Project Management Expert in Asana: Rebuild My Consulting Board in 3 Live Sessions

JOB DESCRIPTION I run a consulting engagement for a manufacturing client. The work breaks into about 20 mini projects across seven groups — messaging, sales motion, pipeline, commercial terms, events, people, and portability. Lots of moving parts, one hard deadline in early October. The content is already in Asana. Two boards exist: An operating board with ~89 tasks sorted by status (In Progress / Next / Blocked / Done), each card prefixed with its workstream. A master board with the 20 mini projects as cards across seven columns, and the actual work sitting inside each card as subtasks. The content is correct. The structure isn't. Two overlapping boards, no due dates, no dependencies, no custom fields, no useful views. I open Asana and can't tell what I'm supposed to do today. I'm not asking you to redesign the work itself — I own the work breakdown and it's right. I need someone who knows project management tooling cold to make it operable, and to teach me to run it. Three things to know before you bid 1. I'm not married to Asana. Full disclosure: I set this up with Claude, and Asana was Claude's recommendation for what I'm doing. I've got maybe a few hours invested and nothing I'd cry over losing. If you're an expert in this space and you think a different platform is a materially better fit for a solo consultant running twenty interlocking mini projects with heavy AI integration, say so in your proposal and tell me why. I'd rather hear it now than a year in. That said, the fixed price below is scoped for building this in Asana — if you talk me into switching, that's a re-scope conversation, not something I expect you to absorb. 2. I'm on Starter, with two seats, and I only need one. I'm a single user, no team. I'm willing to upgrade the plan if it genuinely improves the outcome — what I don't want is to pay for seats I'm not using. So if your recommendation depends on an Advanced feature like portfolios, make the case for it and tell me what it buys me that Starter can't. If Starter is enough, tell me that too. I'd rather you talk me out of spending money than into it. 3. This board is operated by an AI agent as well as by me. I use Claude every day for this project, and it's connected to Asana through an API integration that reads and writes tasks. It works, but it doesn't maintain the board as well as it should — and I suspect the structure is a bigger cause than the AI. So build for machine-readability as well as human-readability: consistent naming conventions, structured custom fields with defined values instead of details buried in prose, one canonical place for each piece of information, predictable subtask and dependency conventions. If a fact only exists inside a task description, the AI can't reliably use it. To be clear on scope: you are not building anything on the AI side. I handle that. I need the structure designed so it holds up when something other than a human is reading and updating it. What I need built Reconcile the two boards into one operating structure. Recommend the approach, then build it. Give me your opinion, not a menu of options. Custom fields for workstream, status, priority, and owner — using defined dropdown values, not free text. Due dates and dependencies across the critical path. The one immovable date is a conference in early October. Rules and automations to keep the board current without me babysitting it. Templates so I can spin up a new mini project, or clone the whole structure for a second industry vertical, without rebuilding from scratch. Saved searches and My Tasks setup that answer three questions in one click: what's due this week, what's blocked, and what's waiting on someone else. A weekly review routine — a recurring task or workflow that walks me through updating the board in 15 minutes so it doesn't go stale. A one-page conventions doc — naming rules, what each field means, where each type of information belongs. This is what keeps both me and the AI consistent after you're gone. Training — three live screen-share sessions, 90 minutes each Session 1 — the build. You share your screen and do most of the work live while asking me the questions you need answered to make good decisions. I want to watch it get made and answer in real time rather than send you a brief and wait. Reserve the last stretch to walk me through the significant choices you made and why. Session 2 — real use, a few days later. I'll have run the board for several days and will bring a list of questions and friction points. We work through them, fix what isn't working, and finish the pieces we didn't get to in Session 1. Session 3 — depth. Show me what I'm not using: automations and rules, reporting and saved searches, template patterns, integrations, and how to clone this structure for a second industry vertical. I want to leave with several things I'd never have found on my own, and I want to build at least one of them with you rather than just watch. Short Loom recordings of the sessions, or a written cheat sheet, would be a plus. What you'll get from me Admin access to the workspace A written brief on the seven groups and how the mini projects relate Fast answers — I'm responsive throughout Requirements Demonstrated builds for real clients in Asana or a comparable platform. Send two examples with a sentence on the problem each solved. Fluent with custom fields, dependencies, rules and automations, templates, and advanced search. Able to explain the tool to a smart non-expert without jargon. The teaching half matters as much as the build. Available for live sessions during US Eastern business hours. Clear spoken English. Nice to have Experience structuring consulting or agency client work Familiarity with the Asana API, or tools that read and write it programmatically (Zapier, Make, custom integrations, AI assistants) Working knowledge of more than one platform, so your recommendation is informed rather than default Confidentiality The board holds client work under an active engagement. I'll ask you to sign a short NDA before granting access, and some names may be redacted. Budget and structure Fixed price: $500 for the build and all three sessions (4.5 hours live), in Asana. Plus up to 5 hours at your hourly rate over the following 30 days for follow-up questions and small fixes, billed only if used. In your proposal, include: your hourly rate for the follow-on, how much prep time outside the live sessions you expect, and your earliest availability for Session 1. SCREENING QUESTIONS I'm on Asana Starter, which means no portfolios. Upgrading to Advanced would roughly double my monthly cost. For one person running twenty related mini projects, do I actually need Advanced? If not, how would you structure it on Starter? I chose Asana on an AI's recommendation, not from experience. If you'd put a solo consultant with this workload on a different platform, name it and give me your reasoning in a few sentences. If Asana is the right call, say that instead — I'm not fishing for a switch. What would you do differently when structuring a board that an AI assistant reads and updates through the API, versus one only a human touches? Link to one build you've done. Describe the client's problem and what you changed. How much prep time outside the three live sessions do you expect this to take?