The Right Problems

Over the years, I've noticed a lot of my (and others') frustrations at work come from feeling like the problems I'm solving shouldn't be problems, or that the problems I'm facing are outside of my control. As I've settled more into my management responsibilities, I've found that the biggest bang for my buck has been to focus on helping folks start solving the right problems and stop worrying about things that are too small or too big and nebulous.

Small, Bullshit Problems

These are problems you encounter frequently in little, annoying ways. Some classic examples include:

  • Why do we keep redesigning our button style every time we implement a new page?
  • What's the real button style? I guess I'll make a new one too, but what should it look like?
  • Who has that file with our brand colors and elements in it?
  • They left the company? Shit.
  • Wait, your team is working on that project? Mine too.
  • I'm interviewing someone today? For what? Who are they? What role is this for?

Yes, these are small problems that, individually, don't mean a lot. But over time and with enough of these piling up, you wind up spending a lot of your design or management time dealing with them. So instead of working on that UX problem, you spend a week designing a new button and arguing in critique about the style (that isn't standardized anyway). Or instead of focusing on asking great questions in interviews, you're too busy trying to figure out who the person even is and how they got in the building in the first place.

Small, bullshit problems in aggregate prevent you from solving the real ones. Whenever I see someone (or myself) dealing with these things, my first instinct is to focus all my energy on removing those issues going forward. There are 45 different button styles and we go through the same rigamarole every time someone makes a new one? Let's build a style guide and spend a week or two arguing about the buttons once and for all. Then let's never, ever think about it again. Interview loops are messy and unclear? Let's codify exactly what our recruiting process looks like and build in steps that are transparent and inclusive. And then let's never have to be confused or wonder what's going on again.

Basically, treat small annoying problems like big, systemic ones (which, if you look at how much time you spend on them overall, they absolutely are). Additionally, empower the people encountering these problems day-to-day (whether they're managers or not) to tackle solving them. They'll clear them out before you even notice they exist, which will save you all sorts of time to deal with...

Big, Outside of People's Control Problems

While small, bullshit problems are bad over time, these types of problems are the ones people cite when they leave your company. For example:

  • What's my role?
  • How do I make progress toward the next level?
  • I'm getting design feedback through the grapevine and can't address it directly.
  • My project got cancelled suddenly and I don't know why.
  • My manager isn't there for me.
  • Things are moving too slowly.
  • I don't feel empowered or trusted to do my job.


These are big problems, but they're just as bullshit as the small ones. No one should ever have to think about these things, particularly because there's just not much they can do about them. If your organization has individuals worried about things like these, drop what you're doing and start to fix them. Remove ineffective managers, start being as transparent and inclusive as possible about changes in organization and strategy, build teams you can trust and empower, give people clarity on their role and set goals with them.

It's kind of amazing the difference in product quality when people can spend less time worrying about this meta-layer of stuff and concentrate on their actual jobs. Additionally, by solving these problems, you'll not only retain great people, but it will be easier to hire more great ones (who can sniff out when things aren't quite right during the interview).

The Right Problems

The reality is that you'll never completely solve all the problems. Solving a lot of the little ones will, at times, give way to larger, meta questions. Tackling the big problems will inevitably lead to a number of small, annoying ones as you evolve and iterate. Also, your organization is probably growing, which means that even if everything is happy and beautiful today, it won't be soon.

The goal, of course, isn't to rid yourself of all the problems (if you think that's your goal, you're going to have a bad time). Rather, it's to be solving the right problems at the right times. Too often we let our problems (at an organizational and individual level) sit and fester, creating a frustrating work experience and ultimately making it harder to resolve when we finally choose to. Organizational debt is a real and dangerous thing. To achieve success, we have to train ourselves to look ahead and proactively identify upcoming challenges and be prepared when they finally show up.