Uplevel Blog

Developers, this is how to prepare for a career development conversation

Year-end discussions often center around anecdotes and broad feelings. This time, come prepared with trend data.
Author: uplevel
Tags: Blog

As the year comes to a close, many managers and developers are meeting for end-of-year performance reviews, or annual check-in conversations. We experienced yet another unusual year of remote work. At the same time, many teams reported having the same or higher output in 2020 than pre-pandemic times, indicating that these conversations still have plenty to explore in 2021.

For software engineers, you might prepare by scanning closed Jira tickets and recording a list of your most impactful projects. Yet, completed work is just one small part of the full picture. Career growth involves discussions around leadership skills, time allocation, and work-life balance. These routine check-ins often miss the opportunity to complement Project Health with People Health—a dual relationship that we consider critical to a healthy work life.

It’s not just what work you’ve done, but how you feel about doing it. How can developers support their career development conversations with the right context?


Being too open-ended with this check-in can ironically lead to less authenticity or clarity. Typically, these discussions start with broad questions:

  • What were this year’s highs?
  • What were this year’s lows?
  • How many of this year’s goals did you meet?
  • Where do you see yourself in one year? Five years?

Those questions simply start conversations that get scribbled into notes of wish lists and reminders: “Streamline focus. Improve cycle time. Spend more time mentoring junior devs.” While all are meaningful goals, they lack specificity. A year later, you might be hard-pressed to accurately quantify “progress” or “achievement.”

Having the right context makes all the difference. Especially for a retrospective that covers a year of work, your memories are often shaded with anecdotal evidence that might not recall the full truth. (That disparity isn’t an inherent flaw, it’s simply how memory works.)

Bring in true quantitative data.


Enter your career development conversation with general and acute topics to ensure that all bases are covered. Yes, you want to discuss the highs and lows; this is also a wise opportunity to touch on smaller points that don’t make your weekly 1:1 agenda.

Here are some key metrics to check quarterly and annually:

Average weekly hours and overtime.

Have you experienced healthy work-life balance? Did things ever truly “settle down” after that Q3 fire drill? Was this year a steady incline from 8-hour days to 12-hour days? Consider the general patterns of your working hours and whether things need to change. (The goal is not to boast about long hours, but to cap a healthy limit—or to advocate for a progressive four-day workweek.)

In Uplevel: Always On captures the amount of work occurring beyond eight hours in a single day. “Above Normal” and “High” signal potential burnout risk.

Agile best practices.

How many of your Jira tickets include descriptions and story points? How concerning is your level of stuck PRs? These practices shape work efficiency and collaboration, which might not be reflected in typical data round-ups, but have a strong impact on well-being.

In Uplevel: Sprint Health provides an overall health score representing output and process, including how this score trends over time. Use the numerous filters in Project Explorer to focus on any particular person or task type, with additional tags and callouts to provide context.

Burnout risk.

Achieving every sprint goal is a positive—unless it comes at the cost of burnout. When looking at work productivity, be sure to address the subjective and objective truths of mental health. (If you’ve passed the “risk” stage and solidly hit burnout, try these recovery tactics.)

In Uplevel: People Health metrics give an idea of elements that contribute to daily wear-and-tear. When Context Switching, Always On, and Interruptions are high, you may want to consider a shift in workload or an early Friday sign-off. There are ways that individuals can reduce their risk, but be prepared for the larger impact to happen at the company level.

Meeting health.

Does a calendar full of scattered meetings get in the way of focused work? Has Zoom fatigue impacted your ability to effectively participate? Quarterly or year-end reviews provide an excellent opportunity for a calendar audit to free up time for Deep Work.

In Uplevel: Meeting Classifier unpacks how much time you spend in meetings, as well as categorizing them for overall comparison. If Monday project reviews are hindering productivity more than aiding it, try moving them online or testing out asynchronous meetings.

Need thought-starters that motivate deeper discussion? Try these questions that go beyond Jira:

  • What motivates you?
  • What accomplishments are you most proud of?
  • What 2021 goal didn’t end up being reached? What were your blockers?
  • What is easier/better for you in a WFH environment? What is easier/better in an office environment?
  • What skill do you think you could be highlighting more here?
  • What kind of work comes easily? What’s really challenging?
  • Where do you hope to improve next year? How can your manager support you?



While we don’t endorse using data to objectively stack-rank team performance, there is clear value in bringing measurable milestones into retrospectives.

One goal-setting philosophy presses on the importance of pairing goals with detailed context. Aptly called SMART goals, the acronym calls for goals to be: 


Through this lens, “Streamline focus” becomes “Work with my manager to load-balance minor tasks and reduce context switching by 25% by the end of Q2.”

“Improve cycle time” becomes “Modify PR approval process to address the current two-day bottleneck and decrease PR cycle time by 10%.”

“Spend more time mentoring junior devs” becomes “Schedule weekly office hours every Wednesday afternoon from 2-4pm to support junior developers and improve team output by 5% or more.” 

The pairing of anecdotes and data can carry these goal conversations forward and set up the next year’s review with a stronger foundation.


You can drive effective career conversations by addressing both your daily work experience and long-term career goals. Patient, honest, open communication paves the road forward for the best results—and developer-empowering data can carry you the rest of the way.