If you’re interested in being a boss, start early. (Gif via )

How women can transition from employee to boss

Advice from a woman in tech who’s climbing the ladder

By Julia Carpenter

Being a boss — it looks hard, right? But becoming a boss — sometimes, that can look even harder.

Within the Pay Up community, this issue comes up frequently: What does it take to be a boss? How should you begin to prepare to lead your own team and to make the transition from employee to manager as flawless as possible?

Last March, Pay Up member Alisha Ramos made the step from Vox designer to Vox’s *director of design* — and she answered Pay Up members’ questions about how she navigated the new challenges, new goals and new directions she discovered during the transition.

[Are you a woman in tech? Join Pay Up today]


Q: What can I do now to position myself to be ready to take on a manager role? What skill sets should I be developing?

Alisha Ramos: That’s a really great question. If you know you want to become a manager, you should look for opportunities to start doing the work of a manager. It depends on your work and your organization, but that can range anywhere from mentoring teammates, to drafting up or formalizing processes, to getting involved with higher-level work (i.e. strategy or hiring).

Once you start doing this work, you can start the conversation of having it formally be recognized as the work of a manager (also it helps if your org has well-defined roles and requirements! Then you know exactly which skills to start developing and what to help out with).

Q: We’ve talked ​*so much*​ in here about the importance of mentors/work relationships and it sounds like this was super key to you, too! Could you talk a little bit about how those things come about and why you find them so valuable?

Ramos: One of the best pieces of advice I got was: if you would like to be promoted, start taking work off of your boss’s plate.

Mentors are so important. I think the definition varies for each person. To me, a mentor is literally just someone you can learn from. That person can be younger, older, newer to the org, older within the org, or work at a completely different company. But you can develop a relationship with them and learn from them. I think a “sponsor” is different because this is a person who sits at the top of the org, or near the top, who can become your advocate and “pull you up” with them. I was so lucky to have a sponsor. But both mentors and sponsors are valuable. (This is a fantastic article about women and sponsors.)

Q: What are some tips for for effectively managing the transition from peer to manager when you get an internal promotion?

Ramos: I stayed within Vox and within my department. When switching from a peer to a manager, things can definitely get or feel awkward. I had been doing the work already of being a manager, and the official switch felt a little more natural because of that.

Because I am friends with some of my reporters, that obviously involves some more awkwardness. But a great piece of advice I got was that in meetings such as 1–1s, you can use the phrase “I’m putting on my friend hat now” or “I’m putting on my manager hat now” and it feels silly, but seems to work really well. I’ve luckily been able to continue developing friendships and healthy manager-report relationships.

It also helps to see your new role as a coach, not as like … a leader or someone “better” than your reports. You are now no longer an individual contributor — you’re now responsible less for the “work” but more for the career growth and performance of your reports.

And viewing my output as my reports’ happiness and career growth has had a really positive impact. And helps me feel good when they’re doing great or improving.

Also, you will be in a lot of meetings! But that’s now your job, so embrace it.

Q: When you become a manager, a big part of your output becomes the output of the people you manage. How do you square that with personal ambition?

Ramos: That is something I’ve been thinking about lately too, as a highly ambitious lady. I think that your output becomes your reports’ performance, career growth, and happiness. So if your reports are doing well, then hey — they make you look really good too.

In terms of personal ambition, it varies for everyone. For myself, I have a vague idea of where I want to be in three to five years, and I think being a manager helps me get there, rather than hinders me, because I now have time to not only spend on my reports’ growth, but I also have the time to think a little more strategically and at a higher-level (in terms of the organization’s business needs, opportunities, etc.) and feel like I have more space to affect change.

Q: How important to you was the process of negotiating title/expectations/salary increase? How was it different than negotiating at other points in your career?

Ramos: Great question. In the past, I had very formal sit-downs and write-ups to prepare for salary and promotions (which is great and effective). With this title change however, it felt more like a collaborative exercise with my boss. And it also felt less “out of the blue” — like it felt like things had naturally progressed to the point where a title change would make sense, given the new responsibilities I had taken on. I think another factor as to why it felt more collaborative is because the company where I work is growing and changing fast, and a lot of the org structure was not formalized. Which is a blessing and a curse.

With the salary increase for the transition, I did a lot of research as well as talking to peers at other companies. But I don’t think that was much different from what I did for an increase tied to a promotion.

Q: How do you handle questions of workplace culture when you’re in management? Say, for instance, that you’re the only female manager in your department: how do you bring up gender issues in a way that lays out the facts in a non-emotional way?

Ramos: I am luckily one of four (I believe?) female managers within the Design Org. I am very close with one of them, and we regularly talk about gender issues, or issues we are facing where we think gender may be a factor. If you feel like you need a “sanity check,” it’s very helpful to reach out to another woman manager. If you can’t find one within your org, it also helps to talk to others in your industry. I am a part of two private Slack communities with women design managers, and it’s been one of the most helpful, insightful sources of strength + sanity checks + advice. I feel you though that being the only woman manager can get tough.

I will say though that … 99.9% of the time when I ask for a sanity check, the answer has been “Nope, you’re not crazy. That’s f*cked.”

Within your org, it helps to have data or hard facts to back up your claims to identifying a problem. Try to think of real life past scenarios. Save emails, save conversations. Show them to your manager or whoever as evidence.

Relatedly, at Vox we have an awesome team who worked on a Code of Conduct that addresses things like microaggressions. It helps to have a place where that sort of thing is clearly identified as something to be snuffed out ASAP.

Q: What would you say has been the one thing that has most surprised you about management life? What one thing do you wish you could’ve better prepped for or known about in advance? For female managers, particularly.

Ramos: I think that I had done a ton of reading (articles and books) about management, design management in particular, in order to prepare for my role. But I don’t think anything prepared me for 1) how emotional it could get, and 2) how much I don’t know about people. I admit I have the tendency to think that I have it all figured out, just because I’ve read books. But I was not prepared for how emotional I could get in 1–1s, for example, when I recognize my reports’ vast improvement in an area.

There’s a woman higher up at Vox who shall-not-be-named who takes pride in crying, especially in meetings. I don’t think I’ve ever cried full-on in a meeting, but I’ve come very close to it when providing positive feedback for my reports. And I finally understood where that woman was coming from about “embracing the cry.” I’m not a very emotional person (outwardly) so that caught me by surprise. Maybe that’s a woman manager thing, but maybe not?

And on the second point, I realized I had a lot of learning to do. I had to learn especially that different people work and learn differently, and therefore your management style with them needs to differ! It took me a while to understand how my reports liked to work, learn, and work with one another. And you kind of have to play coach with them in figuring it out together. At first it was a bumpy process, but now I feel more confident in understanding how they work and grow as individuals!


Have you navigated the transition from employee to manager? What lessons would you share with others? Tell us in the comments!


Pay Up is a private, Slack-based community dedicated to fostering conversations about the gender wage gap. It was formerly managed by the Washington Post.

Show your support

Clapping shows how much you appreciated Pay Up’s story.