About DrillUp

Why this exists

Engineering careers stall for reasons that have almost nothing to do with engineering. People who write excellent code get passed over, absorb impossible deadlines, avoid the conversation about their salary for another year, and find out at a performance review that a problem had been building for months without anyone telling them plainly.

None of those are knowledge problems. Most people know roughly what they should say. The gap is that these conversations happen rarely, matter enormously, and offer no opportunity to practise - you get one shot at the raise conversation, live, with your actual manager, with your adrenaline up.

DrillUp exists to remove that constraint: a place to have the conversation badly first, somewhere it costs nothing.

Who writes this

I'm Dmytro B. I'm a software engineer and a co-founder of DrillUp. The app is built by the founding team; the playbooks on this site are written by me.

Where a page describes a script or a framework, it is because I have either used it or watched it work. Where the evidence is thin or the advice is contested, the page says so rather than presenting one opinion as settled fact.

I write these playbooks in a personal capacity. Nothing on this site is written on behalf of, or about, any employer, team or colleague. Every script and scenario is composite - assembled from patterns that recur across engineering organisations, not transcribed from real people or real conversations.

How the app works

DrillUp is an iOS app. You take a short assessment covering how you work, how you communicate, how you handle conflict and what you want from your career, and it builds a picture of where your gaps are. From there you get one focused drill at a time - a realistic scenario, your response, and specific feedback on what you actually said.

There is also a reflection and journaling side, because the pattern in what you keep struggling with is usually more useful than any single piece of feedback.

On AI

DrillUp uses large language models to generate scenarios and give feedback on responses. We publish what that means in practice, including what data is involved, in how we use AI.

Contact

Corrections, disagreements and requests for playbooks that do not exist yet are all welcome at [email protected]. If something on this site is wrong, I would rather know.