‘I’m Stuck in Endless Interviews With a Company That Can’t Make Up Its Mind’

By Alison Green

Dear Boss,

I’ve been going through rounds of interviews for a job, but every time we reach the point where an offer should be made, the process is extended by yet another lengthy meeting with the senior staff.

To say this process has been long is an understatement. This began in October when I applied to a different position and was asked to interview for a new, full-time role within the same organization. The first interview was relatively straightforward and lasted an hour. The second was somewhat non-traditional, included a lot of “getting to know you” questions, and lasted an hour and a half. The third included two managers and the head of the organization, was scheduled for 7 p.m. and began after 7:30 p.m., and lasted 2.5 hours.

Despite these quirks, I have continued on because they have repeatedly expressed their intention to hire me and have confirmed that they are not interviewing other candidates for the position. Furthermore, I am desperate to escape the industry in which I currently work, and have zero other prospects for achieving that right now.

Following the long evening interview, I was brought on for a paid trial work day (which actually went fine). After that, they scheduled another evening meeting to discuss revisions to the original job description. That interview began 45 minutes late and ended at 11 p.m. with questions about when I could start and promises to send me the official job offer the following day.

Just when I thought I had FINALLY reached the end of this process, I instead received a request from them for ONE MORE meeting, again slotted for two hours! I have agreed to it, but expressed that I am anxious to get this show on the road.

At this point, I am pretty frustrated. I’m excited to take on the work they say they want me to do, and having that work on my resume would almost certainly allow me to find a good job more directly related to my chosen field in the future.

They are a very small organization, so it’s not corporate bureaucracy holding things up … so what is going on? I’m starting to feel like there is no finish line here and I’m just wasting my time. What should I do? I’m sure I should have walked away long ago, but I really can’t keep working in my current industry any longer, and outside of this my years-long job search has been fruitless.

Good lord.

There are a ton of red flags here.

Three interviews isn’t unreasonable, especially for a small organization where fit is crucial, but scheduling you for 7 p.m., starting a half hour late, and then keeping you there until past 10 p.m. is absolutely not okay.

But then after that, another long, evening interview? One that started 45 minutes late and went until 11 p.m.? And now yet another request for an additional two-hour meeting? Five interviews total, plus a paid trial day? And this latest one after they promised you a job offer was coming after the last one? That’s not reasonable and it’s not respectful of you or your time. This isn’t how good organizations hire.

But the silver lining is that they’re giving you incredibly useful information about what it would be like to work there. They’re showing you that the organization and/or these managers have an inability to make decisions, a disregard for people’s time (and believe me, if they’re inconsiderate when you’re a candidate, it’s going to be worse once you work there), and perhaps a worrisome amount of comfort with chaos and flying by the seat of their pants.

Take those two late evenings and what they say about how the company operates. Are you okay with the prospect of being pulled into meetings that go on well into the night with little notice? (I’d judge that differently if you had asked for an evening interview to fit your schedule and they’d warned you ahead of time it could go late, but it doesn’t sound like either of those things is the case.)

This is always the way to look at aggravations in an interview process: What do they reveal about the employer and what it might be like to work for them? That’s especially true when you’re seeing a pattern. One disorganized element of a hiring process — fine. We all have bad days. But when you see an ongoing pattern of disorganization, disrespect, or indecisiveness, that’s something to take seriously.

What’s more, the red flags you’re seeing would be concerning with any employer, but because this is a small organization, it’s highly likely that you’re only seeing the tip of the dysfunction iceberg. When small organizations go wrong, they tend to go very wrong. Because they don’t have the same checks and balances as larger businesses do, incompetence or toxicity in a small organization generally will have an outsized impact on your day-to-day quality of life at work.

I know you want this job to work out — you’ve had a long job search, and you want to get out of your current industry. But don’t let that eagerness blind you to what it will be like to work there if you’re hired.

At a minimum, be vigilant about doing some serious due diligence on this organization before accepting any offer there. Make sure you really dig into the culture, the hours, the expectations, the management … because the data you have so far on those things isn’t good, and it’s crucial to know what you’d be signing up for.

If you still want the offer, though, at the end of this upcoming interview you can say: “We’ve had a number of meetings now and I want to be up-front that it would be difficult for me to continue carving out time to meet. Do you feel you have everything you need from me at this point to make a decision?” And if they contact you for yet another meeting after that, it’s beyond reasonable to say, “We’ve met five times and I’ve done a trial work day. I’m really interested in this role, but I have other commitments that I can’t keep taking time away from. If there’s something specific that we haven’t addressed yet, and is it something we could cover by phone instead?”

But really, pay attention to what they’re showing you.

Leave a Comment