Being the boss lady.

Being the boss lady.

School started two weeks ago around here. Even though my kids aren’t starting until after Labor Day, we’re in transition mode, thinking through what we want our fall routines to look like.

We have a lot of pieces to put in place. My husband and I both work outside the home (though my hours are minimal at this point). We homeschool our kids, and manage their extracurriculars. My self-employed gig—as a writer and blogger—is begging for more time.

Right now, we’re thinking through what kind of schedule we’ll keep and what kind of help we’ll need. About two years ago, when Will went back to a more-or-less regular 8:00-5:00 job, we started hiring regular help for things like childcare, laundry, and homeschool assistance.

And I’m getting some help with the blog, too. Will has always helped with the back end; now I’m thinking through just how much photo processing and technical stuff I can outsource. Additionally, I’ve got a redesign in the works and bigger projects that could use a helping hand.

It’s become clear to me, as we think about hiring people for this season, that being the boss doesn’t come naturally to me. I’m not even good at being my own boss some days. (Honestly, I’m kind of hard to manage: I fly by the seat of my pants, dread decisions of any sort, and don’t cut myself enough slack.)

I’m not good at asking for what I want from people. I’m not even good at knowing what I want from them.

I suspect this has everything to do with personality: as a recovering people-pleaser and an enneagram 9, I don’t feel cut out to be the boss lady.

I read a book this week (that one of you recommended—thank you!) called Creative You: Using Your Personality Type to Thrive. It’s about bolstering your creativity by learning more about your personality type, but I found its insights helpful as I think through what kind of structure will best suit us in the coming year.

The book is centered around the Myers-Briggs personality types. I’m an INFP: the idealist, the healer, the muser.

I highlighted the heck out of Creative You, because the author nailed my type.

As an Intuitive (N), my strength lies in exploring possibilities and finding relationships between seemingly random things. I’m good at taking the long-range view; not so good at the details.

I’m an excellent starter and a horrible finisher. The authors put it well: NPs are “an endless lightning storm of ideas, but the bolts don’t often strike the ground.”

I can dream up 1000 ways to approach a problem, but am horrible at deciding on The One Way to move forward. And when I do decide, I do it slowly. I need lots of time to mull things over.

I seek harmony, dread controversy, and hate telling people what to do.

In short, I shouldn’t be anybody’s boss.

But I’m in a position where I need to be.

I knew all these things about myself, but seeing them in the book in black and white was so helpful, if more than a little sobering. I was reminded of why I struggle so much with being the boss lady—but why it’s so important that I do so. I need the help, especially from people who aren’t like me.

Reading the book, I was reminded of how much I’ve learned about managing myself, and others—even if I don’t always put it into practice.

As far as managing myself, I’ve learned that:

• I do well with schedules and routines, even though they don’t come easy.

• I need deadlines. I love deadlines, because they help me follow through.

• If I wait until I feel 100% sure before I make a decision, I’ll miss the opportunity to make it.

• All the good intentions in the world don’t get me anywhere unless I have a plan for following through.

• Even though I work for myself, I need grounded, detail-oriented people on my team—friends, employees, colleagues—to talk things through, help me figure out what I need, and keep me accountable.

As far as managing others, I’ve learned that:

• It’s important to ask for what I want from the people I’m managing. I’ve heard smart women leaders say this is often hard for women to do. It’s definitely hard for me.

• In order to ask for what I want, I have to figure out what I want, remembering that I’m not going to feel 100% sure about what that is. (See above.)

• I shouldn’t apologize for asking people to do their job. This is ridiculously hard for me. Like, I-should-talk-about-this-in-therapy hard.

• I need grounded, detail-oriented people on my team—designers, accountants, homework checkers—to notice the details, catch my mistakes, and help execute on the follow-through, whether that’s for a blog post or my daughter’s math homework.

(I’m very curious about what these lists look like for other personality types.)

In thinking through my conflicted feelings about being the boss, I’ve realized how many of us take on that role sometimes, even though we don’t think of ourselves as being such. I’d love to hear about your experiences with being the boss lady (or boss man, of course), and welcome any tips you have for being a better boss. 

P.S. 35 things I’ve learned in 35 years, and self-awareness makes everything better.

P.P.S. I wrote a book about personality! In Reading People: How Seeing the World through the Lens of Personality Changes Everything, I walk you through 7 different frameworks, explaining the basics in a way you can actually understand, sharing personal stories about how what I learned made a difference in my life, and showing you how it could make a difference in yours, as well.

Books mentioned in this post:

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46 comments

  1. I definitely am uncomfortable in boss mode. But I do quite well bossing myself, which is probably why I have trouble trying to tell other people what to do: because I assume they have as much self-command as I do. Or that they *should*. Ugh.

    So I get irritated with my kids when I have to tell them what I feel are obvious things. Or my husband. Because I keep thinking, “Why don’t you already know (as I do) that this is what you should do?”

    I need to get over that. 🙂

    • …. also, I score very high on the conscientiousness scale. The only other member of my family who does is my oldest son, so we understand what a curse it can be. Just the other day I told him such. To know what is the right thing to do and to usually be counted on to do it… ah, it’s a heavy burden. Because you want others to do the same!

  2. Jenn says:

    I can’t tell you what other personality types go thru, cause I’m the same as you. Thousands of great ideas without the fortitude to see them through. That is my biggest weakness. Accountability partners and deadlines are a must. Other wise I would never get anything done!

    I’m moving Creative You to the top of my reading list. Thanks

  3. Sara K. says:

    I need to read Creative You! I have always loved the study of personalities. It was my favorite psychology class I took in college, and I think I still have the textbook 🙂 What you described above about the Intuitive type sounds very much like me. I tend to look at some of those traits as flaws in myself so I would like to learn how to turn those into positives!

  4. Emily says:

    My reluctance to embrace being the boss I think has much to do with my age. I wonder with each passing year, though, whether I will ever feel like I have “arrived” (I doubt it) or have the confidence to say, “Okay, NOW I fully know what I am doing and should be in charge.”

    I try to remind myself what I do have that makes myself qualified. I may not have years of experience, but I do have degrees relevant for my job and formal training.

    Working under many different bosses (many of them female) has helped to me to appreciate there is no one way to be boss. Much of it is a style thing, and we each have different strengths and weaknesses. I am working more towards being more and more Emily than I am towards some abstract ideal of who a boss should be. Personality factors into this hugely, I believe–which is why I too love learning about myself, how I work, and what makes me tick.

  5. Kelsey says:

    Wow, I completely identify with all those things you listed! The last time I took a Myers Brigg test my result was ISTP, but the result is different every time. Probably because I can never make up my mind about anything. 🙂 I think it’s time I took it again.

  6. Jeannie says:

    Anne, I just took that book out of the library before going on vacation and brought it with me. The early chapters are really interesting and helpful; I’ve had to set the book aside for the time being, but I plan to read it more attentively and thoroughly in the coming days.

    • Anne says:

      I’d love to hear what you think. It’s not the best book I’ve read on personality, but I just really loved the way they phrased things about my own type.

  7. Christina says:

    Sing it, sister –

    “I shouldn’t apologize for asking people to do their job. This is ridiculously hard for me.”

    I can’t even begin to explain why this is true, but I feel this way EVERY time I hire someone to complete a task for me. I run my own business, and, like you, things are growing and begging for more attention, and I find myself outsourcing more and more. This is fine, in theory, but WHY oh WHY do I feel guilty when clarifying expectations, explaining tasks, etc.?! (cue desperation!)

    I hadn’t put this into words until I read it this morning. Thanks for the “ah-ha” moment (and now I want to find a therapist!). 🙂

  8. i’m an INFJ (at least last time when i took the test) and feel like i’m reading about myself here…wow! i’ll have to check this book out. managing people is something i’ve been thinking about lately as i have a new student worker starting in my area at the library, and i want to get things started off on the right foot with her. i’m a chronic apologizer, and am trying to get better at it, but i shouldn’t apologize for asking someone to do their job. it’s a disservice to us both!

  9. Jamie says:

    As an ISTJ who has been a manager professionally, the number one thing that comes to mind is to be honest, direct, and prompt about addressing it if there’s a problem. As awkward and agonizing as it feels at the time, it’s so much better for everyone in creating a positive and stable work situation.

    Also, just as a side thought, if you’re intentionally trying work with people with different perspectives (us crazy detail-oriented types), there’s an excellent chance that:
    (a) they actually really want to do whatever you hired them for; and
    (b) they are invested in (and rewarded by) doing it well.

    If that is the case, you asking them to do their job – with enough detail and feedback to do it well/better – is something they’re thankful for! Not sure if that helps at all, but thought it was worth throwing out there.

  10. Betsy says:

    “I’m not even good at being my own boss some days. (Honestly, I’m kind of hard to manage…” This made me laugh out loud, but it describes me exactly!)

    I didn’t know you worked outside the house in addition to all the other hats you wear. Is that also a creative-type job?

    Thanks for the book recommendation. It’s going on my list immediately!

    • Anne says:

      Not creative at all (well, most days). I work for a law firm. I keep scaling back my hours; at this point it’s very part time. I have a transition coming up in that regard and I’ll blog about it one of these days. 🙂

  11. Corby says:

    One thing I learned in the corporate world. I like being the worker bee. It’s okay not to want to be the boss.

  12. ailikate says:

    “If I wait until I feel 100% sure before I make a decision, I’ll miss the opportunity to make it.”
    This. There are several big ones looming and I really needed to hear this. (I’m on the line between INFP and INTP) Book requested.

  13. D says:

    One thing I do with the contracts I write for my office is that I tie a deliverable item to the payment we make for it. Even for hourly contracts–if we commission a software developer to help program something for us, he may get paid hourly, but we pay X amount for the delivered program, based on a reasonable estimate of the hours it should take.

    I am trying to move this concept to babysitters, which has been hard. Babysitting can be such an informal thing. A lot of our neighborhood teens are uncomfortable talking about how much money they want to earn for the job. I want to pay someone for playing with my kids, and maybe making them a pizza–not for texting on their phone while my kids watch a movie on a gorgeous day. I was able to make this work when we hired regular summer help to watch the kids. It turned out pretty good for our first stab at it.

    Good Luck!

  14. Ana says:

    YES! I also have trouble asking people to do what their job requires of them. I’m not forceful enough, too apologetic in my asking, and I take my anger (on the thing not being done) out on everyone EXCEPT the person who should be doing the job (i.e. my husband and other co-workers will hear me rant and rave, but then I tend to chicken out giving appropriate feedback to the employee). I have identified this as something I need to work on this year at work, but I can see how it is relevant in my personal life as well (with the kids’ daycare, babysitters, housecleaners).

  15. Kate says:

    Ooh, I need to read that book! I’m also an INFP and very uncomfortable in a boss role, especially as I’ve become so cynical about my job. Thanks for the recommendation and the wise words.

  16. Rebecca says:

    Thanks for sharing this. As a fellow 9 and INFP, I’m always looking for better ways to do just about everything. Ha! I often suffer from analysis paralysis as well. Best of luck!

  17. Megan says:

    I LOVE your blog so much! It’s as if you know the exact things I struggle with in my head, but I have no clue how to verbalize! When I had a certain job 5 years ago, I pretty much worked on my own, but within a large company. my boss begged me to become a supervisor and thought I was insane for not wanting to advance my career and finances! I could never put into words why I was so happy staying at my mediocre position ….but you just explained it perfectly….I should never be boss lady! I know I am quite capable…but the thought of having to tell other people what to do makes me want to run and hide under my bed!

  18. Karlyne says:

    There’s something I’ve always hated about being “the boss”. I don’t mind the facts of a job, the “Here’s your job description.” part. But I don’t like babysitting adults. And I think the reason why is that I hate “managing” people- I always feel as though I am manipulating them into a behavior that they should already have mastered! I much prefer to be the boss with no employees…

    But, teaching and training kids is high on my list of fun things to do; I think it’s important and a great use of my time. It’s a big difference for me, although it seems an odd distinction, doesn’t it?

  19. Hannah says:

    I am an INFJ and I think that sometimes it makes me a poorer homeschooler. Here’s why: I boss my own self and am very conscientious. So when my kids act childish or foolish and don’t do what they’re supposed to do, it’s easy for me to be outraged. I think, Why can’t they just know what they’re supposed to do and do it? I’m learning more about my personality and to rely on the Lord. So it’s slow-going, but we’re making progress, I think.

    • Anne says:

      I see what you mean, yikes! I hope having self-awareness on this helps you compensate in healthy ways—instead of pulling your hair out. 🙂

  20. Beth Anne says:

    LOVE this post and your insight into your personality, Anne! I have to say that as I was reading I kept thinking, “you need a Sarah!” I am you, and my sister is the steady, follow-through accountant. We work so well together in that way, and because we’re sisters, we can be brutally honest with each other when we need to be! I am really hoping that you find your “Sarah” soon. You’re exactly right in looking for others who are different from you – who complement what you bring to the table.

    I haven’t had to deal with being the boss lady in our current business, but at other jobs when I was training new employees, I would always give “correction” in the form of a compliment sandwich. “So, you’re doing an awesome job at being friendly and making the patients feel at ease, but I really need you to do x, y, z, this way. But keep up the good work on W.” I’m not sure if you have the ability to interact in person or over Skype, but a smile and a friendly voice can go a long way when it comes to offering feedback. (I know… it sounds really cheesy!) I always go back to Dale Carnegie’s How to Win Friends and Influence People and remember that kindness and respect can go such a long way and that, to be honest, the more someone likes and respects you, the more they want to do their very best work for you.

    I can’t picture anyone not liking or respecting you, so I think you already win on that one!

    Best wishes as you continue to work out being the Boss Lady and I can’t wait to see what big projects are coming up next!

    • Beth Anne says:

      P.S. We just skyped with someone today who said that for the VA’s they use on O-desk, they create screen-shot videos for them so that when they have questions or forget, they just refer back to the videos and they’re good to go!

  21. Anne says:

    I can relate to this!

    On the flip side, I just hired a house cleaner, and she was very kindly emphatic about telling her if there was something I was concerned about/something else I wanted cleaned/etc. She said she would rather know what I wanted done than not know, which could allow for tension to build up and spill over. It sounded like she spoke from experience, and I appreciated where she was coming from because I really like to understand people’s expectations of me (in a healthy way, if you know what I mean).

  22. Ashlie says:

    I needed this today. I teach elementary school and our year started yesterday. I’m in the very awkward position of needing to manage/instruct another adult who technically doesn’t work under me but is in my classroom. I really resent needing to confront this person about certain issues when I just want to focus on the most important part of my job, which is teaching the kids. I’m trying to find my voice and speak even when it’s shaking. It’s nice to know that other people who are successful and strong adults still struggle with this.

  23. Marcy says:

    What about this list for other INFPs? Because there’s variation even within types.

    I’m an INFP, and I identify with most of this, but I keep coming back to your comments about not being good at the details and shaking my head. I don’t know if it’s because the author of Creative You only nailed your particular version of this type, or because of course you’re presenting the material as it specifically applies to you, or if… it’s something else going on here?

    I think the thing with INFPs is that we’re good at the details we *really care about.* Not only that, but everyone tends to minimize their strengths, so when we *are* good at the details we don’t see it that way, we just see it as kind of an “everyone can do that, right?”

    Take reading comprehension. I bet you’re AWESOME at the details of reading comprehension! And the minute details involved in reading another person, even though much of it is intuitive and unconscious! Again, we minimize our strengths. Maybe especially when they’re intuitive, I guess.

    I’m good at spelling details (among other things), and if you’re not, that’s not actually because you aren’t detail-oriented, per se. I don’t think. (Though, unless your husband or someone is helping you with that? Pretty sure you’re awesome at spelling and grammar details, because as far as I can remember your posts are always impeccable, and I think I would’ve noticed if they weren’t.)

    We’re… not always as good at the *practical* details, true. That’s more of an S thing. But when the details have anything to do with the ideals in our heads and what we see as meaningful and true and beautiful, watch out! 🙂

    I mean, I hear you on the “I’m good at taking the long-range view; not so good at the details.” I just don’t know if that’s exactly the two things that are opposed here. “I can dream up 1000 ways to approach a problem, but am horrible at deciding on The One Way to move forward.” That sounds like TOO MANY details, to me! 🙂 The difference between Js and Ps isn’t that Js are good at detail and organization and Ps aren’t, even though it can look that way on the surface. The difference is that Js are good at action and principles where Ps are good at data and observation. ( http://www.alittlebitofpersonality.com/2013/10/the-cognition-process-in-stick-figures.html ) We get SO hung up on all the details and all the possibilities, that it’s really hard to decide and act on them all.

    So… I guess it’s really just a wording issue I’m quibbling with? But it’s a detail that’s important to me, dang it! 😀

    Um. Sorry for this novel of a comment! >_> Please don’t take it as criticism, I hate conflict too, that’s not what I’m trying to do here! ::embarrassed face::

    • Anne says:

      Your last line made me laugh!

      Thanks for the prompting to think about this more. So let’s see: you’re right, I’m a good speller and a certified grammar geek. (I never thought about that as a personality thing; do you think it might be?)

      Third paragraph: very interesting.

      Maybe what I should say is I can be detail-oriented when I need to be. But I really, really hate it, and so I lose patience, and just move on to the next thing. So I can handle details, but I would really rather not. And I’m often oblivious to the practical details because I’m off in dream land….

      And this is me to a “t”: “We get SO hung up on all the details and all the possibilities, that it’s really hard to decide and act on them all.”

      • Marcy says:

        Oh good! 🙂 (I say, belatedly…)

        And you’re welcome, no problem! Yes, I think it might be a little bit. A personality thing, that is. I mean, I don’t think personality types actually *determine* certain interests or skills, but it seems like certain ones do tend to fit with certain types. Seems like I’ve seen a lot of INFPs recently who are either good writers or good graphic designers. Or both, sometimes. Those are the kinds of details we tend to love! Obviously being a good writer doesn’t necessarily mean good spelling and grammar, but I think INFP writers are more likely to care about it than some other writers.

        But yeah, practical details, especially the kind where you have to DECIDE BETWEEN THEM? And maybe tell people what to do?! UGH! 😀

        “And I’m often oblivious to the practical details because I’m off in dream land….” Yeah, I’d much prefer to think about the details of a dream world, too. 😀 And even then, not like… the physical details for the setting of a novel. The characters and motivations though, YESSS. 😀

        Hmm, just went on the Epic Thread on Facebook about personality types and cognition steps, looking for something that related to this, and found this other thing instead. Understanding, first, that the theory this Thread is based on adds one new component to the T/F spectrum, compared to what most stuff talks about with those — T is about use of things, F about meaning. So one person (an INTP) says, “And of course INFPs should trust that they can look at absolutely anything – particularly any *concept* – and instinctively understand what it means. And also, remember that most people can’t rely on that – it’s actually a magical superpower, or at least seems that way from here.”

        Yup, good at meaning details.

        Oh, maybe this was the other thing. We were talking about nonverbal thinking, and then how INFPs may think nonverbally in their first cognitive step, introverted Feeling, and then translate into words for people in the next step, extroverted iNtuition. And then someone said,

        “I am constantly trying to translate the feelingcolorpicturescenenuancecontext threads in my head (with some words or phrases mixed in, especially if I am rehearsing speaking) – into stumbling, awkward sentences.

        “It always feels like a really inadequate approximation, and like… single petals pulled from a vast field (with light and temperature and wind etc), and then laying those petals out on a blank white surface, and hoping that someone might be able to guess at what kind of place they came from… or something like that.”

        And then someone else, talking from there about why maybe INFPs are often good writers: “I’m leaning towards us being less likely than most to settle for the first words that we think of, more likely to keep trying to craft something to hit that elusive mark?”

        And then later after *that*: “If Ne is largely about making connections, then it would be about making connections between our feelings – including our feelings of what words mean! – so those of us INFPs who are extra fond of thinking of the precise connotations of words would indeed connect words to our other thoughts rapidly and naturally!

        “:takes step back to try to figure out whether Ne = connections is really an appropriate simplification and whether that fits with the “pinging” description:”

        So anyway. That got a little beyond just talking about INFPs and details, in the context you were talking about, but it was fun. 🙂 And does relate back to spelling and grammar being a bit of a personality thing maybe, too. So it is relevant, this isn’t too long at all! Yeah! 🙂

  24. According to the personality profile tests, I’m an INTJ. I don’t like any situation long term where I’m not in charge, but since I prefer not to constantly be around other people, this points toward the smaller scale entrepreneurial life, vs. trying to battle up a corporate ladder.

  25. Ashleigh Anne Payne says:

    As a fellow NP (E/INFP) and a doctor (I AM the boss lady!), I have to laugh. I too struggle with telling other people what to do and apologizing when I ask them to do something I sense they won’t like. And then I feel guilty about it for a bit. But I have to work on turning up my J characteristics to get organized, and letting others help me with deadlines and prioritizing what needs to get done right away. AS part of a physician leadership retreat when I was in training, we went thru the Meyers Briggs and dissected how our types affected our relationships with our patients, colleagues, and others, and this has tremendously helped me as I have grown in my career and life. Thanks for the post!

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