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Measuring What Matters (Not Just Productivity)

Milestones, deadlines, and clear goals are essential to know where we are going and when we arrive.

We get into trouble when we measure and set objectives to feel productive.

Our world does not allow time to step back from our daily lives and gain perspective. If you can make it happen, it is truly a privilege to have this insight.

Since most of us can never calibrate our processes by stopping and assessing, we read, listen to, and watch the great thinkers and teachers who craft their own path and learn from them what they do.

If we can give back as we gain, we will all be mentally and spiritually in good shape.

This article contains some game-changing realizations gained along my path as a software engineer on teams building everything from IT solutions to consumer and business software. Structure that supports dynamically is a skill and a tool worth cultivating amid uncertainty.

The Courage to Fight for What's Right

The coolest part of being on a team with other passionate builders is the ability to argue through the solution and the best approach without getting hurt feelings.

The process of productive disagreement is not familiar to most of us in ordinary life.

We are super conditioned to take any argument as personal, a threat, inappropriate, or even disrespectful.

Basically, we are a society (globally) conditioned to be polite followers. This conditioning has been necessary to maintain order in hierarchical systems and has built our world.

Today requires new ways of thinking, departing from the comfortable familiar when discomfort means productive growth, and extreme collaboration across ALL disciplines and diversities.

Consider a small team deeply invested in the project deliverables due before the end of the quarter; the work is important, potentially life-saving. The lead engineer discovers a flaw in the system design, a major security vulnerability. The fix will take months, the stakeholders have committed to the current deadline.

The only correct option is to push the project back. If no one dares to argue for the correct path, a product will ship to hundreds of customers who themselves provide care for thousands.

At an unknown time in the near to mid-term future, the security vulnerability is exploited and tens of thousands of patient records are leaked onto the dark web where their personal information, birthdate, social security numbers, medical history, spouse, number of pregnancies... is bought by malicious actors in an evergrowing sea of online crime.

The original team is fired once the company manages the initial damage of the stock price plummeting and canceled contracts. Know when to argue, raise the flag early and often, one battle has nothing on the war on damage caused by negligence.

Creating Safe Spaces for Dangerous Ideas

Collaboration is a skill, and so is letting go of what is comfortably familiar but not working for you.

Once you start to look for it, you will know the places you are leaning into comfort by default. Default is easy; transformations are hard.

Paradoxically, problem-solving, by its nature, requires discomfort, while ideas are only shared freely when emotional safety is established.

Most of us do not even realize we are operating in a heightened state of anxiety before additional inputs are added.

The first step to emotionally safe teaming is to feel safe enough to take risks with our ideas and to be vulnerable with our team.

We cannot do this if we are harshly judging ourselves without realizing we are even doing it.

How can we make a safe space for our teammates, friends, and family members if we come from a place of comparison and judgment?

Many of us have felt this from our families our whole lives, and it may be the first time we have the opportunity to be creatively vulnerable when we are part of a highly functioning team, whether as software engineers or otherwise.

Once you have felt the good, you see the bad clearly (thanks to my therapist).

Start with you and how you treat yourself when you get something "wrong" or fail to meet your own targets. Do you give yourself grace and find paths to improvement, or do you abuse yourself with judgment and comparison?

Everything good about human communication starts with safety. Safety requires no bullies, no egos, and neutral language, which is challenging to maintain when passion enters the room. We are passionate because we care, which is a positive. Our passion fuels us, but does not drive our actions. When we keep the focus on the value of the work, when we carefully listen, clarify understanding, and get clear on our strong opinions and those we can let go of, we are ready to create space for the hard work that high-functioning teams can do. The work of creating the best is not done by people working in fear.

Numero uno is where everything must begin. Start with you, love yourself, and then you will be able to hold space for others.

The Creative Funnel: From Chaos to Clarity

One of the reasons NoRules is my mantra in tech and creativity is that I know most solutions will require a lot of garbage picking until the shiny object is discovered.

I know, I love metaphors.

In this scenario, garbage picking means throwing ideas at the wall, like pasta noodles (another metaphor for you there).

If you get all precious and defensive about every little idea, you are not going to take risks and try out some garbage. This means you won't make space to learn at the ideation phase, and you will probably commit to a substandard solution sooner than you should have.

If you think there are rules about ideation and creativity, you will get stuck in the editor's office reworking ideas that can't breathe.

Ideas are common, action is unusual.

Think of the phases of creating as a funnel. The widest part, call it top, is where the brainstorming happens. This is a no-critics, anything-goes, no-rules phase. Ideas benefit from a central theme to coalesce around but as I said, no-rules. Get the whiteboard, the post-it notes, and the Sharpies and get creative!

One constraint that keeps a team focused and respects everyone's time is to set a hard time limit and allow people to move around, doodle, and access their creative minds in whichever way feels good to them. Safety is critical for creative flow.

Consider adding a warm-up exercise and a short reflection at the end or later. After the timed brainstorming, curating the ideas into more structured taxonomies will narrow your funnel further.

Leave room at each phase of creation for check-ins, whether your team is 10 or 4, if you are more than one, you should hold daily check-ins or standups, named thus for the brevity intended.

Two questions are sufficient: "What are you working on today, and do you have any blockers?" Blockers are what you might suspect, issues to be dealt with that your teammate knows can help with.

If you never tell her, she will never know. That is it.

Don't be precious or defensive about your ideas. Someone else will write a book about the same idea you have, but they aren't you, so it won't be the same book.

Elizabeth Gilbert has a wonderful story about this in her fantastic book on creativity: https://www.elizabethgilbert.com/books/big-magic/.

Don't be afraid to try things and learn what works and doesn't work early on.

Engineers and designers use all kinds of crazy materials and processes to force themselves outside of structured thinking and get the idea juice flowing.

The Stanford D School is the mecca for this sort of strategic creative play and a fantastic resource for materials and process guides.

End of Pt. One

next week:
Part 2: The Human Side

  • Choosing Your Guides (And Becoming One)

  • Dropping the Armor: From Solo to Symphony

  • Staying Curious in Uncertain Times

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