I will go down with this ship
May 28, 2014 10:40 PM   Subscribe

How does an insecure person become a good manager? Is it possible? -

Hi MeFi,

So, in some kind of insane stroke of luck, I got a new job and a promotion at a startup a few months ago. It's in an industry I love, with lots more pay and autonomy (though the position itself is more of a "I have experience in this area but it isn't my dream job" sort of thing. More on that later.)

I love the folks at my startup, although it's very, very grassroots at this stage still and I'm basically building a department from scratch. I recently asked for help in the form of a new employee, without realizing that, well, I'd have to manage this person.

She's been here for about a month, and I am totally SHITTING THE BED on this. I'm in my mid-twenties and have never managed another person before (I still have trouble getting to work on time without stains on my shirt). How does one...go about delegating and explaining things and challenging and motivating people? For example, I recently realized that I'd been hoarding some work unnecessarily because I didn't want to have to go through the motions of delegating and monitoring. This is bad. She mentioned to me today that she's not sure what's required of her and that she wants to feel like she's needed/helping make the company better. (All good things, yes? I feel horrible for not being able to facilitate this!)

I'm in charge of department strategy, and I feel like I'm always behind on what's new/current in our industry. I need to make time to research new ideas and always present new solutions to things to our boss. How do you all stay current and engaged? Conferences? Reading articles as soon as you get in? Keeping notes?

Complicating factors:
- I have a nagging feeling that I don't deserve this position, pay raise, title. I sometimes feel like my bosses didn't know what they were doing when they hired me, and I think the insecurity across sometimes. I feel like I'm still a baby in this knowledge area.
- Not too long ago, at my last job, I was in this girl's position and had a boss with my title. I'm extremely sensitive to the way I was treated and am consciously trying to NOT be like my former boss, who was very smart and proactive but often times anal-retentive to the point of insanity. I always have her in my head and it's probably hurting me more than helping me, honestly.
- The company is VERY small and I'm still figuring out how to get myself organized, not to mention another person. A lot of times, things get thrown at me at the last minute and I'm figuring out solutions on the fly. This can be difficult with a second person in the mix. My boss is essentially the CEO of the company, so he's typically crazy busy himself. I'm thinking of using a project management system for the two of us (like Trello) because right now I only use a notepad/pen and it's not really working anymore. (Any recommendations, by the way?)
- It's not my dream job. I'm actually trying to wedge myself into a different part of the industry, although I know that's a transition that's (probably more than a few) years away. This is what I work on at night/on weekends. That being said, this is a solid opportunity in itself, due to the people involved and the projects we work on.

I'm rambling now, but I'd really love to hear any insights on the topic. I guess my questions in summary are this: How did you improve your management skills, especially as an insecure and/or unsure person? What can I do to ensure our team is firing on all cylinders? How did you get you and your team organized and make sure you're always ahead of the curve in your industry?

posted by themaskedwonder to Work & Money (15 answers total) 48 users marked this as a favorite
First of all, insecure people can be managers, successful ones even, they do it all the time. Here's how I know: Everybody is a little bit insecure. EVERYBODY. You become more confident and a better leader and manager by making mistakes and learning and improving and gradually getting more accomplishments under your belt.

To answer your specific questions at the end:

How did you improve your management skills, especially as an insecure and/or unsure person?

I learned that I needed to separate "me" from the work. You can always break everything down into objective, concrete pieces. Everything you do needs to be about the work. Take every concern that you have about yourself and your ability and turn it into an action you can take to try to improve that insecurity. Start with a goal as high falutin' and fluffy as "I need to be ahead of the curve in my industry, I can't get behind on trends." You can turn this into "I will present a top 10 list of emerging techniques in the industry with an analysis to my boss once a month." When you think "I can't be a bad boss for my direct report," turn this into "I will give my direct report clear goals, check in with her one on one 2 times a week." When you say "I don't want to be micro-managey like my last boss," turn this into "I will establish a specific process and framework for what my expectations are on assignments so that she has clear direction and won't feel micro-managed or surprised by my feedback."

Start to retrain your thinking from "I am" or "I need to be" to "I will". All your concerns about whether or not you're good enough? Who cares? The work matters. What you do matters.

What can I do to ensure our team is firing on all cylinders?
This is just too broad of a goal. What does "firing on all cylinders" mean to you, exactly? Breaking this metaphor down, "firing on all cylinders" means that your engine is operating at full power. First you need to... well, frankly, build an engine. You need to define your department's goals, short term, mid term, and long term. Then break that work up and determine a process for how you will work on that with your direct report. Then determine a process for how your department will interface with other parts of the organization. Then you will be firing on all cylinders. That's going to probably take you a really long time. Like, a really long time.

How did you get you and your team organized and make sure you're always ahead of the curve in your industry?
These are not the same goal. Getting your team organized is one thing. Being ahead of the curve in your industry is another. They are certainly related, and good on you for seeing that, but they don't just come together. Regarding organization, I would say that the best place to start for you may be to establish a solid and predictable workflow and clear role ownership. This means, people involved know the following:

Who requests the work to be done and how do they do it?
Who decides when it needs to be done?
Who prioritizes the work and says yes, no, and when it will happen?
Who manages a plan of record and where does it live so people can easily see it?
Who decides when the work is good enough to be called "done"?

Regarding being "ahead of the curve in the industry," I think that's maybe a little bit of buzz talk. I really don't know exactly what that means in objective terms. Do the best work you can and you'll probably be ahead of the curve.

Above all - try to stay calm at all costs. If you don't know an answer, if you feel like things are spiraling out of control, don't panic! Do your best not to take your failures personally or tell yourself that you're not cut out for this, that you don't know what you're doing, that you're a failure, blah blah blah. It's just going to make things harder for you and it does not serve you in the slightest. Keep your eye on the work that needs to be done and doing it as well as you can, and you'll be fine. :)
posted by pazazygeek at 11:11 PM on May 28, 2014 [9 favorites]

I'm not the expert you're looking for. I'm new myself. But I got new role, and 4 people, so, as you can understand, there was absolutely 100% no way I could do everything myself. Even though I keep trying.

Each time we had a new task, I took the first one, wrote notes on how I solved it (that I put in a wiki), next time we had that task, it got handed off to someone else. I only dealt with stuff that no one else could do, yet.
I wrote it up with the intention that any other Team member would have enough basic information to compete. I also assumed they weren't idiots, and it wasn't public facing info, so it wasn't super detailed, it was just links to relevant forms, websites, phone numbers, call and ask for 'blah' service. If it wasn't detailed enough, they could ask me, and I'd add just enough information that no one had to ask me questions.

Keep handing off tasks until she can't pick up any more, basically. This leaves you more free for having random stuff thrown at you. Then either pick things back when needed, or, actually, familiar tasks are easier than new.

Have you got her sitting next to you? Why not? There's only two of you.
Very easy, boring form of training: Get her to sit next to you for the next task you 'could' hand off. Talk about what and how you're doing it, and if it's a problem, especially the steps you're using to figure it out (So, I don't know, but it looks a lot like Blah task, so we'll see if there's anything in the BlahLogger system). Get her to start off a taskwith you watching, then on her own, with you checking, then - Go! Trust that she can do it, and you're ready to leap in and save the day if there is any problems.
Make it clear that YOU are the Too Hard basket, if there are problems, she just has to let you know, so you can pick it up.

Point out that you are new too! That you are figuring this role out, and that you have the experience that means you'll pick it up faster (because you will), but that you are learning how the company works, and that you'll let her know things, as you figure them out.

You can only work with the knowledge you have now. You kind of have to forge ahead anyway. If something is incorrect, you just have to know that you will do your best to correct it, and make sure it doesn't happen in future.
posted by Elysum at 11:34 PM on May 28, 2014 [4 favorites]

First time manager? Have a daily meeting with her in the morning to set her up for the day. It doesn't need to be overly formal, but you need to structure it. You get there an hour before she does an prepare for your meeting with her. Have tasks and due dates. No one likes to be the boss's out basket - which is what happens if you delegate tasks is a disorganized manner or "watch me then do it on your own."

Every day ask her:
- Do you have enough to do?
- Do you have enough CHALLENGING work to do?
- What tools do you need that we have not provided?

A crucial function of managing is being able to organize yourself and the work of the department. Get organized and give her some structure. As she gets used to the work you'll need to do less organization for her.
posted by 26.2 at 12:08 AM on May 29, 2014 [4 favorites]

This is kind of stereotypical impostor syndrome. You're not alone, and your insecurity may not reflect the reality of the situation.

Chances are your bosses are as in over their heads as you are, especially if it's their first start up.

If I were you, I'd start by writing down all of the least thought-requiring tasks you have to do regularly and start the process of documenting them, one at a time, and handing them off. It probably looks like a huge pile of work, but the more you do, the more time you'll have to do more of them.
posted by empath at 12:26 AM on May 29, 2014

The best managers I've had made an effort to get to know the people they manage. Make sure you talk to her to get a feel for what she's interested in, what she hopes to be doing, why she's there, etc. Find an excuse to talk to her about her interests (personal or professional) every so often. You don't need to try and be her best friend, but a little friendliness goes a long way towards being someone she wants to be managed by.
posted by nalyd at 3:36 AM on May 29, 2014 [1 favorite]

I'd recommend reframing this in your own brain first. Here's what I'd try to hang on to if I were you: "This job is a great opportunity for me to learn management skills. One of my most important tasks in this job is to teach myself how to be a better manager. No matter what happens in this job, I will definitely walk away with new and better management skills!"

The way you really make your brain believe this is to make yourself a training plan and follow through on it. I'd actually recommend starting by reading / listening to these two resources, which I've found extremely useful, and seen others use with success. They're not focused on theory, but on very practical tools for understanding your work and doing it well.
- Manager Tools Basics Podcast. This will give you in-depth advice on a set of 4 bedrock practices: one-on-one meetings, delivering feedback, coaching, and delegation.
- Behind Closed Doors. This is a great book for getting a sense of how a good manager works in the day-to-day and the long-term. It's far more thorough than the podcasts, but it's similarly practical.

Once you've checked out the information in the podcasts and book, I think you'll be in a better place to set yourself some concrete (and SMART) goals, and start to work on them.

Once you have a plan, I'd also say it's worth it to get your own boss on board, if at all possible. Share the fact that it's one of your goals to become a better manager, and you've come up with a self-directed plan to do so. Check in with your boss regularly about your progress, and let him help and offer additional resources if they're available. There might be money available to send you to trainings; there might be books or resources your boss knows of; your boss may have useful advice. AND ... because this is a new company, I bet that the work that you're doing to train yourself could become the start of a program to train all new incoming managers. Learning to be a good manager is a very, very worthwhile thing for you to do, and I'm sure your boss (so long as he has any kind of sense) will be pleased and impressed that you're putting in the thought and the work.
posted by ourobouros at 3:40 AM on May 29, 2014 [1 favorite]

She's given your clear feedback. One is simple - "I need more to do" and it's difficult to speak to that without knowing exactly what your day entails. So just make some of your job, her job. Think about the things that take up portions of your day that don't need access your specific brain, and teach her to do them.

I have one piece of advice about the second part "I want to make the company better" - it's important to tell her, out loud, that her ideas about how to improve things are always welcome. And then act on that promise. If someone feels listened to, and has some ownership of the work they're doing then half the battle is won in the "firing on all cylinders" front. Consider the difference between working daily on a spreadsheet that someone else designed, and working on one that you've set up for the way your brain works, and even with the colours you like! Perhaps they achieve exactly the same thing in the same amount of time, but I think you care more about the outcome with the second one.

And good luck - you can do this! The fact that you cared enough to ask the question supports it.
posted by birch effect at 4:14 AM on May 29, 2014

Document document document.

First, you take a quiet hour or so (and you might have to do this on your own time at home -- welcome to management) and think about what you and the company want from your subordinate. Write it all down, but revise heavily as you go. Break down tasks as much as you can. Make them concrete things ("Deliver X report to Head of Accounting weekly. Deliver Y report to Head of Research monthly." rather than "Deliver reports as required."). Concentrate on the "What" more than the "How" -- let your subordinate impress you with some radical new method that works better than yours.

Once you're done with that, type it all up nice and neat, preferably in a bulleted list, preferably organized (by frequency works well; so does by topic). Run it by one of your fellow managers for a sanity check, then by your subordinate to see whether she has any suggestions (emphasizing suggestions here -- you are still in charge).

Now run it by your boss (and yes, bosses need to know what people two levels below them are supposed to be doing, even if "knowing" just means they read their job description once).

Once it's "approved," present it to your subordinate as an Initial Review. Sign it and have her sign it. Give her a copy. Encourage her to go over it monthly to see whether she is living up to it.

Conduct a Quarterly Review with her. Note how she is living up to your expectations, adjust them as necessary, and sign off on it. Give her a copy of each Quarterly Review.

Now her Annual Review will be easy. You just do another Quarterly Review, start another list of expectations from that (but put another hour-or-so of effort into it), and hey presto. You have a logical, neat, simple system for monitoring and reviewing her work.
posted by Etrigan at 4:32 AM on May 29, 2014

Your subordinate is a woman, not a 'girl'. Thinking of her as a fellow professional may also help you a manager.
posted by Dashy at 5:33 AM on May 29, 2014 [2 favorites]

First off, needing advice/guidance as a first-time manager is a total thing! Just look at all Google results!

Second, something that really helped me as a first-time manager was religiously reading Alison Green's Ask A Manager blog. In fact, a number of us in my office have a discussion group where we just talk through some of the questions she gets and think about how we would handle the situation.

To get you started, here are just a few relevant questions:

Can you be a good manager if you’re shy?

New managers and authority

Advice for new managers (Number 7)

Most important advice for new managers

Seriously poke around in her archives. Any time I have a major work problem, I start there to see what advice she has. In general, her approach (clear, direct, realistic, pragmatic) lines up really well with the average MeFite's tendencies.
posted by whitewall at 5:53 AM on May 29, 2014

A task that you delegate will never be done just the way you would do it. Learn to accept it. If you don't accept other people's work, you'll have to do everything yourself -and your subordinates won't have anything to do.
posted by SemiSalt at 5:59 AM on May 29, 2014

If this is such a very small start-up, I think you need to spend a few minutes considering this: where do you think your person will be in one year or 5 years?

What I mean is, is she just a clerk/secretary/assistant type person, or does she have the skills to participate in the creation of the company and/or to do your job if she had the time to learn it? If the company grows over the next year, will she still be a clerical assistant or will she be the head of her own department?

I think, based on the answer to that question, you have 2 different paths to choose from. If she will be the head of her own department, then I think you should treat her more as an equal - work together to figure out what work your department needs to produce each day/week/month and divvy up the tasks to achieve that. You're the boss and the senior so you get the final say, but her input should be fully considered.

If she's really just an assistant, then yes, all the advice above about managing is the right way to go. But you don't do the documentation - she should do that. You show her in person what needs to be done, ask her to create a process doc for the wiki and then you review it and show her what to change.
posted by CathyG at 7:00 AM on May 29, 2014

Response by poster: Not threadsitting, but:

Dashy -- I'm a female and usually refer to myself as a "girl," and I have a bad habit of doing this to other women, too. (This is dumb, but it's probably because I sometimes have trouble referring to myself as a "woman"! Perhaps it connotes some kind of maturity/wisdom I don't feel like I possess.) I wasn't trying to imply that I think there's a professional gulf between us, but I appreciate the language check, as it's not something that I tend to be aware of. I will be better about that from now on.
posted by themaskedwonder at 7:37 AM on May 29, 2014 [1 favorite]

So, I manage a team of 100+ engineers doing product development and have been an engineering manager since 1988. And, I remember the night I came home from work thinking I would get a promotion to first level manager (I was 27 at the time) and sobbing in my partner's arms because I was so scared and felt so incapable. And, I'm female and manage male-dominated (90%+ male) teams and work in a male-dominated environment. Some folks who have worked for me think I'm one of the best managers they have had. [For others, like ones I've had to fire, I'm the worst.]

Yes, I think insecure people can become good managers, but for me, it has taken a lot of internal work to be able to do so. I've had to overcome my own fears of not being good enough and still, even after all these years, I still have these fears crop up.

There are a lot of good books and podcasts out there on being a manager. One thing I would add is to see if you can find a mentor, ideally someone not in your company, who you can go to for advice. That transition from individual contributor to first level manager is a tough one, and I think it's helpful to talk things over with someone you trust and respect.

The other thing I would add is to "fake it til you make it". Think of people who you respect -- could be real, could be fictional -- and think about how they would handle situations as they come up. I had the opportunity to work in a Fortune 100 company for the first 20 years of my career, so I had a lot of examples to choose from, and I could channel a little of this person and a little of that.

You can do this!
posted by elmay at 12:41 PM on May 29, 2014 [2 favorites]

Nthing fake it till you make it. Two things helped me in making the transition from an insecure twentysomething to a manager. Well, three things, but the first two are linked.

One way to think of a manager role is to think of it as a leadership role. You are taking charge of somebody, even if it's that one person.

So firstly, think of a leader you admire. It needn't be somebody world-changing like Nelson Mandela (my idol was Optimus Prime. I kid you not, I still have the Transformers movie poster at my work desk, albeit now hidden away under the desk instead of desperately displayed on the cubicle wall). Think of why you'd like to follow a leader like that. Pick out the points that you think you could fake reasonably well were you to say, act in a skit featuring said leader.

Secondly, realise that the person you are managing is expecting you to lead. Your own employee said as much when she said she's not sure what's required of her and that she wanted to feel needed. When you delegate work to her, you're fulfilling her expectations of you. When you think of it like that, it becomes much less intimidating to delegate work. It becomes less like you putting a burden on someone else, and more like you fulfilling yet another duty. In this case, your duty is to your employee to lead her and guide her in completing the work that you assign her.

Thirdly, find out what kind of leader you are. I had to go through management training to find out my leadership style (nuturing leader), so you might want to ask your boss to send you for something similar. I can't quite remember what the other leadership styles are - one of them was a visionary leader, and another was a strategic leader. Once you know what kind of leader you are, you'll feel like you actually have something to sink your teeth into. You have an identity as a leader and it's much easier to go with the flow of your leadership style. Over time, this identity and the identity of your idol identified in the first step will merge, and you'll have your own leadership style and identity that you're comfortable with.

Of course, although I phrased my answer in a very definitive "you will" sort of way, your actual mileage might vary. Still, it's worth a try, I think.

To address the imposter syndrome issue: I always feel like I'm behind in industry news too. I compensate for this by being ahead of the curve in other ways, like the use of computers (people in my line of work are not always very computer-savvy). This can actually make you look even better than if you were up to date on industry knowledge, because so long as you have a basic knowledge of the industry, you're meeting expectations. But excel in an unexpected area (preferably relevant to your work, of course), and suddenly you're outstanding.

Keep at it, you'll be fine!
posted by satoshi at 8:44 PM on May 29, 2014 [1 favorite]

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