This post is a work in progress. It includes my answers to common "cultural-fit" job interview questions. The image above shows the outdoor version of my home office.

Note: Many of these questions are quoted from the reference list at the end of this document. Citations are coming soon!

What are your career goals?

My career goal is to engage my strengths (such as  persistence and love-of-learning) and pursue my values (such as diversity and sustainability).

As a youth, I thought of building a pro-social video game to teach people social and emotional intelligence. Years later, something like that continues to appeal, because it is in the cracks between technology and psychology. If I could squeeze in a contribution to environmental sustainability, then I would be living my dream life. Of course, few of us live a dream life, so achieving a reasonable approximation is enough.

What role? Often I have told colleagues that I would like ideally to be the technical lead to whom the architect comes for advice.

What company culture? The ultimate culture is evidence-based, stands on the shoulders of genius, and follows known community best practices. An example of this is to use Guarding Minds at Work as the basis for creating a healthy culture. Another example is to use Rapid Development or Accelerate as the basis for creating a system of software development management.

What values? My primary career values are sustainability and diversity. From this come all of my other career values.

If I achieved what I really wanted, I would continue to live on Salt Spring Island, working remotely as a technical lead and/or senior software developer. My work days would be Monday to Thursday, with core hours from 10 am to 4 pm, filled with solving technical and social problems (or challenges if you like) using evidence-based skills. My colleagues would be engaged in an adventure of personal growth that balances work and life. The work would make a very small contribution toward a lush and peaceful world.

What are your strengths?

My best friend tells me that my top professional strengths are...

  1. Thinking outside the box.
  2. Adhering to best practices.
  3. Persisting at problems and doing whatever learning it takes to solve them.

Here are some other takes on my strengths.

Persistence. According to the VIA Survey of Character Strengths my top strength is persistence.

You work hard to finish what you start. No matter the project, you  "get it out the door" in timely fashion. You do not get distracted when  you work, and you take satisfaction in completing tasks.

Love of Learning. The VIA also attests to my curiosity and interest in the world.

You are curious about everything. You are always asking questions,  and you find all subjects and topics fascinating. You like exploration  and discovery.

The VIA survey also gave me three other top strengths.

  1. Humour and playfulness.
  2. Capacity to love and be loved.
  3. Fairness, equity, and justice.

The latter two mean that I am community-oriented and have a strong tendency toward treating all people equally.

The following photograph represents my top five strengths. It shows persisting in the setup of our compost at the cafe. We've connected a hand truck to our bike rack so we can transport the composter from our house to the cafe. I loved learning about the the various composters on the market. The electric car and composter demonstrate my commitment to fairness, equity, and justice through sustainable practices. It certainly takes a sense of humour and playfulness to drive around the neighbourhood at less than 10km/hr with my wife preventing the composter from falling. And hey... who can find such a wonderful, supportive spouse without having the capacity to love and be loved.

Despite my humour and playfulness in life, I tend to be focused and professional in the workplace. While I joke around with colleagues, my top priority at work is to get things done.

At work my style is best suited toward:

  1. Doing something rather than persuading or managing others.
  2. Working autonomously rather than working as part of a highly interactive group or working with close supervision.
  3. Working with facts/science rather than subjective material.
  4. Working with clear goals rather than on vague or ambiguous tasks.

Also, despite being outgoing, my personality is introverted.

What are your weaknesses (or opportunities for growth)?

My best friend tells me that my top professional weakness are...

  1. Going with the flow when it's going sideways.
  2. Interpreting indirect or colloquial messages.
  3. Thinking inside the box.

Here are some other takes on my weakness.

  1. Persuading or managing a group. I am better at doing something. That said, I have training in management, influence, communication, and assertiveness.
  2. Working in a highly interactive team. I am better at working autonomously or with a small group of focused colleagues. In highly interactive groups, I tend toward exhaustion and over-stimulation.
  3. Working with close supervision. I am better at working autonomously toward clear outcomes within time boxes.
  4. Working with highly subjective material. I am better at working with scientific, factual material. (Oddly enough, in my life I am a voluminous reader of classic literature.)
  5. Working towards vague goals. I am better at working toward clear finish lines. When someone sets a task, I ask questions to clarify deliverable outcomes.

What is a recent example of when you really demonstrated going "above and beyond" or "exceeded expectations" on a specific project or task?

When our team decided to use the CQRS/ES architectural pattern, I went above and beyond by finding a conference on the topic, registering for the conference, paying for it myself, and taking one week of unpaid leave to attend the conference.

Another example of going above and beyond is in team communication. In the last six months or so, our team decided to do most communication in our project management tool instead of in Slack. When the team forgets to do this, I currently take the initiative to copy/paste/format the conversations from Slack into the project management tool. The team has appreciated this.

Here are two more examples. As part of our team conversations about which Git branching/merging model to use, I took the initiative to read community resources and compose a blog post on the topic: When our software development cycle lost velocity, I took the initiative to work with a junior developer to research existing patterns, perform an evaluation of company needs, and choose the most appropriate development cycle for the team.

Going above and beyond and exceeding expectations is part of my DNA. If we're in an interview, ask me about these situations too:

  1. Learning OpenID Connect by contributing to open source with Kevin Chalet.
  2. Contributing to StackOverflow to improve my technical communication skills.
  3. Presenting to the community on Git, ASP.NET Core, and DevOps.
  4. Seeing a cognitive behavioral psychologist to improve my workplace skills.

What is a new skill you’ve learned, a book you’ve read or training you’ve done in the [the year 2020]. Why was it important to you? How have you applied what you learned?

In the last year, I earned the TypeScript gold badge (200 answers, 1000 up votes) on StackOverflow. This was important to me, because in my most recent role, the back-end Web API uses TypeScript. Earning this recognition helped because it taught me real-world TypeScript expertise, increased the strength of my network of TypeScript A-players, and gave me practice explaining complex TypeScript concepts.

In the last year, I also attended a CQRS/ES conference in Vancouver. This was important to me, because this architectural pattern underpins the entire back-end system in my most recent role. Attending the conference helped me learn canonical patterns for designing, implementing, testing, and maintaining such a system. It further strengthened my network of A-players in the CQRS/ES world.

What is your proudest moment as a people leader. What made it so memorable? What impact did it have on others?

This narrative is shifting gears from software development to coffee shop management. In the last four months, I have taken on the challenge of re-opening a small coffee shop during COVID-19. This is a community project of mine, and it is not my primary employment. A main challenge has been to encourage mask use inside the building. What's made it memorable is that it's drawn on twenty years of learning in social psychology including assertiveness and influence skills. We've created several signs and landed on this message, “Most people wear masks in this building. We appreciate it. Of course, it's totally up to you.” This is the third iteration of the sign. The impact has been outstanding; our mask wearing adherence in the building is well above 90%. The sign is informed by research by the social psychologist Robert Cialdini. In addition to crafting the passive messaging strategy, I have also been engaging with individual customers with clear, direct, respectful communication. This is meaningful because it is possibly saving lives in the community.

We also built some tents for the pandemic outdoor seating.

What is a difficult conversation you had as a people leader. What made it challenging? What did you learn from it?

Situation: My software development team was designing the authentication and authorization system for a new customer-facing web application. The management at the time was under pressure to release quickly.

Task: My role was to design and implement this security layer. Management asked me to take a shortcut that I knew would jeopardize end-user privacy. I needed to explain the situation to management and protect our end-users.

Action: My plan was first to explain the privacy risk to my manager, and second, if necessary, to set a boundary that, if this was the management's choice, I would not be the person for the job. This was challenging, because I was, in effect, preparing to say no to my employer. After my explanation of the security hole, management was not convinced.  The way I approached my follow up was to await a time when my manager and I were one-on-one.

Result: The manager received my boundary calmly when I explained that, "I appreciate that this is the way you would like to go forward, but given the security concern, I am not the guy for the job." After management had some time to consider this, we ended up implementing the security in a way that did protect end-user privacy. The team maintained respect for everyone involved.

I learned that calm, clear, patient, and respectful boundary setting can help people think through decisions more carefully.

Also ask me about these situations:

  1. Staying the course to complete conversion of CoffeeScript to TypeScript.
  2. Encouraging Civility and Respect in a workplace that had bullying.

What type of work environment or people empower you to do your best work?

Evidenced-based, professional cultures empower me to do my best work. An example of this is Westrum's generative organizational culture. Here are some references to specific cultural practices that I have found empowering in remote teams.

Default to asynchronous team communication. That means less use of instant messenger and more use of project management software for task communications. A great discussion of this pattern is here

Communicate about psychological health and safety. When we are in a sensitive situation, it can be helpful to read about best practices for conflict resolution and legal requirements for companies. A wonderful resource is

Spend time to craft succinct messages. Most communication benefits from being concise, clear, and considered. For instance, unless it is very urgent, it helps to collect three questions instead of asking one question every 15-minutes. Similarly, it helps to craft an precise technical question with a minimum reproducible example.

Schedule intense meetings at least two hours in advance. Software developers need to switch between operating on a computer to relating to a human being. Meetings go a lot more smoothly when every developer has time close out a task before interacting with the team.

Casual chit-chat among surgeons helps to maintain rapport. On my current team, we often keep Zoom open without really talking to each other much at all. This gives the sense of being in the same room and allows for casual conversation. The art here is knowing that, in these situations, the content must remain light, easy, and fluffy. This reminds me of the casual conversations that we sometimes witness among surgeons during open heart surgery!

Are you the next member of our team and want to be sure we don't miss something important we should know about you?

Four months ago, I purchased a local cafe that had closed because of the pandemic. My weekends since then have involved retrofitting it for the COVID-19 pandemic. This has been an enormously meaningful community project, and it has provided a weekly break from my ongoing role as a software developer.

From the tender age of 13, my hobby has been sleight-of-hand with playing cards. It's safe to say that I am an expert amateur. My YouTube channel ( contains videos that demonstrate sleight-of-hand with playing cards.

What is your home office setup?

I have a lovely home office that I have been curating over the last ten years of remote work. On a yearly basis I have been adding a high quality addition to the space.

In the early days, I added a Herman Miller Sayle Chair. It is ergonomic enough to keep up with my persistence.

Next, I added the HumanScale Float Table. It is a spacious, mechanical up-down table.

After learning that three-monitor setups are the most productive, I started first with the Human Scale Single Monitor Arm and then a Human Scale Two Monitor Arm. This of course necessitated monitors, and I went with three 24" by ASUS monitors (two landscape, one portrait). Initially, the three monitors required an eVGA UV Plus 39 adapter. Recently, though, I switched to using a Lenovo X1 Extreme and Lenovo Docking Station. This is an amazing three monitor setup!

In between the new table and the Lenovo machine, I added further ergonomics with a HumanScale Foot Rocker that keeps the body in motion and a split keyboard. My keyboard choice is the Kinesis Freestyle Two Keyboard because it throws nicely into a backpack.

Finally, my most recent purchase has been a Sennheiser Noice Cancelling Headset. This is phenomenal home office productivity.

After a recent renovation, the office now has a large picture window with a view of the ocean and our front garden; from time-to-time deer cross the window! The room started as a garage with concrete flooring, which we have now replaced with heated composite floors (faux wood). There is a bathroom off the corner and a separate entrance.

All this means that at work, I remain productive and out of the way of my family for the entire workday.

What questions, if any, do you have for us?!

  • What does this job involve, exactly?
  • What are the top skills an employee in this job would have to have?
  • What significant changes has this company gone through in the past five years?
  • What values are sacred to this company?
  • What characterizes the most successful employees this company has?
  • What future changes do you see in the work here?
  • Who do you see as your allies, colleagues, or competitors in this business?

Additional Cultural Fit Interview Questions

From Thinkific's guide to the first interview.

  • What have you accomplished in your recent roles?
  • Who are your references? What might they say about you?
  • What is your salary expectation?
  • When will you be available to start, if we were to offer you a position?
  • Have you had a lot of short stints? Taken a long break to travel? Became a new parent? If there’s anything you want to clarify about your previous experience or gaps in your resume, let us know here!
  • What excites you most about being a member of our team? How do you believe your skills would be valuable in this role?
  • Think about a specific time you faced a work challenge that you didn’t have an answer to or solution for right away. What was the challenge and how did you persevere to solve it? What did you learn?

From What Color is Your Parachute.

  • Tell me about yourself.
  • What do you know about this company, business, or organization?
  • Why are you applying for this job?
  • How would you describe yourself?
  • What are your major strengths?
  • What is your greatest weakness?
  • What type of work do you like to do best?
  • What are your interests outside of work?
  • What accomplishment thus far in life, gave you the greatest satisfaction?
  • Why did you leave your last place of work?
  • Where do you see yourself five years from now?
  • What are your goals in life?
  • How much did you make in your last job?

From the Koru7

  • Grit. Tell me about a time when you wanted something so badly, you were unstoppable pursuing it? (How long did you stick to it?)
  • Rigour. Tell me about a time you used data to make decision. (How complex was the data and the thinking?)
  • Impact. When did you have a measurable (quantitative) impact on a job or organization? (What were your trade-offs and prioritization?)
  • Teamwork. When working on a team, what is hardest for you? What about a time you worked on a difficult team? What was your role and experience? What makes you happiest and effective when working with others? What would your best friend say is your top strength and weakness? (Do you know your strengths and weaknesses? Can you empathize with others?)
  • Ownership. TODO Add questions about ownership.
  • Curiosity.  TODO Add questions about curiosity.
  • Polish.  TODO Add questions about polish.


Bolles, R. N. (2018). What color is your parachute? 2019: A practical manual for job-hunters and career-changers.

Smart, G., Street, R., & Tantor Media, Inc. (2008). Who: The a method for hiring. Old Saybrook, Ct.: Tantor Media, Inc.

Forsgren, N., Humble, J., & Kim, G. (2018). Accelerate: The science behind DevOps : building and scaling high performing technology organizations.

MacConnell, S. (1996). Rapid development: Taming wild software shcedules. Redmon: Microsoft Press.