a big mortgage (say, $300k). And you also have $100k saved up that you're currently putting into some pretty safe investments (e.g. US government bonds, or perhaps even just a CD at a bank for negligible interest). By not putting the $100k into paying off your mortgage, you're essentially doing the equivalent of borrowing $100k (at whatever your mortgage rate is) in order to invest it. That's ultimately a risky move, even though many, many people do it (including myself many years ago). It just seems so "safe" -- but it really isn't.

I don't know all the specifics, but I believe #3 is likely best (borrowing from your own retirement, assuming you can and will pay it back, and that the interest/etc is paid to yourself and also has some tax benefits, probably). #2's not great for a few reasons: it's high interest, and it's also ultimately going to hurt your ability to get a mortgage as well (because banks will account for all of your liabilities when deciding how much to loan you).

Don't worry about the issue of "taking money out of compound interest gain" (in #3) -- because you're ultimately doing so in order to avoid #2; if you did #2, you'd essentially be borrowing money at 6.7% in order to invest it in your retirement (at whatever rate it's earning right now; and very few people are really getting anywhere near 6.7% in low-risk gains these days).

What I don't know is whether #1 might even be a better choice than #3. If you haven't bought a house before, I believe some laws in the US allow you to borrow from a 401(k) in order to make a first-time home purchase (once again, paying the interest to yourself). If that's the case still, and if it applies to your retirement account, then #1 sounds better than #3 even -- because you keep your money in your tax-free retirement account over the next 2 years earning interest, and then you borrow from your retirement account only when you're ready to buy a house. You might investigate this path; if everything lines up like I suspect it will, #1 is strictly better than #3.

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