DEV Community: Will Barrett

Engineering Team Red Flags and What They Mean

Will Barrett — Mon, 23 Mar 2026 23:49:01 +0000

We’ve all seen stressed-out and poorly performing Engineering organizations. Over my years in technology, I’ve seen the same red flags pop up repeatedly, with predictable results. I’m sharing the top 9 signs I look for, along with what they usually indicate, in the hope that others who see the same signs will better understand them and see the next steps to resolve them.

Fear In the highly unstable world of technology, fear is far too common. Engineering teams are sometimes prized assets of an organization and sometimes expensive cost centers. At most organizations, they are both, depending on who you talk to. But fear is corrosive.

It impedes trust and hinders productivity. It pulls attention away from the work and creates conditions for negative politics to thrive. Signs of fear appear in faces and body language. They show up in defensiveness and insecurity. They manifest in politics. They mean that staff don’t feel secure in their roles.

Usually, they are afraid of threats to their livelihood, standing within the organization, or the loss of opportunities. Calming these fears with honesty, transparency, and fair dealing is one of management’s key responsibilities.

Constant Firefighting When everything is constantly going wrong or leading to reactive action, it is always a symptom of systemic problems. It could be poor tooling, rushed releases, or a culture that rewards heroics over one that supports consistent progress.

This type of environment will burn out staff, lead to turnover, and hinder the consistent delivery of value to users. In this type of environment, enforcing 5 Whys meetings, slowing the feature release cadence, and holding staff accountable for implementing the systemic change required are the only ways out.

Often, the business side of the organization will have a hard time accepting this because they are already frustrated with the current state and want immediate progress, not slower delivery.

Uneven Stress and Ownership When a small number of people hold all the responsibility or are on the critical path to accomplish anything, it creates unhealthy dynamics on the team. Some team members may be coasting while others grind towards burnout, or knowledge and power may be hoarded by a few to whatever ends.

Either way, allowing the pattern to continue will result in team churn and lower velocity. Managers need to take action to even things out and restore balance to the team. Groups are most successful when everyone pulls their weight and is allowed to optimally contribute.

Roadmaps That Are Mismatched with Reality Most commonly, I see roadmaps that would require a miracle to complete within the allotted time. Usually, the executive team is pushing for everything right now, and the staff handling implementation feels they have no leg to stand on to push back. The results are predictable: burnout, blown deadlines, and low-quality work.

Giving developers agency to provide roadmap feedback and to build in buffer time for polishing software before release are non-negotiable. Forcing leaders to stack-rank their priorities is a harder pill for executives to follow but swallow, but it’s the only surefire fix I’ve seen.

When there is only one top priority, everyone can focus on delivering it and give it a strong chance for success. When there are five or more, most staff can’t even consistently remember what they are. We humans, are limited creatures, and our working memory is painfully finite.

Lax Security Passwords on Post-its. Everyone has root access. The password management system is a Google Sheet. Lots of accounts are shared. Whatever the signs, lax security means that staff don’t take user trust seriously.

These organizations may be too self-absorbed, more worried about how they will get rich than about how they impact the lives of their users. The solution is to refocus on the users—be grateful for them, and treat their trust with care.

A CISO and training are the most common solutions, but in reality, all but the most inexperienced team members already know what should be done and only require reminding of their responsibilities. Once that’s done, all that’s usually left is answering disagreements over the level of care/paranoia to exercise. A few well-worded policies will do the trick.

No One Knows “Why.” The people doing the work don’t have a clear sense of the reasoning behind the work they’re doing, or don’t see it as valuable. This is a clear sign of weak leadership or poor decision-making by those leaders. In this situation, staff may appeal to authority to justify their actions, citing leadership opinions rather than data or insights from users.

The solution to this problem is two-fold. First, develop a clear “why” and share it. The “why” should center on the user, ideally incorporate data, and be clearly understood in terms of the value generated. Second, share the “why” consistently and broadly with the team, repeating yourself until little confusion remains and you hear others repeating the why without prompting.

Sloppy Engineering Empty or outdated READMEs, poor test descriptions (or no automated tests at all), manual build and deployment processes, out-of-date packages or containers, flaky tests, poor development processes—really, the list on this one gets long, but we’re not looking for just one sign. We’re looking for a cluster of poor practices that add up to the team being sloppy or delivering shoddy work.

There are several causes for this. Inexperience, disengagement, or constant time pressure are the usual culprits. Inexperience is fixed with education. Constant time pressure is fixed by building the business case for improving technical systems and quality. Disengagement is the hardest nut to crack. It requires identifying and removing demotivators while also creating the right conditions for motivation, which vary from person to person.

After that’s done, scheduling in cleanup time and paying down the debt will be required.

Process Paralysis
Every change takes many sign-offs and approvals, which are hard to get or frequently delayed. Complying with process requirements consumes a large share of developer time. Even small, clear wins are drowned out by red tape. Every small error adds to the process load, stacking on the teetering mass of paperwork. We have to ask — why is the organization so risk-averse? Once we understand the motivations, we can pull out the scissors and start removing process checks and approval levels until we reach something close to industry standards or the minimum required by the company’s compliance framework.
Resignation
Either a team that is turning over for better jobs, or even more commonly, a team that has given up on trying to change things. You might see half-hearted retros where no one tries to push for changes, or the same items come up week after week with no follow-up or resolution. Staff may be gaming metrics or checking boxes rather than showing up with a drive to win. Engineers may be keeping their heads down rather than standing up for what they believe. When staff see a systemic failure to change and improve, they will stop pushing for it and eventually give up, looking for greener pastures. This red flag indicates deep problems in how the team is run that need to be addressed. It’s the most general of all the signs and indicates that whatever is wrong has been wrong for a long time.

Conclusion
Looking for and resolving red flags is a key responsibility of Engineering leaders. Building and maintaining a successful Engineering organization depends on creating an environment where people want to engage in their best work. Tending to the garden by proactively monitoring for challenges and providing swift resolution creates trust on all sides and gives both the business and staff members more of what they need. While some believe that the industry as a whole falls into the same traps, I have seen organizations that exhibit few or none of these flags. Building productive and effective Engineering organizations is worth the effort and is more possible than many believe.

My 30 Favorite Tools as a Fractional CTO for 2026

Will Barrett — Wed, 03 Dec 2025 16:25:16 +0000

I’m always fascinated by the daily rituals and tools that others use to thrive in this world. Here’s my list, and why I use each one.

Part I. Electronics

You can’t be a technologist without Technology. My relationship with technology is complicated – no one who has deep experience with computers and internet systems has a simple set of feelings about software, hardware, and how they impact us. I try to manage the impact of the tools on my thought processes, not just optimize for maximum productivity. Of course, computers and technology, when built and used well, are a force for good, but they can also be massively distracting and expensive boondoggles that slow us down, addict us, and infuriate us. These demand constant self-control from the user. Here are the tools I prefer for a mindful approach:

Apple MacBook Pro, M1, 16”
This is an old machine by computer standards, but it does everything that I need. It runs the development environments for every app I’m working on, gets me into and out of video meetings, and holds a charge for a whole business day. Upgrading computers regularly is no longer necessary unless they break. I plan on using this one until either I can no longer upgrade its operating system or the hardware gives out. Despite the improvements in iPad software, a laptop computer is still a basic necessity for everyone working in technology. Turning off notifications, being mindful of time spent in Slack or in consumption, and approaching the computer constantly with intention are critical.

iPad Pro 11”, M1 & Apple Pencil
Just because I use a 16” laptop doesn’t mean I always carry it around. My iPad lets me handle most tasks that don’t involve programming and take the occasional meeting, while weighing less than half as much as my MBP. I also prefer reading on an iPad, so most of my document and code review happens on this machine. I tend to leave my MBP at my office and carry the iPad back and forth. The other main use for my iPad is as a substitute for my cell phone. I lack self-control when it comes to checking messages and Slack, so I found removing the option from my cell phone was the best way to keep myself in check.

iPhone 13
Yup, 4 generations behind the current model. It’s my favorite color (green), works fine, and does everything I need it to, which is mostly play Spotify, make and receive calls, and load Google Maps to get me where I need to go. If I could downgrade to a flip phone, I probably would, but maps are too useful. Having an always-available internet connection in my pocket can be challenging for self-control. I think the constant distraction is almost offset by constant access to the world’s information. By the way, any app that sends me a marketing notification gets uninstalled. I don’t want to be interrupted. My clients know that in any true emergency, they need to call me.

T-Mobile Cellular Hotspot
I used to blow through my phone’s hotspot data allowance each month. Eventually, I broke down and bought a dedicated hotspot to use on the road or when away from home or office. It’s an investment in freedom and the ability to work from wherever I like, without having to hunt down a free Wi-Fi connection. I use it to work from my car by the ocean, from libraries, from park benches, and anywhere else I like. Its second use is as a backup internet source when the Comcast landline network goes down at home, or my office fiber is on the fritz. If it gets me one more hour of billable time per month, it is worth the investment, and I’ve always been able to justify it.

Olympus TM-720 Audio Recorder
This is an upgrade from my even older DM-620 recorder. I misplaced it and decided I was tired of carrying an extra connector cable. Yes, my iPhone can take voice notes and even transcribe them, but it can’t do so hands-free because there are no physical buttons to start or stop the recording. I use the recorder to capture ideas while driving, dictate content, draft documents, and record occasional in-person interviews. It is small, light, has decent audio quality, and is affordable enough that I won’t cry too hard when I lose it. This tool lets me work while walking in the woods, away from cell reception, and modern transcription tools make turning the resulting recordings into text quick, painless, and free.

Apple AirPods and AirPod Max
AirPods for on-the-go, Max for at home. The primary purpose of their use is to keep client conversations confidential. Less necessary is listening to music while I work and podcasts while I do chores.

Section II - Software

Never have we had so many great options available. Most of these tools are things I’ve been using for years. Some are so central that I don’t know how I would manage without them.

Todoist
Todoist is the center of my day-to-day workflow. It is my second brain, and to date, I’ve created and completed over 48,000 individual tasks – a nice vanity metric that Todoist is all too happy to provide. My wife and my assistant have access to my Todoist instance. No one else is allowed. Todoist tells me what I need to do by when and gives me the mental space to think, rather than trying to remember what to do next. I recommend that everyone have their own tracking system for their work, separate from what their employers provide. It gives us all an internal locus of control over our time rather than an external one. Of all the options in the market, I think Todoist is the best suited to this purpose.

Spark 3 Email Client
The death of email, much promised, will never happen. It’s just too ubiquitous to ever die. I have around 10 different email accounts for different purposes. Some are tied to different clients, some to different projects. They filter into 5 inboxes, which my assistant and I collaboratively manage. Spark is not the best email client on the market, but it is the best option for managing multiple email inboxes when you have an administrative assistant.

Google Chrome with multiple profiles
Personal, business, and one for each client. I never seem to open the right profile on the first try. This tool needs a rethink, but migrating away from it will be a real pain. I tried Arc, but didn’t like it. Firefox is slower, and Chromium tends to have more bugs. This is not my favorite system, but I haven’t found anything better.

DuckDuckGo Search Engine
Why? So I can turn off the AI results and advertisements. They’re not generally helpful and waste time, attention, energy, and water. Google search results are not what they used to be, and this is the best alternative I’ve found. Note to others in software: if I want AI, I’ll talk to an AI. No need to cram it into everything.

TogglTrack
Time tracking is an unfortunate necessity. Toggl Track works on just about every device and platform, and its reporting is flexible enough that I can pull exactly what I need. I can also copy meetings from my calendar as time entries, which makes keeping track of time a little easier. I used to use Tyme for Mac and iPhone, but the lack of Windows support became an issue for some of my collaborators.

Google Workspace
Now that my time is spent more on management than programming, this is the center of my work. Everyone needs documents, spreadsheets, calendars, and email (if only for iMAP and SMTP access). Most of my clients are Google-based, though I do have one on Microsoft.

CalendarBridge
Along with having 5 inboxes, I also have 5 calendars. Managing this is probably the most annoying part of my work. CalendarBridge is a relatively simple utility that copies appointments between calendars and automatically manages my availability. This saves a lot of time and headache by reducing the percentage of the time I’m double-booked. It also anonymizes my meetings so that clients with access to my calendar only see free/busy information, except for my meetings with them.

Fantastical
This is the best calendar program that I’ve found. Lately, I’ve been mostly using it as a client to jump into meetings. I may remove this from rotation soon and return to Google Calendar for better scheduling features. Fantastical gets confusing to use with multiple calendar sets, and its scheduling interface tries to do too much in too little real estate.

WisprFlow
Sometimes, writing something out takes too long, and WisprFlow is a great solution to the problem. We can speak far faster than we can type, and for quick emails and Slack replies, WisprFlow is a game changer. Their mobile keyboard for iPhone and iPad really eases text entry and smooths out what can be a frustrating experience. I don’t always use this system, but when I do, it can be amazing.

LinkedIn
I meet a lot of people through this platform and find it very helpful as a networking and sales tool. It’s currently my primary platform for publishing as well, though this will certainly change in 2026.

Linear
Linear is the best option I’ve found for managing Engineering projects. It does everything I need it to, and a little that I don’t. It’s an opinionated tool for managing software projects, luckily I agree with most of its opinions.

vim & tmux
I still haven’t found a better alternative for software engineering. I find AI to be intrusive rather than helpful, so I see no appeal in Cursor or similar tools. I’ve never enjoyed working in IDEs, no matter how advanced, though the JetBrains toolchain is the best of the bunch.

Apple Notes
For times when I need a scratch pad, digital notes, or a manually updated dashboard, this is the quick, easy solution. It reliably syncs across all my devices, does just enough not to get in the way, and can be used with an Apple Pencil on the rare occasion it’s necessary.

Slack
Worse than email, better than text messages. I prefer to only dip in a few times a day, but this is an industry requirement. My favorite use for Slack is communities of practice like Rands or Jade Rubick’s communities. For companies, Slack is frequently an interruption machine that does more harm than good. So, I try to encourage thoughtful posting rather than dashing off every thought that comes to mind.

Section III – Writing Materials

Much of my work as a fractional CTO falls into two categories: making good decisions about strategy and communicating them clearly. I also write marketing content for my own practice and for a couple of other projects I hope to release in 2026. Writing is core to my thought processes – taking notes by hand and working in the physical world lets me process information more deeply and understand more aspects of the problems I’m focused on. While many people are bouncing their ideas off of ChatGPT (which is convinced all humans are brilliant savants who never come up with a bad idea), I prefer to write out my plans and thoughts, then send them to my collaborators, who can tell me how wrong I may be.

Apica CD Premium Notebook & Galen Leather Cover
This is my daily note-taking device. I capture TODO items, scribble during meetings, and write down important points when I’m preparing for a decision or getting ready to do something that requires precision. Breaking down programming or other complicated tasks, writing my daily journal entries, etc. They all happen here. This is my log of thoughts, feelings, professional, personal, and other progress, and the ugly, unfiltered reactions to everything that happens in a day. Don’t read anything in this notebook – it’s all half-baked.

Rhodia 8.5×11 Lined Pads
When I’m going to write a rough draft by hand, this is what I reach for. I have one of these in my bag with me at all times so that I can scratch away at some rough draft in moments on the train, or when sitting around with nothing better to do. I like the feel of the paper, and I grew up writing on 8.5×11 in school. The cover helps keep them from being destroyed by the constant coffee spills I make.

Lamy AL-STAR Fountain Pens
I like fountain pens, though I use cartridges these days. Nothing else writes as smoothly or comfortably. I like the paper clip on the AL-STAR; it keeps the pen from getting lost easily, and the weight is just about right. The cost isn’t too much to worry about – I always lose my more expensive pens after a few months, but I have never lost one of these. The Lamy Safari is a little too light for me, but it does in a pinch. I also like that these are big pens – I’m not very tall, but I have relatively large hands.

Pilot Precise V7 Rollerball Pens, Fine
For when I can’t use a fountain pen. Airplanes mostly. The occasional moment when my fountains are out of ink. It’s acceptable. I keep a red one in my bag for marking up drafts.

Underwood GoldenTouch Typewriter, 1960s
I like to type rough drafts at times; the inability to edit makes me think ahead and keeps me from editing while I write. Sometimes it skips spaces, and it’s annoyingly loud for my family, but it makes me focus. There is no YouTube, HackerNews, Reddit, or anything else. Just me and what I’m trying to say. Good for when my hand cramps from using my pen for too long. This lives on my office desk, and is used most mornings before my first meeting. OCR gets the pages into Google Docs for editing later.

Library Cards
Don’t ever trust important decisions to someone who doesn’t read. As much as we’ve benefited from information access on the internet, we still retain more of what we read when we read on paper in books. E-Paper or iPad reading results in less retention, according to some research. Libraries are still relevant for all of us, and represent well-edited (compared to the internet) sources of information and deep thought. I try to finish a book a week, and many of the ideas I pick up are useful to my clients. The iPhone isn’t a bicycle for the mind, but libraries sure are.

Section IV - Finances

QuickBooks Online
This is my solution for accounting and invoicing. I started with the free version of Wave Accounting, but the lack of classes eventually led me to switch to a different platform. I don’t like the new reporting system they’re building because it has many accuracy issues, but the old-school reports work great and are time-tested.

A Bank with Physical Locations for Checking and Credit Cards
Sometimes, as a business owner in the US, you still need to walk into a bank and speak with someone. I started with an online-only bank, but as soon as I needed a notarized bank letter, this approach broke down. Some Government entities still expect you to bank with a brick-and-mortar, so that’s what I do.

Checking Account with an Online-Only Bank
I think it’s smart to keep a backup transactional account, just in case something goes wrong with the primary. I’ve kept my online-only account and now use it only for emergencies.

An Online-Only Business High-Interest Savings Account
I hold my cash reserve here. Same theory as personal finances – make your money work for you, at least a little bit. I’m surprised more business owners don’t do this for their cash reserve.