Rain Boots and Sandals

There are many strategies that can lead to project success. It often pays dividends to consider alternatives, even when the proposed paths are wildly different.

My current random cycling goal is to ride every street in my home town of Santa Barbara, CA. This has led to a lot of evening and weekend bike rides through every neighborhood in the city, one cul-de-sac at a time. I have also ridden in a wide array of weather conditions.

A few weeks ago I was slogging along through a neighborhood in the foothills during a light rain. I was a bit wet, a bit cold, and wishing for the rain jacket that I foolishly left behind. During the ride I happened upon a pair of people out for a morning walk.

They were each happily walking through the rain and running water on the street. They each had a different approach to the problem though. One wore waterproof boots that rose to almost her knees. These rubber boots were certain to keep out any water on the ground. Feet dry – mission accomplished.

The second person took a different path forward: they wore sandals. Their feet were 100% soaked, but they hardly seemed to care since they no longer needed to worry about preventing water intrusion. Their toes may have been a bit cold, but they didn’t have to worry about the water anymore.

So, keep your mind open to alternative approaches as you solve problems. You never know when it might be time to remove your boots and throw on your sandals. Just remember your jacket…

Photo: Rainbow over the east side of Santa Barbara.

They’re always getting recruited

It is naive to think that your engineers aren’t getting pinged constantly about new job opportunities. You should act like it.

I have an admittedly love/hate relationship with LinkedIn. It is an infinitely useful tool for building, indexing and maintaining a professional network. It can also be a morass of sales and recruiter spam. I am admittedly part of that problem, having sent hundreds of recruiting emails to interesting candidates. Everyone I have talked with reports the same thing: recruiters are constantly sending them messages on the site.

I won’t lie to you – it bothers me that people are out there constantly tempting my team members to leave. Recruiters can sing any number of siren songs to find the right leverage. Need money now? Boy, do we have a great signing bonus. Looking to improve your total compensation? Let’s chat about our equity vesting schedule. Want an interesting technical challenge? We have a new team spinning up and you can hack to your heart’s delight. The grass is totally greener on this side – just sign here…

So, what can you do with the knowledge that recruiters are banging on the door of all your engineers?

It doesn’t matter. Nothing new is needed. You focus on fundamentals.

Your forever-goal is to create the kind of team that people would hate to leave. The kind of team that people doubt can be replicated elsewhere. The kind of team that always presents unique opportunities to engineers. These goals will be true whether recruiters are pinging your people or if their inbox is completely empty.

Your people will leave you. Your best people will leave you. I am never hurt or offended when I know that people are leaving for a new opportunity that I can’t provide them. I am hurt, and potentially offended, when people leave for reasons that are entirely within my control. Build the team that you would hate to leave and you will be halfway to your goal already.

Photo: Arch Rock on the east side of Anacapa Island within Channel Islands National Park.

“What else?”

Ask “what else?” and keep asking until the room is silent.

Program management gets a bad rap at times. Ask twelve people what a program manager does and you will get a dozen different answers. The best description I ever heard was from a career talk during an internal Amazon technical program manager (TPM) conference: “I don’t know what program managers do, but things seem to go far better when they are around”.

One of the best TPMs I ever worked with had a pro-tip that he swore by. It is so simple that it seems obvious, but it is still a rare occurrence in meetings. After we had worked through the meeting agenda he would ask “ok, what else?”. That would inevitably lead to a missed agenda item that should have been discussed. “Great, thanks. What else?” Someone would volunteer that there was a risk that hadn’t been documented that should be. “Awesome, what else?” Suddenly an engineer would share that we need to talk with our third-party vendor. “Fantastic, what else?”

“What else?”

I am convinced that these two magic words have saved more projects than I have fingers.

Asking “what else” changes the focus of any meeting from simply completing the agenda to truly understanding the state of the project. It also communicates that the goal is to suss out all challenges and blockers, not just to check things off of a list. This subtle shift is powerful.

Don’t be a slave to your agenda. Focus on success of the project. Make sure that all challenges and blockers have been discussed. Ask “what else” until it hurts. Ask it three times in a row. Ask each person individually. Whatever it takes to get a shared understanding of ground truth.

Photo: Ball made of used bike tubes in Breckenridge, Colorado.

The Punctuated Equilibrium

Always be at the top of your game.

Performance across teams always tends to increase as review season comes around. Individuals know that they are about to be evaluated by their manager and, consciously or unconsciously, they ramp up their output. I see it as an attempt to put their best foot forward and a chance to capitalize on recency bias. All in all, it is a very smart move.

But it is not a smart move. You need to be at the top of your game, always.

Opportunity is a random process. You never know when the unexpected will happen and a previously satisfied business need is now a business need unsatisfied. If that happens during review season, and your stats are up, then what an amazing coincidence. If it happens outside of review season, and your stats are off, then you have missed an opportunity.

Like many, I have often thought of career progression as a linear march. You continuously move in a straightforward fashion toward the next level, occasionally getting promoted. With more experience, I now see career progression as a kind of punctuated equilibrium. Things are relatively stable until such time as they are not and dramatic change can happen very quickly. The goal, your goal, is to always be well-positioned for those periods of change.

I feel this is important because this randomness has shaped, and perhaps defined, my personal career. The first time I became a software manager was when my then-current supervisor decided to leave the company for a new gig at Apple. He went to the CEO’s office and tendered his resignation. After some discussion, and an attempt to retain him, the CEO asked “how should we handle your replacement?”. My supervisor responded that “Craig has been really crushing it lately and has relevant experience”. The rest is history.

Anticipating your question, no, this was well after that year’s review season.

Time and again I have observed people who have missed opportunities because they weren’t positioning themselves to be prepared for it. There is a lot of power in acting like you belong at the next level because you never know when that opening will appear.

You will always have a down day here and there where nothing seems to click. That is natural and can’t be avoided. Don’t let off the gas though, even if it looks like opportunities are sparse. As Robert Abelson famously said “chance is lumpy”.

Photo: Lightning strikes the Santa Ynez mountains north of Santa Barbara, California.

New Beginnings

Hello Internet friends. I’ve missed you.

A new weblog is both a roar and a whimper. It is a roar as the author plants a flag in the ground and definitively states “I have something to say”. It is a whimper because there is no audience and therefore nobody listening.

I blogged for seven years as a cognitive neuroscientist at prefrontal.org. Across 117 posts I discussed everything from mundane current events to deep dives on scientific topics. Some percentage of those posts are of questionable quality, but there were a few gems in the mix. My weblog work introduced me to some amazing people, got me invited to conferences, and led to a few invited papers.

It has been eight years since my last blog post. Why (re)start now? Why scream into the Internet void at all?

Maybe I have something to say again. Maybe.

I’ve been in the software industry for over ten years. I have had several successes and an even greater number of failures. I have worked as an engineer and as a manager I have worked at small startups and the largest companies in the world. I have embarrassed myself in front of CEOs and vice presidents. I have been promoted due to skill and promoted due to luck. I have also had role models who demonstrated both what to do and what not to do. Putting it all together, I finally have experiences to share that are worthwhile.

So, if I have something to say, then who am I speaking to? Who is the audience?

Ultimately, I think I am writing for myself, ten years ago. I would love for this to be the weblog I wish I had when I first got into software management.

As I stepped into management for the first time two things became immediately clear. First, I was in way over my head. I just didn’t have the skills or previous experience to make management immediately successful. Every day was an effortful push to figure things out. Second, my own blissful ignorance is what enabled me to say “yes” when I was asked to lead my first software group. It is also what enabled me to carry on when the going got tough over the next few years.

There were a handful of books and weblogs that were critical in those early days. They helped orient me to the role, taught me what to value, and helped me avoid some rookie mistakes. These resources helped me scramble up the learning curve far more quickly. Today, ten years later, I give those authors a huge amount of credit for their assistance.

Now, it’s my turn to give something back.

Photo: A view to the south from the top of Gaviota Peak in the Santa Ynez mountains.

Launch

Starlink Mission. Cape Canaveral Space Force Station, Florida. September 18th, 2022.
Provided by SpaceX. Licensed under CC BY-NC 2.0.