Have you ever start­ed a new job and regret­ted it with­in months? Wished you’d asked more ques­tions before you’d excit­ed­ly said “yes” to the job offer?

Ever not been able to choose between two job offers because you did­n’t know enough about either job?

Ever said, “If I’d known that, I’d nev­er have tak­en that job”? Ask­ing at least some of these 27 ques­tions can help you avoid new-job remorse.

You need to know whether you’ll enjoy the job

Dur­ing the inter­view, if the inter­view­er asks, “Do you have any ques­tions?” ask: “What would my imme­di­ate pri­or­i­ties be?”

You’ll need to know you’ll be suc­cess­ful.

Nei­ther you nor your new employ­er will be hap­py if you can’t meet your employ­er’s expec­ta­tions. Ask:

— What will you want me to accom­plish in my first thir­ty (six­ty) days?

— What will tell you one month from now that you’ve hired the right can­di­date?

— What are chal­lenges you expect the per­son in this posi­tion to face?

— How will you eval­u­ate my per­for­mance?

— What is the biggest chal­lenge fac­ing this depart­ment right how?

As a sec­ondary ben­e­fit, ask­ing these ques­tions shows the job inter­view­er you care about meet­ing employ­er expec­ta­tions.

You can even ask, “Do you have any hes­i­tan­cy in hir­ing me?” If your inter­view­er answers, you can address the inter­view­er’s unspo­ken con­cerns or at bet­ter pre­pare for future inter­views.

What will it be like work­ing for this man­ag­er?

Your man­ag­er has a large impact on your career. Can you trust and respect this man­ag­er? What’s his/her man­age­ment style? Before you land a job with a hands-off man­ag­er unavail­able when you need guid­ance, or a man­ag­er who expects dai­ly brief­in­gs or oth­er behav­iors you con­sid­er micro­man­age­ment, ask:

— How often will you and I be com­mu­ni­cat­ing and what type of com­mu­ni­ca­tion do you pre­fer — email, text, in per­son, or phone?

— Once I’m ori­ent­ed and have won your trust, what deci­sion-mak­ing respon­si­bil­i­ty will I have?

— What is your vision for the depart­ment?

What will your employ­er expect from you?

Will this job ask more of you than you’re pre­pared to give? Ask:

— How reach­able will you want me to be on week­ends or evenings?

— What’s a nor­mal work­day and work­week?

— How much busi­ness trav­el will I do?

What can you expect from this employ­er?

— What advance­ment oppor­tu­ni­ties exist for some­one in this role?

— What pro­fes­sion­al devel­op­ment oppor­tu­ni­ties does this employ­er pro­vide?

— Does the job include a work from home option?

— What is the cor­po­rate struc­ture and where do I fall with­in it?

— How does the com­pa­ny deter­mine salary ranges for remote work­ers and is it dif­fer­ent for in-office or hybrid work­ers?

— How impor­tant is this posi­tion to the over­all suc­cess of our com­pa­ny?

— What ben­e­fits does the ben­e­fits pack­age include?

— Can I meet some mem­bers of my team before I start?

— What are the most impor­tant projects the team is work­ing on?

Dodg­ing a bul­let

Bet­ter you uncov­er prob­lems before you start a new job. Once you’ve received an offer, you can ask HR or the hir­ing man­ag­er:

— Is this a new posi­tion or how did this posi­tion come to be open?

— How did this com­pa­ny fare dur­ing the pan­dem­ic? What safe­ty pre­cau­tions have you put in place? What are some ini­tia­tives you’ve put in place post-pan­dem­ic to han­dle hybrid and remote work?

— What are the main rea­sons employ­ees stay at or leave this com­pa­ny?

Ques­tions to ask your­self

Most impor­tant­ly, ask your­self:

— What about this job excites me?

— Can I pic­ture myself doing this job and being hap­py doing it for at least two years?

When and how to ask ques­tions

When you ask these ques­tions, keep your tone pos­i­tive and inter­est­ed. Notice the effect of your ques­tions and be care­ful not to grill or to touch a nerve. Word your ques­tions to show you care about the job and meet­ing the employ­er’s expec­ta­tions, and not just the com­pen­sa­tion and ben­e­fit pack­age. Final­ly, if you don’t like the answers, breathe a sigh of relief. You’ve dodged a bul­let.

Lynne Cur­ry writes a week­ly col­umn on work­place issues. She is pres­i­dent of Com­mu­ni­ca­tion Works Inc. Send your ques­tions to her at https://workplacecoachblog.com/ask-a-coach/.