NeutralPickHow to choose the best project management software for your team: questions to ask vendors
This guide is for a small team choosing project management software to plan work, share tasks and track deadlines, often moving from email, chat and spreadsheets. The best one is the one your team will actually keep using. The questions below help you compare vendors in the same way.
In this guide, a vendor is a company that sells project management software.
Why a sales demo is not enough
A project management demo shows a tidy board with a few tasks. Real teams are messier, for example:
- half the team keeps using email and chat, so the board is out of date,
- a feature you need, such as timelines or guests, is only on a higher plan,
- clients or freelancers can't be added without paying for a full seat.
So ask about these in writing, and ask every vendor exactly the same questions. Then you can compare their answers directly.
Before you contact any vendor
Write down your answers to these four points. They decide which questions in the checklist matter most to you.
- How your team works. Projects with deadlines, ongoing requests, client work, or repeating tasks.
- Who will use it. Your team, plus any clients, freelancers or other teams who need to see or add things.
- What it must connect to. Your email, calendar, chat, file storage, or time-tracking tool.
- How you like to see work. Lists, boards (cards in columns), timelines, or calendars.
The checklist
The questions are in three groups. Must have means a problem here can stop your team using it, or make it costly to leave. Nice to have means it makes a real difference for many people. Optional means it only matters to some people. When you open the checklist in NeutralPick, you can move any question to a different group to match your answers above.
- Must have
- Shows work the way your team thinksOn the plan we'd buy, can we see the same tasks as a list, a board and a timeline or calendar, and switch between them?Different people prefer different views. Timelines are often only on higher plans.
- Simple enough that everyone uses itCan a new team member create, assign and update a task without training, and do you offer a free trial for our whole team?The best tool is the one people use. Try it with a real project and your whole team, not just one person.
- Clients and freelancers at a fair priceCan we invite clients or freelancers to see or work on chosen projects, and do they need a paid seat?Guest rules vary a lot. Some tools charge a full seat for anyone who logs in.
- You can take your projects with youCan we export all projects, tasks, comments and attachments at any time, in files other tools can open (such as CSV)?This is what lets you move later. Some exports leave out comments or files.
- Control over who sees whatCan we keep some projects private to certain people, and control who can delete or change them?Matters as soon as you have client work or private projects.
- Nice to have
- Connects to the tools you useDoes it connect to our email, calendar, chat and file storage on the plan we'd buy, without paying for a separate service to link them?Connections save copying between tools. Check which are built in and which cost extra.
- Notifications you can controlCan each person choose which notifications they get, by email, app or chat?Too many notifications get ignored, which defeats the point.
- A phone app that worksCan people see and update tasks, and add photos or files, from the phone app?Matters for anyone who works away from a desk.
- Templates and repeating tasksCan we save a project as a template and set tasks that repeat on a schedule?Saves setting up the same work again and again.
- Who is too busyCan a manager see each person's workload and deadlines across projects?Helps spread work fairly and spot problems early.
- Optional
- Time tracking, if you bill by the hourCan people record time on tasks, and can we export it for billing?Only matters if you bill clients by time.
- AI features you controlIf it has AI features, are they included in the price, can we turn them off, and is our data used to train them?Some AI features cost extra, per user or as usage credits. Check the privacy terms.
The button opens this checklist in NeutralPick. There you can:
- Remove the questions that don't matter to you, add your own, and move questions between groups.
- Add each vendor you are considering.
- Send each vendor its own private link, so they answer every question in writing. Or, if you have already had a sales call or a product demo with a vendor, fill in their answers yourself from what they told you.
- See every vendor's answers side by side.
Want to see what a finished comparison looks like first? See an example comparison with three made-up project management software vendors.
Answers to look at carefully
Vendors often answer the points below in vague terms. When you get a vague answer, ask the follow-up question shown here. A vague answer often means the honest answer is "no" or "only partly".
- "Unlimited projects". Ask: which features are limited on this plan, such as views, guests, storage or automations?
- "Integrates with everything". Ask: which connections are built in, and which need a paid connector or a higher plan?
- A price per user. Ask for the yearly price for your whole team, including guests who edit, after any first-year discount, and whether you pay for a minimum number of seats.
- Leaving later. Ask: what can we export, including comments and files?
What to do with the answers
- Put all the vendors' answers side by side.
- Look at the Must have questions first. If a vendor answers No to something you marked as a must-have, remove that vendor.
- If a vendor answered "Partial" to a must-have, ask them exactly what is missing.
- Run one real project with your whole team in the trial of each one left, and ask the team which they would keep using.
Why use NeutralPick to compare project management software vendors
- Every vendor answers the same questions. Each vendor gets its own private link to your checklist and answers in writing, so you can compare their answers question by question.
- All the answers in one table. You see every vendor's answer to every question side by side, instead of searching through emails and call notes.
- No vendor can pay to influence it. There are no adverts, no paid placements and no "featured" vendors. No vendor can pay to be shown to you or placed higher.
- Free, with no account. You don't need to sign up or pay anything.