Achilles' Heel Retrospective
Two of the oldest stories about hidden weakness, turned into a sprint retro: the vulnerability everyone knows about, and the risk that got in looking like a gift.
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The board
01
ACHILLES' HEEL
What's our single biggest vulnerability right now?
02
TROJAN HORSE
What snuck in looking like a win, but is quietly hurting us?
03
SHIELD
What's protecting us this sprint?
Achilles was invincible everywhere except one heel, and Troy fell not to a siege but to a gift its own soldiers wheeled inside the walls. This retrospective borrows both stories for one reason: teams are rarely hurt by the risks they're already watching. They're hurt by the one exposed spot nobody protected, and the one that arrived disguised as good news.
Achilles' Heel names the vulnerability the team half-knows about already — the single point of failure everyone quietly works around instead of fixing. Trojan Horse names something sneakier: a shortcut, dependency, or 'quick win' that looked completely safe going in and is quietly causing damage now that it's inside. A Shield column keeps the sprint from reading as all danger, naming what actually held the line.
When to use an Achilles' Heel Retrospective
- Teams that keep circling the same known weak point without ever prioritizing a fix for it
- After adopting a new tool, library, or process that felt like a win — a good moment to check for hidden costs
- When a retro needs a memorable, non-corporate framing to get people to actually name the risk out loud
- Reliability- or security-minded teams who already think in terms of single points of failure
How to run an Achilles' Heel Retrospective
- 1
Name the battlefield
Before writing, the facilitator states what's at stake this sprint — the release, the system, the deadline the team is defending. In Retromik, put it in the board's focus question so it stays visible above every column.
- 2
Pick one heel
The format asks for the single biggest vulnerability. Several heel cards are fine while writing, but use the vote to choose one.
- 3
Look for Trojan horses among recent wins
Ask the team to revisit last sprint's quick fixes and easy yeses. A Trojan horse usually looked like a win when it came in.
- 4
Name what the shield is made of
For each Shield card, ask what makes it work. A protection the team understands is one it can keep, or copy for the heel.
- 5
Give the heel a defender
End with an owner and one concrete step for the chosen heel, and decide what to do about the top Trojan horse.
Anonymous writing, voting, grouping and action items work the same as in any Retromik retro.
Example cards
What good cards look like for a software team. Specific, about the work, never about a person.
ACHILLES' HEEL
- Only one person can deploy the payments service.
- No alerts on the nightly import job.
TROJAN HORSE
- The quick caching fix that now serves stale data.
- Saying yes to every small request from Sales.
- A tool we adopted to save time that now needs its own maintenance.
SHIELD
- Good test coverage on checkout.
- The weekly sync with Support.
A 45-minute agenda
- 0–5 minName the battlefield
- 5–15 minWrite cards silently
- 15–20 minVote, and pick the one heel to defend
- 20–35 minDiscuss the heel and the top Trojan horse
- 35–45 minAgree a defender and a first step
Common mistakes
- The heel column becoming a long risk list. The format is about one weak spot.
- Using Trojan horse to blame whoever made a past decision. Talk about the decision, not the person.
- Skipping the Shield. It shows what's already protecting the team.
- Ending without an owner for the heel.
Frequently asked questions
What is an Achilles' Heel retrospective?
A themed retrospective with three columns: Achilles' Heel (the team's known, single biggest vulnerability), Trojan Horse (something that looked like a win but snuck in a hidden cost), and Shield (what's actually protecting the team). It gives two different shapes of risk their own column instead of lumping every problem together.
What's the difference between Achilles' Heel and Trojan Horse?
Achilles' Heel is a vulnerability the team already knows about but hasn't fixed — a single point of failure everyone works around. Trojan Horse is a risk the team didn't see coming because it arrived disguised as something good: a quick fix, a new dependency, or a process change that seemed like an improvement until it wasn't.
Isn't this just Strengths, Risks, Learnings with different names?
The columns rhyme, but the framing changes what people write. 'Risk' invites a generic list; 'Achilles' Heel' asks for the one thing that could actually take the team down, and 'Trojan Horse' specifically hunts for risk disguised as good news — a category most retros never surface on their own.
Is the Achilles' Heel template free?
Yes. Retromik is free — create a board with the Achilles' Heel template and share the link. Guests join without an account, and cards stay anonymous while people write.
How do you spot a Trojan horse?
Look at things that arrived as wins: a shortcut that saved a day, a tool that solved one problem, a request that was easy to say yes to. If it now costs the team time, quality or focus, it's a Trojan horse.
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