Brainstorming Project Retrospective Ideas

Creating a project retrospective should be fairly easy now that we've created a story bank. The key is mapping the job description with skills you want to highlight, and choosing a project which highlights those.

Step 1: Determine skills to highlight

In an interview scenario, it's good practice to highlight your strengths while addressing what may be perceived as weaknesses. The project retrospective is no different.

Let's run through an example. Say two candidates are applying for an Engineering Manager role in Payments Infrastructure at Stripe. The responsibilities and requirements for the role are:

Candidate 1: One year of engineering management experience at Square, a direct competitor to Stripe. Before becoming an EM, she spent several years as a payments engineer and tech lead learning the ins-and-outs of finance and payment processing technology. Although formal EM experience is limited, she always went out of her way to share her knowledge and learn from cross-functional peers and help her teammates.

Candidate 2: Seven years' engineering management experience and two years SWE experience at Apple. Before that, five years' experience as a SWE at a healthcare company. He's a seasoned manager with experience delivering complex projects, though infrastructure experience is limited. His team members have consistently gone on to do great things following his mentorship.

Sample skills assessment

Candidate 1, while lacking in formal EM experience, has deep domain-specific knowledge of Stripe's technology, business, and competitive landscape. She should highlight this, as well her ease working cross-functionally. She may not have formal recruitment or performance management experience, but she can highlight the informal ways in which she's helped her teammates grow — thus contributing to the healthy, supportive, and challenging company culture Stripe is building.

Candidate 2 is clearly an effective manager. He should highlight the consistent personal and professional growth he was able to coach his reports through. Seven years is long enough to develop deep and nuanced management philosophies, so he should choose a project through which he can demonstrate his style. While he doesn't have much infrastructure or payments experience, he's clearly adaptable, having successfully switched industries.

Step 2: Brainstorm a list of projects

Once you've got a sense of how you can best portray yourself as a match for the job, it's time to brainstorm projects. This should be quick if you've got your story bank ready. Go for quantity during this first pass.

Step 3: Select the top three

Now, go back to the job description and think about projects that show off the skills you chose to highlight. Make sure the project is big enough that you'll be able to address your weaker areas and answer follow-ups.

For example, Candidate 1 above might select:

• The project that convinced her boss to promote her to engineering manager in the first place. A complex project where she really stepped up and learned on the fly. It doesn't hurt that this project is heavily technical and relevant to Stripe.
• A successful cross-functional project in which she acted as engineering liason, representing her team's interests gracefully among multiple other groups.
• A recent or ongoing project in which she's had to coach her new team through difficulty. She may not be able to speak to results yet, but she should be able to speak to her management skills and technical knowledge of payments.

Candidate 2 might select:

• A large, high-visibility project which resulted in C-suite recognition of his team's exceptional work. As a result, a key team member received a big promotion.
• A slightly smaller project, or perhaps a stretch assignment that ultimately became a big win for the company due to his adaptability and innovation.
• A project during which many things went wrong, and he had to make difficult decisions. This project offers many opportunities to showcase his technical knowledge and people management skill, while talking through trade-offs (always a winner in interviews.)

Do's and Don't's

• Do choose a project that you're excited to talk about. Enthusiasm always makes for better, more memorable interviews.
• Don't select projects older than 2 or 3 years. Interviewers will want to dive deep and the details should be fresh in your mind.
• Do take care not to overstate your own importance. EM interviews are more about the team, less about you individually.
• Don't be afraid to choose projects that had issues. Interviewers are very interested in how you handle adversity.
• Do pick a project that was successful and had measurable business impact.
• Don't pick a project if you weren't directly responsible for it or weren't actively involved.