“New Job, First Week – Seven Questions You Should Always Ask”

“Give thanks for unknown blessings already on their way.” 

– Native American Saying

ACTUAL “CASE HISTORIES”: It just never ceases to amaze me: new employees encounter needless difficulties – and lose out on significant benefits – for one simple, yet avoidable, reason: they simply fail to ask a few important questions during their first week on the job. 

At some companies, employee benefits begin the first day on the job; at other companies, benefits don’t begin until after three months of full-time employment. Some employers provide healthcare benefits beginning on the first day of the next calendar month after hiring, while 401k eligibility does not commence until a full year of employment has been completed. 

At other employers, all employees have probationary periods, but are never told of that fact. And, at still other companies, you are given a stack of papers to sign during the “onboarding” process, but never offered a copy of what you sign. It’s all very confusing, and made even more confusing by it being the start of a brand new job when you’re confronted by a veritable “blizzard” of new information.  

The number of difficulties that arise, and the amount of legal fees that are sometimes unnecessarily incurred to correct these difficulties, are so much greater than you might imagine. For this reason, every new employee would be wise to ask the seven questions we set forth below during his or her first week on a new job.

LESSON TO LEARN: Information is always valuable, and even more so when put to good use. But first you have to acquire that information. In the context of new employment, it is usually the case that, “All you have to do is ask.”  Of course, asking should always be done politely, in person, or if preferable, in the form of an email. Of course, follow up may become necessary.

Sure, in the beginning of a new working relation, you don’t want to appear distrustful or confrontational, but the questions we recommend you ask are not “edgy,” but instead sure signs that you are prudent, thoughtful and attentive to detail – all attributes of a valuable employee.

Savvy, sophisticated and successful workplace “negotiators and navigators” know and appreciate the truth in the saying, “More data, better decision.” And you should, too.   

WHAT YOU CAN DO: When starting a new job, you have lots on your mind. However, certain questions are more important than others.  These seven questions are the ones we suggest you “Do Not Forget To Ask”:  

1. “May I please have a copy of everything I sign, for my records?” –  Examples of some of those things “I-think-I-might-have-signed” during your employment “onboarding” process include (a) non-competition agreements, (b) confidentiality agreements, (c) agreements to give a certain amount of pre-resignation notice, (d) agreements requiring you to resolve disputes using certain procedures, often arbitration, (e) beneficiary designation forms for life insurance policies, and (f) agreements to repay certain monies paid to you – sometimes even years later – if you leave under certain circumstances. And there are many, many more. Each of these might become quite important to you at later times and in presently unanticipated circumstances. It is a great idea to ask for, and retain, copies.  

2. “How can I get a copy of the Employee Handbook?” – Most, but not all, employers have an Employee Handbook that contains many of the “rules of the road” for the employment relation. Those “rules” just might affect who you date, whether you use company email and for what reasons, and even what you can do and can’t do if you are harassed or accused of harassing someone else.  

Some employers keep their Employee Handbooks on their website, and some hand out copies to new employees, but most just have HR tell you on one of your first days on the job, “Make sure you read it.” In fact, many employers require new employees to acknowledge, in writing, that they have had an opportunity to do so. Get a copy of yours, and read it thoroughly, as it just might get you promoted if you do, or fired if you don’t.  

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3. “When do each of my Employee Benefits commence?” – Whether it is (a) coverage for medical, dental, disability or life insurance, (b) eligibility for 401k, profit sharing, tuition assistance or savings plans, or (c) accrual of vacation, commissions or PTO, it is important that you don’t err regarding the date each commences. These are valuable and significantly so; you surely don’t want to find out that the expensive dental work you had done on day 89 of your employment was not covered by the dental coverage that commenced on day 90.        

4. “What are the names, phone numbers and email addresses of Contact Persons for my questions about (i) Payroll, (ii) Benefits, and (iii) General HR?” – This question is simply self-explanatory. These are the people you will most likely need to speak with during your first few months on the job. Best to have their contact information now, for ready reference later. 

5. “Where can I find out about Policies and Procedures regarding (a) vacation, (b) sick days, (c) expense reimbursements, and the like?” – If the Employee Handbook provides the “rules of the road,” your employer’s Policies and Procedures are the “highway’s regulations.” As an analogy, we all know that it violates the “law” to drive 100 miles an hour on the highway, but did you know that you can be fined $250 if your car’s headlights are dirty? 

At work, these seemingly “smaller” rules can easily trip you up, and lead to a surprisingly painful  “fall” from grace. If you need a permit to park in the employee parking lot, or submit petty cash receipts no later than three days after the end of a calendar month, better to know them now and obey them. Trust me: successful careers have been lost due to such seemingly innocuous issues.  

6. “How can I get access to the written ‘Plans’ for 401k, Employee Stock Options, Bonus, Commissions, Severance and similar employee programs?” – Chances are low that you will ever read through the Plans that set forth the details of your eligibility for, and entitlements under, your employer’s workplace programs. But the chances are quite high that, sooner or later, your attorney and accountant may need to do so for you. Finding out where they are accessible if and when you may need them is a good practice to follow. Knowing what they say is even better.    

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7.Will I be asked to sign a Non-Compete or related agreement?” – Last but not least, we add in this question about non-competition (often called “non-compete”) agreements. It is quite common these days for employees to be required to sign a Non-Compete agreement. There are three good reasons to ask this question at the commencement of a new job: (i) If the answer is “yes,” better you know it now, and be best prepared to respond to that request when it comes; (ii) If the answer is “no” or “We don’t think so,” you have a good argument to resist the imposition of a non-compete agreement in the future; (iii) either way, having a record of sorts that this was “foisted” upon you during your first week or two on a new job can prove helpful to later efforts to have a non-compete voided by a Court, if you ever land up there in a non-compete dispute.     

When asked to sign a non-compete agreement, consider asking for release from it, or modification to it, in order to protect your career. How can you respond? How should you respond? Our “Model Letter: Response to Request You Sign a Non-Compete” shows you “What to Say, and How to Say It.™ To obtain your copy, just [click here.] Delivered by Email – Instantly!


SkloverWorkingWisdom™ emphasizes smart negotiating – and navigating – for yourself at work. Negotiation and navigation of work and career issues requires that you think “out of the box,” and build value and avoid risks at every point in your career. We strive to help you understand what is commonly before you, and to then understand what to do to achieve greater rewards and greater security at work.          

Always be proactive. Always be creative. Always be persistent. Always be vigilant. And always do what you can to achieve for yourself, your family, and your career. Take all available steps to increase and secure employment “rewards” and eliminate or reduce employment “risks.” That’s what SkloverWorkingWisdom™ is all about. 

*A note about our Actual Case Histories: In order to preserve client confidences, and protect client identities, we alter certain facts, including the name, age, gender, position, date, geographical location, and industry of our clients. The essential facts, the point illustrated and the lesson to be learned, remain actual.     

Please Note: This Email Newsletter is not legal advice, but only an effort to provide generalized information about important topics related to employment and the law. Legal advice can only be rendered after formal retention of counsel, and must take into account the facts and circumstances of a particular case. Those in need of legal advice, counsel or representation should retain competent legal counsel licensed to practice law in their locale.  

Sklover Working Wisdom™ is a trademarked newsletter publication of Alan L. Sklover, of Sklover & Company, LLC, a law firm dedicated to the counsel and representation of employees in matters of their employment, compensation and severance. Nothing expressed in this material constitutes legal advice. Please note that Mr. Sklover is admitted to practice in the state of New York, only. When assisting clients in other jurisdictions, he retains the assistance of local counsel and/or obtains permission of local Courts to appear.  Copying, use and/or reproduction of this material in any form or media without prior written permission is strictly prohibited. All rights reserved. For further information, contact Sklover & Company, LLC, 10 Rockefeller Plaza, New York, New York 10020 (212) 757-5000.    

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