Crucial questions and negotiating skills

Wait, Don't Take That Job! (Yet)

Before signing that job offer, here's what you should ask yourself, your potential boss, and the HR department.

To some, the lure of receiving a monthly salary after months of job hunting is enough that they will sign the first offer they get.

But, taking a job entails much more than getting a paycheck. Once you sign that dotted line, you're agreeing to the company's culture, schedule, and more. Not to mention, you're agreeing to work with your new boss and coworkers—whether you like them or not.

Even as a freelancer or a contract worker, you're still committing to dedicate your time to this company. It's something that you should be proud to mention in your resume or portfolio, that you can use to take you somewhere.

But, when anxiety around finding a job kicks in, paired with the sudden thrill of having landed an offer, there are often questions we leave on the table. Before you commit to a new job, asking these critical questions will help you figure out if you're making the right decision. Remember, good things take time.

Questions to Ask Yourself First

When you're job-hunting, any opportunity in your field can seem worth looking into. This can lead to some fabulous opportunities, but also some questionable ones that might become your crazy job story in the future. Now, with that offer in hand, you might want to ask yourself these questions before moving along in the process.

Are you genuinely excited about this job?

When you've been job-hunting for a while, it can be very exciting to get that offer. At last, you're finally looking at the prospect of more financial stability. But, before accepting, put that paycheck aside. Are you genuinely enthusiastic about the job, and see a future full of opportunities and skill developments within the company—or are you just saying yes to the first offer that pops up? For those lucky enough to have multiple offers on the table, assign a number 1-10 to each based on your excitement level, and where you see the greatest career development happening for yourself.

Does the position use your skills appropriately?

Sometimes, people stuck in a career rut tend to settle for less. Do your best to match your job search with your talents and passions, and don't underestimate yourself. If you must wait a bit longer to find the right job, and can afford to wait, it will always pay off. Additionally, consider whether your place within the organization is reflective of your work experience. Taking an entry-level job, when you were previously at a mid-senior level, could jeopardize your professional path.

What are your non-negotiables?

Job offers are a negotiation, and you better come prepared with your non-negotiables. For example, if you're not willing to go below a specific salary, or perhaps you want to work a certain number of remote days per week, whatever your requests are, make sure to be open about them once you receive an offer.

How will the career move position you for further success?

When analyzing a job offer, make sure you know how it will help you advance in your career. Look for opportunities that will help catapult your professional life and take the next step in your career, whether that's finding your place in a new industry or setting your sights on a senior role. Imagine your future resume, and what position you might hold ten years down the road. Can you see this position being a stepping stone towards your ultimate goals?

Are you happy with the salary?

Even though money is not everything, you still need to be happy with the salary, and it needs to sustain your lifestyle without putting you into a pit. When you feel underpaid, you'll most likely end up dreading your job and in a career rut that can hurt your professional development. Have a reasonable expectation, and make sure to bring up your compensation needs during negotiations.

Is the company reputable and stable?

Before saying yes to any offer, make sure you do your due diligence. Looking at the company's track record can save you from potential disaster. Accepting a job at a startup or a company that has had bad behavior in the past can leave you stuck and without payment. The first places to look for a company’s track record are on LinkedIn and Glassdoor to find out what their employees have said about the work environment.

Questions to Ask Your Potential Boss

From small to large corporations, at one point in the interview process, you'll probably meet your potential new boss. It's up to them to decide if you're the right fit to join their team. Look for personality traits that signal if they're the type of boss you'd want to have. Then, ask the right questions to make sure you don't end up with someone that's a nightmare to work with. Remember, interviews are supposed to be a two-way street. So, when they ask, "do you have any questions for me?" please politely reply, "as a matter of fact I do," and ask these questions.

What will my everyday responsibilities look like?

Have you ever read a job description? They often seem written in another language and disconnected from the actual work. In essence, you will have to be able to handle all the company’s expectations and maintain a positive, productive attitude. Instead of focusing on the job description, ask your new boss to give you a rundown of a regular day. If this sounds like something you're comfortable doing, and you feel everything else in the offer aligns with their synopsis, then you might be on the right path after all.

What's the onboarding process like?

Onboarding is the process in which new applicants are taught about the company's history and goals, as well as the skills and processes they need to familiarize themselves in order to be a productive team member.

Just about every company has its own onboarding process. Some include shadowing a coworker for a week while they explain everything that needs to be done. Others include month-long programs that blend in-classroom trainings with on-the-job experience. If a company is lacking a strong onboarding experience, you may want to think twice. This is important, because you deserve to feel comfortable and confident that your new boss has given you all the necessary tools to succeed in your new role.

What are the goals of this job? How will you measure my success?

Larger companies often have key performance indicators (KPIs) that are used to measure everyone's success, including the company's. Smaller companies might have check-ins every so often to make sure what you're delivering is up to the company's expectations. Keep these in mind, and ask exactly how these evaluations will be used in the future. Some use them to backup promotions and salary raises, while other companies just do them to keep employees on track.

What will my schedule be? Are you flexible?

Never assume a job is from 9 to 5. In fact, when it comes to a job, never expect anything. Especially if you're getting paid by the hour. Make sure to ask about the schedule and whether or not your new boss is flexible with your time. If possible, try to ask your new coworkers this last question, as your boss might say one thing but in reality be the complete opposite.

What are your expectations in how we communicate?

Have you ever been asked to receive company emails on your phone? What about installing apps like Slack, Trello, or Microsoft Teams? Yes, some companies expect workers to be available almost 24/7. But, is that doable? Ask about the company's expectations when it comes to communication and “off the clock” the time. Develop a clear idea of what they want from you, as it might save you both a headache and your job in the future.

What goals do you expect me to achieve? What's my timeline for those?

Finding your groove at a new job is not just a “press play” type of thing. It takes time. At first, you might need training wheels until you feel secure enough to handle situations on your own. But, when are the training wheels supposed to come off? By week 1? Three-months in? Knowing the answer to these questions will let you know how your new boss sees your path within the company, and provide a quick snapshot of your job. If you like what you hear, then moving on with negotiations might be the right thing to do.

Questions to Ask HR

Lastly, it’s time to ask HR a bunch of questions. They're the ones taking care of all the operational details there to make your life (hopefully) a bit easier. Don't feel intimidated to ask HR questions, as they should find your interest and knowledge reassuring. Plus, it will safeguard you from a mess in the future.

When do you want me to start? When do you need my decision?

Before you accept any offer, there are a few things you have to consider. From your resignation notice timeline to relocation time before you start, these are all things that will affect your schedule. Remember that you can always negotiate a later starting date, if necessary.

What types of benefits are included and when does my eligibility start?

Compensation packages include everything from health care, dental insurance, transportation benefits, and so on. Yet, not all these benefits kick in from day one, as most companies want to wait to see if you’ll make it through the training period. Other benefits like gym memberships, daycare, and so on are also worth considering, especially if you already pay for these services on your own.

How much vacation and sick leave do I get?

First of all, you want to know if the company differentiates between PTO and sick days, as some companies group these together. You'll want to ask if these days increase when you get promoted, if they roll over to the following year, or if they can be exchanged for cash when left unused. The more you know, the better idea you'll have about the company's work-life culture.

How long do employees in my role last?

While it would be exciting news to hear that the last person in your potential new role moved up the career ladder, it would be disheartening to find out the position has been a revolving door. If employees are coming out as quickly as they're coming in, that's a big red flag. Watch out for these, as it may be difficult to tell while the company is trying to win you over.

Do you offer any flexible work programs?

Define what flexible work program means to you and ask about it. This could be something as leaving early every other week to pick up your children from school, to working remotely two days a week to help with your commute. You'll be surprised how many employers are willing to allow flexible work programs when they believe they have found the right person for the job. This can also be part of your negotiation strategy, so keep this in mind.

What about a parental leave policy?

This one is so important, especially if you're planning on having a baby soon. How much time will you have to get acclimated to your new child? Remember all the previous questions here, and consider negotiating a flexible work program if you do have a baby.

Ask about other perks

Offices are turning to so many other perks to lure in employees. There may be bring your dog to work days, unlimited snacks, freshly-brewed coffee, nap pods, and even spas. These perks can add to the appeal of a job listing, especially when they include teambuilding efforts like corporate retreats and so on.

What happens during slow cycles?

While the answer to this question won't be 100% accurate, it's worth to see what will happen in this scenario. Every industry has its slow cycles, and some workers worry about losing their jobs, especially if they're freelancing, which is totally understandable. Some companies already know about their different cycles and prepare for this. In retail, that means fewer hours for workers. In agencies, that could translate into more time for training and education, and so on. Try to get an honest response from HR or someone else within the company. If you're looking for a single and steady source of income, fluctuating workloads might not be the right fit for you.

Can I get this in writing?

When you start a job, you're asked to sign a million and one documents. Ask for one significant document in return—everything you agreed on, in writing. While people often get an official offer letter, this document typically has only the salary and starting date. Request documentation that includes the different perks, the arrangements of your flexible program, your vacation and sick days, the timeline for your benefits to kick in, and everything in between. This ensures that you have a backup if at one point you do need to prove that such terms were once approved.

Preparing for accepting a job offer involves much more than writing the perfect resume or crafting the ultimate elevator pitch. It also means asking the right questions. Come prepared for your next interview and set yourself, and your employer, up for success. The last thing you want is to accept an opportunity that you'll end up regretting from the start.

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