Things go wrong, and they always do.

Working in an early-stage startup, I have my fair share of near-breakdowns and office walk-outs from all the negative energy resulting from things going wrong. Clients calling in angrily to complain, coworkers getting frustrated, broken things not getting fixed on time. Shit happens, and sometimes, they happen all at the same time.

I’ve been thinking about this issue for quite some time now and have been doing some mental experiments. I have so far come up with a 3-step heuristic on how to best handle these situations.

Keep Calm

This is not as easy as it sounds when many of the office phones are ringing, colleagues demanding answers, teammates relying on you for solutions, and other commitments all demanding your prioritized time and energy all at the same time.

So my first step is try to keep calm. What works for me is doing a “forced mental reboot” where I temporarily step out of the chaos zone for a few minutes and breathe deeply, empty my head, and prepare to face the incoming challenges.


Upon returning to the chaos zone, first thing I do is gather all the information related to all the issues at hand. Then I force rank all the issues by priority in terms of business impact. Clients come first, colleagues come second, personal tasks come last — I haven’t clearly thought through why this is how I judge business impact, but it’s been working so I’ll stick to it for now.

After force ranking all the issues at hand, it’s time to get your hands dirty and tackle the problems one by one. I think the critical point here is to really tackle the issues one by one and not multi-task. Multi-tasking often causes new issues as well as half-fixing current issues.

Briefing and Proposal

I don’t like treating a fixed problem as “done” even when it’s completely fixed. It feels irresponsible and dangerous, dangerous because I’ll have this looming threat at the back of my mind of it happening all over again.

So I have developed this habit of writing detailed status reports to all the parties concerned. It consists of a breakdown of what happened and a proposal on how we will prevent the same issues in the future and how we can do better.

The contents of the report mostly follow this outline:

  • Apology for what happened
  • Timeline of events
  • Current status
  • Root cause of the issues
  • How we’ll do better
  • Another apology
  • TL;DR

And yes, TL;DR is a must. You’d be surprised at the percentage of the population who never reads lengthy emails.