Short version: Having a boss measure how toxic the environment he or she creates is wrong.

Generalized: Toxic environments are difficult to report on from inside. Empower your employees.

Ultra-specific request of managers: One person who is afraid of making mistakes is too much. Consider this specific measure of your work environment and consider others in this series.

Part of being in a toxic work environment is that you are afraid to mention it. Yet, it is that very environment which is decimating productivity.

There are a large number of factors which contribute to work environments which are not healthy…

Short version: Assign tasks in a transparent manner

Generalized: Visibility to task definition, priority, and assignment allows for better organization of work

Ultra-specific request of managers: Watch out for duplication of effort, for the appearance of favoritism, for consistently discarded effort, for consistently changing priorities, and for consistently missed milestones despite people putting the work in. These are likely a result of task assignment problems.

This is a software engineering article.

For the moment, imagine you’re working in a bookstore:

• You start to take an inventory of the reference section, and, while you step away for a short break, someone…

Short version: It is the part of the process which is not documented which causes delays

Generalized: Deadlines are as feasible as the tasks they are set for are understood

Ultra-specific request of managers: Remove these words from your vocabulary, except for in extremely specific cases:

• “simple”
• “should”
• “But I know how to do it.”

We were in the home stretch of a project which had all the hallmarks of failure: introduced mid-sprint with other commitments on the line, little or no planning, no comprehensive team schedule or document, deadlines made without team acceptance, tasks introduced as people thought of…

Short version: The definition of insanity might be doing the same thing over and over again while expecting different results. Or it might be doing an untested new thing and expecting better results just because it is new.

Generalized: Do not assume that people resisting a change are resisting all change.

Ultra-specific request of managers: Explain the reason for change without focusing just on what lack of change is and assuming that is “good enough”.

I was talking to my manager about team workflow changes which were rolled out with a lack of:

• transparency
• definition
• cost/benefit analysis

He told me…

In late February or in the first week of March, I cannot remember, I signed the visitor’s list to enter a tech meetup in Kendall Square and walked into an unfamiliar scene:

It was the end of the beginning of 2020 in Cambridge, when the snowiest time of the year begins to yield to an eventual spring. The meetup’s hosts, with uncomfortable laughter, asked participants of the meetup not to shake hands. Folks were awkwardly elbow bumping. Clear bottles of hand sanitizer were on every tabletop.

As an introvert who needed to get some programming done before the talks began…

Abbot and Costello Team Leadership

For those of you who do not know the classic Abbot and Costello sketch “Who’s on First?”, I recommend starting there.

Those familiar know this is not how you want a team working on tasks.

Let me tell you how this might look on an actual team —

Alice, Bob, Chuck, David, Erin

You want the following items taken care of on top of everyone’s regular duties:

a) a major documentation initiative

b) improve your integration workflow

c) formalize the communication between your team and Sales

d) the thing nobody wants to do because it is so much manual effort for little payoff

So you…

May 31 was my one year anniversary at what I had decided would be my dream job:

• Python engineering
• Tech team leadership/managerial oversight of a small team
• Startup culture

This got me out of a strictly Oracle/strictly DB-developer tech-team lead pigeonhole, and it allowed me to grow in ways I wanted to grow while helping the company I’ve worked for grow — using my decades of best practices to help bring change there.

I learned a lot over the past year.

The area I’d like to focus on in this account for now is management anti-patterns.

Why anti-patterns?

For me…

I’ve received countless interview rejections in the past year for in-person interviews. It is part and parcel in the life of a forty-something software engineer.

It must be the constant sense of rejection, or maybe all the chemicals I’m taking to work a day job and do take-home programming assignments on nights and weekends [along with meaningful side-projects and participate in the open-source community], but I have begun to hallucinate interview rejection emails.

Here are some of my favorite imagined ones:

1. NUMBER ONE MOST FUN PLACE TO WORK BOSTON!

Hello applicant!

The team loved meeting you in person. Jake, who…