behavioral

Question 1

Tell me about a time when you mentored someone.

Answer 1

S: 5–6 months after I joined, our team lost two members, creating a knowledge gap.

T: I was asked to onboard two new hires and help them ramp up quickly.

A: Led walkthroughs of the app, answered questions, and escalated unclear areas to team leads for accurate info.

R: Both hires became productive quickly, and the process deepened all of our understanding of the system.

E: Fast-paced, collaborative team with minimal documentation—required initiative, communication, and flexibility.

Question 2

Tell me about something you’ve spearheaded/led the charge on at work.

Answer 2

S: Our internal, client-facing team manually entered filing data using our system, which was slow and repetitive.

T: Streamline and automate the filing process to reduce manual effort and improve turnaround time.

A:

• Built an Excel template for structured data input
• Used a legacy dispatcher system to pick up filled templates
• Developed an ETL pipeline to automate filing creation, data aggregation, and validation

R: Cut filing time by ~70%; users simply fill the template and drop it into a folder—everything else is handled automatically.

E: Legacy-heavy environment; needed to work around existing systems while improving internal user efficiency.

Question 3

Tell me about a time when you took it upon yourself to give feedback to someone who was holding-back the team.

Answer 3

“have not experience this but my approach would be very polite

ask if there’s anything going on that is hindering their work

ask how I can help their work, if possible”

Question 4

Tell me about a difficult technical challenge you encountered. How did you navigate it?

Answer 4

S: A legacy client’s Excel macros broke right before a filing deadline, blocking their workflow.

T: Fix the VB macro code so the client could complete their filing on time—despite my lack of VB experience.

A:

• Learned VB syntax and Excel debugging tools on the fly
• Used breakpoints and watchlists to trace and correct logic in the macros

R: Fixed multiple macros same-day, restored data aggregation in the spreadsheet, and enabled a successful client filing.

E: High-pressure, client-critical situation with unfamiliar tech—required fast learning and independent problem-solving.

Question 5

Tell me about your side projects.

Answer 5

S: After a college interview with the Brooklyn Nets, I wanted to deepen my skills in Python, APIs, and web development.

T: Build a project to analyze NBA stats and recommend optimal player lineups for specific game scenarios.

A:

• Used Flask to build a web app
• Pulled real-time data using the nba_py API
• Created backend logic to run situational statistical analysis

R: Built a tool that recommends the best 5 players for scenarios like “4th quarter, down 5, vs. the Nets.”

E: Independent, exploratory project post-college—motivated by curiosity and a desire to improve technical depth.

Question 6

Tell me about a project that didn’t go according to plan (shifted priorities/deadlines/budget).

Answer 6

S: For our ETL system, validation logic was originally scoped for 2 weeks—but the timeline was cut to 1 week to allow more testing.

T: Deliver all validation code for the ETL pipeline within the shorter 1-week timeframe.

A:

• Rigidly planned my work and prioritized critical paths
• Put in extra hours to meet the deadline

R: Delivered the code on time; a few bugs surfaced during testing, which I addressed shortly after.

E: Fast-moving dev cycle under shifting priorities—taught me to aim for early delivery whenever possible to allow for unexpected pivots.

Question 7

How do you negotiate scope/requirements across teams?

Answer 7

“having worked in 3 different teams (all at once at one point), I managed my bandwidth by explicitly making my bandwidth known across all teams

prioritized which scope was more important

prioritize which tasks were more important”

Question 8

How do you stay educated on best-practices/industry trends?

Answer 8

• instagram, reddit
• subscribed to bytebytego - technology newsletter
• linkedin learning

Question 9

How have you worked on your weaknesses and developed your strengths?

Answer 9

most notably quit my job and started interview kickstart

Question 10

Tell me about a time when you received feedback that was difficult to hear.

Answer 10

S: In an annual review, my manager pointed out that the completeness of my work wasn’t where it needed to be.

T: Improve the thoroughness and reliability of my code and deliverables.

A:

• Took the feedback seriously, even though it stung
• Joined a new team and learned from a lead dev whose code quality I really admired
• Adopted his habits for writing airtight, detail-oriented code

R: In the following year’s review, my manager called out my significant improvement in completeness.

E: Feedback-driven, collaborative environment that supported growth—reinforced the value of learning from strong peers.

Question 11

Tell me about a time you had to deliver on a tight deadline.

Answer 11

S: We shortened the ETL validation phase from 2 weeks to 1 to allow more time for testing.

T: Complete all validation logic for the ETL pipeline within 1 week.

A:

• Rigorously planned my workload and focused on key validations first
• Committed extra hours to ensure delivery on the tighter schedule

R: Delivered the validations on time; found and fixed a few bugs later during testing.

E: Agile, high-priority project environment—reinforced the importance of early delivery and baking in buffer time.

Question 12

Tell me about a time you fell behind or missed a deadline on a project. How did you respond?

Answer 12

S: I had just joined a new team and took on more tickets than I realistically could handle.

T: Deliver 4 new APIs plus other sprint work, despite not yet being fully familiar with the codebase.

A:

• Spent long hours during the last 1.5 weeks of the sprint to get everything across the finish line

R: Completed the work, but with less polish and fewer improvements than I would’ve liked.

E: Fast-paced sprint environment—taught me to be more realistic and transparent about my bandwidth to avoid compromising quality.

Question 13

Tell me about yourself.

Answer 13

“backend focused engineer with 5 years of experience

computer science degree

worked at ACA where I was a part of 3 different teams, delivering different kinds of products

looking for an opportunity to expand my skillset and knowledge and be part of a engaging team and contribute to more meaningful, higher visibility products”

Question 14

Tell me about a conflict you had with your own manager. How did you approach this?

Answer 14

Situation:
“soon after joining a new team, during a sprint, I was asked by my manager to take on a few more items than I was comfortable with

given that it was a new code base that I was still getting comfortable with and knowing other tasks that I had for another project, I explained that I might not be able to do it

she still wanted me to take on the tasks anyway

end of the sprint was coming close and I still had a long ways to go

she was disappointed in my progress at that point”
Task:
create a couple new APIs
Action:
“I discussed with her that I took on too many tasks that exceeded my capacity (knowing myself as a developer)

she mentioned that I still have to get the work done regardless

I ended up finishing the work in time

we had a discussion after the sprint where I explained my realistic capacity to get quality work done

I also mentioned that I could improve my orgranization and time-management to be more productive”
Result:
agreement that I was given too many tasks and I should take on what I’m comfortable with

developed a better time-management system for me to complete tasks

Question 15

Tell me about a time you overcame a conflict with a team member.

Answer 15

Situation:
“one of my lead devs explained to code something up as IQueryable instead of reading the data directly into a list ahead of time

I realized that that method was inefficient due to it having to make numerous calls to the database as opposed to one large call (we needed all the rows anyway)”
Task:
use IQueryable instead of reading the data directly into a list ahead of time
Action:
we had a screenshare where I walked him through a debug of the code where it was visibly clear that IQueryable was much slower than preloading all the data
Result:
we used my way which resulted in seconds faster processing

Question 16

Tell me about a time when you had a conflict with your team or the direction your team was headed.

Answer 16

Situation:
“my first team I was a part of, Regulatory Reporting, had no more developement in the future

frustrated because I was only doing maintenance work”
Task:

Action:
spoke to manager about how I was unhappy about just doing maintanence work
Result:
joined Security Master team that was complex and fun to work on

Question 17

Tell me about a time where you had to resolve a conflict between two or more of your team members.

Answer 17

“have not done this but I know I am very empathetic

can understand both points of view and come up with an objective solution”

Question 18

Why are you looking for a new job?

Answer 18

• Looking to explore other possible roles for me in tech
• Want to leverage my experience but also try something different than heads down coding
• Architecting seems like a natural progression for my career

Question 19

How would you describe yourself and why do you think that you should be hired by Grammarly?

Answer 19

a. I would say, or would like to believe (lol), I’m intelligent, hard-working, friendly, and empathetic.

b. I think I would just be a really solid addition to Grammarly. Someone that can be relied on all the time to get all my work done efficiently, and also someone who can bring new thoughts and ideas to the table.

Question 20

What was your experience one time when you were asked to help a colleague in an area out of your sphere of responsibility?

Answer 20

Situation:
* Teammate asked if I can help see why our dispatcher wasn’t working

Task:
* Help teammate

Action:
* Said I can help in a few minutes -> did a screenshare with him to solve the issue

• Update config file to point to the right database -> fixed issue

Result:
* I’m always happy to help out a coworker so it was a pleasure for me

E - Environment:
* ACA Group - new team with a lot of initiatives

Question 21

Share an example of a time you failed to succeed.

Answer 21

Situation:
* Two weeks away from launching our PFRD ETL system

Task:
* Complete validation for the PFRD ETL system in a week so we can have a full week of testing beforehand

Action:
* Worked on it but it wasn’t fully complete by the end of the week

Result:
* Manager was disappointed but I worked all weekend, Monday and Tuesday to complete the validation. Finished by Tuesday

• learned: to get things done earlier just in case they need to be done sooner

E - Environment:
* ACA Group - new team with a lot of initiatives

Question 22

What would be your ideal team to join in Grammarly

Answer 22

Medium size team around 6-10 people. I like this setting because it feels like everyone knows each other better and knows what everyone is working on. Allows for easier communication

Question 23

Could you tell me about a time when a decision you made didn’t work out? What did you learn from it?

Answer 23

A lot of my code that I wrote early on in my career was not fully thought out before I wrote it. It resulted in a log of bugs and a lot more work in the end. When I joined Security Master team, lead dev was inspirational in the way he wrote code which was very thought out and very fault tolerant. I learned to be more thoughtful and intricate with my code, so that it would be more fault tolerant

Question 24

What is your most memorable challenge from your past experiences?

Answer 24

Creating the PFRD system. It was my first real project that I was assigned to do. It involved creating upwards of 50 stored procedures, validation for all the data, training our clients how to use the system, and being the main point of contact for any questions

Question 25

Tell me about a time you had to work closely with product managers. How did you balance technical concerns with business goals?

Answer 25

**S – Situation** * Worked on developing an SIU tab for a client in the claims system. **T – Task** * Needed to work closely with product managers to translate their vague requirements into clear technical work, while balancing delivery deadlines and maintaining code quality. **A – Action** * Helped break down ambiguous product requests into well-defined technical stories. * Flagged complex or risky features early and suggested splitting them into smaller, manageable tickets. * Collaborated with product managers to align the project scope with realistic deadlines without sacrificing code quality. **R – Result** * Delivered the SIU tab on time with high quality. * Maintained a good relationship with product managers through clear communication and realistic planning. **E - Environment** * Vertafore

Question 26

Have you ever had to explain a complex technical concept to a non-technical stakeholder?

Answer 26

**S – Situation** * I had to create a Flood tab in a claims module for a client. * After I delivered the tab, the client tested it and complained that the validation process erased all fields after an error, causing frustration. **T – Task** * I needed to explain why the validation behaved that way and what it would take to change it, in terms the client could understand. **A – Action** * I explained that the validation behavior was part of the base system’s validation logic, which resets fields after a validation failure by design. * Clarified that modifying this behavior for their customization would require an additional 2–3 hours of development effort. * Made sure to communicate this in simple terms without heavy technical jargon, so the client understood the trade-offs. **R – Result** * The client agreed to the extra work, and I updated the logic to preserve the entered fields after validation errors. * They appreciated the clear explanation and the quick turnaround on the fix. **E - Environment** * Vertafore

Question 27

“How do you collaborate with non-technical stakeholders?”

Answer 27

**S – Situation**: * At Vertafore, I worked on projects that required daily coordination across multiple teams — project managers, the builds team, directors, and fellow engineers. **T – Task**: * My responsibility was to deliver features and fixes that touched not only code but also SQL stored procedures and deployment workflows. **A – Action**: * I regularly clarified scope and requirements with PMs, worked with the builds team on environment deployments, and aligned with teammates and directors on implementation details. This communication helped prevent misunderstandings and kept us moving quickly. **R – Result**: * Our workflow was smoother, and we had minimal negative feedback from clients once deployments went live. **E - Environment**: * Fast-paced enterprise insurance software where accurate deployments and client satisfaction were critical.

Question 28

“Why Origami Risk?”

Answer 28

* I like Origami's mission to simply risk & insurance * As an engineer, simplifying things is what I strive for (aka less manual work) * Tech-first approach is something I'm drawn to * Growing company where I can learn and grow a lot as well

Question 29

“Can you give an example of when you challenged the status quo?”

Answer 29

**S – Situation**: * At Vertafore, I had to create a new screen to log claimant actions. My boss had an approach to add columns to the custom claimant table but I suggested instead to create a new, related table **T – Task**: * Create a new screen to log claimant actions **A – Action**: * I spoke up and he mentioned that would be a better idea which I implemented **R – Result**: * Successful implementation with easier to read relational data **E - Environment**: * Vertafore

Question 30

“How do you measure outcomes versus outputs in your work?”

Answer 30

* Outputs = deliverables (code, tickets closed). * Outcomes = business/client impact (reduced downtime, faster workflows).

Question 31

“Where do you see yourself growing in the next few years?”

Answer 31

* Short-term: strengthen as an associate solutions architect, learn the product deeply. * Medium-term: grow into a solutions architect role, mentor new hires. * Long-term: lead initiatives that improve architecture consistency across clients.

Question 32

“What do you look for when joining a new company or team?”

Answer 32

Collaboration, autonomy, learning opportunities

Question 33

“What motivates you in your work?”

Answer 33

* Impactful outcomes (solving client problems, improving processes). * Growth opportunities, working with smart/collaborative people. * Curiosity + solving complex problems.

Question 34

“If you joined Origami, what’s the first thing you’d want to learn or understand?”

Answer 34

* Understanding the Origami product (architecture + workflows) * How to be an impactful architect with impactful contributions/ideas * Learn about Origami culture, standards, and best practices

Question 35

"How do you stay current with technology?"

Answer 35

InfoQ → tech news ByteByteGo → tech email subscription about system design methods Reddit/Instagram → shows you stay connected to real-world dev chatter, not just official blogs.

Question 36

"Have you ever managed multiple clients at the same time?"

Answer 36

**S – Situation**: * At Vertafore, I regularly manage multiple client accounts simultaneously, each with unique issues and deadlines. **T – Task**: * Constantly ensuring clients' asks/needs are met **A – Action**: * Typically, each request has a "Vertafore Priority" level. But if they had the same priority level, use personal judgement based on urgency, and business impact (can they file claims, etc). * Always communicate and be transparent about timelines and potential delays * Set expectations early and proactively provide updates **R – Result**: * Successfully managed several client relationships at once without missed deadlines. * Consistently received positive feedback for clarity, responsiveness, and professionalism.

Question 37

"How would you deal with a customer who wants to be especially prioritized?"

Answer 37

**S – Situation**: * At Vertafore, sometimes clients would request escalation **T – Task**: * Had to assess the clients request **A – Action**: * Internally judge if it's worthy of escalation * Provide transparency of how prioritization works (if their business cannot function, then it will be prioritized) * Always provide realistic timelines and proactive updates **R – Result**: * Reduced client frustration by showing empathy and ownership. * Earned trust even when I couldn’t change the priority order.

Question 38

“What if the customer isn’t satisfied with your response?”

Answer 38

**S – Situation**: * Client was unhappy with response about not being able to escalate **T – Task**: * Keep client happy while maintaining Vertafore process **A – Action**: * Acknowledge frustration * Explain limitations and how our prioritization works * Provide workarounds, or alternative solutions if they exist **R – Result**: * Preserved trust and satisfaction even when outcomes weren’t ideal * Built a reputation for calm, empathetic, and solution-oriented communication.