Calling all calendaring wizards!
December 28, 2017 8:02 AM   Subscribe

I have been tasked with designing and implementing a calendaring solution for my team's needs. We are 4 engineers, 1 QA person, and 1 project manager. We need a calendar that allows us to schedule 6 weeks (1 development cycle) of discrete engineering tasks in a manner that allows an at-a-glance view of the entire cycle. Ultimately, we want to use the calendar as a visual organizational tool that allows us to see whether our scheduled tasks will overload our QA person at any point in the cycle and adjust accordingly. More details below.

Relevant details:

- The tool we use needs to be compatible with both Mac and PC.

- When viewing the calendar, we should be able to easily tell which tasks belong to which engineer.

- When tasks are scheduled over multiple days, the task should visually appear as an unbroken bar over multiple days, rather than as "start" and "end" bullets on the start and end days only (this, for example, nixes an Asana calendar).

- It should be easy to edit the duration of a task.

- We do not need to "invite" one another to tasks within the calendar (unless there's a compelling reason I haven't thought of to leverage same).

- It should be a literal calendar, not a ticketing management tool (e.g. Jira, Waffle). N.B.: We manage our development cycle tickets (individual tasks) via Pivotal Tracker. I have exhaustively canvassed the universe of tools that exist to make Pivotal integrations with calendars possible; nothing currently out there works for our needs, primarily because of limitations in Pivotal's setup. Changing ticket management platforms is not an option. Please assume as such :)

- As far as calendar management goes (i.e., do the individual engineers manage putting their own tasks on the calendar, or is there a Calendar Overlord who does all of this?) nothing is set in stone, although I'm leaning the Overlord direction because of generalized teammate-specific calendar grouchiness.

Finally: I really, really, really, really, really want to use something other than Google Calendar. This is for two reasons: (1) the Google Calendar UI is a monster garbage fire; (2) our company as a whole already uses multiple Google calendars, which would make for a lot of annoying checking and unchecking of calendars when members of my team wanted to look at solely our team calendar.

I am open to hearing about all other calendaring tips, tricks, and solutions you've got up your collective sleeves. Thanks, y'all.
posted by sevensnowflakes to Grab Bag (15 answers total) 3 users marked this as a favorite
You should look at products called "project management software" rather than just calendar apps. It will provide such things as a critical path analysis that exceed what you get from a calendar plus a variety of graphic reports on project status.

I was exposed to Microsoft Project long ago. It seems to have grown into an expensive behemoth, MS-style, but I bet some Mefite can recommend simpler, cheaper options.

These thing work if the group has the discipline to keep progress accurately updated. That's a big ask in many workplaces.
posted by SemiSalt at 8:30 AM on December 28, 2017 [1 favorite]

Are you looking for a Gantt chart?

I only have passing familiarity with Pivotal (an old job had migrated away from it), but there's often a Gantt chart feature buried somewhere in these trackers. Unfortunately, they're often only retrospective, which is not actually useful.
posted by hoyland at 8:58 AM on December 28, 2017 [2 favorites]

Wrike is somewhat expensive but in my so-far limited experience with it, should do what you're after.
posted by supercres at 9:10 AM on December 28, 2017

Yeah, this is really not a calendar per se, more like... an additional layer of project/product management to schedule specific tickets. As a PM I have to really question why you're doing this when you're totally locked into pivotal, but I trust you when you say you really don't have a choice. I also seriously question the reasonableness of mapping in calendar terms *exactly* when each team member is going to work on each task - that rarely aligns well with real-world software development - but, again, I'm going to move on and assume you've got an accurate set of constraints out of your control.

What I'd probably do in your position:

* Grab a PM tool that allows very specific calendar-day scheduling of tasks, probably Asana.
* Task an unfortunate soul (or an entry-level junior PM type staffer) with periodically mirroring all Pivotal tasks into Asana. The Asana tasks would be very simple and probably just consist of a title, assignee, and link to Pivotal for all the details.
* Update as often as needed.
* Team members consult the Asana calendar as often as needed to tell what they/others are working on.
* Advocate endlessly and frantically to move from Pivotal to a ticket tracker that lets you accurately reflect your process. Jira plus some well-chosen plugins would be my first choice but there are plenty of alternatives depending on the details of the rest of your process.

I've used Wrike in the past for major projects - it will do what you want, but it's also insanely expensive and has a number of shortcomings when applied to software development, so I'd recommend against it for this purpose. In all seriousness, the money you'd spend on Wrike could be better spent on a slice of an hourly administrative person to manually handle more work.
posted by Tomorrowful at 9:23 AM on December 28, 2017 [1 favorite]

I think Asana is the tool you're looking for as well.
posted by warriorqueen at 9:35 AM on December 28, 2017

Hi all. Some thoughts:

I also seriously question the reasonableness of mapping in calendar terms *exactly* when each team member is going to work on each task - that rarely aligns well with real-world software development

Yeah, me too. I'm not the PM, but the PM knows this is true. Nevertheless, the idea is to try and corral the devs as much as is reasonably practicable, giving our QA person at least a rough idea of when particular tickets will be finished so that her work can be spread throughout the dev cycle in a saner way.

Asana is the tool you're looking for

Nope, afraid it isn't. As noted, Asana only allows for the entry of start and end points that do not visually stretch a task over multiple days.

Thanks for your thoughts so far. Keep 'em coming.
posted by sevensnowflakes at 10:58 AM on December 28, 2017

There is nothing better than a wall with post it notes, sticky notes, names and etc. Period. Everyone can see it. There is no question as to what is done, and the document store lends its self to multiple attachments and properties you don't get out any conventional system I've used thus far

You can't do deep analytics on it, but *everybody* sees what is where, when something is done, and who has what tasks and responsibilities. Every piece of software that I have ever used - pivotal with slack, jira, project + one note, and a few other custom ones have all had one fundamental problem in that there is no way to adequately visualize everything at once - especially not on a monitor, and definitely on a mobile phone.

Pivotal has no time component in a due date / milestone manner - otherwise I might recommend it. Jira is so heavily geared in some weird ways that it just - it just bogs down life in automated emails and status updates until everyone is numb to them and ignores them.

Lastly, all of these agile systems live in the make believe world where all other groups you interact with that aren't agile understand a sprint and a scrum and how to get things done within your group, that there aren't emergencies or fire drills, or other ephemera that side tracks and takes down all your hard and fast dates laid out in the initial project planning.

If everybody has to walk past your paper wall of death - everybody knows that there is no fucking way they are going to weasel their rinky dink snowflake request in on your group - and if they do - their dirty laundry request is out in the open for everyone involved to publicly shame.

There are some things software does well - project management is not one of them.
posted by Nanukthedog at 11:24 AM on December 28, 2017 [8 favorites]

When I had a similar need, I made do with Tom's Planner. It will create gantt charts that allow you the at-a-glance view that you want. It's not the perfect solution, but I found it was the best for me.

The next best solution was using an excel spreadsheet and marking columns as weeks, and rows as jobs (or people), then either filling in cells or drawing boxes on top of the cells (drawing made them easier to move).

Good luck!
posted by hydra77 at 1:23 PM on December 28, 2017

This sounds a lot like Smartsheets to me
posted by rebent at 2:08 PM on December 28, 2017

You know what -

You're obviously some species of software dev team. Can you just... build it? You have a problem, you probably have either the right kind of developers or (I'm guessing) people who wouldn't mind picking up some more skills, and this isn't a huge technical lift. You need to hit up the Pivotal API to grab the tickets, you need a UI to attach start/end times to them, and there are a zillion calendar display libraries of varying quality out there to pipe your visually-overlapping blocks of time into. Stick the whole thing on a small cloud-hosted instance, wrap it in some basic authentication for privacy, store your duration data in a tiny SQLite or Mongo DB... I'm not saying it's trivial but if you've got a very specific problem that's requires a hyper-specific solution, and it doesn't neatly align with what the market already provides, and you're unwilling/unable to change your practices to suit the available tools - why not roll your own tool?
posted by Tomorrowful at 2:29 PM on December 28, 2017

As a software engineer, the only system I agree with so far is the physical post-it-notes-style solution. I can't think of anything that fits your exact model (which I think is... ill-advised due to reality not lining up nicely on dates) out of the box, so you'd need to spend time writing/customizing a solution to fit your needs, and a system like this is only good if everyone's on board with using it and keeping it up to date, so I'd essentially prototype using paper before spending time locking yourself into it by coding up something.

I guess the follow-up question might be what leads you to believe that this sort of system would be helpful for your team. Is this style of visualization mostly for your PM's benefit, or is this something everyone needs? Would it be possible to wire something up to an existing task-oriented tracking system and spit out a calendar, and just run that report as needed?
posted by Aleyn at 2:51 PM on December 28, 2017 [1 favorite]

My team has been using Roadmap for what sounds like the same purposes. The things we like about it: each team member has a swimlane so you can easily see how many tasks each person has as well as if someone has none (most of the charting tools we looked at relied on someone being assigned a task to show up in the calendar, no tasks = no representation in the view). Easy to drag and drop tasks from one team member to another. Easy to change task length. Continuous line for as long as the task takes.

Things we don't like about it: it has a terrible UX and no documentation which requires some blind fumbling around in the beginning to get the hang of it. You can exclude weekends automatically but not holidays. Due to its pricing structure, you either have to set up your account so there is a Calendar Overlord or everyone logs in as the Calendar Overlord as only paid admin/manager accounts can make edits once you are out of the free evaluation period.
posted by jamaro at 2:53 PM on December 28, 2017

You're obviously some species of software dev team. Can you just... build it? ... Why not roll your own tool?

This only ever ends one one of two ways.
(1) You and your team get completely derailed doing this and it's the downfall of the company, or
(2) You do it really well, pivot, and it ends up actually being your product.

The latter has been known to happen, but it's not exactly the most common outcome.
posted by dmd at 3:53 PM on December 28, 2017 [1 favorite]

Heh, I wish I hadn't mentioned software engineering. We have a post-it board and it is awesome! But that's for the engineers/PM! They don't care when - as in, the specific calendared date - the tasks get done, only that they get done during the cycle.

This calendar - not ticket tracker - isn't for the engineers, it's for our awesome and totally overloaded QA person. Our QA person cares about specific calendared dates, because having a calendared map will help her manage her time over multiple weeks.

(Yep, I proposed rolling our own, but the reality is we just don't have the resources to do that right now.)

I've been playing with a Gantt app all day and it's just the thing I needed. Thanks all!
posted by sevensnowflakes at 4:01 PM on December 28, 2017

I worked for a company that did this on white boards. Every dev had a 5x2 (we worked in two week sprints) grid written in permanent marker on the board, each with a small corner box for a date -- think bowling scores for the visualization of each box in the grid.

At the start of each Sprint, each dev wrote (with dry erase, inside their permanent marker grid) a date in each box, ticket numbers on each day they planned to start each ticket, and an arrow drawn across boxes through the day they thought each ticket would be done.

Every morning thereafter, each dev adjusted ticket numbers and arrows to reflect their current expectations, based on what had happened the day before.

As you search for a software tool, I suggest you give this approach a shot, only looking two weeks ahead. You already have a team using post-its etc. on a board, so this is just a little more daily overhead, and you can work out some important things right away that will also be relevant to calendar software, like:

- does the dev team think giving exact date estimations lock them into an unreasonable commitment, or do they understand the dates are only meant for ongoing qa planning?

- does this calendar approach really help the one qa person it is intended for, or will this turn out to be more trouble than it is worth (and better solved by looping them further into daily ceremonies, allowing qa work to spill into the next sprint, etc.)

- is this something more knowledge from the devs in front of a wide audience solves, or is this something the qa person should or must own in order to get real value from it? (i.e. once you start doing it, where does all the heavy lifting get done to make it genuinely useful?)

Once you're doing this with markers, and working out the issues/determining the usefulness, you'll get a better idea for how much better things might get with an aligned software tool. I just suspect it's a bit early for jumping into software, unless you've already done a similar exercise and answered lots of questions as noted above. And no, the PM "solving" qa's scheduling concerns by asking for a calendar is not enough of an exercise.
posted by davejay at 11:16 AM on December 29, 2017

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