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How Startup CTOs Fight Christmas Holiday Work Stress

December 15, 2016

The festive season is approaching, and although most of us look forward to some downtime (human, not technical), many are also stressing out trying to finish that never-ending to-do list before going on vacation. So, the 100 dollar-question is: how do you get your team to work efficiently, prioritize the right projects and get shit done while deadlines are piling up and your backlog is longer than Santa’s wish list? And how do you make sure that your security work isn’t neglected due to lack of time?

Web security firm Detectify and cloud task management tool Trello have interviewed startup CTOs and team leads about their best tips for greater efficiency.

Nataliya Remez: “We have a silent agreement to not promise more than we can achieve”

Works at: Web agency Young/Skilled
Role:
Team Lead
Twitter: @nat_remez

As the CTO/team lead, is it noticeable in your team that the holidays are approaching. If so, how?

It definitely is, we are getting a lot of last-minute requests from customers that want to have changes in place just before the Christmas sales campaigns. Usually those changes require both a lot of time and resources from us since the updates are needed on the entire app/infrastructure.

What should CTOs/team leads keep in mind during times of increased workload and upcoming vacations?

First of all, make sure to put off some time to ask your teammates about upcoming vacations, add them to a shared calendar and inform everyone about them. Try to set the right expectations in advance, both internally and externally. We have a silent agreement to not promise more than we can achieve. All communication with clients goes through our Customer success managers, who inform them that our speed will decrease due to the absence of team members.

What kind of work routines do you have in the team and what digital tools do you use to structure your work?

We are using Trello boards and workflows for almost everything, starting from Must have-features and Product Roadmap to Support. We also have Developer Team Boards such as Fast Track board and Sprint board. Also, we found a way to integrate our boards with GitHub issues and statuses through gitlo.coFor meetings, we use Google Hangouts.

An example of a IT / Admin Support Trello Board

How do your security routines look like before/during the holidays?

We are following our regular rules and agreements which include proper SSL implementation and we use Detectify to security test the websites for some of our clients.

How do you get started in the best way when you return to a never ending to do-list after vacation?

It’s always a good idea to have a short daily sync-ups with the team and 1×1 with your managers.

Your best tips for working efficiently and getting shit done?

Make a plan and try to follow it together with your team, at least for 2-week periods.

Johan Norrman: “Make sure that the tasks and projects you are returning to are stimulating”

Works at: Web security firm Detectify
Role: CIO
Twitter: @johannorrman

Meet the Detectify Team: Johan Norrman

As the CTO/team lead, is it noticeable in your team that the holidays are approaching. If so, how?

Our focus is on trying to finish current projects in a good way before going on vacation. We all know how difficult it is to get back to half-finished code and trying to remember where you were and how you thought before you went on vacation.

What should CTOs/team leads keep in mind during times of increased workload? Are there any common mistakes that one can easily make during such circumstances?

Start focusing on upcoming deadlines earlier than planned because they always come faster than you think. Do not rush things out to production before the holidays. It often means that stuff is being released unfinished or untested. Instead you should schedule releases after the vacation when everyone is back again.

What kind of work routines do you have in the team and what digital tools do you use to structure your work?

Like many other development companies, we try to find a balance of sufficiently long development cycles and a good number of supportive tools. We are operating in a Kanban-like tool that allows us to track our progress in the various tasks we are working with. I think it is more important to find a tool that everyone is comfortable with, rather than finding one that has all the features.

Test around a bit to find a tool that works for you, there are several task management tools such as Trello, Favro or Swedish Qlutter that we use.

Do you have any remote workers in your team? How do you include them in the daily work and how do you follow up their work effectively?

⅓ of our tech team is working remotely, which places high demands on how we communicate, so that people receive the right information even if they are not physically present. Almost all our communication is written so that everyone can take part, and some meetings are also done via video link.

How do people work during Christmas?

An important part of our product is always trying to stay ahead of hackers, so we must always monitor forums and channels where security news are released. Fortunately for us, it is not only in our company’s but also in our private interests to follow these channels, which means that we often do not see it as work …

Since Detectify has employees of all sorts of nationalities the staffing won’t be a problem, all our teams will be manned during Christmas and New Years. We are not planning for any major releases during the days when the tech team is reduced in workforce.

And how do you make sure not to forget about your security work?

We work with security in many dimensions, but for example, we continuously monitor channels where security updates are released, we also make sure that our own security monitoring is up and running and up-to-date. Somebody should always be on call, even during Kalle Anka (watching Donald Duck on Christmas Day is a Swedish tradition).

How do you get started in the best way when you return to a never ending to do-list after vacation?

The most important thing is to make sure that the tasks and projects you are returning to are stimulating. That there are exciting things to get your teeth into, new features waiting to be released, new components waiting to be developed. Returning to an old to-do list never feels stimulating.

Keep in mind that January is the one month of the year when most people change jobs … plan accordingly.

Your best tips on working efficiently and getting shit done?

“Start stopping, stop starting.” To let people finish their projects is among the best stimulus there is. Make sure to allow people to finish what they have started working on. No matter how strange it sounds, people become more effective when they are working with few things and can finish them properly, rather than working with many parallel tasks that they never finish.

Cecilia Borg: “We use physical representations of project timelines on every team’s scrum board”

Works at: Looklet
Role: CTO
Twitter: @CeciliaBorg

As the CTO/team lead, is it noticeable in your team that the holidays are approaching. If so, how?

In early November, it becomes clear that there are only three sprints left until people go on vacation so the project group begin to tighten their operations. The stress level rises slightly and it is important to remind everyone to focus on what’s important. Don’t try do more than you can handle.

What should CTOs/team leads keep in mind during times of increased workload? Are there any common mistakes that one can easily make during such circumstances?

It’s all about expectations. Be realistic about what you think you can deliver, and inform people involved in time. If you have a habit of revisiting the annual plan each month, you have a few weeks to calibrate the expectations of stakeholders and groups who depend on you. Talk to them about what needs to be done and you’ll know what to focus on over the last weeks of year.

What kind of work routines do you have in the team and what digital tools do you use to structure your work?

Looklet works a lot with innovation and creating solutions to problems that no one has tried to solve before, which makes it difficult to estimate how long projects will take. Therefore, we work as thoroughly and quickly as possible to identify blockers, delays or problems. We work a lot with different physical representations of project timelines on every team’s scrum board. We also use the wiki tool Confluence and Google Slides.

How do people (in the dev team) work during the holidays?

We take into account that we will shut down feature development for two weeks to give people time off if they want. In addition to that, we have staff in place and on call for client support.

How do you get started in the best way when you have been on vacation and return to a never ending to do-list?

The problem occurs when you’re working against a mountain of tasks, go on Holiday gasping for air and return to the same mountain. Make sure to begin your vacation on a good note, be happy about the things you have accomplished (you have always accomplished more than you think) and feel excited to finish or begin projects that are the most important when you return.

Your best tips on working efficiently and getting shit done?

I’m working the days before Christmas and New Years and I have a clear list of things to do that’s been laying around during the years. Some of those things are difficult to get started with, so I usually to break down the whole projects in different tasks and “subgoals”, so that I won’t postpone the whole project.

Chad Fawcett: “Security and monitoring is one of those things that you can’t pause just because people are out on vacation”

Works at: Trello
Role: SRE Team Lead

As CTO-manager, do you feel you can tell that holidays are approaching on your team. If so, how?

I came from a fairly long history of working in consumer e-commerce prior to joining Trello, so as the holiday season approaches I still have moments where I feel like I should be more stressed and locking things down in prep for a huge increase in traffic related to holiday shopping, but in that regard, we have it a bit easier here.

The holidays themselves aren’t the cause of a huge abnormal spike in traffic activity. A lot of Trello’s users use it for work so, if anything, growth can level off a bit during the vacation heavy days. That said, the holidays aren’t without their own challenges. Everyone on the team takes off some around the holidays and New Year’s but Trello still has to stay running 24/7 and we still want to make sure it’s performing well.

What should CTOs/team leads keep in mind during times of increased workload? Are there any common mistakes that one can easily make during such circumstances?

The engineers I work with are pretty amazing at managing their time and projects and prioritization. I think the key for us is providing good visibility into what’s going on in the team and the company as a whole in terms of the goals, initiatives, projects, and challenges. When everyone on the team has that info, it becomes really easy for people to prioritize the right things to work on to keep the company moving forward in the same direction and for everyone else to know what they’re doing.

What kind of routines do you have and which digital tools do you use to streamline your work?

Trello itself is the main tool we use keep a shared perspective to make sure we’re all on the same page. At any time everyone on the team can see what everyone is working on, what they plan on working on next, and any identified issues or requests that no one has grabbed yet. Each team is able to use Trello in the way that best suits their team’s workflow with team specific boards.

Company Overview Board (copy and make it your own)

Outside of Trello itself we use a number of tools, often along with a Trello Power-Up to integrate it into the team board. To name a few, we use Slack for real time discussions, GitHub, and Zoom.us for video and screen sharing. Detectify provides us with regular automated security scans and we use Pager Duty to manage our on-call rotations and alerting.

Do you have any remote workers in your team? How do you include them in the daily work and how do you follow up their work effectively?

A significant portion of Trello’s workforce is remote, including me. While our headquarters are in New York, at last count, we hail from 29 cities across 7 time zones (speaking 20 different languages). Because of the distributed nature of our company, there generally isn’t a separate set of methods and practices for remote workers, they’ve just become our methods, period.

Trello itself is all about providing a shared perspective, so it’s well suited for our distributed team. There are a number of ways where we’ve made conscious decisions with our practices to make sure we keep remote people on equal footing however. For example, if a group of people are having a meeting and even one person is remote then everyone hops on a video chat individually. That way you don’t have a group of people in a room with one or two remote people thrown “up on the wall” on a projected video chat where it’s harder to participate at the same level..instead everyone is on video and can have equal voice (zoom.us with gallery view is awesome for this).

How do people (in the dev team) work during the holidays?

Most things don’t change. While maintaining an awareness of people’s availability and travel plans, people continue to get stuff done and use the same workflows and tools we always do to track where we are. Pager duty (for which we use PagerDuty) is one of the few place where we change things up a bit. While everyone takes vacation days, we still have to have several people on call at all times for our monitoring systems and alerts.

Normally our on-call rotation changes weekly, but around the holidays that would mean that just one or two individuals would get stuck handling pager duty while everyone else relaxed with eggnog and candy canes and hockey. So we share the love during those couple of weeks while taking into account everyone’s plans so that no one has to be the primary for more than a couple days and when they are it’s on days that work out for their schedule and plans.

How does your security work look like before / during the holidays?

Security and monitoring is one of those things that you can’t pause just because people are out on vacation. I don’t feel like the holidays really change our approach since it needs to be one of constant vigilance regardless of the time of year. A lot of people are trusting us to protect their data, so we take privacy and security very seriously.

If an automated Detectify scan were to detect a critical high severity issue, we would need to react to remediate it right away, whether that was on a random Tuesday at 11am or on New Year’s Day.

Example of a Detectify report page 

The same holds true for reports from researchers through our bug bounty program, which we manage through HackerOne, and any of our real time security monitoring. So if the people who own those channels are out on vacation, they make sure they’ve got coverage so anything critical isn’t waiting until they get back.

How do you get started in the best way when you have been away and come back to a long list of things to be done?

Short lists and achievable goals! On the Site reliability team, we have a “Next Up” list that’s a nice easy way to pull out tasks and projects from our Issues and Requests and Planning lists that we plan to work on next. Putting what I plan to work on when I get back there before I leave on vacation helps refresh my memory when I start back up.

Site reliability – SRE team specific example board

That, and carving out a nice quiet chunk of time on the first morning I’m back to go through notifications, email, and the like to get back up to speed before diving in.

Your best efficiency tips on getting much done?

Context switching is a huge time killer, for me at least. The more I try to multi-task, the harder it is to focus well on the task at hand, and switching gears itself takes time and mental energy. I still find myself juggling because we all wear multiple hats, but if I can at least keep it to a relatively small number of concurrent tasks I don’t get overwhelmed by the context switching itself.

Big time blocks help too. We try to avoid having too many recurring meetings, but the ones I do have I try to schedule right before or after when people break for lunch or the like as much as possible so that they’re not right in the middle of a potential big productive block of time. That can of course be a challenge when the team is spread across multiple timezones, but you do the best you can.

Productivity and security go hand in hand and if you are a productivity nerd looking for a way to make your security work more efficient, we’re here to help you out! Detectify integrates with Trello, allowing you to see your security reports on your favourite to-do list.

Go hack yourself, Kanban style!