Does Your Startup Feel Chaotic? Good.

As long as you're cultivating the right kind of chaos

Via Lucas Crespo

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Kate here. No one goes into a startup thinking that there won’t be some amount of chaos—myself included. Today we’re thrilled to publish a new piece about startup chaos by Jean Hsu, whose post about ask vs. guess culture hit number one on Hacker News. Jean is a vice president of engineering with whom I had the opportunity to work at Medium, where she was an early engineer. She’s been writing about startups for a decade and founded a coaching and leadership development company for engineering leaders. In this piece, she distinguishes between the good startup chaos—what she calls necessary chaos—and the bad—or unnecessary—and offers advice on how to reduce the latter.

Startups are inherently chaotic. There are a lot of unknowns, and teams need to navigate uncertainty as startups grow. New data might require you to re-order your roadmap, or you may fail several times as you experiment to find product-market fit. Sometimes, you’ll need to pivot your product to respond to a change in the market. In more extreme cases, you’ll need to pivot your entire company strategy.

Some of this chaos is good. It leaves room for creativity, gives team members more agency, and keeps your organization flexible. I call this necessary chaos

What doesn’t work is unnecessary chaos, borne by a lack of planning. Unnecessary chaos eats into any bandwidth for necessary chaos, which is the lifeblood of startups.

To be clear, no startup is completely without unnecessary chaos, and the gray area between unnecessary and necessary chaos is wide. However, in my experience as a vice president of engineering at several early-stage startups, I know firsthand the importance of not giving in completely to unnecessary chaos.

In this piece, I lay out methods for startups to identify unnecessary chaos, learn how to manage and reduce it, and make room to take on necessary chaos.

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Unnecessary versus necessary chaos

In my 13 years working at startups, I’ve witnessed many examples of unnecessary chaos—here are a few.

A major release has been planned for months, but launch communications—new positioning, website copy, customer email, blog post—are reviewed at the last minute.

A manager reschedules 1:1s every week because of ongoing conflicts, and they don’t take the time to find a recurring slot that works.

There are meetings with no agenda or structure, and there are often follow-up meetings.

CEOs artificially manufacture deadlines, fire drills, and strategy pivots to force execution on their team. They don’t always provide new information or context as to why. Sometimes, these pivots lead to frequent reorganizations that break apart effective teams. A red flag is when a recent hire goes through multiple teams and managers within a year at the company.

Although there have been ample opportunities to provide feedback, someone swoops into a design file as a feature is about to launch, questioning its basic premise and functionality.

There are controversial 1000-plus line pull requests submitted the day before someone goes on vacation.

If you’ve worked at a high-growth startup, many of these examples will sound familiar. Of course, not all chaos is bad. Even the best-laid plans require adjustment, and sometimes even complete re-thinking. That’s where necessary chaos enters.

Necessary chaos embraces the uncertainty inherent to startups. Here are a few examples:

As growth accelerates and larger teams are needed, people stretch into new roles, teams scale and split, and new processes are formed.

After a promising call with a potential new customer, the product roadmap is re-prioritized to incorporate features that will help the team close the deal.

A bug bash held before launch reveals UX issues that weren’t originally surfaced. The team diverts resources to fix it before rolling out the feature more broadly.

Market fluctuations lead to team restructuring and reorganization.

A product manager goes out on parental leave, and designers and engineers need to adopt more product thinking and project management skills for a few months.

A serious production bug slips through the cracks. Monitoring catches the increased errors and pages an on-call engineer to fix it.

Necessary chaos is important—people who gravitate towards startups tend to be excited to tackle it. 

Unnecessary chaos can ruin a startup’s equilibrium

Unnecessary chaos is unsettling. Often, it creates a culture of low trust and frustration.

You might trust your teammate less if you’re constantly asked to urgently review requests that don’t need to be urgent. You might be tempted to tell them that poor planning on their part should not constitute an emergency on your part.

But its impacts are far-reaching. Unnecessary chaos can reduce your bandwidth for managing necessary chaos. When necessary chaos comes up on a team that hasn’t figured out how to handle the unnecessary, team members can be low energy, frustrated, and resentful.

I find unnecessary chaos particularly maddening in meetings, when one or two people derail it and no one steps in to rein in the conversation. Over time, I found that instead of sitting back, tuning out, and complaining about the meeting afterwards, I could be the one to step in and get the discussion back on track. I soon found myself nominated as facilitator for most team meetings, as my coworkers trusted that I would keep unnecessary chaos to a minimum.

On the other hand, when a team has worked to reduce unnecessary chaos, team members are often more motivated to take on the necessary, whether it involves strategy shifts or late nights to get something out the door. These teams trust that changes in plans come with good reasoning. There is a built-up history of transparency, communication, and planning, and team members assume the best of leadership.

Tactical ways to reduce unnecessary chaos 

If you’re an individual contributor, you can reduce unnecessary chaos by communicating effectively, which might mean regular updates to team members regarding progress. Resist the urge to hide in a hole if your work starts to slip. Ask for help so that others are not caught off guard when they find out your project is behind. Rather than unstructured, stream-of-consciousness writing, opt for structured written communication in templated tech specs or product requirement docs.

If you’re running a meeting, create predictability and structure. If you create space for open discussion, facilitate aggressively to keep the discussion relevant and aligned with the meeting’s purpose. Structured constraints can help team members feel safe enough to bring up and engage with real topics, especially those dealing with necessary chaos.

If you’re in a position of leadership, try to be a steady presence for your team. During transitions such as restructurings or layoffs, manage careful communications to reduce any feelings of being blindsided. 

Communicate clear and thoughtful plans that give people something to anchor onto, while establishing that plans may and will change in response to new information. During team re-orgs, I’ve coordinated with other leaders to create communication timelines, detailing when people will hear about the upcoming changes either individually or as a team. As each interaction occurs, the responsible party checks it off the list so others know that it’s happened. This prevents situations like a manager hearing from their direct report that they’re going to be moved onto another team, which is understandably unsettling.

Whether you’re an individual contributor or a team leader, the following prompts might be helpful to consider:

  • How can you reduce the likelihood of people being blindsided or caught off guard? 
  • What expectations can you set ahead of time (for a meeting, for a sprint, for a quarter, for the year) with your team? 
  • What processes would create more predictability and structure?

Reduce—not eliminate—unnecessary chaos

When your on-call rotation has well-tuned and actionable alerts, your engineers will understand if they are occasionally woken up in the middle of the night to look into a production issue.

You may find that your team is excited to be all hands on deck to get an unplanned feature out for a lucrative customer after a few months of steady and well-planned feature releases. 

If you consistently show consideration for your coworkers’ time, last-minute urgent requests are viewed positively. Even when it’s inconvenient, they will be eager to help you out, knowing that the last-minute request did not come from poor planning, but rather from an unexpected need.

Then, you can start to tackle the important part of startups—necessary chaos.

Jean Hsu was most recently the vice president of engineering at Productable and Range. Previously she was an early engineer at Medium. She writes about navigating life with a career in tech at Tech and Tea

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