A guide to scaling enterprise SaaS product and engineering teams, from $0 to past $100M ARR.
One of the most harmful behaviors I’ve observed in ineffective leadership is a tendency to add chaos when one enters a room. Chaos comes in many flavors: A decision was reached about an important architecture question weeks ago, but someone suddenly insists that you revisit the project’s fundamental goals at the 11th hour. An executive insists that their project is most important, and pushes it onto the roadmap. Or maybe you leave a productive meeting without concrete next steps, and are right back where you started in a week.
My litmus test for effective leadership: any room that you enter should have more certainty and a firmer plan by the time that you leave it. Good leaders can walk into a situation where people have lost track of their goals and get everyone aligned on a clear path forward. They remove unimportant details, distill complex situations to their essence, and get the right decision-maker to make a call – even if it’s not them. They’re able to not only stop bad plans before it’s too late, but get them moving again in the right direction.
Usually, chaos-causing behavior is unintentional and comes from a good place. Often people are just missing context, or haven’t developed a rhythm for making sure that projects and plans stay organized. In rare cases, it can arise for less savory reasons: someone wants to flex on others by diverting a conversation to a favorite topic or forcing a change of plans.
I’ve been guilty of causing my share of unnecessary chaos, and have always regretted it. However, I was fortunate enough to also have a number of teammates who weren’t shy about calling me out for this over the years. I’ve since built a grab bag of practices on how to be better:
And most importantly: The fancier your title, the more you must avoid causing chaos. If Bob the Intern frantically flip-flops on the plan for his summer project, people will patiently help him towards a good path and perhaps make sure he has less caffeine tomorrow. If Bob the CEO flip-flops on his strategy, people will capsize the ship trying to enact his will. Remove chaos and you and your team will be happier and more successful.
Previously published here.
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