Advice on Being a Boss

Getting to the C-suite isn't always as easy as it seems -- being a boss can be trying in new and challenging ways. Whether you need some help getting to be a boss, or now you're a boss and need advice on things like delegating and managing subordinates -- we've got you covered.

How to Delegate to Subordinates

What are your best tips for a new mid-level manager for how to delegate to subordinates, readers? We’ve had a lot of conversations about how to be a boss, whether you should aim to be liked or respected as a boss, how to delegate work to your assistant, and we’ve also rounded up general reading for leadership resources for women — but it’s been a while. So let’s discuss how to delegate to subordinates. Here’s Reader C’s question:

I have a request that I don’t think has been directly addressed in a post. I’m a mid-level Big Law associate, and I was wondering if you (and the hive) had some general advice for adjusting to the newer role of delegating to junior associates. I’m more friendly and generally willing to walk newbies through concepts, but I think I end up getting taken advantage of and not as respected as the more standoffish associates. How do I strike a balance?

Great question. A few easy tips for how to delegate to subordinates:

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How to Keep Track of Work To-Dos

how to keep track of work to-dosHow do you keep track of different task items at work, readers? What are your best tips for how to keep track of work to-dos? Reader E wonders…

I would love a post on how people keep track of work to-dos. Do people write down their assignments on their calendars, keep a paper to do list? Some other system?

Great question, E! We’ve talked about different tools for time management, how to organize your office, as well as how to choose a great planner, and how to find a system like Getting Things Done, but I don’t think we’ve talked about how to keep track of different work to-dos. My own system is kind of simple (she said, preparing multiple bullet points) — OK, it’s not terribly simple, but it KIND of works for me. I could definitely improve, though, so I’m curious to hear what works for you guys!

Here’s the best ways I’ve found to keep track of work to-dos (and to-dos in general):

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The Best Online Women’s Management Training

online women's management trainingManaging people is hard. And managing people as a woman brings its own complications and considerations. Management and leadership training specifically designed for women can help, but if traditional in-person training isn’t an option for you, there’s plenty of online women’s management training out there, and that’s what Reader K is looking for. She asks:

Do you have any suggestions for online leadership/managerial training programs for women (or anyone really)? I am a government lawyer stepping into a managerial position and there is no formal training beyond my past experience watching my supervisors. I would like to take a more proactive step toward developing better managerial and leadership skills, but don’t know where to start. Thanks!

Great question, K! It’s been a couple of years since we talked about resources for becoming a better manager, so this is a great time for an update. (We’ve also discussed online classes for working women, executive presence for women leadersdressing like a managerimposter syndromedelegating work, and whether you should be friends with staffers.)

Here’s our list of online women’s management training (plus some general training for everyone):

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What to Get Your Assistant for Administrative Professionals’ Day

what to get your assistant for administrative assistants' day 2017PSA: Administrative Professionals’ Day is April 26, 2017 — what are you getting your assistant? 

In the past, we’ve taken polls on administrative professionals’ day gifts before, talked about how and what to delegate to your assistant, and swapped stories of amazing assistants — our roundup of gifts for your assistant (or how to buy jewelry for your assistant) may also be of help to you.  Comments on this thread had some great ideas for what to get male assistants.

If time allows this year, and your assistant is always freezing, you may want to consider a gift from Barefoot Dreams — this poncho avoids the “will it fit” question, and allows easy typing and more.  It’s $88 at Nordstrom.

Of course, you can always go with my friend’s system of flowers and cash — as she explained it, she got the floweres so everyone in the office knows you appreciate your assistant, and cash to keep the assistant happy.

Ladies, let’s talk: do you work with an administrative professional? Are you getting him or her a gift this year? (Does anyone have any good tips on how to avoid the “office housework” issue of the junior woman often being the one saddled with organizing a group gift to a shared assistant?)

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How to Use a Personal Assistant

Have you ever wished you could offload some of your life to someone else, whether it’s household chores, online research, or other drudgery, but have been unsure how to start? We recently got a reader question wondering how to use a personal assistant (and how to find a good personal assistant!), so let’s discuss. Here’s the question from Reader S:

Life and work are busy and I find it difficult to “get it all done.” I hear it’s possible to hire a personal assistant whom you can ask to research/compare homeowners insurance options, be there when the cable guy comes to install, so on. I found a blog that makes a compelling argument that this is not only a time AND money saver, but it doesn’t tell me HOW to find an experienced PA. Plus, how do you learn to delegate in a way that doesn’t take more time than just doing it yourself? Thanks!

GREAT question, S — so let’s discuss. (Pictured: Daddy Warbucks’ assistant extraordinaire, Grace Farrell, getting it all done in one of my favorite childhood movies, Annie.) We’ve talked about what to delegate to an assistant before, as well as talked about the kinds of things you can outsource to a virtual assistant through Fiverr or a U.S.-based virtual assistant service like Fancy Hands or Task Bullet — over at CorporetteMoms we also talked a bit about working with a personal assistant (in a “how to throw money at the work/life balance problem” kind of discussion). If you’re leaning towards trying a virtual assistant, you may also want to read this classic Esquire piece (reprinted in The Four Hour Workweek and now on Tim Ferriss’ site); this post on how to hire a virtual assistant also looks great.

But sometimes, virtual help just isn’t enough — so let’s discuss how to use an in-person personal assistant. A friend of mine, C, actually used to be a personal assistant to a wealthy businessman, so I reached out to her to ask her thoughts on both HOW to find a personal assistant, and how to USE a personal assistant.

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Help! My Assistant Talks Too Much

Help! My Assistant Talks Too Much!We’ve talked about the chatty boss before, but Reader N has a slightly different question: how to deal when your assistant talks too much? Reader N wonders what she can say to discourage her chatty assistant:

What are some ways to end a conversation with people at work that work for you? I have a new assistant, who is fantastic at the job! But she is VERY long winded for the smallest things (e..g, dropping off a file) & ends up on very long tangents completely unrelated to work. I understand that part of her need to chat with me / be friendly with me has to do with me being the boss,but need to be able to get work done during the day. I want to keep things friendly as she is helpful.

We haven’t talked about this problem in far too long — I still remember a fellow lawyer who used to “pop in” my office for what became two hour gabfests in the middle of the day. (Funnily enough I haven’t heard from her since we stopped working together.) Here, the added dynamic of the chatty coworker being your subordinate makes things a bit more complicated from an etiquette standpoint, but not unworkable.  Obviously, you can just tell her sternly to “please let me do my work” or actually sit her down for some bigger conversation about her talkativeness being disruptive — and because you’re the boss, the direct approach is absolutely fine. Readers in our discussion of chatty coworkers suggested saying things such as “hey, now isn’t a good time to chat, but I’ll stop by later” — but if you don’t actually ever want to hear her 45 minute theory about Westworld, that may not work either. (Or, Westworld aside, maybe you just prefer to keep a healthy distance and not be friends with your subordinates.)  But: of course you still want to be friendly and have a good working relationship.  This may take us back to our discussion of whether women bosses should aim for being liked or respected, but here are my top tips for solving the problem of when an assistant talks too much in a non-direct, friendly way:

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