Dan Short (he/him)
Director of Engineering at Virtuous
Updated: 20 March, 2025
Director of Engineering at Virtuous
Updated: 20 March, 2025
Under Construction: I'm working on converting this to 11ty to play with static site generators.
My Manager README is a document that helps introduce you to my management style, philosophy, and expectations. The intended audience is primarily anyone who reports to me, though anyone is free to read it - or even provide feedback on it! Please treat it as a reference and guideline for how I will conduct myself as a manager and what I expect from you.
This document is aspirational. This is how I strive to be. I’m not perfect. I have made and will continue to make mistakes. I urge you to hold me accountable for my promises, and I’ll do the same for you. Without your feedback, I will not be able to improve as a manager.
If I were going to put my management philosophy on the cover of a book, it would be “Servant Leadership.” My job is to make sure that you can do your job. I want for you the same thing I want for my family; for you to be happy, healthy, and successful. Here’s how I judge if I’m doing a good job:
I also strive to create a Leader-Leader environment (as opposed to a Leader-Follower organization [see Turn the Ship Around ]). This style of leadership is particularly important in a fully remote environment, where we aren't always in the same room, and there is little to no direct supervision. When working remotely, team autonomy and clear communication become even more critical. I've found that successful remote teams require:
I can't be involved in every decision, so I rely on my team to make the decisions they can and then let me know where they're going. I won’t be micro-managing or assigning specific things for you to work on. I’ll work with you to define the goal and let you decide how to get there (with help from me when and where you need it).
Another important part of ensuring that you’re happy, healthy, and successful is ensuring that I’m helping you resolve conflicts across teams or technologies. If there is a difference in approach or a misalignment on goals, it will be my job to ensure that your opinion is heard and that there is clear articulation of the potential approaches and documented tradeoffs to help us make informed decisions with our trio partners. The cliché about Product and Engineering being constantly in tension is a cliché because it's often true. It's my job to help Product understand the constraints under which we're operating, and to ensure that Engineering knows the priorities and can help move Product's priorities forward as quickly and efficiently as possible. Cross-functional alignment isn't always easy, but it's always possible.
When security or vulnerability concerns arise, I ensure they get proper attention and aren't sacrificed for speed or features. Building this balance between security, functionality, and usability is a delicate art that requires constant attention from leadership, and a clear communication of the importance of these fixes to stakeholders outside of Engineering and Security.
Trying to get consensus in large groups is the enemy of progress. We may need to commit to an approach in cases where myself, you, a partner, or the team will not agree with it. It is my job to drive a clear direction for next steps so that we can keep moving forward. I will work to keep everyone accountable to the decision that was made and escalate when that is not the case. While we may have to go backward and readjust, we will have the learnings from the first approach taken and can apply that to our second attempt. My ultimate goal is to keep forward momentum.
Transparency, curiosity, humility, trust, and a sense of humor.
I need to know what’s happening, and so do you. I will push the “why” of decisions down to the team as soon as possible, and I’ll leave the “how” to you. You should always know where we’re going and why we’re going there, and I’m going to lean on you and the team to help figure out how to get there. I am always here to help navigate that process, but those of you closest to the problems are best suited to find the solutions.
Conversely, I need to know what you’re working on and what problems you may be having. This doesn’t mean that I need status updates from you twice a day, but if something isn’t going to plan or a plan is changing, I need to know about it to make any necessary adjustments to account for those changes. If something is going to take you three weeks longer than planned, I shouldn’t hear about it 2 days before it’s due.
Give me plenty of heads up, as I’ll be doing the same for you.
I also want to make sure that everyone is communicating, async, a lot. All conversations around the work should default to public spaces and only be moved into a private space if the conversation is disruptive to other processes or may cause confusion for people outside of a smaller group.
I do very little engineering work any longer and spend most of my time focused on learning about how to be a better leader. This means focusing on how to support the team, how to make sure we’re planning properly, and finding new ways to keep my teams happy, healthy, and successful ( there it is again! ).
This means that I’m taking the time to learn new approaches to old problems, and I expect my teams to do the same. I want everyone to approach problems with curiosity, not preconceived notions, and be willing to challenge both their own and their teammate’s assumptions. It’s perfectly acceptable to have strong opinions, we’re all smart people, but they should be loosely held and open to challenge.
If you don’t hear me say “I don’t know” at least once a day, you’re probably not paying attention. I’m well aware of my own limits and will never lead you to believe I know something I don’t. If you assume I’m fully versed on a topic then you may put too much weight on a decision I’ve made based on inaccurate information. If you lead me to believe you know something you don’t, then I’m going to lean on your supposed expertise and we may end up in a bad spot. We all need to understand each other’s limits to ensure that we’re making the best choices possible when solving problems.
I’ve led, and continue to lead, teams working on technologies with which I have zero experience. In order to make that work, we have to lean on trust.
I’m going to tell you the truth. All the time. Even if it sucks. I expect you to do the same. This doesn’t mean that I’m going to be harsh or unsympathetic. I am always going to lead with compassion and empathy, but I’m still going to deliver the truth. I want you to be open and honest with me, even if it’s uncomfortable, and we’ll lean on each other in the process.
I’m also going to always assume good intent in async communications. It’s too easy to take an off-hand or careless comment as a bald-faced attack. I’ll trust that you’re being compassionate and candid with async communication until you lead me to believe otherwise.
I don’t take myself seriously… life is too short. I’m happy to make fun of myself and lean on humor as a way to de-escalate tension and help people understand when I’m being serious or light-hearted in our async text-based work environment. I will /giphy the hell out of a conversation where it’s warranted (Kristen Bell and Schitt’s Creek gifs are my love language).
As a leader in technology, I recognize that trust is earned through consistent attention to security and privacy. Throughout my career, I've emphasized a few key principles:
I encourage teams to integrate security thinking from the earliest design phases and make it part of our definition of done. In practice, this means regular security reviews, encouraging team members to raise concerns, and working closely with security specialists to implement best practices.
The most secure systems are those built by teams who understand that protecting user data is part of delivering value, not an obstacle to it. This mindset creates the foundation for software that users can trust with their most sensitive information.
I won’t ask you to do something I’m not willing to do or hold you to a standard to which I don’t hold myself. I also won’t take advantage of something that I don’t also allow you to take advantage of.
TODO:
Communication expectations
Work hours/flexibility
Work quality
I’ve said before that I don’t put too much stock in personality types, but 16 Personalities gets pretty close (I think) as an Assertive Advocate (INFJ-A). Here’s my full profile on 16 Personalities.
You and I will have 1:1s every week or two, depending on your needs. Your 1:1s are your 1:1s, and we’ll discuss the topics that are most important to you. We’ll keep a record of these topics in a shared document, and you will drive the meetings. Expect me to ask questions and probe around the areas of your interest, but we’ll keep on topic and I will endeavor to not turn these into status updates (unless that’s what you want).
I hold rotating skip-level 1:1s with my manager’s direct reports, ideally speaking with each IC once every month or two. Skip-levels are primarily to make sure that communication is making it through the organization and that we all have a shared vision of where the product and processes are going. This is also an opportunity for individuals in my organization to come to me with issues with their manager or colleagues that might not be filtering up.
This is also an opportunity for you to get to know me and my particular management style if it’s not already spreading out through the organization. You can ask me about my favorite coffee (I’m not picky) or what I’m growing in my garden, in addition to business strategies and long-term roadmaps.
For me personally, no news is good news. I sometimes don’t do a good job of letting people know they’re successful and meeting expectations because if something is going sideways I’ll reach out to you directly. This can sometimes lead to a perceived lack of communication from my direction. I work on over-communicating to try and alleviate this particular flaw, but I still need practice.
I’m a generalist; I know a little bit about a lot of things. I probably don’t have the deep knowledge of specific languages or technologies that you have. That’s why I hired you 😀 ! I’m really good at getting to the meat of a problem or asking probing questions to get to the core of an issue (five whys). Lean on me for troubleshooting, getting to the root of an issue, and making sure that we’re answering the right “why.” I’ll lean on you for the technical know-how to make it all magic.
TODO: Talk about conflict avoidance, and how I overcome this by being (sometimes) uncomfortably blunt.
Social Media
I’m a mentor on PlatoHQ
I have drafts of articles to post on LinkedIn and Medium, but the imposter syndrome is real, and I haven’t posted on my blog since I posted about not posting on my blog.
I grew up in north Texas, moved around a bit with the military, spent time in Oregon and California, and settled in the Austin, Texas area in 2006. I convinced my (now) wife to move from her home state of California, and she’s become a converted Texan. I have an adult son looking to get into the movie-making industry. He got married on May the 4th, 2022, and I am now officially old.
When I’m not at work, I’m usually spending time with my wife and close friends. We cook every meal at home, have a backyard garden where we spend hours to save 10s of dollars on groceries, and enjoy making things to make our nest even cozier. We like being away from the metropolitan hustle and bustle but being close enough to attend a concert or musical when the mood strikes.
In 2022 we gook a month-long road trip around the North East US and absolutely loved it. I’m looking forward to spending more time traveling in the future, and exploring the world with my lovely wife.
I love tear-jerking dramas and gratuitous action flicks, and pretty much anything in between.
I listen to just about any kind of music except for opera and twangy country (I grew up in Texas, but I’m a city boy).
I also spend quite a bit of time reading, whether that be ways to improve myself or escapism in fantasy and sci-fi. You can see everything I’ve read or am reading on my Kindle on my GoodReads list.
Work in progress, may be ugly
We lose the habit of reading because we’re afraid of wasting our time. We think we need to be productive and “on the go” at all times. But people are not machines, and you are nourished by naps and fiction and basking in sunlight, no less than by food and drink.
— Owl! at the Library 😴🧙♀️ (@SketchesbyBoze) September 2, 2021
