What I’m Paying Attention to as We Head Into the New Year

The stretch between Christmas and the New Year has always been a strange and useful pause.

The calendar hasn’t flipped yet, but the pressure eases just enough to think. Projects slow down. Meetings drop off. You get a little space to reflect without immediately turning that reflection into a plan.

This is usually when I take stock of what’s actually worth paying attention to.

Less Noise, More Signal

There’s no shortage of predictions right now. Every week brings another “AI will change everything” headline, another tool launch, another bold claim about the future of work.

Most of it is noise.

What I’m paying closer attention to is quieter:

  • Where teams are still struggling, even with better tools
  • Where automation helps, but also where it gets in the way
  • How often humans are still doing invisible glue work between systems
  • And which problems keep showing up no matter how advanced the tech gets

Those patterns matter more than any single product announcement.

The Gap That Keeps Showing Up

One thing I keep seeing is a growing gap between capability and clarity.

We have systems that can generate code, route work, summarize decisions, and automate entire workflows. But many teams are still unclear about why certain work exists, who should make which decisions, and when software should act versus pause.

More capability doesn’t automatically lead to better outcomes. In some cases, it just makes existing problems happen faster.

That’s the space I find most interesting right now.

What I’m Intentionally Not Rushing

There’s a strong pull at the start of a new year to rush toward answers.

I’m resisting that.

Some problems benefit from speed. Others benefit from sitting with them a little longer. Understanding how people actually work, where judgment shows up, and where things fall apart, takes time.

I’m okay with that.

Looking Ahead, Quietly

As we move into the new year, I’ll be sharing more of what I’m observing as these ideas take shape. Not polished conclusions, but real thinking in progress.

If you’re curious where that goes next, I’ve started talking out loud in a few places beyond this blog. You’ll find links on the site if you want to follow along.

No pressure. No sign-ups. Just conversation.

Sometimes the most useful thing at the start of a new year is simply paying attention.

A Peek Under the Hood, How I Think About Building the Next Generation of Dev Tools

When I first got into software, there were no libraries waiting for us. No package managers. No Stack Overflow. No copy-paste from GitHub.

If you wanted to build something, you built it. Top to bottom.

If I needed to talk to another system, I opened a socket. I connected via TCP. I handled the protocol. If something failed, I debugged it at the wire level. Applications were handcrafted end to end, and you were responsible for everything you shipped.

That experience shaped how I think about software to this day.

From Building Software to Assembling Software

As my career progressed and I started hiring engineers, I noticed something changing. We stopped teaching people how software works and started teaching them how to assemble it.

That’s not necessarily bad, but it does change the skill set.

When I built hiring assessments, one of the things I always tested was algorithms. Not because I expected everyone to be writing sorting routines every day, but because algorithms tell you how someone thinks. They reveal reasoning, tradeoffs, and how a person approaches a problem when there isn’t already a solution handed to them.

Over time, that kind of thinking became less emphasized. We got very good at wiring packages together. We got worse at understanding what was actually happening underneath.

That shift matters more than most people realize.

Automation Isn’t New, Context Is

Long before AI entered the conversation, I used to tell teams the same thing over and over. I can automate almost anything, but we need to start with people.

You let humans run the process first. You iron out the edge cases. You understand where things break. Then you automate the boring, repeatable parts and kick the exceptions back to humans.

That model has worked for me for decades.

What’s new now isn’t automation. What’s new is that software can finally understand a little bit of context. Not perfectly, but enough to participate instead of blindly executing instructions.

That distinction is everything.

The Real Cost of Babysitting Software

At one company, I had a peer who was incredibly good at keeping things running. Customers were happy. Issues were handled quickly. From the outside, everything looked fine.

When he eventually left, I dug into the system and realized how much time had been spent babysitting instead of fixing root problems. Not because he didn’t care, but because there simply weren’t enough hours in the day.

The company didn’t push for deeper fixes because the work was getting done. In reality, they were paying a premium for reactive support instead of investing in durable solutions.

That experience stuck with me.

Software that constantly needs human babysitting isn’t efficient. It’s expensive. And worse, it hides the real cost behind “everything is working.”

How My Thinking Has Changed

Today, I care less about features and more about intent.

Where does intent originate?
How is it preserved as work moves through systems?
What happens when that intent becomes unclear?
And when should software act versus pause and ask for help?

These questions matter more to me now than which framework is trending.

Some principles I won’t compromise on anymore:

  • Tools should preserve intent, not just produce output.
  • Automation without context just accelerates the wrong outcomes.
  • Humans are not a failure mode, they are part of the design.
  • Software should adapt to people, not force people to adapt to it.

Why This Is Finally Possible

For most of my career, software was deterministic because it had to be. That made context preservation incredibly hard.

Now we have systems that can reason, summarize, adapt, and operate with uncertainty. We can design workflows that branch. That pause. That escalate. That involve humans when confidence drops.

This doesn’t replace judgment. It finally gives judgment a place to live inside the system.

A Quiet Tease

I’m working on something that reflects all of this.

It’s shaped by decades of building software the hard way, watching teams struggle with invisible friction, and seeing how often people end up doing work that tools should have handled better.

I’m not ready to talk about it publicly yet.

But if modern dev tools feel powerful and exhausting at the same time, we’re probably thinking about the same problem.

More soon.

Rest in Peace, Coach

Still trying to get my head around the Chiefs loss in Super Bowl LV, this morning I get an alert on my phone that Marty Schottenheimer, long time coach of the Kansas City Chiefs, has passed away at the age of 77 due to complications of early onset Alzheimer’s Disease.

I wrote about the coach and his battle with this disease 5 years ago in my article titled “One Play at a Time“. Today it is very sad news to hear that he has passed away. I just wanted to write something to say, “Rest in peace” to him and think about his family at this time. Coach had a giant family in Chiefs Kingdom, and I know he will be missed by many.

To me, Marty was the epitome of a football coach. He looked like a coach. He sounded like a coach. You could watch the Chiefs play and always see the man coaching. He was constantly talking to players and trying to motivate them as men. He was a great coach. He won over 200 games in his career. He only had two losing seasons across a head coaching career with 4 NFL teams.

Marty was a good as it gets when it comes to being a coach, a leader, and a man. He was a leader of men. He will truly be missed. I will always remember him and think fond thoughts of the man that taught me the game of football. My dad got me into watching the 49ers in the 1980s. In the 1990s, my dad introduced me to Chiefs football with Marty, and my views on football were forever changed.

Rest in peace, Coach. You earned it.

Virtually Yours!

Due to the COVID-19 global pandemic we are all living through at this time, I’ve decided to grow my side hustle into a real business. The name of the company is Transcendent Software. Don’t feel obligated to click through or feel like I’m trolling you for my services. For some background, I originally started this business in 2009 to make some extra money and help some friends with different projects from time to time as things came up. My goal with my career in technology has always been to make the world a better place through the use of technology, so this fit right in with my personal mission statement.

One of the service offerings I am most excited about is a Virtual CIO / Virtual CTO Service. If you are not familiar with this, it is sometimes referred to as vCIO, Fractional CIO, Part-time CIO, or something close to that. The service is geared for small to mid-sized businesses. I would be able to serve as CIO or CTO for several companies at one time. We would agree to a fee and hour limitations, but I could help them out and eliminate the need for a full-time employee when it would be very cumbersome for them to take that salary on. The nice thing is that I would still fulfill every aspect of leading an IT department, but not be as involved in the day-to-day part of the business.

If you’ve been reading me for any time throughout my career and my several attempts at blogs, I have spent the better part of my career as a CTO (Chief Technology Officer). When I wasn’t that, I usually carried IT Manager or IT Director in my title, because the management side was part of my job for almost my entire career.

I started my career as a Software Engineer I, but within a year on the job I was really starting to design our systems, and very shortly after took the title Chief Software Architect. When I was given the responsibility of running the IT department as well, I was then IT Manager / Chief Software Architect and eventually Chief Technology Officer.

So, back to the Virtual CIO / Virtual CTO Service, I am very excited to be offering this service to small to mid-sized businesses. It gives me the opportunity to take what I’ve done for several companies over the years and be able to do it for even more companies in many different industries. I think the role can be applied into any business, even businesses you wouldn’t think would be in need of technology leadership. Another thing I am excited about is that eventually, it will allow me to bring on other resources to do the same role and keep pushing my mission of making the world a better place through the use of technology one vCIO gig at a time! I’m psyched and ready to go!

The Right Stuff

I know it’s been a long time since I last posted, but I think it is relevant to discuss training and education, especially in software development. This has been a topic weighing on my mind a lot the past several years.

In the past 20 years since I made the leap into my career path, I have witnessed many changes in technology. The microprocessor and the internet have taken over nearly every facet of our daily lives. It is quite remarkable where we came from to where we are today, and to think it has only been that short of a time while I’ve been a professional.

When I first started writing software, we didn’t have the rich toolsets we have now. We had some very basic compiler suites, or command line compilation using a text editor to edit the source files. We also didn’t have the libraries available today. Most problems we had to solve from scratch. Finally, to top it off, we didn’t have Google to save the day when we needed that snippet of code to hybridize into our own solution. We had to know how to write algorithms to solve problems. The solutions weren’t handed to us, and we weren’t coddled to the answer via great tools that auto complete our lines of code, and format our code and give us instant feedback to errors or omissions without compilation and trial and error.

I may sound like an codgidy old man, and maybe I am, but I think having to solve problems from scratch taught my generation a lot about problem solving. I think this is the magic bullet that is missing from the college curriculum, work training programs, or coding bootcamps. I think all of those things are great, and there is some foundational stuff there, but these folks are missing out on algorithm design. This is the foundation for which all software works. You have to be able to solve problems. You can’t just rely on Google or great tools to solve them for you.

So, here I plead to anyone affiliated with these software development educational programs, spend some time on bubble sort or binary search. Teach your students about how to extract a subset of text from a string, or how to increment numbers exponentially. Spend some time on conditional logic, and order of operation. All of these things have value, and while pretty basic, they are the building blocks that we are skipping over to get to the cool IDE or the latest tool or JavaScript library.

What Yoda taught me about being a mentor

Like I mentioned in my blog post, What I’ve Learned from Mr. Miyagi, the elderly, wise, green alien creature from the Star Wars saga, Yoda, was another model for how I learned to be a great mentor. I didn’t know it at the time, but while I watched The Empire Strikes Back when I was a young boy, I was learning many life skills while I dreamed of being Luke Skywalker flying an X-Wing, commanding the force, taking on the bad guys, and learning to overcome the dark side, and in particular, Darth Vader.

Yoda was introduced into the story when Luke Skywalker crash lands into Dagobah, a swampy forest planet. After a moment trying to gather his surroundings, Yoda arrives in scene as a quirky, curious, alien creature who speaks in broken english, but still shows some sarcastic and quippy wisdom when he speaks. For instance, when Yoda asks Luke why he is there, after some banter, Luke states, “I’m looking for a great warrior.” Yoda immediately in his broken english language states, “Great warrior? War’s not make one great.”

You can watch the entire dialog above, but the truth of the introduction is that Luke is overconfident, and almost cocky. He has many thoughts about how everything works, how he is supposed to become a Jedi Knight, how his destiny is supposed to pan out, and in reality, he has much growing up to do. Luke is like many of us when we start out on our career paths. We have a small education and maybe some bits and pieces of real world experience, but in practice, we don’t have much experience at all.

Many of us, when seeking mentorship, are ready to receive it. Luke, on the other hand, was not. He argues with Yoda and Obi Wan Kenobi’s force ghost about whether he is ready to be a Jedi Knight or not. Eventually, they all agree he will finish what he starts and become the Jedi Knight he is meant to become. This submission of will is important, because being a good mentee is about submitting to the process, knowing that in the future you’ll be able to expand your wings and fly on your own.

Yoda trained Luke on calming his mind and approaching challenges in a clear frame of mind and to stay focused. He also taught Luke small concepts and allowed him to build upon them later, even though he didn’t know why he was doing them in the first place. This idea of foundational building was something I explored with how Mr. Miyagi trained Daniel in The Karate Kid. This was the same with Yoda. He started by having Luke move small objects with the force. Later in the training scenes, he had Luke try and move his X-Wing from the swamp as it began to sink. He utters some of his best lines during this scene, “No. Try not. Do or do not, there is no try.” or Luke saying, “I don’t believe it,” when Yoda uses the force to move his X-Wing from the swamp and Yoda replies, “That is why you fail.”

I use these same techniques when I mentor. I often only give out bite size pieces of information which are enough to get the job at hand completed. This allows my mentees to become masters of that technique faster, and later one we can connect the dots. Keeping things simple is a core value of mine. Not only is it the best way to keep things progressing, but there are many times I learn new techniques as well. As I have explored in many of my previous posts, including Teach a Man To Fish, I point out that the best leaders and mentors surround themselves with smart people, and allow them permission to fail. Everyone gets an opportunity for growth this way.

In conclusion, Yoda and many other wise sages in many movies taught me much about how I mentor today. Lessons such as keeping things simple, staying focused and submitting to the process are all key to growth. We will explore this more in the future, but for now, venture out and try these things out for your teams.  May the force be with you.

What I’ve Learned From Mr. Miyagi

Like many kids who grew up in the 1980’s, I learned a lot about life from two wise sages. First, was Yoda, the green, grumpy, 900 year old Jedi master, who trained Luke Skywalker to reach his potential and overcome against all odds to destroy the dark side forever (Well, at least until Episode VII came out in 2015, because the dark side somehow came back again). I often quote Yoda to my wife’s dismay with, “No. Try not. Do or do not. There is no try.”

We’ll tackle Yoda in a future post, but in the interest of staying more grounded in reality, I’d like to focus on my second choice, and that is Mr. Kesuke Miyagi or Mr. Nariyoshi Miyagi, as he went by both names in the movie series. For the purposes of how I knew him, Daniel Laruso, his student in most of the movies, called him Mr. Miyagi, so that is how I knew him as well.

Mr. Miyagi was a fictional character, but the things he did and said in the three Karate Kid movies (I know there was a fourth one much later and then a remake after Pat Morita died featuring Jackie Chan as the Karate mentor) were very much things that shaped who I am and how I live my own life, even today. I constantly find myself quoting Mr. Miyagi as well. “Walk on the road? Walk right side safe. Walk left side safe. Walk middle, sooner or later get squished just like grape.”

Mr. Miyagi seemed to always have a solution, but I think it was just a confidence in his response, even if he didn’t know how the outcome might play out. In the first movie, there was a scene on the beach where some racist drunk guys didn’t want to move from their spot so Mr. Miyagi and Daniel could leave. They had taken up shop on Mr. Miyagi’s truck and had placed several empty beer bottles there. Mr. Miyagi asks them to remove the bottles so they can leave and they refuse. He then proceeds to Karate chop the beer bottles in half, and the guys remove them and scurry off. Daniel asks Mr. Miyagi how he did that, and he simply replies, “I don’t know. First time.” You can watch below, skip ahead to about 2:36 for the scene.

This scene is perfect Mr. Miyagi with a little humor and humility, simplicity and yet in complete control. This is a theme with Mr. Miyagi throughout the entire series. Another scene that demonstrates this is when he takes Daniel to the Cobra Kai dojo to talk to the bully kids and their sensei in hopes that they might leave Daniel alone. When Mr. Miyagi realizes this won’t happen he volunteers Daniel to fight in the All Valley Karate Tournament in return for no more bullying. The sensei agrees. After leaving Daniel is furious that he has to fight, and Mr. Miyagi says something to the effect of, “I just saved you two months beatings!”

Mr. Miyagi taught Daniel lessons using cryptic methods, but it all came back to simplicity. I’m sure nearly everyone knows “Wax on. Wax off.” or “Sand the floor.” or “Paint the fence.” or “Side to side”. These being his way of instructing Daniel in the basics of self defense. He also had him do manual labor to build strength and endurance.

Mr. Miyagi understood how to live a rewarding life, even though you knew throughout the films that he struggled with this himself. He was an immigrant and veteran of World War II. He lost his wife and unborn child during the time he was away at war and never really let go of this, and while they never stated it directly in the movie, they definitely implied he probably battled some sort of alcohol abuse grieving these losses. He at least commemorates the anniversary each year by dressing up in his military uniform and by getting hammered to the point he passes out. Daniel finds him during an anniversary and sees a side of his friend and mentor to show he is just a man with flaws who is doing the best he can.

In the second movie, we discover that Mr. Miyagi also had a relationship before he left Okinawa. He and his best friend were going to fight to the death over a woman, and Mr. Miyagi knew he couldn’t kill his friend, so he gave up his love and left the island. When he returns he finds that he still loves her and she never married and never stopped loving him either. Of course, as these things go, he leaves to go back home at the end, but he and his friend patch up their relationship before he leaves, and all is well (I guess?).

Mr. Miyagi, while a man with flaws, also shows great wisdom in the entirety of the series (even the fourth film I suppose). He says statements of simplicity and devises simple challenges to get his points across and be the best mentor and friend to Daniel he can be. As a leader, there is much to be learned from Mr. Miyagi’s approach to leadership. Keeping things simple is often the best way to empower those you lead to take ownership themselves and become the best they can be while you nudge them in the right direction from time to time.

One Play at a Time

Today brings sad news that former NFL head coach, Marty Schottenheimer, is suffering from early onset Alzheimer’s Disease. There are plenty of news sources reporting that he has been suffering from this terrible disease now for about five years.

Legendary NFL Coach Marty Schottenheimer Selling Carolina Mansion ...

As a Kansas Citian who is still in his 30’s (barely), my formative years were spent watching Marty lead the Kansas City Chiefs using awe inspiring quotes about getting the gleam, igniting the rocket ship, or taking it one play at a time. His voice was familiar to me, as every time I turned on the radio or television, I couldn’t escape his voice saying, “Nothing stops a Trane”, as the spokesperson of Trane HVAC systems. His voice was so familiar he seemed like someone I knew, like a long lost uncle.

Marty was an iconic figure in my mind and to me was the epitome of a head coach. He was known for Martyball, with his run dominated offense and outstanding defenses. He even got a polka song written for him! He led talented and not so talented teams to really good records. He only had two losing seasons in his career, his final one in Kansas City in 1998, where the promising season derailed and finished at 7-9 and his second season in San Diego in 2003, where they went 4-12, but followed that record in 2004 with a 12-4 record and first place finish in the AFC West.

Schottenheimer smitten with Thomas from the start - News - The ...

With all of his success, he still kept things very simple. He was very focused on the task at hand and didn’t get caught up in looking backwards or forwards. This is something I try and do in my career and life. In any situation, you only have control over your next action. You can’t hit the undo button and get another shot at what you already did and you can’t skip forward and change the future.

Marty Schottenheimer's congratulatory message for Andy Reid | The ...

This is the lesson that I learned by watching Marty Schottenheimer coach the Kansas City Chiefs in the 90’s. His teams were so good at moving onto the next play and not dwelling on the past. I can recall countless times I watched defensive stands, last second field goals, blocked kicks or kick returns for a win. If you think of all of the times you have failed before, you’ll never be prepared to succeed when called upon. This is what Marty represents to me. He now has an incredible fight ahead of him as he undergoes experimental treatments and continuing loss of his faculties as this disease progresses. Knowing Marty from being the fanatic observer I was, I know he will continue to live his life one day at a time and appreciate every moment, because that is all he can do.

Go get ’em coach!

Build Your Team With Character First

So much can be said about character. To me, it is the number one thing I look for in another person in any walk of life, not just professionally. Character is our moral fiber. It is what makes us who we are and it provides us what we need when we are at our whit’s end.

Mark Twain said, “It is curious that physical courage should be so common in the world and moral courage so rare.” I don’t know if it is so rare or it is just not advertised. Doing the right thing, being paitent and kind, being strong when the chips are on the line, these are things that just aren’t talked about. They are exactly the types of things I look for in those around me.

I am a huge football fan. My team I root for is the Kansas City Chiefs. In 1998, after a very good run in 1997 and a 13-3 regular season record and a disappointing loss to the division rival Denver Broncos in the divisional round of the playoffs, Marty Schottenheimer was going all-in to try and win a Super Bowl. He brought in several players of questionable character, but with above average talent. This move backfired and Marty experienced his first and only losing season in his coaching career, going 7-9. Marty went against his moral fiber and brought in players purely on talent. He never did this again in his other coaching stops. He only had one other losing season.

In my own career, I have spent much of the interview process talking with the candidate. I’ve been known to take a candidate to Starbucks and buy them a coffee and just try and get to know them. During nice weather, I might take them on a walk through the trails by our offices if their shoes are up for it. This approach tells me more about the person and I also get a feel for their qualifications. I can always coach them up or teach the person a skill, but I can’t teach them to be a person I trust with the operation and execution of my future and the futures of those I work with.

In short, when looking to who to surround yourself with, look to character before talent and you’ll do much better in the long run. I’ve mentioned George Washington as one historical person I’ve looked up to as a leader. He was quoted as saying, “It is better to be alone than in bad company.” There is so much truth in this short statement.

Teach A Man To Fish

Everyone has heard the expression, “Give a man a fish and you feed him for a day; teach a man to fish and you feed him for a lifetime,” or some variation of this. In fact, it’s been quoted, paraphrased, blogged, memed and parodied so many times, it hardly seems blog post worthy anymore. The phrase itself is a fairly novel concept. The real reward in life is learning to be self sufficient and to not be dependent on others. This is truly where happiness comes from. A new penny loses it’s shine eventually and is just a penny, but if you know how to make that one penny into many pennies, the reward is so much greater. Blah, blah, blah, etcetera, etcetera, etcetera. We all know this, right?

When I got started in IT leadership, I was so obsessed with making sure things were handled to my standard that I hoarded much of the work. I would tell myself that I was protecting my employees from having to deal with such things, but in actuality I was hindering their development. There was the occasional employee I felt so comfortable with that I would hand one particular project to them and let them own it, but for the most part I felt like I had to have my hands on everything that was going on. I felt if I didn’t do this, we would fail. I felt such ownership over every piece of software, hardware, process, or procedure that I couldn’t let it go.

I can still remember having several conversations with my boss about delegation. We talked on the subject often, and I understood that it was something I needed to get better at, but I sure didn’t know how. How do you own something, and be responsible for it’s success and yet let other people do it? This concept was hard to grasp. It was hard to grasp for him too, but we both vowed to get better at it.

washington-meeting-his-generals-war-is-hell-store

I remember seeing a program about George Washington once, and on the program they talked about his leadership style. George would gather those whose opinions he valued, hear them out and make a call. I visualize them in a circle around some old 1700’s wood table made from a tree trunk, standing of course, in full dress for the period. I picture them with their wigs and hats. George would address the group with the issue, and then he would back off and let them all talk about it. He would observe and in the end I picture him clearing his throat to a silence of the crowd and just telling them how it is. George took the opinions and ideas and formulated his own idea and then that is what happened. That is my image of a good leader. The thing was, George had those around him that he trusted to provide value. How did he get to that point? Sure you could say it was because he served in the trenches with them. You could say it was because George always had the absolute best around him at all times. The truth probably is that George did his best to teach them all to fish. He made them better, so in the end he was better at his job.

fish

To come full circle, I think we can learn something from George Washington. For us to be the absolute best version of ourselves, it is our responsibility to teach everyone around us to fish. In business, now, I think I do a much better job of this. I give everyone who works for me the permission to fail. In fact, I encourage it. I want them to try to solve problems on their own. I tell them that my door is always open to talk through what they are working on, but in the end, they are the ones working on it. I will not do it for them, even at the expense of the project or a deadline. In my early days, I had no problem sitting down at my employee’s workstation and running through the solution to whatever problem they were working on and not thinking twice about it. Each time I did this, I was setting them back days, weeks, or months in their development and maturation as a technology professional. To be the best leader I can be, it is up to me to make those around me the absolute best they can be. If I do this, in the end, we will all reap the rewards of learning to fish.