I'm wondering if this type of tool exists. Basically, I am senior dev of a 3 man dev team at a non-tech company. I maintain 60 or so web apps for our 300-400 users (all internal apps) as well as act as jack of all trades when it comes to SQL, IIS, self hosted and cloud hosted windows server boxes, VMware, etc. Basically, I have a lot of spinning plates.

We are in active development but we get interrupted a lot. Like, a lot a lot. Because of this, we don't really work based on deadlines but more on timelines. Upper management knows that things get priority over other things and we have to move things around and pivot a lot, so as long as we can explain why a project took 6 more months than we projected, it's fine.

So having said all that, I'm looking for a timeline system similar to gantt but I want the ability to have more than one "timespan" per task/row.

So for example let's say I'm building a to-do app and one of the tasks is to figure out the theme/color scheme of the app. I think this will take 3 days, and I don't really need to be more specific than that, they aren't trying to micro manage. However, I got interrupted and pulled off the project in the middle of that task, so I worked on it for 1 day, I had other things for 3 days, and I came back to finish the last two days.

In this case, in a gantt chart, your task can only be one "timespan" per "row" and in order for me to chart what actually happened, I need to add multiple subtasks to that task and the task ends up taking 3 rows of space.

This is rough to read and annoying to have to rearrange and insert new subtasks and rearrange subsequent tasks along the timeline.

Is there a tool out there that handles this more "ad-hoc" scheduling that I'm looking for?

Ideally what I would like is for me to be able to put together a full estimate of time for the project (say 3 months) with the ability to cascade schedule changes down when a task in the middle goes on longer than expected or gets interrupted.

I would like to have categories or color mapping so we can see which timespans are interruptions and which are tasks done and tasks to do.

Am I asking too much? Does gantt have this ability and I've not found the right vendor?

Right now my temporary solution is excel but it's a beating to have to go shift things every time I have an interruption, I feel like I spend more time explaining what happened than I do actually programming, haha

Edit: I've seen things like Monday.com and Microsoft project, but these are really heavy and too specific for my needs, I don't want a lot of context or setting up a kanban board or anything like that, I just want effectively an interactive timeline with simple "I'm doing this for x days" and not much else in terms of percent complete, details of the task, sprint integration, etc.

Think trello in complexity, just time-based and sideways 😅

I don't want to be a project manager, I don't have time for that - I just need the ability to quickly track interruptions and be able to use it as backup if upper management comes poking around

Input wanted for an article.

Let's say that your company is considering the purchase of an expensive new application to help in the company's software development. The demo looks great, and the feature list makes it sound perfect for your needs. So your Management arranges for a proof of concept license to find out if the software is worth the hefty investment. The boss comes to you to ask you to be in charge of the PoC project.

I'm aiming to write an article to help developers, devops, and testers determine if a given vendor's application meets the company's needs. The only assumption I'm making is that the software is expensive; if it's cheap, the easy answer is, "Buy a copy for a small team and see what they think." And I'm thinking in terms of development software rather than enterprise tools (e.g. cloud-based backup) though I suspect many of the practices are similar.

Aside: Note that this project is beyond "Decide if we need such a thing." In this scenario, everyone agrees that purchasing a tool is a good idea, and they agree on the baseline requirements. The issue is whether this is the right software for the job.

So, how do you go about it? I'm sure that it's more than "Get a copy and poke at it randomly." How did (or would) you go about designing a PoC project? If you've been involved in such a project in the past (particularly if the purchase wasn't ideal), what advice could someone have given you to help you make a better choice? I want to create a useful guide that applies to any "enterprise-class" purchase.

For example: Do you recommend that the PoC period be based on time (N months) or workload (N transactions)? How do you decide who should be on the PoC team? What's involved in putting together a comprehensive list of requirements (e.g. integrates with OurFavoredDatabase, meets performance goals of X), creating a test suite that exercises what the software dev product does, and evaluating the results? ...and what am I not thinking of, that I should?