The Contoso Convergence, Episode 1: The Summons at Waterdeep Docks

An Advanced Dungeons & Dynamics 365 session. Episode 1 of 14.

Every consulting engagement has an origin story. Most of them start with a kickoff call, a signed SOW, and someone on the client side saying “we’re really excited to get started” in a tone that suggests they are not.

This one starts at the docks, at dawn, with a folder that’s still warm from the printer.

Welcome to the Contoso Convergence. This is the campaign we’re running here on the blog: a full Advanced Dungeons & Dynamics 365 session, told in fourteen episodes, following a five person party sent to rescue a D365 Finance & Operations go live that has already failed twice. If you’ve ever lived through a stalled implementation, you’ll recognize the dungeon. We’ve just given it a party and some dice.

Here’s the party, for reference:

• Thorne Ledgerkeep, Paladin (Functional Consultant, Finance). Cannot tell a lie about a trial balance. Weak against scope creep.
• Vex Nullpointer, Rogue/Artificer (Technical Consultant). Picks locks on legacy integrations. Allergic to undocumented customizations.
• Sable Query, Wizard (Solution Architect). Casts Data Mapping at range. Vulnerable to “just one more report” requests.
• Captain Marge Dunwell, Fighter (Project Manager). Frontline tank. Immune to fear, mostly immune to steering committees.
• Ai. Cassiopeia, grey collar party member, an AI agent bound to the Wayfinder’s Network. Casts Copilot Suggestion. Cannot be blamed in the retro, which everyone resents.

They work for the Waterdeep Trading Company. Their assignment: Contoso Coffee Roasterie, a mid market roaster whose D365 go live has now stalled twice, and whose current state can be summarized by one line on a whiteboard that nobody has erased.

Let’s begin.

---

The Session

GM (Dessa, dispatching the party): Contoso Coffee Roasterie. Third go live attempt. The first two consultants who touched this engagement now work in agriculture. You leave at dawn.

Thorne: What’s the scope?

GM: That’s the thing. Here’s the SOW. It’s forty one pages. Page seventeen is missing.

Vex: (flipping pages) Page seventeen is always the page with the integration list on it. Always.

Sable: I’ll cast Data Mapping when we arrive. Can’t do it blind.

Marge: Team, standard rules. We document the golden path, we do not perform the golden path. If Contoso’s demo deck has a slide that says “and then the order just flows through,” that slide is lying to us.

Ai. Cassiopeia: I have ingested the prior two consultants’ status reports. Both end mid sentence.

The party arrives at Contoso’s gates. The receptionist hands Thorne a folder. It is warm, as though recently printed in a panic.

Receptionist: They’re expecting you in the war room. Also, go live is in six weeks.

Thorne: The SOW says twelve.

Receptionist: That was the old go live date.

The party is led down a hallway that smells faintly of burnt coffee and cold pizza. Someone, at some point, taped a printed banner to the wall that reads “WE ARE ALMOST THERE.” Someone else has crossed out “ALMOST” and written “NOT” above it in marker.

The war room door creaks open. Inside, a whiteboard covered in red ink reads only:

“WHERE IS THE MARGIN GOING.”

No question mark. Nobody in the room has energy left for punctuation.

---

Why this scene, why first

Every stalled implementation has a version of this moment: the point where a new team walks in and the first thing they learn is that the paperwork doesn’t match the reality on the ground. A missing page seventeen. A go live date that’s moved without anyone updating the SOW. A room that’s been living inside the same unanswered question for months.

None of that is dysfunction, exactly. It’s what happens when a project runs long enough that the documentation stops keeping pace with the truth. The SOW says twelve weeks because that’s when someone last had time to update it. The scope says one thing because rewriting it would mean admitting how much has drifted. Nobody’s lying. Everybody’s just too busy surviving the current sprint to fix the paper trail.

Marge’s line matters here, and it’s the whole thesis of this campaign: document the golden path, don’t perform it. A demo that only shows the happy path teaches the team nothing about the exceptions they’ll actually live in. That’s not a throwaway rule for a fictional party. That’s the difference between a go live that holds and a third failed attempt.

We’ll come back to that idea more than once over the next thirteen episodes.

---

What happens next

The party has a whiteboard, an unanswered question, and a go live date that just got six weeks shorter. In the next episode, they meet the Contoso stakeholders, including a woman named Priya who nobody introduces by title, and the party learns that somebody has been quietly running the real numbers in a spreadsheet the entire time.

Next episode: Episode 2, The Shadow Ledger (coming soon)

---

If any of this feels familiar, that’s on purpose. This campaign is built on the same framework behind Gamifying the Enterprise: Game Mechanics for Continuous Proficiency, available now on Amazon: https://www.amazon.com/dp/B0GY3VWLVX

And if you want to run something like this for your own team, not the dragons, the actual configuration, the AD&D365 guides are the place to start: adnd365.com/start