5 Things to Negotiate at Work (That No One Ever Does)

Recently I got my real estate brokers license and worked my way onto an amazing team with Douglas Elliman here in NYC. If you know anything about the real estate business, you know that your ability to negotiate is a key factor is making your clients happy and therefore being successful. With this in mind, I knew that I would have to negotiate my commission split with my team leader not only to ensure that I made good money, but so that he could see that I had the confidence in myself to ask for what I thought I deserved.

The same can be said for most industries – and just as you should negotiate your salary when you’re first starting out at a new job, you should demonstrate your worth and be sure to negotiate other working arrangements intend of just taking what they offer you — because trust me, they will try and get away with giving you as little as possible. Of course I’m not insinuating that you should start making demands during your initial interview or when you’re new to a job, but once you’ve become a little more valuable to the company you have a bit more leverage.

1. A more flexible schedule

Dream of not having to sit in your sterile office surrounded by your annoying co-workers day in and day out? It’s not so crazy to ask for a specific modification, like working from home on Fridays or leaving an hour early twice a week, especially if you’re not someone who is easily replaceable. It’s smart to ask your HR department or supervisor if there’s an existing flex time policy in place or if they would consider your request. Back up your argument for why this will work with a plan of how you’ll be able to better perform your duties under these revised hours or circumstances – maybe you’ll use the time for networking or you’ll be using the time for inspiration for projects. Put it in writing if you have a more formal relationship with your supervisor, and if you’re faced with some push back, offer a trial period to give you a chance to prove this thing is working before it becomes something permanent.

2. A promotion

Did you know that you don’t need to wait for your annual review to ask for a promotion?? Get crazy. Live a little — especially if you feel that you’ve added value to your employer recently and deserve to move up in the ranks. Remember, the longer you wait to move on to your next position, the longer it’s going to take you to move towards your other career milestones. Start putting together your recent accomplishments and ways that you’ve been exceeding expectations recently (for more tips on this read my post on how to ask for a raise).

3. Training support or classes

This is a pretty easy one to negotiate since you are essentially asking your boss to help you get better at your job and essentially make him more money too. The bonus is that the skills you acquire will be transferable into other jobs you may apply to in the future and thereby making you more valuable. Adult education classes and other training classes are available at most colleges, and educational conferences are great ways to improve yourself – and if you’re a solid negotiator, you can get your company to pay for them.

4. Maternity leave

Unlike my native country Canada which gives a full paid year after popping out a baby, the U.S. remains anti-baby making for anyone with a job. Paid maternity leave isn’t legally mandated, which explains why so few companies offer leave beyond the three months. The good news is that some companies may allow you to negotiate what is called a ‘soft re-entry’ to work — which could mean arranging to work just a few days a week or arrange to work from home a majority of the time for the few months after the paid leave ends. Consult with HR to ensure that the reduced hours don’t negatively impact your health insurance benefits.

5. Vacation time

Since most workers get only ten measly days of paid vacation time, but require many many more to lessen the chances of having a complete meltdown – this is something that you should definitely try and negotiate. When your up for review, use this as a chance to request the extra days off by explaining how you’ll minimize the effect of your absence on the company, or how the time off will positively impact your performance. Be mindful to not ask for time off during a busy time of year,

6. A hot assistant

I’m joking obviously. Unless he’s a Ryan Gosling look-alike. In which case negotiate the sh*t out of that arrangement.



  1. As you mention, it’s all about leverage. You have to prove your value to the company before they will consider giving you things like these, and once you get what you were asking for you need to prove that your performance will not be negatively impacted so they don’t take it away. I’ve been able to negotiate some of these things myself including a promotion, a flexible schedule where I come in early and also leave early to beat traffic, and the ability to work from home twice a week. Now if only I could get them to hire Kate Upton as my assistant!

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