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Work Advice on Avoiding Early Meetings and Bad Bosses

Send questions about the office, money, careers and work-life balance to Include your name and location, or a request to remain anonymous. Letters may be edited.

I’m a white woman in middle management at a somewhat stodgy nonprofit that has been grappling with doing more to advance racial equity. I’m hiring for a relatively junior position and have put a fair amount of work into recruiting a diverse pool of candidates. It worked! The unquestionably best person for the job is a Black woman.

I’m worried that if she takes the job she’ll grow frustrated at our still not very “woke” culture and the pace of change. I know from her social media presence that she’s quite outspoken on issues of race, which I think would be great for our organization — but potentially really draining for her.

Second, I’ve struggled with the Black women I’ve collaborated closely with in the past. (I regret to say I thought of them as “difficult.”) I know now that this is a function of my own internalized racism and cultural expectations, but am unsure about what I should do differently to become a better manager and co-worker — to this woman and all the people of color I work with. How can I help her feel supported and help her to thrive, even as I know both the organization and I have lots more to do?

— Anonymous

Why do you think this capable, talented woman needs you to rescue her from a position for which she willingly applied? It’s condescending to assume she won’t be able to handle your office culture. I can assure you there is nothing about your workplace she hasn’t already experienced elsewhere. Your anxieties are … misplaced. As you note, she’s the best woman for the job. She’s going to be fine, or not, but she’s an adult. She doesn’t need you to protect her from reality.

You should support her the way you would any new co-worker. Make sure she has the necessary tools to do well in your organization. Set her up for success, with clearly defined expectations. Provide mentorship. Don’t tokenize her. She is a professional, not a mascot.

Ultimately, I think you’re worried about the discomfort and, perhaps, guilt you will feel when she has to work and, ideally, thrive in your problematic workplace. The best thing you and your colleagues can do is to create a supportive environment for all employees, one that is focused on inclusion and equity for all. That means thinking not only about recruitment, but retention. What will it take to evolve your workplace from where it is now to where it should be? What will it take for people of color to want to work at your organization and have room for advancement? You mention that your organization changes slowly, but that is not immutable unless you allow it to be.

In terms of your interpersonal issues with Black women: You’re going to have to do the work of figuring out why you’ve had contentious relationships with the people you’ve worked with and what you can do to avoid that in the future. It will require rigorous self-reflection and being mindful of how you perceive and treat the Black women you work with. It is difficult to say what, specifically, you should do differently because I’m not entirely clear on what you’ve done in the past. The short answer is to do the opposite of what you did previously and to hold yourself accountable.

My department works remotely, and we each choose our set hours, so long as they are within an hour or so of 8 a.m. to 5 p.m. My colleague has chosen 8 to 5. However, when I try to schedule an 8 a.m. meeting, he says it’s too early, and a little later is OK if I don’t mind him eating breakfast. He says mornings are hard because of his morning workouts. He suggests meeting at 9 a.m. Am I old-fashioned, thinking colleagues should be ready to work during their work day, unless their calendar is marked busy or out of the office?

— Anonymous

No one should ever schedule an 8 a.m. meeting. That is, indeed, far too early. People need time to ease into the workday. Now, your colleague probably shouldn’t have shared that he needs his mornings for his workouts but if we have learned anything from the pandemic and the ways workplace culture is evolving, it’s that we are more than our jobs.

Most of us can handle our work responsibilities well and be human, making time during the workday for family, for fitness or for personal interests. Stop micromanaging your colleague. His schedule is not your concern. Surely you can be a bit more flexible with setting meetings. It sounds like he is willing to do the same. It’s all going to be OK.

I am an English teacher in a public school. Post-pandemic, many teachers here are asking if this is a viable profession anymore. We had three catastrophic hurricanes during the pandemic to make home life and school life even more difficult. Before the pandemic, our state was consistently ranked among the worst for children’s educational outcomes as well as for teachers’ salaries and working conditions. I work at a public school that was once considered a decent place to work, but pandemic upheavals brought us a new principal.

He’s just so bad. Autocratic, micromanaging, always right, insecure and inexperienced bad. Two teachers retiring in the middle of the year and one straight-up quitting in September bad.

I’m guessing my work friend won’t let me do something as passive-aggressive and self-destructive as anonymously give him a book on leadership for the holidays. He’d probably guess it was from me, and I doubt he even reads books. He’s an anti-vaxxer who exposed staff to Covid-19 and lied about it, so I’m pretty sure learning from experts is not his jam.

But for every worker who has this secret fantasy (it can’t just be me!), can you share some favorite books about leadership? If just one boss finds a new idea under their tree — if it could lead to creating positive work spaces, treating workers with respect and sharing authority and decision-making — it would be worth a try, right?

— Anonymous

I’m sorry to hear about your horrible boss. We’ve all had one and it’s the worst, particularly when you have few employment options. I’m a big believer in the power of reading, but there are some people who are so maladjusted that not even great literature can help them. That said, while I am not at all familiar with conventional business books about leadership, I do have some unconventional suggestions that will serve anyone well.

My suggested reading includes: “The Fire Next Time” by James Baldwin; “Notes from No Man’s Land” by Eula Biss; “The Empathy Exams” by Leslie Jamison; “All About Love” by bell hooks; “Odes to Common Things” by Pablo Neruda; “Thick” by Tressie McMillan Cottom; “Voyage of the Sable Venus” by Robin Coste Lewis; and “Borderlands/La Frontera” by Gloria Anzaldúa. These are books that have expanded my understanding of the world in profound ways, and I firmly believe that kind of expansion is what empowers people to be better in all ways.

I landed what could possibly be my dream job as an engineer working from home. I love the work and my manager is a good guy, but I have a couple problems. He’s not always very specific about what information he wants. He will say something like “what’s the update with X-manufacturing site?” I am not sure what kind of information he’s asking for, though I think in his mind he knows what he wants.

Second, I don’t always understand him very well. He is from India originally and has a really strong accent, and following him gets more difficult the faster he speaks. How do I navigate this without seeming either incompetent or racist?

— Anonymous, Mich.

Congratulations on landing your dream job! When your manager is overly vague in his requests, simply ask for clarification with specific questions that will, hopefully, elicit the information you need. I imagine that if you do this enough, he will begin to provide more precision in his directives.

In terms of understanding, you have to listen actively and carefully but you can, again, ask for clarification, with directed questions. Taking notes also helps so you have a written record of what you do understand. You can repeat back what you’ve heard so that your manager can confirm that you’ve understood him or amend what you’ve repeated as needed. I understand your concerns but it is not incompetent to seek clarification, and it is not racist to need some time to acclimate to an unfamiliar accent.

Roxane Gay is the author, most recently, of “Hunger” and a contributing opinion writer. Write to her at

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