How I got 7 Job Offers in 8 Weeks (Part 3: Finding the Right Job)

I’ve made a few big leaps in my career so far from finance consulting to product management to software engineering, and I just finished another job search. I’ve had successful negotiations, and made (sometimes stressful) decisions between very different companies. After writing about my strategies for getting into the interview room and preparing for interviews, I’ve gotten tons of questions about my job choices and career transitions. How do I uncover exciting job opportunities, get assigned to the team I want, and decide which offer will meet my needs?

Interviewing is such a consuming process of impressing them that it’s easy to lose sight of what you need. Each of my job transitions has refined my method for defining priorities and identifying the best fit for my next role. With learnings from my most recent search, I want to share my strategies with you.

Caveat: Not every job search affords the luxury of being choosy. Maybe you’re short on cash or escaping a toxic workplace, and you just need ANY job, yesterday. If your financial situation forces you to accept your first offer, I see and respect you. BUT, after celebrating your employment and taking a breather, summon the energy to keep interviewing and find someplace you really want to be (while collecting your new paycheck). You owe it to yourself to have food on the table and be happy. :)

1. Take notes on your way out

As soon as I know I’m going to leave a job (or even a team), I take notes on the place I’m leaving. What did I like? What would I never want to deal with again? What could have been better? And I save my notes somewhere I can find them later.

These notes are observations about what matters to you, and you’ll use them to find an even better fit next time. Often when I leave a job I’m so exhausted I just want to sleep for two weeks straight, but don’t wait to do this. The more time that passes, the less you’ll recall the specifics. You need good notes to remember why you left and guide future job searches.

Note: If this is your first job search ever, you’ll have to take your best guess at what’s important to you. If this is you, I’d highly recommend putting strong support and mentorship high on your list. You can also ask someone with more work experience to suggest qualities to look for in a junior role in your field. Don’t be afraid to search for potential mentors on LinkedIn and buy them coffee!

2. Identify what matters to you

Your needs will change over your life and career. Maybe five years ago you cared most about work that was exciting and spiritually fulfilling, but now you need more flexible hours to take care of a family member. What are your priorities right now, for this search? What can’t you do without, and what can you not tolerate? This is your bottom line. Use your notes on past likes and dislikes as a starting point. Prioritize what qualities you’ll be vetting for as your bottom line, and what else you’ll keep an eye out for.

I transitioned careers not too long ago, so in my last job search my bottom line was all about training, mentorship, and strong career support. There were also things I was unwilling to accept — for example, I knew I would not join a team where I would be the only woman engineer. I explicitly wrote down what was most important to me to find: my small handful of must-haves and dealbreakers, and all the other nice-to-have qualities.

3. Interview them, too

What do you do when your interviewer asks, “do you have any questions for me?” If you just lob over some generic softball questions to seem prepared, you’re losing the chance to do some real vetting. Always be ready with a list of questions you actually need to know the answers to, and write down their answers so you don’t forget.

Specific questions that reflect your values also make you more hireable, so don’t be afraid to ask tough ones. After interviews I’ve gotten glowing feedback about challenging questions I’ve asked, saying it showed that I was discerning and self-aware, and had a genuine interest in finding a mutual fit rather than just impressing them.

Picking the right questions is VERY tricky: an interviewer will usually give you a positive spin on any question you ask about their workplace. So you need to think about what questions will get the information you need to reach your own conclusions.

Start with your bottom line qualities you’re looking for, and try to come up with 1–2 questions for each that will help you really understand how each job differs on that point. My main rule of thumb is to ask for specific information, rather than an opinion. That way, I can interpret the information myself and decide which job is best for me. For example:

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• Too general: “What do you think of the onboarding process here?”
• Better: “Can you walk me through the onboarding process? What else do you do to set up new folks for success?”

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• Too general: “How does everybody get along on the team?”
• Better: “What qualities do you appreciate in a team member? How would you describe the team dynamic? Is there anyone here you hang out with outside of work hours? How often?”

4. Interpret their answers carefully

Never leave them the opportunity to say, “It’s all good! I haven’t heard any complaints.” Don’t be afraid to dig deeper if their answer is too general to give you the details you need. You can ask right then if there’s time, or make a note to ask in a followup conversation later if you get an offer.

When I ask the right question, I try to notice things like:

• Is their answer thoughtful and detailed, or generic? Does it seem like this is something they’ve thought about before, or like my question is the first they’ve heard of it? This is a signal of whether it’s something that this workplace really values.
• Do the things they describe sound like they would meet my needs?
• Does the interviewer seem uncomfortable answering the question, or like they’re making excuses for something? Or are they excited at the opportunity to describe something this place does well?
• Are they willing to be real with me about what they wish were better? This might be a positive sign of an environment that fosters psychological safety and honest feedback. If nothing else, at least it gives me more information.
• How does it compare to when I asked the same exact question at other interviews? You should be doing this so you can compare notes apples-to-apples on who best meets your needs.

5. Be willing to wait

Before starting my last job search, I took a look at my finances and decided how long I was willing to wait to find the right fit. I held myself accountable to that timeframe and was ready to turn down offers that would have compromised on my bottom line, as long as I knew I had time to spare.

It can be distressing to turn down a job offer that’s “pretty good.” But if you know what really matters to you, it’s worth the wait. Mentally prepare to say no if the job or work environment doesn’t meet your bottom-line priorities. You will always have to compromise on other nice-to-haves, but don’t compromise on your bottom line unless you’re truly out of time.

Most opportunities should also be flexible if you simply need time to decide. I’ve often made a request like this:

“I’m so thrilled to have this offer, thank you for the opportunity! I am still in the interview process with other opportunities, and don’t feel comfortable making a decision without all the information from everybody. I expect to have a decision by ; can I get back to you no later than then?”

Some offers may demand a decision in as few as 1–2 days. In most situations, this is a manipulative tactic to force your hand, and a glaring red flag. If this is how they treat you when they’re showing you their best side, how will they respect you as an employee? If it’s a small company with one job opening, they may need a quick answer to move to their next choice if you decline — though, they should still be flexible with a couple extra days if you’re really on the fence. Know that you’re worthy of some time to get full information about your options and make a life-impacting job decision.

6. Use your post-offer power

You will never have as much power at your job as during the time between receiving an offer and signing it. You know they want you, and their goal now is to get you to say yes. Don’t be afraid to ask for everything you need to make an informed decision.

Be truthful and direct

In my most recent job search, before signing an offer, I made specific requests about what I wanted to work on and what I wanted in a team. Don’t leave them guessing! I would say something like, “It would be easiest for me to say yes to an offer if…” Often they would be able to work something out.

This isn’t manipulative if it is truthful: I was honest about what mattered most to me, so that they knew how to meet my needs. If the alternative is turning them down, it’s better to ask for what you want and give them the opportunity to try to make it happen.

Ask your awkward questions

Some questions can be uncomfortable to ask in an interview. For example, I wouldn’t want my highly specific questions about work-life balance to give the wrong impression about my work ethic. Recently I even had some ethical questions about one of the companies I was interviewing with, but didn’t want to come off as too critical of their business model early in the interview process. It’s okay to save these up and ask them after you get an offer, once you’re in the seat of power.

Meet your team

Your relationship with your teammates and your manager will probably have a higher impact on your satisfaction than most other aspects of the job. One company wasn’t planning to assign me a team until after I started, but I told them how important it was to me to know what my team was before signing an offer. Did I get matched with a team after I asked? You bet.

Then I asked to set up separate one-on-one meetings with 2–3 members of the team, plus the person who would be my manager. I asked the team members about the manager and the team dynamics. I asked the manager similar things, and tried to get a feel for our interpersonal dynamic if I were their report.

This all might sound way too demanding. Many people have a big fear: what if they rescind my offer? I have never heard of this happening so long as you’re respectful. Be honest and gracious in asking for what you need, and remind them how excited you are about the opportunity.

Lo and behold, everybody was happy to set up meetings and answer my extended questions. Remember — they already interviewed you, and they want you. You’re deciding whether to invest years of your life in this place. You’ve earned the right to be informed.

7. Negotiate

A job opportunity will almost never give you their best offer upfront, no matter what they say about it. If you want something, now is the time to negotiate. There are tons of extended resources online about how to negotiate and this is not one of them, so please look those up! My tiny reminders are:

• Have other offers. Competing offers make it much easier to negotiate for salary, benefits, or whatever else you want to ask for.
• Think outside the box. There are lots of negotiable parts to an offer in addition to salary. Is there room to budge on equity or vacation days? Do you wish your title was different? Maybe you’d like to work remote one day a week? Make a list in priority order of all the things you could negotiate on, because those all could be on the table if you’re willing to ask.
• Reiterate your interest. Make sure to stay positive and engaged. When negotiating, remind them how excited you are about the opportunity.
• Be careful before you commit. If you say “I will accept my offer if you do [x],” you need to mean it, or else you could burn a bridge if you change your mind. You can negotiate without committing by saying something like, “This would make the offer much more attractive to me” or “This would make it easier to say yes.”

Bonus: After saying yes

I started doing something new at the suggestion of a mentor. After starting a new job, I schedule a date in the future to consider how things are going in my current role. Otherwise it’s easy to forget to make space for reflection. This could be around the 6-month or 1-year mark, but it should be when you expect to be somewhat settled in and past the honeymoon period. You can even take a day off of work to have some solitary focus time if your other free time tends to be busy.

If things are going well, carry on and schedule another for next year! If you’re feeling dissatisfied, this is an opportunity to identify why. You don’t necessarily need to jump ship: consider whether you can make changes in your own approach to your work or talk to your manager or another decision-maker about addressing your concerns. If you feel like you’ve tried everything but some fundamental need is going unmet, it might be time to see what other opportunities are out there.

It can be scary to acknowledge when something isn’t working out. But you need to give yourself a chance to notice how you feel, and be honest with yourself and others about your needs. It’s perhaps the most important step to keep reaching for the right fit over the course of your career!