Q: I have weekly phone meetings with my boss to discuss projects, deadlines and issues — including anything personal that could affect work. I have always believed this person to be sympathetic and supportive. However, over the past six months, these conversations have become uncomfortable, as my boss discusses the mental health of others on the team.

I have tried steering the conversation away from this type of discussion, but my boss keeps coming back to what is none of my business. This person also makes a point of announcing at management meetings that various team members have “ongoing challenges and difficulties” necessitating careful monitoring, and that, for this reason, all requests must go through them first. I’m fairly confident most of my co-workers would be surprised by these characterizations. I have my own life challenges, but am unwilling to discuss this with my boss as I now realize I may receive the same treatment. I feel complicit in breaching confidentiality. How do I shut this down? — Anonymous

A: There are few things worse than an indiscreet person. You are right to be wary of sharing anything personal with your boss who has a strange fixation on the mental health of the team. I am not sure why they have started doing this in the past six months. Maybe they’re dealing with problems in their own life, so it’s easier to focus on the issues of others.

Regardless, discussing your colleagues’ personal issues with you is inappropriate and it is no wonder you feel uncomfortable. Clearly, steering them in other directions has not worked. It is time to be more direct and say you are not comfortable discussing private, personal information about your colleagues and would prefer to stay on task.

The credential trap

Q: I have decades of experience and earned my way to vice president with one of the premier organizations in my field. My time there ended because of pandemic restructuring, but it was an amazing experience with talented colleagues and a robust alumni network that has been generous with endorsements and connections.

I’ve gotten to second-round interviews for senior positions at new companies but have been stopped by the college degree question. I did attend community college but never earned a degree. For whatever reason, that track wasn’t emphasized or encouraged for me. I got to work and made my way.

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How do I effectively — but in a nondefensive way — push back on this requirement? I’ve got a lot to offer in a hot field (supply chain) and I can’t allow something that should’ve happened over 30 years ago to get in my way! — Christine, New York

A: Too many companies worship at the altar of credentials and, in doing so, overlook incredibly qualified candidates who could benefit their organizations. Clearly, you’re experiencing the fallout. The best thing you can do is highlight your decades of experience. Your résumé is your credential. There is nothing you could learn at college that you haven’t already learned over the course of your career.

Also, make sure your references are willing to talk about your experience, highlighting your contributions over the years. Of course, your real challenge is putting yourself in a position to be able to make the case for your employability. You can highlight your experience in a cover letter and in an interview. But also rely on your network. Let people know you’re looking for senior positions at organizations who value experience and are willing to consider someone without a college degree. Good luck!

Task troubles

Q: Typically, I take something off my to-do list if I’ve done my part and any further steps are left in the hands of other people. This works well until someone drops the ball and those further steps aren’t done. A few times, I’ve been left to put out a fire because of an incomplete task that was no longer on my radar.

Do you have any suggestions for how I should keep track of all these things — or if I even should? Part of me thinks I should keep a running list to try to avoid disasters, but part of me thinks it’s not my problem and I can’t fathom how to keep track of all these items. — Lauren, Maine

A: I don’t know if you should keep track of other people’s responsibilities, but if you’re putting out fires, you probably have to, just to make your life easier. It’s not your problem when other people drop the ball, but it also kind of is.

There are all kinds of systems and software that can help you with project and task management. I personally use Todoist and Trello so my team and I can keep track of multiple timelines, tasks, who has ownership of those tasks and so on. For the most part, it works very well to be able to see what’s going on with each project.

Once you set up a system, make sure to familiarize everyone with responsibilities on how to use the system, so they have no excuse for not following through. I would also think about accountability. What are the consequences when someone doesn’t fulfill their responsibilities? How can you make it so that your colleagues have to clean up their own messes?