Three Types of Management Problems

The busiest time in my career so far was spent at a startup in growth mode. This is a deeply chaotic time in the life of a new company as there’s so much opportunity to expand, so much to do just to keep the lights on, and not nearly enough people to do it. There are a million tasks that demand your attention, and the structure to get them all done doesn’t yet exist. Doing everything during this time isn’t possible, so you need to brutally prioritize.

During this growth phase, management is all about solving problems – not only your own, but more importantly your team’s. Solve enough of the right problems and you’ll succeed. Solve too few of the most important problems and you’ll go out of business.

One of the first questions that I focus on when someone on my team wants to gameplan a problem is whether the situation is likely to improve, get worse, or stay the same with time. Over time I’ve found that this perspective is helpful in adding clarity, especially when you have too many problems to solve and will need to triage aggressively. When combined with an assessment of the raw severity of an issue, a view into whether a problem will improve or deteriorate with time is key to prioritization.

Problems that get worse the longer that you put them off should usually be handled immediately. For example: if your product is churning customers faster than it’s acquiring them, every day saps a little bit more of your income and incrementally reduces your ability to maneuver. If someone on the team is being particularly toxic to somebody else, every day that you put off correcting the issue is another day that you’ve normalized the behavior, and another opportunity for something really terrible to happen on your team.

Deteriorating problems also compound and cause deleterious downstream effects. If you have increasing churn, you’ll slowly accrue detractors in the marketplace and eventually hit a critical mass where a poor reputation also impacts new customer acquisition. If you have a toxic team member, eventually they’ll cause someone to quit, adding a hiring fire drill to a management problem. These problems are like cancer – even if the impacts aren’t yet severe, you should handle them as quickly as possible while they’re still tractable.

On the other hand, some problems are stable – they won’t get better or worse with time. Examples include:

  • Our user account settings page is really ugly, and remains heinous every day that we don’t touch it. However, it has low traffic and isn’t business critical for most customers.
  • Expense tracking is a mess, and takes up a bunch of manager time every month.
  • A database service reliably pages around once a month. It doesn’t cause a production incident, but it does require someone to babysit it.

The most important thing to note about these situations is that some stable, low-severity obstacles can be kicked a surprisingly long way down the road without screwing up your business. Stable problems require a plan, but they don’t have a high chance of becoming fire drills. If deteriorating problems are like cancer, these problems are like having bad knees – important to plan for, but only requiring immediate resolution when the severity is high.

And finally, some problems simply get better on their own without any intervention, or at least have a good chance of fixing themselves. New teams are having difficulty gelling and operating as a unit – with time, many teams will adapt and work better. Someone on the team is bright but doesn’t have experience on your mobile technology stack – given time, they should be able to learn. This principle applies to very broad classes of problems as well. For example, challenges around product marketing or positioning can often get solved by a team simply running many sales cycles and seeing what sticks – teams tend to improve at telling their story over time.

These potentially self-resolving problems are actually the most important to identify, because you can sometimes solve them by ignoring them. It’s almost always worth finding them and fixing them last (or not at all), in order to save time for the much more significant problems that one needs to solve elsewhere.


Knowing what tasks or situations to prioritize is hard, especially when you’re busy. When deciding where to spend your time, consider the dimension of whether problems are going to improve, deteriorate, or remain stable over time.