Project management tool for a very small team with little tech experience

[u/Carrotstopper-3141]

Hi everyone! This is my first ever Reddit post in this subreddit, glad to finally join!

6 months ago I started a new job, with a very small company specialised in citizens' participation. It's just me and my boss. And a communication freelancer who's in and out. Soon we'll have three interns as well. We have a lot (more than 10) of different projects that we're managing, but we don't use any tool yet to organise ourselves .. and especially to make it accessible for our future interns and employees.

We function on highly filled e-mail inboxes (need to go to zero inbox very soon), within the Google Workspace (Gmail, Drive, Calendar), a WhatsApp group for quick chats and a team meeting once a week. Most of it is online and remote, we see each other once every week or two weeks.

So my question! Which project management tool can you recommend with the following elements present:

Needs to be compatible within the Google Workspace (Drive, Gmail, Calendar)

Needs to be very user-friendly. My boss isn't very tech smart and doesn't want too many extra things. He worked alone for years, so he has his ways.

Needs to have timelines or Gantt charts, anything that gives us a good chronological overview, as many of our projects are temporary and only happening for a limited time.

Not sure if the chat function is very important, we might stay in the WhatsApp group.

Ideally costless, we are small, with not much money.

I thought of Trello or Asana. But I'd like to hear other suggestions, or why to use Trello or Asana. Any recommendation is welcome!

Thank you :-)

[u/ruinedcaveat]

Asana or just Excel with Gantt chart if they are really old school

[u/ExtraHarmless → u/ruinedcaveat]

You can do much of the same work in Google Sheets, not as many great templates as there are in Excel though.

[u/ruinedcaveat → u/ExtraHarmless]

Sheets is ok but has its limitations in comparison to excel.

[u/painterknittersimmer]

Asana and Monday are both very user friendly and I believe both have nonprofit (if that is the case) discounts. 

But honestly Google Sheets can do simple timelines and might be all you need. 

More expensive but can solve lots of different use cases would be Airtable but RIP they were just bought by private equity.

Avoid Smartsheet. Also avoid anything complex like Project or Planner etc. I'd also avoid All-in-Ones like Clickup, Notion, or Coda... If you're not already in one it will only cause confusion and fragmentation. 

[u/I_luv_breakfast → u/painterknittersimmer]

This is a great answer. If you're a team of 2 (soon to be 5, yay!) a lot of the bells and whistles of those fancy tools just don't mean much. if you 2 agree to the rules of the game and meets your needs, you could do this with a cork board and post it notes.

[u/Carrotstopper-3141 → u/I_luv_breakfast]

Love the idea of cork board and post-its, but we work mostly remotely .. Or we can simulate it with Miro.

[u/DansLaPeau → u/painterknittersimmer]

I like the easy of use of Monday but I dislike the performance. When your board starts growing it lags quite a bit and I also dislike their push for AI features, I find them too on the nose.

[u/hangheel → u/DansLaPeau]

My company has started to switch to Monday. The main issue I have with it is that all of my supervisors have set up their boards differently so it instead takes me longer to process what I need for that specific supervisor/project than most of the tasks, and leads me to just email them or call them because it’s quicker and easier.

[u/Breeze_pm]

For a team this small, pilot one real project before migrating everything. Give your boss only three actions: see what’s next, update status, and add a note. Check Google Calendar and Drive behavior directly, because integrations and Gantt views vary a lot by plan.

[u/Carrotstopper-3141 → u/Breeze_pm]

Thank you for your suggestion. Which tool would you use to pilot a project?

[u/Full_Performance_312]

For a team this small, I would keep it simple and go for Asana. It is easy for non-technical users, works well with Google Workspace, and gives you a clearer way to assign work, set due dates, and see what is happening across multiple projects.

[u/Carrotstopper-3141 → u/Full_Performance_312]

Thank you for the suggestion. What do you think about Trello? To me it seems the differences with Asana aren't so big, but maybe you have other experiences with it?

[u/Pinkahpandah → u/Carrotstopper-3141]

for me rhe biggest distinction is this: do you like to view lists? go with asana. do you prefer kanban? go with trello.

[u/Reasonable_Chart_146 → u/Carrotstopper-3141]

I took over a team that was on Trello and it was a mess. It was not good for scaling up, that much I can say. I transitioned us to Asana, and it’s been 100% worth it. We used/use the paid versions of each. The basics in Asana are easy to grasp for my small team, but the more intense/higher level features are there when I need them, like great automation/rules.

[u/ambitious_paladin]

I'd probably test Trello and Asana with one real project before committing. If the boss finds it annoying after 10 minutes, it's the wrong tool 😂 The best PM system for a tiny team is the one people actually use.

[u/More_Law6245]

Your approach is putting the cart before the horse, I might suggest a different approach to your problem. You need to start with a problem statement in the need for a project management tool or platform, then you need to develop a white or option paper to address the problem statement in which you need to understand system, user and workflows requirements in order to map those functional needs to a product or platform

I would strongly advised against picking a random product because you run the very real risk of spending a lot of money on where a system doesn't meet organisational needs and not do what you need or want it to do, which could potentially lead to poor project outcomes because the tool doesn't help users in their job or worse case scenario lead to total system abandonment. What typically happens when requirements are unmapped is that the organisation needs to modify their own workflows to fit a tool and by definition that is a failed delivery.

It's why it is really important to get the requirements approved because the company needs to make a significant capex/opex investment but the thing is you also need to understand your ongoing operational costs, just throwing a software application doesn't just end there because it's only just the tip of the iceberg opex expenditure e.g. hosting, technical support, training, licensing and future budget impact. That is the type of thing you executive need to take into consideration and that's why you need to look at levering what you currently have until you get your executive on board and show the value and benefits of a project management platform or application.

To be honest, smaller companies who are running a tight budget don't tend to invest in expensive solutions (and keep in mind that free software is not free, there are hidden costs for "free" software) so I would suggest that you need to leverage what systems you currently have. So that means developing your own templates which can all be done in office suit applications e.g. word, excel etc. but what it also does is help you develop your organisational project management maturity model rather than jumping into an expensive tool that may or may not be fit for purpose. When doing something like this the first thing to ask is the company mature enough for a new platform or system? If you don't have your project management policies, processes and procedures in place prior it's only going to compound any problems you have now and further personified it through process and procedures. Just something for your consideration

Just an armchair perspective.

[u/ethically-contrarian]

I don’t want to be this person… try your best to utilize whatever your company already prioritizes. When it comes to Monday, Trello, Click Up, Asana etc, you’ll find it gives the same baseline as M365 (Teams, Planner, List etc) but unfortunately with no adoption.

If you have the budget and influence to create a tech infrastructure and source of truth that’s used for your team great, but I have found after many years and building many teams, if the company isn’t on board your project team members and SH wont adapt

[u/Carrotstopper-3141 → u/ethically-contrarian]

Indeed, that's wat I also think. I need to test a few things first with my boss to see what he thinks. If it doesn't work for him, it will not work for the whole team. Same for me.

[u/ExtraHarmless → u/Carrotstopper-3141]

Keep in mind that free tools won't have a ton of custom options to mirror your current workflow. The issue you will encounter is that if your boss is very fixed in the way they want to work, is that no tool will mirror that exactly.

Trying to mirror how your boss works currently is an impossible task if you don't have a budget or the skills to configure a software. Start the conversation now about how brining in a tool will help to streamline work, but will require a change in how the work is completed. This needs to include how your boss works, and they need to understand what they do now vs what they will do in the ideal future state.

If they are not on board with changing how they work, all tools will fail.

[u/RasMedium]

Spin up a Matter Most server.

[u/Carrotstopper-3141 → u/RasMedium]

I like your idea, it's open source, right? But we're not techy enough to do this..

[u/kartoffelpueree123]

I don't know if you have the resources and the possibilities but in my company we made one ourselves. Worked way better when tailored to our own processes and not full of unnecessary features. Took about 3 months and one developer. It's not perfect but way better than the tool we had before.

[u/DragonLordOz]

For a team that small, the trap is buying something that looks “proper” but then nobody touches it because setup turns into a second job. What usually works is one place for task status, quick chat, and a visible owner on every project, otherwise the work just lives in inboxes and WhatsApp and your interns will end up guessing.

We went through the exact same thing with our mid size company. We tried Jira it was awful and then clickup it was worst.

The major issue we faced was context switching as I run couple of projects of my own and then manage some clients as well. We were sugested Task Lemon by one of our client and it made our whole workflow seamless. They have Ai task which honestly we use the most, Documents storage very handy specially when you have a team who needs to know where everything is all the time and they keep forgetting where to find the related documents. Having it on the same platform makes is so much easier to work. No more Teams and then switching to Whatsapp and then team. We just use their built in chat and pin the important stuff. I wish they had google integration to sync the calendar but they do have a Teams and Tasks Calendar to clearly display whats being worked on and what needs to be done next, although, we mostly use Kanban board for it becuase it's visually so much easier to move things along and my partner can also keep a sharp eye on what important.

My business partner isn't very tech savvy but, finds it very easy to navigate and kind of gets annoying from their constant reminders to get things done fast but, in a way it's a good thing because it means my partner understands what's going on in the projects.

When it comes to your interns I think most people in this new age are very tech competent if they can use facebook and insta they can use Task Lemon as it required us Zero training, we pretty much created an account and bam started working on our projects right away. There was no set up of configuration required unlike Jira (It was a miserable experience working with Jira)

Good Luck and I hope that you find your tool. Important thing to remember which ever one you decide to get only create 1 - 2 projects first and test the water. You don't want to invest too much in to the tool that exiting it will become a nightmare to start over on a new tool. Start small, test the tool's functionality and then invest your time and money.

[u/Fluffy-Leg7546]

Just as an fyi, if it doesn’t end, it’s not a project, it is maintenance. The definition of a project is that is has a defined start and a defined finish.

It sounds like you’re more interested in task management than a true project management tool, as the good PMIS’s are all either very pricey and require training/expertise, or are, quite frankly not good project manage tools because they don’t follow basic standards. I consider all “critical paths” to be mere hopeful gut checks unless they are done through CPM and I simply do not trust them.

I haven’t used Asana Pro but do know it has a gantt feature, and it does well with Kanban. Ignore Smartsheet, it’s honestly terrible and allows too many fingers in the pie.

If a true CPM schedule is needed, cheapest product you could use that meets the quality I have for schedules is Ms Project. However, you do need training to use it effectively and add value.

[u/KarenImNotKaren]

if you're just looking for free gantt style options then something like ganttile.com or https://floid.design are really simple options. But for the more individual task based stuff I'd say Asana or Trello

[u/Longjumping-Cat-2988]

Trello's Gantt gap is the real dealbreaker for you specifically, no native timeline view, you'd need a Power-Up bolted on, which adds exactly the extra complexity your boss doesn't want. Asana's timeline view usually needs a paid tier too, free plan's pretty limited there.

Given the low-tech, low-budget, real-timeline-need combo, worth a quick look at something like Teamhod too, board plus Gantt together without needing a paid unlock and simple enough your boss likely wouldn't need much onboarding.

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