The upside of being a hard boss

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As the Empire has grown from just me and a dev, to just me and the dev and an intern, to just me and the dev and an intern and another editor, to just me and several editors and a couple devs and a community manager and a sales rep and a freelance designer and the server guy who helps out, it makes sense that I’d be getting a super rough crash-course in people-management.

I spent over a decade toiling in the corporate marketing world before breaking out into small business ownership, but none of my gigs involved managing staff. I was usually a creative contributor, meaning I was focused on cranking out STUFF, not managing people. This means everything I’ve learned about management has been via trial and error, stumbling around and fucking up and trying to do better.

The biggest lesson I’ve learned is that, as a manager, I don’t do anyone any favors by not being a tough boss. I’m not a MEAN boss — I like to think the worst my staffers put up with is low-grade sexual harassment as the result of my foul sense of humor (this seems to be relatively consensual, so I don’t think it counts as true harassment, but you should ask my editors/mods if any of them are crying into their pillows at night).

So while I’m not a MEAN boss, I think most of my staffers will tell you that I am not an easy boss. My standards are probably higher than they should be given what I can pay, I’m online all the time and expect even my part-time staffers to be available all the time too, and when something isn’t done well… I’ve learned to be pretty blunt about my disappointment.

Of course my immediate goal as a manager is to get good results out of people, but my secondary goal is to give my staff bad-ass job skills that hopefully advances their careers in directions they want to go. Both these goals necessitate not dancing around it when someone’s failing. Not only do I do my own business goals a disservice when I put up with poor performance, but I see it as doing the staffer’s career development a disservice.

As a touchy-feely West Coaster, it’s difficult for me to confront people with negative feedback — heck, even giving constructive, pro-active feedback feels like I’m being “mean” sometimes. But I try to always give a clear idea of what and how the result could be improved, and I try to couch most negative feedback in the context of what’s working — this part is great, but this part is falling down. I really appreciated when you did this, but when you did that, I felt like you weren’t quite measuring up.

I used to not be this way, but sadly I learned the hard way that padding my feedback based on staffer’s feelings was a quick road to ruin. The first time I had to let someone go, I got feedback about a lot of confusion. I hadn’t been clear enough each time I was disappointed, so when I finally said, “Enough,” it felt like it came out of the blue.

Now I try to be very VERY clear every step of the way when I feel things sliding off the rails. It’s never easy letting someone go (I lose sleep and end up crying almost every time), but as I’ve learned to be more straightforward and honest with my negative/constructive feedback, it’s resulted in less confusion from staffers being let go. The last time I had to let a staffer go, the response was basically I get it. I wish I didn’t because then I could be all pissed off, but I understand completely. It still broke my heart, but at least there weren’t any confusions about what was happening or why.

I guess the moral of the story is that being a hard boss feels difficult and mean in the moment, but ultimately serves everyone better in the long run. Me and my delicate West Coastiness are still getting used to the idea.

Comments on The upside of being a hard boss

  1. You’re right – being a softy doesn’t do anyone favors. That’s not to say a hard boss is a jerk about everything, just that the hard boss knows what they want and how they want it, and will communicate that to employees. Employees working under hard bosses (ok, stop chortling about all the dirty innuendos that can be made here) are rewarded with a real sense of accomplishment when they do well and the boss compliments their work – they know it’s the truth, and not just padding. Also, hard bosses (heh) are easier to work for because they can earn employees’ respect. I’ve worked for total pushovers and it was awful. My productivity suffered merely because it COULD, and the boss never batted an eye or inspired me in any way to do better. Why bother putting in 50 hour work weeks, when I’d get the same reaction/reward as when I worked a 25 hour week? Why spend 10 hours writing copy when a 2-hour slapdash job was satisfactory? When I finally got fed up and quit that job to move to Philly I swore to myself that if I would never again work in any capacity for a person who didn’t deserve my respect. Give me a hard boss any day!

    • And a big +1 to what Kissa said–I’ve found bosses who are interested in investing in my skillset and career *and* expect top-notch product get the best work I can do. The ones who pay lip service to giving me new things to think about, to stretching my limits, and to keeping me busy tend to get lip service back.

      …And this thread just got 100% more innuendo’d.

  2. In California, it doesn’t count as sexual harassment until you ask the person bothering you to stop, and they continue.

    And I like to think the Empire fosters an environment of beneficial, mutually assured lechery, not sexual harassment. 😉

  3. I’m totally with Sarah. It’s beneficial, mutually assured lechery. 🙂

    Honestly, I don’t think you’re a “hard boss” so much as an “involved boss.” Like Kissa and Sarah, I appreciate having a boss who has expectations of me. If my grad school professors expected me to up my game, then why shouldn’t someone who actually pays me? To be honest, it is a level of respect. If the boss respects their employees enough to be aware of the work they’re doing and the work they should be doing, that says a lot. If you ever work at a job where your boss doesn’t really seem to invest any effort in you and yet expects you to be working your behind off, you will quickly see motivation fail. I watched my direct boss quit after bad treatment that included a lack of work put into addressing issues or dealing with them and then an ambush at a performance review that focused on the negatives but didn’t give ANY recognition of the positives.

    You may have high expectations, but you also give a lot back to your staff. Not just in “thank you”s but also in actual opportunities, feedback, growth and commitment. You also encourage ROWE. I am all for working smarter, not harder, and your recognizing that your employees’ time is valuable not just at an hourly rate is impressive.

  4. Thanks so much for this Ariel. I’m another one who cries herself to sleep after giving tough feedback or letting someone go. Just can’t help it and am always conflicted between feeling like a lame-o because I can’t hold it together vs. feeling like a jerk b/c it happened at all. So glad to know I’m not a party of one in that respect and that maybe it’s a normal thing!

    Am totally lapping up everything on OBE!

  5. Struggling with this myself right now! Thank you for your perspective. I’ve been tip-toeing around some issues recently and this post couldn’t have come at a better time.

  6. It’s *tough* being a boss with a staff to manage. It’s particularly hard when your staff is comprised of your peers (as is the case with me) — you don’t want to be the bossy-pants mean person, but if you have certain standards (and have to report to your own higher up about them yourself) it can get a little rough because sometimes, it seems as though there’s no way to frame things in a positive consider-this-a-learning-experience way without either seeming like an ass (because they’re your peers, not whippersnappers or something), or corny.

    Sometimes, you just have to say it straight to people, even if its wildly, wildly, wildly uncomfortable. I remember the first “This cannot happen again. Ever. Totally unacceptable” conversation — I felt *awful* but… was the job that was done. And it sucks.

    I guess the thing is…you’re right. Padding sometimes just doesn’t cut it. That’s not to say I’m pro-mean-ness, but I’m pro-honesty.

  7. I also have pretty much taught myself how to manage people – my own boss has been very supportive on the one hand, but he also is largely absent, so I don’t get a lot of face-time and he no longer knows our staff and our shop with the same intimacy that I do.

    After learning my lessons and self-correcting from the “soft” boss I previously was I sometimes feel like now I swing too far in the other direction. I feel like I still haven’t quite hit the right balance between the two, but it’s something I am working on, and I try to go into every staff interaction really consciously aware of it.

    I’m a much better, more capable boss now than I was when I started managing over 2 years ago – but it’s an ongoing process, and whenever I make a mistake I try not to beat myself up about it, but rather to just learn from it and move forward.

  8. I’m currently dealing with a boss who knows what she wants but doesn’t know how to communicate it … leading to a silly amount of passive aggression. And I’m not really sure how to deal with it, being the person she’s paying and all.

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