The career growth conversation is one of the most impactful things an EM can do, and one of the most poorly executed. Done well, it gives engineers clarity on what to focus on and a sense that someone is invested in their long-term success. Done poorly, it is a vague “you are doing great” that leaves the engineer wondering what their actual path looks like.
Why these conversations matter
- They keep your strongest engineers — top performers stay where they see growth
- They surface gaps before performance review — no surprises in calibration
- They identify what your team is missing in skills or scope
- They are how trust is built between you and your reports
Cadence
One dedicated career conversation per quarter. Distinct from regular 1:1s. 60 minutes. Both prepared.
What to ask
Six questions that consistently produce useful conversations:
- “Where do you want to be in 18 months?”
- “What kind of work energizes you most?”
- “What kind of work drains you?”
- “What skill would have the biggest impact on your career if you developed it?”
- “What is missing from your current role?”
- “What support do you need from me?”
Listen more than you talk. The goal is to understand their model of their career, not to impose yours.
Mapping growth to the level rubric
Every company has a level rubric (E3/E4/E5 at FAANG; SE I/II/III at most others). Walk through it together:
- What expectations are they consistently meeting?
- What expectations are they meeting some of the time?
- What expectations are they not meeting yet?
The “not yet meeting” categories define the growth direction. Be honest. False reassurance is unkind.
Setting growth goals
Quarterly growth goals should be:
- Specific to the rubric or skill gap
- Measurable (artifact, demonstrated behavior)
- Realistic for one quarter
- Aligned with team needs (what you ship and what they grow on overlap)
Examples:
- “Lead the design and implementation of feature X” — for someone growing toward Senior
- “Mentor a junior engineer through their first complex project” — for someone growing toward Staff
- “Write a deep-dive on Y system and present at the engineering all-hands” — visibility + technical depth
Common mistakes
- Promising promotions you cannot guarantee: “If you do X, you will get promoted next cycle” — calibration may say otherwise. Frame as “if you do X, I will advocate for promotion.”
- Skipping the hard truths: “You are doing great” when there are real gaps. Reports lose trust when calibration surprises them later.
- Generic feedback: “Be more visible.” Useless. Be specific: “Present a design at the architecture review next month.”
- Career conversations only at review time: reactive, defensive. Make them proactive and quarterly.
The lateral move
Sometimes the best career step is sideways — to another team, another role, another type of work. As their manager, support this. A report you support to a great lateral move becomes an advocate for you forever. A report you blocked from a move becomes a leak.
The promotion conversation
When a report is approaching readiness:
- Tell them explicitly: “I think you are 1–2 cycles from promotion. Here is what would close the gap.”
- Document the gap with specific examples
- Quarterly check-ins on the closing of the gap
- Build a portfolio of evidence (artifacts, peer testimonials)
When a report is not approaching readiness:
- Be honest about what is missing
- Ask what their motivation is — sometimes the answer is “I want to feel valued,” and recognition or comp adjustment is the real ask
- Offer alternative paths if promotion is not the right fit
The “I want to switch tracks” conversation
An IC wants to become a manager. A manager wants to go back to IC. A backend engineer wants to do ML. Take these seriously.
Steps:
- Understand the why. Sometimes the underlying need is different from the proposed move.
- Discuss the realities — pay, scope, learning curve.
- Identify a low-risk way to test the new track (a small project, shadowing, a temporary rotation).
- If they decide to commit, support the transition fully.
Frequently Asked Questions
What if I do not have a clear growth path for my report?
Be honest. “I am not sure what your next promotion looks like in this team. Let us figure it out together. Some options: lateral to team Y, deepen in domain Z, take on cross-team scope.”
What if my report wants a promotion they have not earned?
Be honest about the gap. Frame it constructively: “Here is what is missing. Here is what you would need to demonstrate. Here is the timeline I would expect.”
How do I handle a report whose ambitions exceed the team’s scope?
Help them find scope inside the team if you can. If you cannot, support a lateral move. Holding them back will cost more than letting them go.