Recent content on Chris Dail
Is this better, or is it just different? This is a question I keep coming back to. One example of this is the light switch. In the 80s, people tried to invent a better light switch. The Clapper fascinated me as a kid. This was a lamp that was activated by clapping to turn it on or off. There were also touch activated lamps where you would touch the base to turn them on or off. Both were different…
I am seeing a trend pushing more software engineers to move into more of a product engineering role. At its core, it is about owning more of the full product lifecycle including taking a bigger role in shaping the solution, not just building it. It is being framed as a new wave. I see it differently. This is a return to form. Early in my career, there was a sharp distinction drawn between a…
I have been using ralph loops to autonomously work through a list of well defined tasks. The challenge that I’ve had is none of the tooling out there was exactly what I was looking for. Existing ralph implementations have issues like context pollution from auto-compaction with the claude recommended plugin. Other implementations out there are needlessly complex and have weak cost management…
Most teams are using the wrong strategy to leverage the benefits of agentic AI in software development. The two most common strategies I see are: do the same thing we always did, but faster with AI, or cut the team because we can do the same thing with fewer people. Either of these may seem effective in the short term, but the best they can do is keep you on a flat trajectory. AI-native companies…
Interviewing is like speed dating to determine who you will marry. There is very little time to develop any deep understanding from either party. Recently, I was interviewing candidates with a colleague who had previously worked with one of them. After the interview, my colleague remarked that they knew this person could have performed better. This is a story that I have seen play out many times.…
I have seen a lot of buzz lately about defects introduced to working code by AI. Some benchmarks show AI creating 1.7x more issues than humans. This is the worst AI code generation, and I expect this gap to close. Even if AI is much better than a human, any change to a codebase has the possibility of side effects . When looking at the cost of any code change to a system, the highest cost was often…
Why are some developers still not embracing AI coding tools? Adopting new tools is inherently risky. This is true of many new tools, but it is especially true of AI coding tools, which require a fundamentally different way of working. So why do some teams embrace these tools while others remain skeptical? In my experience, it comes down to two things: time to think and the ability to fail. Time to…
2026 is going to be an exciting year. We saw just the tip of the iceberg on what AI coding tools can do in 2025, and now the floodgates are open. AI has fundamentally changed how fast software can be built. This means smaller teams can ship higher-quality software and quickly. We are going to see an explosion in new software products hitting the market in all categories. With increased…
Have you ever heard something like “How did they not know about X? I communicated it last week.” I often see leaders say they have communicated something with a team, but what they really mean is that they did some talking or maybe fired off an async chat message. Think about basic radio communications. You cannot simply turn on a radio, blast some message out into the ether and assume…
Is it wise to start a Computer Science degree in 2026? Is AI going to take all of the software development jobs? These are especially relevant questions for me as my son graduates from high school this year. This is the advice I gave him. I believe it is a fine choice to take Computer Science in the year 2026, provided the following two things are true: You love it - The days of this degree…
Recently, I wrote about the value of senior developers in an AI world . What are the most important skills a software developer should focus on in this world? Here are my top 3… or perhaps top 7 because the last one has 5 parts. System Architecture and Design Context is king when it comes to designing systems. You may have planned the most elegant and “correct” architecture,…
Will AI replace senior developers? This is a common question people are asking today as AI coding tools become increasingly sophisticated. Instead, the aspects that make a senior developer a great developer remain unchanged in the world of AI. It has been said by many that AI raises the floor and not the ceiling. What this means is that the best developers will become even more differentiated from…
The Model Context Protocol (MCP) represents a significant advancement in AI assistant capabilities, enabling seamless integration with external tools and services. However, as MCP adoption grows, so do the security concerns surrounding credential management. The authorization services and OAuth flows may solve the problem for many HTTP-based MCP servers, but little exists for local services. I…
When you are asked to take on a task that you do not feel is possible, your instinct might be to say “no” and explain why. A more effective approach is instead to shift from “No Because…” to “Yes and here is the impact of that.” I’ve spoken with some leaders who struggle with pushing back on things or feel like they are constantly pushing back on…
I predict that in the next few years, we will see a huge wave of resignations in software companies. We are in a period where the opportunity cost of leaving a role is high. There are few postings in the job market, and there are many people who are looking for work. The consequence of this is that people who are interested in moving on are sticking around a lot longer than they otherwise would.
My formative years in tech were in the era of Slashdot and Linux becoming mainstream. Being a Microsoft hater (aka Micro$oft) was very popular at the time. Bill Gates was on the way out, handing the reins to Steve Ballmer and the company motto, at least externally, was Embrace, Extend and Extinguish . The company prioritized lock-in and leveraging their dominance, and open-source was not part of…
Startups are under a lot of pressure to deliver fast. This often necessitates the accumulation of technical debt. Many articles have been written on why it is essential to pay off technical debt. Fewer speak to circumstances for keeping debt or evaluate what areas of tech debt should be prioritized. In my experience, software developers often overvalue the benefits and impact of fixing tech debt…
I have noticed a trend that many brilliant people struggle to advocate for their ideas effectively. Often as engineering or product leaders, you need to propose a technical or product solution, recommend a vendor or make some sort of choice that you need buy-in from others. In all of these cases, the ability to “sell” your idea is critical. Here are the top 4 things you can do to take…
I was chatting with someone from a startup last year, where it is normal for team members to put in extra long hours (60+ hour weeks). The founder and CEO said, “I wish it wasn’t like this, but it is what we need to do right now.” I was a bit shocked by this. He knew it was not healthy but did not see any alternative. Marvin Let me tell you a story about Marvin (name changed).…
I have seen a flurry of bad job-searching advice on LinkedIn recently. Here are some of the top ones I have seen and what to do instead. Stop applying for jobs that are advertised. Everyone else is. The people who are advertising jobs are the ones who are hiring. Very few people are sitting on open positions without posting them. Yes, competition may be high for these roles. Instead, focus on how…
I am an engineering leader with a proven track record of scaling teams and delivering business results. Experience ranges from startups to Big Tech, including a successful exit and scaling teams from founding engineers to 50+. I am currently a Senior Director of Engineering at Dash Social , leading Product Engineering. I focus on building quality products that delight customers through a pragmatic…