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Will Tyndall avatar
Written by Will Tyndall
Updated over a week ago

Evaluate + Negotiate Like an Insider

How to negotiate salary and pick the right post-military job for you

The phone’s ringing. It’s the recruiter. He can’t wait to share the good news.

Congrats + game over!

Not so fast. You didn’t work so hard in the military and push so hard in your search just to take the first offer that comes over the transom. Instead, make sure all that hard work leads to a new job that you’ll want to work equally hard in by evaluating and negotiating the offer carefully.

Start by getting as close to certainty as possible that this is a job you’ll love. To do so, put on your job detective hat and focus on the three key drivers of job satisfaction:

  • Will you love doing this work?

  • Will you love working with these people?

  • Will you love working in this organization?

Will You Love Doing This Work?

Job-seekers tend to focus on all the fringe aspects of a job: Look at these stock options! My family and friends are going to think I’m awesome! And I can’t wait to eat all that free sushi!!!

We call these “fringe” aspects since, even though they loom large as a job-seeker, they quickly fade to the periphery as a job-doer. After all, if you’re knee-deep in boring spreadsheets by Week 2, no amount of free sushi is going to compensate for work that just doesn’t inspire you.

Which is why you need to get super clear about what you will actually be doing all day. So be sure to ask your prospective boss the following questions:

  • What are the first three projects you’ll want me to take on?

  • How likely is it that these projects will change?

  • How do you evaluate success on this kind of work?

  • Will I have the autonomy to set my own projects at some point?

Then, just like you did in the Find Your Path section, you’ll want to take some time to reflect. Close your eyes and imagine yourself doing the specific projects you’ll soon be tasked with. Then notice how your body responds without the interference of stock options or free sushi. Because if you find yourself salivating at the prospect of taking these on, that’s awesome. But if you feel yourself already reaching for the Snooze button an extra time, well, you’ve been warned!

Will You Love Working with These People?

While you’ve hopefully gotten a good feel for your prospective teammates during the interview process, there’s one person who can make or break this job. Yup, your boss.

So to make sure your boss is more Dead Poet’s Society and less Devil Wears Prada, it’s time to do a little cyber-sleuthing. Here’s how:

  • Check out their profile on LinkedIn.

  • Notice that in the right-hand column, there’s a People Also Viewed section.

People Also Viewed
  • Chances are that these are the people they either work with now or in the past.

  • Focus on the people from their past (you’ll likely already have met their current teammates) and find their email addresses on

  • Then reach out to them with a very simple request: “I’m considering taking a role with X. As someone you’ve worked with in the past, would you be eager to work with them again?”

  • While you won’t hear back from everyone, we’ve found that this simple framing tends to produce genuine responses. Because while someone might be OK with recommending a bad colleague to a total stranger, they’re often more honest when it comes to their own desires. So anything less than an enthusiastic “Heck, yeah!” should be seen as a warning sign.

Will You Love Working in This Organization?

Culture is a tough thing to pin down. While it can be easy to conflate it with the cool office design or a Casual Fridays policy, it’s really more about what kind of person fits within an organization. For example, if you’re an incredibly driven Type A, you may get frustrated with an organization’s slow, consensus-driven approach to decision-making. Whereas if you’re more of a Type B team-builder, a cutthroat, results-driven culture will feel like oil to your water.

So while you can start by reading Glassdoor reviews of your potential employer, you really need to get a perspective from someone who knows you or the cultures you’ve been in already. Here’s how to do that:

  • Go into LinkedIn’s Advanced Search filters and set the Past companies field to your prospective employer. This way, you can talk to someone who doesn’t have skin in the game. In general, we find that when someone pays your health insurance, it’s hard to bash them too much... :)

Past Companies
  • First run a search for 1st degree connections. See if you can find someone who knows you AND the company you’re considering. If so, they can give you a good feel for how the company might feel relative to your preferred MO.

  • If you don’t know anyone who used to work there, try searching for people from your branch of the service who used to work there (by adding it to the Search box). That’s because they can give you an apples-to-apples comparison of how, say, the Coast Guard feels vs. Colgate.

Search by branch of service
  • And if you can’t find anyone who knows you or your context, feel free to reach out to someone who used to work there in as a close a role to yours as possible. For example, try searching title:”project manager” to focus on folks from that team. But to really elicit a sense of what it’s like, don’t ask them to describe the culture since that can be like asking someone to “Describe air.” Instead, ask them to tell you a story that reflects how the culture was different from other places they’ve worked. And now you’ll have a visceral feel for what it’s like on the inside.

Search filtering

Negotiate with Leverage + Data

So you’ve done your due diligence and everything checks out: the work, the boss, the culture. You just can’t wait to get started.

But now imagine that on Day 1, you find out that your new teammate is making 50% more than you to do the same work. Not feeling so motivated after all, huh?

To prevent this unhappy discovery and to kickoff the new job with confidence, here’s how to negotiate with strength - but in a way that doesn’t burn the very relationships you want to build.

  • When you first receive an offer on the phone, make sure to nail down two dates: When you’ll have the offer in writing (usually just over email) and when you need to decide. This way, you have a clear timetable for the negotiation.

  • Now, if you’ve been applying to a new job every single day for a few weeks, chances are that you’ve got at least one other opportunity in the works or at the offer stage. This is great news by itself - but even better if the recruiter knows about it.

  • So make sure that you introduce this leverage after the offer is made, if you haven’t already. All you have to say is: “You totally made my day! I’m considering one other opportunity at the moment but will definitely give this offer serious consideration ASAP.” This does two important things for you: It respectfully shows your gratitude to your prospective employer but also lets them know that they can’t take you for granted.

  • Next, check your offer against two sources: Glassdoor’s salary data for that specific role at the company and LinkedIn’s salary data for that general role in your area. This will make sure that the company isn’t lowballing you against its own standards AND that it isn’t out of whack with the overall market for your skills.

  • When you conduct your comparison, make sure to consider the full package - including equity, if offered. The easiest way to compare equity to salary is to figure how much it’s worth today (don’t hesitate to ask the recruiter!) and then assign it a probability for the future. For instance, if you’re getting Restricted Stock Units (RSUs) at a big, stable company, these are the closest thing to pure cash. While the firm’s stock may go up or down, you can generally estimate that the future value of those shares will be similar to what they’re worth today. Whereas, if you’re getting options at an early-stage startup, you should not only figure out what they’re worth today but also take into account that they may grow considerably (about 1% of seed-funded companies become worth $1 billion or more) but are more likely to not grow at all (about 70% of these companies either fail or never go public/get bought). So if you’re not comfortable with this level of risk, you may want to apply a similar discount rate to the value of these options. And if you really want to geek out on how this all works, check out this detailed report on options from our friends at Andreessen Horowitz.

  • If the company’s offer is lower than its median pay for that role, the market’s median, or your other options (including staying with the military), just ask them if they can beat that number. Of course, be sure to give them the highest of those three data points (including your Regular Military Compensation) since the first rule of negotiation is to anchor them in the best possible direction (i.e., the first counter-proposal becomes the number that all future bids will center around).

  • If the company’s offer is already higher than everything out there, it still doesn’t hurt to ask for something since companies expect you to negotiate (and if you’re applying for a sales or supply chain role, it would look bad if you didn’t!). It doesn’t necessarily have to be salary-related, since that’s often the hardest number for a company to move. Instead, consider asking for a bigger bonus to defray relocation costs, a larger stock grant to show your alignment with the company’s success, or even more vacation days if you’ll need to travel far to visit old military friends around the world. Even if you don’t have data to draw upon, providing a personal need for any of these requests converts it from an arbitrary pursuit to a highly rational one.

  • But definitely don’t feel like you need to keep pushing things beyond the point of satisfaction. You’ll be much happier at work knowing that you’re compensated fairly and that you’ve got a good relationship with your teammates than knowing that you squeezed every last cent out of the negotiation at the expense of your reputation!

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