Before you ask your boss anything, figure out where do you want to go? And I don’t just mean in your career.

Then from that figure out, what does your ideal career trajectory look like in the next few years?

Do you want to be an L2? a sysadmin? DevOps? Do you want to keep working for an MSP, or maybe into a company with a dedicated IT team. Also consider if your tech career progression isn’t the most important thing, maybe it’s family, maybe it more time for a hobby, that’s ok too.

When you have a clear picture of what you want to do, communicate that and ask what you can do for the company that also helps move you toward that goal.

They probably won’t be moving you into your target role immediately, but any decent manager will help you move towards your goals, with training, mentoring, or other opportunities for skill building.

Some bosses are shitty and will try to keep you in roles that are the best for them, These bosses usually respond with a focus on your flaws, they will tell you why you’re not ready for whatever the next step is and offer no support or guidance to help you change whatever they cite. If you have a boss like that, start looking for another job.

Keep in mind the company has their own goals, you need to be prepared to be flexible they’re not going to move you into a role they don’t need. But as long as your manager isn’t a total dick, they’ll move you as close towards your goal as they can within the limits of the company’s goals.

Especially in this field it’s pretty common to need to move to another company to keep moving towards your goals. If you haven’t progressed to a new level within a year or two start applying for L2 role (or whatever else you want) at other companies.