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 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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Executive Presence for Women Leaders

Executive Presence and How to Get It (Or Fake It) | CorporetteHow would you define “executive presence,” particularly for women? Have you worked to build your executive presence? What are your best executive presence tips? Here are some qualities of women with executive presence that Corporette readers have mentioned during conversations that have taken place in the comments:

  • having a “cool, calm, and commanding” presence
  • being a skilled public speaker
  • appearing put-together (clothes fit well, hair is neatly styled, etc.)
  • seeming “knowledgeable but not a know-it-all”
  • staying cool in a crisis
  • showing confidence
  • having an attitude of “the buck stops with me”

Earlier this year, we discussed new research that showed that looking “put-together” and exhibiting “good grooming” can boost women’s salaries (even more so than being considered attractive), and a couple of years ago we talked about a study that stated wearing more makeup makes women look more competent. Today we’ll go beyond that to take a closer look at executive presence and what it means for women leaders at work. (In the past, we’ve shared posts on imposter syndrome, the difference between confidence and arrogancebeing taken seriously when you look young, and books and resources to help you become a leader and a better manager. We’ve also discussed the book The Confidence Code.)  

According to research from Sylvia Ann Hewlett, the founder and CEO of the Center for Talent Innovation, executive presence is composed of “how you act (otherwise known as gravitas, the most important quality), how you communicate, and how you look.” A 2013 Business Insider article describes it with 7 Cs: composure, connection, charisma, confidence, credibility, clarity, and conciseness. Hewlett (whose book we link to below) says that executive presence “accounts for as much as 28 percent of a woman’s success” (!).

These definitions sound straightforward enough, but cultivating executive presence requires women to walk a very fine line, thanks to the maddening contradictory messages we receive about how to act at work. You know: If you don’t ask for a raise, you’re blamed for the gender wage gap, but if you ask for a raise, you’re viewed as “greedy, demanding or just not very nice.” If you act with confidence and strength, you’re “too aggressive” or “a bitch”; if you don’t appear assertive enough, your behavior is interpreted as weakness. (As social psychologist Dr. Heidi Grant Halvorson puts it, the typical dichotomy for women is “competent and cold — that’s the bitch — or warm and incompetent — the doormat who no one takes seriously.”) Of course, this predicament extends to physical appearances, too; research shows that women with “unkempt nails” lose executive-presence points but that those with “overly done” nails are also viewed negatively. Faced with this “damned if you do, damned if you don’t” minefield, some women are paying $2,000 to $5,000 to attend special workshops on executive presence.

Putting all of that aside for a moment, here are a few concrete tips on exhibiting executive presence at work:

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Should Your Work Friends Include Your Assistant?

Should Your Work Friends Include Your Assistant? Do you socialize with your assistant or secretary? Do you consider him or her to be among your work friends? Or do you keep your relationship with staffers friendly but avoid turning it into an actual friendship? If the relationship has swung too far towards “friendship,” how do you bring it back to “collegial”? Reader N wonders…

How do you reformalize a working relationship with your secretary? I work in law and I have been cognizant about not talking down to my secretary, who is also a young female. I have noticed recently she has interpreted this to mean we are “friends,” which is fine. Recently, she has seemed to step up her attitude, and does not make requests of me politely. I don’t want my niceness mistaken for passiveness or that she does not need to respect me the way she does others who were not as nice.

Hmmmn… tough question, Reader N! With Administrative Professionals Day observed this Wednesday it’s a good time to revisit the issue. In general, I think it’s fine to be friendly with staffers and other subordinates, but the closer the relationship gets, the more complicated it gets. One reader wrote to us a while ago where she was the only female lawyer, and the group of female secretaries was being very welcoming — in that case, where she already had an uphill battle to be/feel accepted with the other lawyers, I think she was right to keep her distance.  Outside of that circumstance, friendship with subordinates can also be complicated because if the assistant screws up, needs redirection or criticism, or just generally needs firmer deadlines and oversight, all of that is easier to do with an arm’s length, professional relationship, without adding more intense emotions of doubt and betrayal (“but I thought we were friends” / “why is my friend betraying me”). (We had a great discussion on whether a boss should be respected vs. liked just last year.)

As to reader N’s question, how can you bring an office friendship with an assistant back to a collegial relationship? I’m curious to hear what the readers say here, but I think the answer is “very carefully.” My $.02 tips:

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How to Delegate: How to Start Delegating Work To Your Assistant

how to delegateLadies: let’s talk about the art of delegating work to your secretary, assistant, or another third party. More and more I feel like knowing how to delegate is key to success in work and life — you can’t micromanage everything. Besides, if you bill by the hour, remember that your client doesn’t want to pay, say, $500 an hour for someone to photocopy something! So: what tasks do you delegate? How did you learn how to delegate, and what are your best tips for women thinking about what they should assign to others? (Previously: we’ve talked about how to show your appreciation to a great assistant, and when to fire a bad assistant, as well as apps like Fiverr that let you delegate some things to third parties.)

For my $.02, for working women with an assistant, I’d seriously look at delegating tasks like:

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The Bad Assistant: When To Switch, When to Fire

When to Fire a Bad Assistant | CorporetteWhat should you do when you’re stuck with a bad assistant, secretary or subordinate — and your assistant doesn’t assist? When is just time to switch assistants, or even fire the person? Reader K wonders:

We are a small (12 people) conservative professional investment firm serving high net worth clients. I recently moved from front office to portfolio assistant. The young woman who replaced me thinks she is doing a great job even though she was told by management that she needs to work on skills. She says she has a photographic memory and doesn’t take notes on anything I try to explain. I prepared “how to'” notes for her, but have had to print them for her repeatedly. She makes “to do” lists but rarely does items on the list. When I try to explain something, she has gotten up and walked off or continues to stare at computer screen. Her history shows that she is constantly on the Internet. I was told to monitor these things, but feel uncomfortable. I am working an extra 15 hours a week trying to do my new job and picking up slack on hers. Needless to say, I am stressed. Management is aware of issues, but not that I am really stressed out over this. How should I handle this?

Wow — I’m sorry, K, that sounds like it really stinks. You say she’s been warned; you say management is already aware of these issues. That all leads me to the following advice:

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