End of year is coming up, and our company did really well. They are investing more $$$ in our organization and are worried people will leave since competition for tech talent is fierce.

My boss asked me point blank what I want my bonus to me. I've literally never had this happen before! I've always just been given something. My initial discretionary bonus (when I joined) was slated at $20K, but I started comparing my Total Compensation to TC at other companies at and I would probably be making like $100K-160K more if I switched. Should I ask for $100K? Is that crazy? I'm nervous about seeming ungrateful and asking for something that is WAY above the discretionary bonus they initially listed when I joined.

Any advice or thoughts would be very much appreciated. Thank you.

Can you ask for a (fat) raise instead? That bonus tax hit differently.. 😬
Oh really? Can you explain more about how the taxes work for bonuses?
raises to your salary for one are taxed at your income rate see here: give you longer term benefits by raising your salary to that level "forever" and give you more power in future positions to increase your base salary.bonuses are taxed typically at 22% + additional rates depending on your state/ country: from experience: a $55k bonus was about $35k actual cash hitting my account. a 36% tax rate in CA, USA when my normal income tax bracket at the time was 28%.source: CPA turned data scientist with a love of personal finance
Couldn't have said it better @jessicap, thank you!Bonus taxes are evil! :( I remember when I got one for the first time, I was so excited until it hit the bank account... my face was a big WTF :)
ughh i know! it is so disappointing, isn't it?!?
Getting a raise is also better because then that's your salary going forward vs a one-time bonus, although companies know this and that is usually why they are often more generous with the bonuses. Is it possible to speak with co-workers at your company as well to see what they're asking for?
You could ask, β€œWhat is the bonus pool, and how many people will divide it?” Also, you will lose about one-quarter to taxes, so keep that in mind. It’s not free money.