How to ask your manager to help you level up

In this episode, Dave and Jamison answer these questions:

1. I have been with my current organization for 5+ years. I like the company and have generally had a good experience working here. However, the last several years I have not really gotten a raise except for the standard “merit raise”, which does not cover inflation, so effectively the last several years I have made less money than the year before. I brought this up to my EM who said there is no chance of the company increasing the merit raises to meet inflation, unless I get a promotion. However, my EM also said there are no promotions available.

   I don’t know if this means the company knows the job market is tough and they don’t have to pay us as much, or if the company is in dire financial straits and unable to keep salaries up with inflation.

   This job market is tough and I don’t know how long it would take me to find a new job, but certainly I will look. My question is basically, how can I go about getting my manager to help me level up to make myself a more attractive candidate for a future job without necessarily tipping my hand that I am job searching.

   On one hand I assume he knows that I might be looking. On the other hand if the company is in a bad position and we have another round of layoffs (we have had several over the past few years), I don’t want to be first on the chopping block because it looks like I have my foot out the door.

   I’m just wondering how much I should make it clear what my goals are to have my EM work with me, or play it close to the vest.

2. I am a Software Engineering Manager with about 12 years of experience. I am a few months into a new role at a medium sized private company. The day I joined I found out that all ICs under Staff-level are international contractors! Surprise!

   My team is mostly contracted “Senior developers”. Nobody is anywhere near what I consider “Senior”. The company has a culture of aggressive performance reviews. However, I’m seeing ICs and other Managers around me who are all seriously below the bar compared to other places I’ve worked in the tech industry. I get a lot of vague pressure from the Director/CTO level to “raise the bar” and quickly exit people who aren’t meeting it. I already fired one person for performance and behavior issues, but I feel like I’m between a rock and a hard place.

   If I’m truly going to hold my team accountable to my and the company’s own published performance metrics, I should fire the whole team. That’s probably not good. Alternately, I can pad performance evaluations to convince my boss that everyone is meeting expectations. This also isn’t good, but feels like what everyone else is doing.

   Also, I’m a little queasy doing aggressive firing and performance reviews for contractors. The company treats them as full time employees (after hours on call expectations, etc) and I’m not sure how Earth lawyers would look at this situation.

   Help!

   Final wrinkle - my last two jobs I’ve lasted less than a year. I wasn’t fired but just haven’t been able to find a good fit for a little while. I’m worried that if I just leave this job 6 months in, it’ll start to look suspicious on my resume.