There was a post this week in a Facebook group where someone asked for advice on whether or not they should negotiate their salary. The post reminded me that I already had a Word document with all the different things I could think of that someone should either inquire about, understand, or negotiate besides salary. The working title is ‘the Ultimate Guide to Understanding and Negotiating a Job Offer.’

I created this list out of necessity in my own life over the years to ensure I understood as much as possible about an offer itself and the company presenting it. This list is not (yet) all-inclusive, and it may not be appropriate to ask every question in every situation. My hope is that you can pick and choose what is important to you from this list and use it to your advantage.

Please give me your feedback! What am I missing? What could be better? Find me on YouTube: search Anthony Drew Gary and on Instagram @anthonydrewgary if you want to send feedback through DM.

Start Date

  • Get this date exactly where you want it. Take that trip or tackle those projects at home before you start.
  • Also be sure to leave enough days to handle the transition with integrity and respect to your current employer. Life is long. Leave on a positive note.

Pay Periods

  • Frequency? Bimonthly? Monthly? Weekly?
  • Is pay current or in arrears? This matters mostly in the beginning. If your current employer’s pay is current and your new employer’s pay is in arrears, you could go 4+ weeks without a check.

Vacation and Time Off

  • How much to start? How long before more accrues? Does it roll over year to year? 
  • If a company cannot give you extra salary but can give you an extra week off, does that work for you?
  • Which holidays are company holidays? 
  • Are there personal holidays or floating holidays?
  • Using ‘prior commitments’ to anchor a minimum number of vacation days on the way in could work. For example, if a company regularly starts at 10 vacation days, yet you have 14 days of vacations already planned for the year.

Health / Dental / Vision Insurance

  • Does the company offer healthcare benefits? Do benefits start immediately? After 30 days? After 90 days?
  • Dive into the specifics of the insurance plans and compare them to whatever you currently have.
  • If benefits do not start immediately, it may be worth asking for help covering COBRA or whatever your plan is for healthcare before new benefits kick in.

Health Savings Account (if available)

  • Does the company setup the account on your behalf or do you setup your own account?
  • If the company sets up the account, can you invest the account balance?
  • Does company match contributions or contribute to the account?

Life Insurance

  • Does the company provide a life insurance policy?
  • Companies that provide this benefit generally provide 1 to 3 times salary. This should come at no cost to you.
  • If the company’s insurance company offers additional life insurance coverage, be sure to price compare.

Cell Phone

  • Is the company providing a device and service? 
  • Do you have to pay for the device?
  • Do they offer a stipend and you pay for your own device and service?
  • If you had a company phone at your prior job, this may be an opportunity to gain in salary if the new company does not provide a phone.
  • A good test here could be if your cell number is expected to be on your business cards or email signature, then the company may pay for it.
  • If you are expected to have your work email on your cell phone, you could make the same case.

Laptop / Tablet

  • Is a device provided? Does the device have 4G/5G service?
  • Is there remote access to company servers from the web?
  • Are there specific software you really want to have? 
  • If there are certain technologies or accessories you want, ask for them up front.

Company Vehicle / Transportation Reimbursement

  • This is very industry specific but worth mentioning.
  • If you are expected to drive to an office and then out to other destinations, make sure you understand how mileage is calculated and reimbursed.
  • If the company calculates mileage reimbursement differently than the IRS, understand why.

Annual Increases / Bonuses / Performance Reviews

  • Make sure you know how the performance review program works.
  • Ask for a range of annual increases and bonuses for similarly skilled employees over the past few years.
  • If their compensation adjustments are in December and you start in June, are you eligible for review in 5 months or do you have to wait 17 months?
  • Is there a profit-sharing plan? How does it work?
  • Is there a pathway to ownership in the company?

Sign-on Bonus

  • I recommend tying this back to a specific event unless sign-on bonuses are common in your industry. For example, if taking this new position means you lose $2,500 worth of non-vested employer match in the 401k of the employer you plan to leave, you can try to make some of that up with a sign-on bonus.


  • Will the company cover or reimburse for gym memberships, massages, yoga, etc.?
  • Learn the company’s maternity and paternity programs. Are they paid, unpaid, or partially paid? What is the duration?
  • If the company does not offer paid maternity or paternity leave, perhaps you can ask to work from home for the first few weeks after childbirth? This may not be appropriate to ask until after you’ve already started the job. I would hate to see someone be discriminated against for intent to start or grow a family.
  • Adjustable / standing desks available?
  • Are there any aspects of wellness that are tied to lowering health insurance premiums?


  • Who manages the account? When can you start contributing? What funds are available?
  • Is there a match? When does the match start? What is the vesting schedule? 
  • Is the 401k Roth or traditional?

Continuing Education

  • Is there a tuition reimbursement policy toward specific programs related to the field?
  • How does the policy work? Is a specific amount of tenure required beforehand?
  • Does the company historically pay for seminars, trade shows, leadership programs, etc.?
  • How does the company handle mentorship? What learning opportunities already exist within the company?

Office Environment

  • Will you have an office? Cubicle?
  • Can you work remotely? From home? From a coffee shop?
  • Where do you park? Cost? Assigned Spaces? Covered or surface lot? Stipend provided?
  • Company Culture? Softball, bowling, golf, or basketball rec leagues?
  • Expected number of hours worked per week. If you are a salaried employee, it is paramount to have an expectation up front.
  • Standard office hours? Is it OK to be 7-4 or 9-6 vs 8-5? Does it matter how many hours you work during the day? Is working at night OK?

Chain of Command

  • Who will you report to? Have you met and spent time with that person?
  • Will you have direct reports? How many? Have you met and spent time with them?
  • Is there a linear progression in title and responsibility? Will you have to blaze your own trail for future promotion opportunities?


  • Frequency? Know how many nights per month you’ll not be sleeping in your own bed.
  • Company Credit Card for Travel? Or reimbursed for personal card spending?
  • What is the meal, lodging, and entertainment allowance?
  • Does company cover TSA Pre-Check or Clear?


  • Ask on the front end for confirmation that there is no expectation to relocate in the next [number] years. If there may be an expectation to relocate, ask what the company typically offers in relocation assistance.
  • Consider having to pay housing expenses in two locations.
  • Consider actual costs to move.
  • Consider Realtor costs, Realtor selection, closing costs, etc.


  • Are there company sponsored volunteer initiatives?
  • Are there days set aside for volunteering that are not treated as vacation?
  • If someone wants to take a week-long mission trip, do they need to take a week’s vacation?


  • Wardrobe Allowance?
  • Pay for LinkedIn Premium Account?
  • Guaranteed Severance Package if asked to sign non-compete? If you’re asked to sign a non-compete, consider spending money on an hour of a lawyer’s time to ensure you’re comfortable with the language.
  • Golf Outings / Sporting Event Sponsorships?
  • Sponsor industry memberships?
  • Bonuses for referring new hires to the company?
  • Work perks from outside companies? I’ve seen everything from an onsite barber and onsite oil changes to discounts at specific retailers and restaurants.
  • Corporate discounts? Daycare partnerships / discounts?
  • Does the company hire interns? Think second generation here.

This list is not yet truly the ‘ultimate guide’ but maybe it can be one day. What needs to be added? Removed? Please leave a comment.


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