When Your Boss Becomes an Octopus in Distress

Ever worked for a boss who’s metaphorically drowning? They’re behind on updates, struggling to keep pace with decisions, and reacting to everything like they’re in a constant rip current.

They start to resemble a distressed octopus, becoming an eight-armed whirlwind, thrashing, reaching, and occasionally lashing out. If you wander into range, one of those tentacles might land on you, and suddenly you’re the reason everything’s tangled.

Here’s how to protect yourself while still helping them swim to safe waters:

Keep your distance… but not too far: Stay in their peripheral vision so you’re available but not in the strike zone. This means being present with regular updates, but avoiding last-minute “by the way” surprises.

Anchor yourself: Be clear on your own priorities and deadlines. When they fling new requests your way, you’ll have a calm, factual way to say, “Happy to do that — here’s what will shift if I do.” This reduces random tentacle grabs.

Toss them a lifebuoy, not a lecture: Offer help in small, easy-to-grab pieces. “I’ve drafted a quick summary for you” is better than “You need to read all 47 of these emails.” They can latch on without feeling overwhelmed.

Guard against sucker damage: Document important decisions and actions. This isn’t about mistrust — it’s about making sure you both remember who agreed to what when the waters get choppy.

Know when to swim away: If your leader is truly in over their head, they may need more support than you can give. Recognise your limits and escalate appropriately, before the whole team goes under.

Helping a drowning octopus-boss isn’t about diving into the chaos with them — it’s about staying steady, creating clarity, and making sure you’re not mistaken for lunch in the process.