big lists does not a good leader make

I’m constantly surveying. I survey the people around me, I survey myself, I survey ideas, I survey my thoughts, and I never stop surveying trends.

In the 2 weeks leading up to Thanksgiving I forcibly made myself conscious of the way people around me were leading others and in some cases, how they were not.

Most of my style comes from a fairly intentional “speak with your feet” thought process.

That is to say that at any given point where I physically put myself (or allow myself to be put) is where I can be the most intentional about who I’m working with and what I’m working on. I struggle with it only because it scales poorly across 4 office locations that span the US so I’m attempting to see trends that work and those that don’t in myself and in others.

That struggle. Spawned this particular question. What trends do I see in those who are effective with their team in multiple locations? I noticed a few things but this blog got too long so I cut it down to the most time consuming one.


Long lists are bull shit.

In the most inefficient conversations about what went wrong on a project that I’ve seen typically involves a huge list of items somewhere including work that the person who made the list would not be doing.

This is not 1 or 2 things but in some cases dozens to maybe even 100 or more items on a list… Dropped off like laundry to be folded.

Whether the list is e-mailed or put into a work repo. It’s still just a list and it represents 10s to 100s of hours of peoples lives.

I get that the ideal roadmap of any project has basically all the information on it and it even is sometimes naturally prioritized based on what is on the top of the list. But 9 out of 10 times it’s too much information and no one reads it. 1 out of 10 people read it and that last person 100% of the time doesn’t get everything right.

So. The 1 person that cared will make mistakes 100% of the time when they execute one of these big lists because the person who gave them the information poorly communicated it. That’s a practice that makes absolutely zero sense.

Keep in mind these lists take forever to make. Whomever made it is probably incredibly pissed and insulted at the end of the process because nothing got done right. This makes matters worse because they probably cared deeply about everything they asked for attempting to make it as clear as possible so that the person executing the list would be set up for success.

So. 2 people work really hard. The end result sucks, stresses people out, and the work has to be done twice.

Too much information means too much confusion and the likelihood of failure very high.

Long lists, long e-mails, and complaining are like kryptonite for your team.

Here’s the issue. When someone drops off these huge lists, very few people read them and those that do are so confused by them that whatever the ideal outcome is… It is really unlikely to happen. Making a big list for someone doesn’t really get anything done.

Getting the desired outcome requires working on the items on the list with your team. 

This simple differentiation is the difference between getting the results you want and getting bad results while making the team miserable.

Engineers who pair naturally solve this problem a majority of the time because the knowledge transfer is so great and they do the work they agree on together. Why there is no good term for people doing it in marketing or legal… I have no idea. I’ll call it just being a good human being and working on problems with people rather than just dropping off lists.

Big lists are a waste of time. Keep them small, keep them intentional, and work on them with your team.

1 thought on “big lists does not a good leader make”

  1. Totally agree Ben, lists are a series of “whats” and the only thing exciting about “whats” is how they’re connected to “whys”. When the why is absent -“typeface isn’t a pressing issue”. Stories, not lists, have preserved profound truths throughout history – perhaps stories provide us with the best construct for wildly successful project launches and companies, after all they’re the shortest distance between two people.

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