I do have a tendency to be unconfident, to ask permission, be deferential, wait for somebody to tell me to do the thing, etc, when I could just do the thing. I tend to assume what I was going to do was wrong, especially if I get any pushback. In part because what I suggest has historically automatically been dismissed, my work and effort downplayed, etc... that doesn't seem to be a problem at my current org but I'm somewhat conditioned to assume that's the feedback I'll get anyway.

Incidentally I've never seen any of those things. At most of the smaller companies I've been at I've been the most senior woman simply as a senior engineer. Reporting to a woman sounds fantastical. I know it happens; I know a couple of female EMs at my current (bigger) company. I've essentially never had a woman in my reporting chain outside who is in the engineering org. (Across 7 jobs and about 15 years of career).

I tend to dress the part anyway and have had interview candidates assume I was the manager and my EM was the IC, but it hasn't been helpful outside of that. At worst, it can cause people to assume I'm non-technical, so it's a dangerous game to play.

I think some people really do need role models, so if you don't see any female engineering managers, it may be harder to envision yourself in that position.

That said, you do need to unlearn a bunch of stuff. You have to (at least pretend to) be confident, do things without permission, be self-motivating, etc. It's going to be very difficult to manage people and have them take you seriously if you can't get yourself to do those things.

I've been in a Technical Leadership position for about 10 years, with the last four having an explicit Manager title. If I were looking for someone to groom as an EM, that person would at a minimum have to show a strong level of initiative. You don't need to be "bossy" but you do need to be able to assert yourself while still considering alternate points of view.

I can point out some of the things you need to be, but I can't tell you how to get there.

I have a couple of questions.

1. What type of product/service has your team been building?

2. What did you do when 10 non-permission-seeking engineers went off in different directions doing their own things?

1. We build a variety of low-power wireless devices.

2. If you're managing people you should know what they're doing, and immediately correct this behavior. I'm a big fan of the phrase "stop doing that" because, yeah, it happens. By now my team knows that they have agency, but if they deviate from the plan to let me know.

One worker acting alone, part time, is unable to tackle very large problems. At the point where the solution needs coordination, it happens.

I need to write a whole blog post about the subject of role models, but basically, yes. Even simple stuff like "how do I dress?" is hard to answer when you don't have role models. Or how do you resist people who talk over you without being seen as difficult?

You're right about unlearning behaviors, though easier said than done. I'm relatively self motivated when I'm not interfered with, but when I get negative feedback can easily get stuck in an analysis paralysis loop trying to figure out "what does my manager want me to do?" It's not a good sign when I'm spending time on the question of if I should even ask him or if that will be perceived as me not intrinsically knowing which will reflect badly on me.

And all that stressing about what my manager wants or how a given action will be perceived looks like laziness at best.

I'll admit, part of what I want out of being an EM is external validation that somebody trusts me to lead something. I've had a lot of bad experiences that really undermine my confidence and make me question myself.

An example: at my last job, I had a coworker who made it his personal mission to slow my velocity as much during code review as possible. One of the more egregious examples - he told me to consider using a regex rather than == to evaluate equality of strings. No particular reason. What resulted was an hours long argument... his main justification was that if I had just spent an hour to benchmark it we could have found out faster than the argument took.

You can imagine how when even extremely basic decisions of yours like that are routinely questioned it sucks out your confidence. The lead of that team explicitly had no interest in mediating this ongoing problem, and eventually promoted that guy to be the team lead so he didn't have to manage it. I meanwhile had to plan all my code around the times he'd be out of the office; I could get a month of work done in a week he was out, because somebody else would review my code. I got a reputation for missing estimates, but my timelines were entirely driven by code review cycles and thus at his whim and availability.

And yes, I repeatedly asked to work with literally anyone else, and it was only when I threatened to quit that anybody at the org actually made that happen.

There's a long history of stuff like that happening to me, and it means that I tend to just wait for somebody to tell me exactly how to do whatever it is, because the way I will do it will be seen as wrong. Who can forget the manager a couple jobs before who admitted to creating fake crises and yelling at us over nothing to keep us motivated?

This org is the first one that has actually respected me enough to do more, and where my manager's main complaint is that I act like I don't have any power, when I do. Everywhere else, it felt like they were really trying to make sure I didn't get any, and it's tough to unlearn.