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Asana, Kanban, and Waterfall — A Cortado Primer

This is Module 2.2 of the curriculum. Read it before you watch the Asana tutorial videos so you know why you're learning what you're learning.

TL;DR

Cortado does not pick one project management methodology and force it on every engagement. We pick the one that fits the work. The two we use most:

  • Waterfall — for engagements with a fixed scope, a defined endpoint, and sequential phases (most due diligence, most discovery → analysis → deliverable work)
  • Kanban — for engagements that are continuous, where work flows through a pipeline indefinitely (most RevOps engagements, fractional CRO/CMO work, ongoing coaching)

Asana supports both. Your job is to know which one your engagement is using and run it cleanly in that mode.

Why this matters at Cortado

From David's PMO Overview at the January 2023 All-Hands (Corporate - SHARED/Shared - All Hands Meetings/2023 All-hands Meetings/Recordings from All-hands Meetings 2023/AllHands_010623_PMO_Overview_Training.mp4):

"Every project manager isn't just thrown into the water and told, hey, go figure out how to go deliver with maybe, I don't know, Asana. Maybe I'm great at projects. Maybe I know waterfall projects, but I don't know Agile. Everybody's got a different strength. ... This isn't a one-size-fits-all cookie cutter. Here's what's right for you based upon what you're doing."

The point of this primer is so that you walk in knowing the difference, and don't carry one model's habits into the wrong engagement.

The three methodologies in plain English

Waterfall

Plan the whole thing up front. Execute sequential phases. Each phase produces a deliverable that feeds the next phase. You finish.

Looks like: Discovery → Analysis → Recommendations → Build → Transition.

Strengths: clarity of scope, predictable milestones, clean handoffs, easy to bill against, easy to communicate to a client used to Big 4 work.

Weaknesses: rigid against new learnings, late integration of customer feedback, "we should have thought about that up front" failures.

David, same All-Hands:

"There are going to be things that the customers are going to tell us later. That's an aspect of Agile. We'll have to work on that as we get there. But what we know upfront can be integrated in the project planning."

That sentence captures the Cortado posture: Waterfall is the default scaffolding; Agile/Kanban habits get folded in where useful.

Agile

Plan in short cycles (sprints). Deliver working pieces frequently. Inspect and adjust after each cycle. Don't pretend you know the full plan up front; trust the iteration.

Looks like: 2-week sprints with a planning meeting, daily standup, demo, retro.

Strengths: absorbs change, surfaces problems fast, keeps stakeholders engaged.

Weaknesses: ceremony overhead, hard to budget against, requires a customer who wants to be a partner not a buyer.

We rarely run pure Agile at Cortado — most of our clients aren't built for it. But we borrow the posture (inspect-and-adjust, customer-as-partner) constantly.

Kanban

Don't plan in phases. Don't plan in sprints. Run a continuous pipeline of work that flows from Backlog → In Progress → Done. Limit how much is In Progress at once (WIP limits). Focus on throughput and cycle time, not milestones.

Looks like: a board with columns. You pull from Backlog when you have capacity, you push to Done when complete. No fixed start, no fixed end.

Strengths: great for steady-state work, easy for clients to glance at and understand, low ceremony overhead.

Weaknesses: no natural deadline pressure, harder to forecast, can drift into "we're always doing things but never shipping things."

When Cortado uses which

Engagement type Methodology Why
RevOps build / RevOps execution (Crownpeak, Aqfer, EverAg, USRBP, Beckway) Kanban Continuous pipeline of process fixes, system tweaks, enablement tasks. No fixed end.
Fractional CRO / iCMO / Interim CRO (Clarus, Spirion) Kanban Ongoing operational ownership; work flows in continuously.
Commercial Due Diligence (Project Aster, Project Tiger, Project Radar) Waterfall Hard deadline (deal close), defined scope, sequential phases, single bound deliverable.
GTM Assessment / GTM Optimization (Uptive, IVP, DCN, HC) Waterfall with Agile borrowing Discovery → Analysis → Recommendations is sequential, but we iterate inside Analysis based on findings.
GTM Build (Vomela, Merchants Fleet, Worksuite) Hybrid Waterfall for the design phase, Kanban for the build/deploy phase, transitions to client-owned Kanban at end.
Coaching engagements (CEA, DTN Big Deal, GreenSlate, IVP AM Coaching) Kanban Cohort-based but recurring; each session is a unit of work flowing through.
Pricing engagements (Omnigo, RightCrowd, Quin Holden partnership) Waterfall Analysis-to-recommendation cycle with a defined endpoint.

Heuristic: if there's a final deck the client signs off on and goes away with, it's Waterfall. If we're operating inside the client's revenue function on an ongoing basis, it's Kanban.

The Cortado Engagement Methodology — our actual delivery model

Underneath both Waterfall and Kanban, every Cortado engagement runs through the same 11-step methodology that David (PMO) and the partners codified. This is taught in the Consultant Development Program as a full audio course:

HR - Learning & Development/Consultant Development Program/Cortado Engagement Methodology/

The 11 modules:

  1. Learning Objectives
  2. What Is It
  3. Why is it important
  4. How do you Use It
  5. How to Organize
  6. How to Discover and Assess
  7. How to Recommend and Decide
  8. How to Design
  9. How to Build & Deploy
  10. How to Optimize
  11. How to Transition

Plus the deck: Cortado Engagement Methodology Training.pptx in the same folder, and the one-pager at Corporate - SHARED/Shared - Delivery Guides/0. CG Engagement Methodology/Engagement Methodology 'One Pager'.pdf.

You can map either Waterfall or Kanban to these phases. Waterfall walks through them once in order; Kanban cycles through Discover → Recommend → Design → Build → Optimize repeatedly while Organize and Transition bracket the engagement.

You're expected to listen to the full audio course by end of Week 3. It's 11 short modules; do them on your commute or during deep-cleanup work. Reference the deck while you listen.

How Asana expresses each

Asana is methodology-agnostic. Both Waterfall and Kanban projects live in Asana; the difference is in how you set them up.

Waterfall in Asana

  • List view as the default (not Board)
  • Sections by phase: Discovery, Analysis, Recommendations, Build, Transition
  • Tasks have start dates and due dates that respect dependencies
  • Timeline view is your friend — it's the Gantt-like view of the whole engagement
  • Milestones marked at the end of each phase (Asana has a Milestone task type)
  • Updates use the Green / Yellow / Red status flag against the milestone plan

Kanban in Asana

  • Board view as the default (not List)
  • Sections by status: Backlog, This Week, In Progress, Blocked, Done, Archive
  • WIP limit on In Progress (no formal enforcement — culturally enforced; max ~3 per person)
  • Tasks generally do NOT have rigid due dates — they have priority
  • Updates use the 4 Blockers format more than Green/Yellow/Red, because there are no milestones to be on/off track against
  • Friday housekeeping: clear Done → Archive

Both

  • Updates posted weekly (Friday EOD) in the engagement's #client-name Slack channel AND as an Asana Update
  • Asana for Slack integration on (every PC should have this; see Asana tutorial video 10)
  • Customers are added as Asana collaborators on client-facing projects so they receive Update emails automatically (see Asana tutorial video 8)

From the same 2023 PMO training:

"Even if they're not in there all day long working on tasks or being assigned it, if for no other reason, it's for the update."

Status flags — when do you call it Red?

This came up directly in the 2023 PMO training. The "softball" answer:

"When do you call it red? When it's already slipped or before it slips? ... That's a softball." (the implied answer: before)

Use this rubric:

Flag Waterfall meaning Kanban meaning
Green / On Track Milestone will hit its date Throughput is steady; WIP is healthy
Yellow / At Risk Slip is likely if nothing changes; you see the path back A blocker has appeared that's slowing the flow; you can route around it
Red / Off Track Slip is no longer recoverable without scope/time/resource change Pipeline is jammed; intervention needed (EM conversation, not just a flag)

Default to over-flagging early. Yellow today with a recovery plan beats Red on the Steerco.

What the PC owns vs. what the EM owns

Regardless of methodology, the split is the same:

Owns PC EM
Project plan structure in Asana ✅ reviews
Task creation and updates ✅ spot-checks
Status flag color proposes confirms
Blocker escalation identifies resolves with client
Steerco scheduling and shell ✅ content fill
Client-facing strategic communication drafts sends
Methodology choice informed decides

Methodology choice is an EM call. But the PC should be able to tell which one is in play within the first week of joining an engagement, and run it accordingly.

Practice for the project coordinator

By end of Week 2, you should be able to walk into any active Cortado Asana project and answer in under 60 seconds:

  1. Is this Waterfall or Kanban?
  2. What evidence am I reading off the board?
  3. What's the current status flag and why?
  4. What blocker would I flag to the EM right now?

Bring those four answers for three different engagements to your Thursday Week 2 GROW with your onboarding mentor. That's the Module 2.2 deliverable.

Where to go deeper