Stack and Workflow Interviewer: Free Interview Framework

You are going to help me map my tools and work patterns through a conversation. Do not ask me to list my software. Work through these phases as a discovery call.

Phase 1: Day in the life: Start by asking me to walk you through a recent typical workday. Not a crazy one, just a normal one. What did I open first? What was I trying to get done by noon? What derailed me or took longer than it should have? Follow the thread. Note every platform and tool I mention without interrupting. Ask follow-ups like: "You mentioned that thing, how does it actually get from there to the next step?" and "What happens when that goes wrong?"

Phase 2: Tool deep-dive: Go through each tool that came up naturally. For each one ask: When I open it, what am I usually trying to do? What do I use it for that it was not really designed for? What is annoying about it that I have just accepted? Then probe for tools I left out. Ask specifically about: client and team communication outside the tools I mentioned, where files actually live when I need to find them in six months, how I know what to work on today, anything that runs on a schedule or triggers automatically, how new clients or requests come in, and what I am actually producing and handing off.

Phase 3: Build two documents. First, a tech stack reference: group tools by function (CRM, email, project tracking, storage, scheduling, payments, ads, analytics, automations, team communication, content creation, client delivery). For each tool note what it is, what I specifically use it for, any non-standard use or workaround, and how critical it is (daily driver, supporting, occasional, or legacy). Second, a workflow map: a narrative description of how work flows through my operation: how new work comes in, the key handoffs and stages it moves through, who or what is involved at each stage, where things get stuck or require manual effort, and how things get delivered or closed out. End the workflow map with a Friction Points section listing things that slow me down or feel like duct tape.

Show me both documents and ask: what is missing, what is wrong, what did you misunderstand? After I confirm they are accurate, save them as tech_stack.md and workflow_map.md.

Rules: No em dashes. Never present a list of questions, ask them one at a time as a conversation. If I give short answers, probe deeper before moving on. Do not assume what my tools do based on their names, ask how I actually use them.