Q: I’ve been interviewing for senior jobs in the nonprofit sector. I’ve been a finalist for three different roles, each of which has had four rounds of interviews. Each organization has asked me to draft between 15 and 20 pages of original responses to screening questions and hypotheticals, and to develop advocacy and legal strategies. Sometimes I get the feeling I’m doing free labor as I give them all my great ideas, hoping to be hired. I understand that organizations need to evaluate what a candidate can offer, but this process is burdensome and feels inequitable as they request sophisticated work product on a short time frame without pay. Is it OK for employers to demand so much of applicants? Is there any way I can challenge this dynamic? — Anonymous

A: Having to jump through an excessive number of hoops to get a job can be incredibly frustrating. It seems like the interviewing process is getting more and more convoluted in many industries. And there are employers out there who are exploitative, essentially demanding unpaid labor from job candidates and getting away with it because they can. Some employers will offer compensation for work product produced during the vetting process, but they are few and far between.

This is a challenging problem because, as you note, employers do need to find ways to determine whether a candidate will be a good fit. A new hire, especially for a senior position, is a significant investment of resources; hiring the wrong person only increases that investment. While some things can be gleaned from interviews, there are criteria that can be assessed only through work product. Within reason, it is acceptable for an employer to make requests of potential hires. The limits of that reason are quite subjective, unfortunately.

I really empathize with your frustrations — so much work with no guarantee of success. Employers hold all the cards, or they did, until the Great Resignation began. You may, perhaps, challenge this dynamic by asking if there is compensation for the work asked of you, but that is risky. I do hope, in time, that employers find a more reasonable way of vetting potential hires, and I wish you the very best in your job search.

The great generational divide

Q: I work for a legal services nonprofit making the transition to the new world of the cloud, video meetings, etc. It feels like a constant battle between the younger people and the more seasoned employees — constant sniping, each calling the other lazy and entitled. As a geriatric millennial, I am constantly in the middle. I hear the complaints from both sides and strive to help each side understand the other’s perspective. Both sides have some good points and both sides are wrong about some stuff. The leadership is barely keeping the place running and has completely abdicated any culture-creating or policy-setting role. That leaves people like me to sort it out. Do you have any suggestions for how to get the two sides to talk to each other in productive ways? The issues aren’t just related to Zoom meetings and Dropbox accounts but cultural shifts as well. I genuinely believe everyone is trying. I have thought about trying to set up a mentorship system to pair people together? Or (when possible) planning more social events? Maybe there are specific resources you would recommend? — Anonymous

A: Honestly, you should tell these people to grow up — this is ridiculous. Yes, change is hard, but it is inevitable. Technology and the ways we use it in the workplace are always evolving. The culture we are a part of shifts, sometimes faster than we can manage. We don’t have to like it, but we do need to adapt.


At the same time, there is much to learn from older ways of working and thinking and being. It’s just lazy for people to shout derivative generational barbs at one another. To what end? It might feel good in the moment, but it only creates a more divisive atmosphere among people with whom we are supposed to be in community. Tell your colleagues this is unacceptable on all sides.

If everyone is genuinely trying, they need to try harder. The mentorship program sounds like a great idea. Frame it as a two-way mentorship system, so everyone understands they have something to offer. I don’t think that mandatory fun will solve this problem, but mandatory maturity might.

Unfair advantages?

Q: I recently had the opportunity to bring three provisional junior members into my team, with the option to progress them to permanent roles after a year if I can demonstrate their importance to the business. Depending on budget, there might be room for only one or two to progress. I’m assessing them on their productivity as well as contributions in other areas. All three are hard workers with great attitudes and high productivity, and I’m currently building business cases to keep each on board permanently. I’ve also received unsolicited praise from three senior managers for one of them in particular — who happens to resemble a young Michelle Pfeiffer. These individuals are all older straight men, which is unfortunately the main demographic here at the upper levels. “Michelle” has in no way behaved unprofessionally — she’s made strong professional connections across demographics — but I’d be remiss in ignoring my suspicions that these men were at least subconsciously motivated by more than professional respect. It feels unfair to the other two junior staffers to offer this praise the weighting it would normally merit but unfair to Michelle to ignore it. Help. — Anonymous

A: Be careful. You’re essentially engaging in the same type of behavior you rightly disdain from your older straight male colleagues. Are you really suggesting that you might penalize your employee because you assume she is receiving positive professional feedback because of her appearance?

People have biases, particularly where looks are concerned. My mother loves to remind me that we eat with our eyes first. This is something of a mixed metaphor, but I think you get my point. Entire books have been written about the advantages beautiful people enjoy in the workplace. I appreciate your being mindful of this dynamic, but if Michelle is indeed performing well, that should be your focus. To compensate based on what you perceive as unfair praise is a slippery slope to head down. You absolutely mean well, but you have no way of knowing if the men praising her performance are really only praising her looks.

Is it possible? Of course. But it’s not fair to punish her for their childish misogyny, if that’s truly what’s happening. All three candidates deserve to be treated equitably. Don’t overthink this.


Ghost story

Q: Earlier this year, I went on a few dates with a guy I liked and thought things were good until he ghosted me. I accepted that he wasn’t that into me and moved on, though I was hurt by the lack of communication. Fast forward six months: He’s introduced as my new co-worker. He had known I worked at this small restaurant and even said, “Hey, I’m glad you still work here!” I honestly don’t mind that he works there. I’m happy to help him when he asks work-related questions. However, he often tries to talk as if we’re friends and has not addressed our past or the fact that he ghosted me. How do I tell him I was hurt when he ghosted me and that I wish to only discuss work matters? — Anonymous

A: Being ghosted feels terrible. Without warning someone disappears and you have no answers. In some ways, this is a fortuitous situation. You have been presented with an opportunity for closure. If you really do want to address this with the Ghost, ask him if you can speak before or after work in a neutral location. Share your feelings and the terms you would prefer for your relationship moving forward.

But before you do that, I want you to really think through what you’re hoping to get out of such a conversation. What goodwill can come from a conversation in both the short and long term? You will unburden some of your hurt, but it might complicate what seems like an amicable professional relationship.

Do consider letting this go, not because he deserves to be let off the hook but because you seem to be in a good place and he doesn’t deserve any more of your mental energy. In the meantime, may the next guy you date be the man of your dreams.