Running a small team means every decision counts. You need tools that actually help your team work better, not ones that drain your budget or waste hours in setup. Project management software sits at the heart of this question. Two names keep coming up in conversations: Trello and Monday.com. Both platforms have loyal users. Both claim to make work easier. But they take very different approaches to getting things done.
This guide breaks down everything you need to know about these two platforms. We'll look at real features, actual costs, and what works best for teams like yours. No fluff, just practical insights to help you make the right choice.
Before diving into features and pricing, you need to understand what makes these platforms fundamentally different.
Trello built its reputation on simplicity. The platform uses a Kanban board approach where you move cards (tasks) across lists (stages). Think of it like a digital version of sticky notes on a whiteboard. You see everything at a glance. The learning curve barely exists. Your team can start working within minutes, not days.
Monday.com positions itself as a work management platform rather than just a project management tool. The software offers deep customization options, multiple view types, and automation capabilities built into its core. It aims to handle everything from simple task tracking to complex workflow management. The trade-off? More power means more complexity.
For small teams, this difference matters enormously. A simple tool that everyone actually uses beats a powerful tool that sits unused because nobody learned it properly.
Cost matters for small teams. Both platforms offer free plans, but they work very differently in practice.
Trello's free plan supports up to 10 collaborators and allows 10 boards per workspace with unlimited storage. You get unlimited cards, which means you can track as many tasks as needed. The platform includes basic integrations and one Power-Up per board.
For a small team just starting out, this feels generous. Ten people can collaborate on ten different projects without paying anything. You can organize marketing campaigns, track customer requests, plan content calendars, and manage product launches all on the free tier.
The catch? You're limited to one Power-Up per board. Power-Ups add functionality like calendar views, time tracking, or custom fields. If your board needs multiple extensions, you'll feel constrained quickly.
Monday.com's free plan restricts you to just 2 users and 3 boards, starting with 200 items total. You can earn more items by referring others (up to 1,000 total), but the core limitations remain tight.
Two people barely counts as a team in most scenarios. You can't bring in your designer, developer, or customer success person without upgrading. The three-board limit means you're constantly choosing which projects deserve attention.
The free plan lacks automations, integrations, and timeline views. These features make Monday powerful, but you won't access them without paying. For testing purposes, the free tier works. For actual daily work with a small team, it falls short.
The Verdict: Trello's free plan wins decisively for small teams. Ten users versus two isn't even close. Unless you're a solo founder with one assistant, Trello's free tier provides actual utility.
Eventually, most teams need paid features. Let's examine what each platform charges and what you receive.
Trello Standard costs $5 per user per month (billed annually) or $6 monthly, offering unlimited boards, advanced checklists, and custom fields. Premium runs $10 per user per month annually ($12.50 monthly) and adds workspace views like Timeline and Calendar, plus advanced admin controls. Enterprise starts at $17.50 per user per month for teams of at least 50 users.
For a 5-person team paying annually:
The pricing stays straightforward. You pay per person, you get the features. No surprises.
Monday.com Basic starts at $9 per user monthly ($12 when billed monthly), including unlimited items and boards. Standard costs $12 per user monthly ($14 monthly billing) and includes timeline views, automations, and integrations. Pro runs $19 per user monthly with annual billing, adding time tracking and formula columns.
Here's the catch: Monday.com prices include 3 users as a minimum. You can't pay for just 2 seats. Even if your team has 4 people, you're paying for at least 5.
For a 5-person team paying annually:
The Verdict: Trello costs significantly less. A small team on Trello Premium ($600/year) spends less than a similar team on Monday's Basic plan ($540/year) while getting more intuitive software. Monday's power comes at a premium that small teams often can't justify.
Your team's time is valuable. Software that requires days of training costs more than just subscription fees.
Everyone focuses on how easy Trello is to use, and there's still no tool that does Kanban-based projects quite as well. Open a Trello board and you instantly understand what to do. Cards represent tasks. Lists represent stages. You drag cards from "To Do" to "In Progress" to "Done."
The visual nature makes Trello accessible to everyone. Your marketing coordinator gets it. Your developer gets it. Your intern gets it. Nobody needs a training session. You share a board link and people start contributing immediately.
This simplicity becomes powerful when you're managing multiple projects. You can glance at a board and see project status instantly. Red cards need attention. Cards on the right are finished. Cards on the left need starting.
Monday.com offers more features, but that power creates complexity. Depending on how you configure your Monday dashboards, the interface can become quite cluttered and hard to navigate. The platform presents multiple view options, numerous customization settings, and extensive automation builders.
New team members need guidance. You'll spend time explaining how different views work, where to find features, and how to set up their workspace. For some teams, this investment pays off. For others, it creates unnecessary friction.
Monday.com's beautiful user interface and robust task management views make it a superior project management tool once teams master it. The question becomes whether your small team has the time and inclination to climb that learning curve.
The Verdict: Trello wins on ease of use. Small teams need tools that work immediately, not platforms that require extensive onboarding.
How you see your work matters. Different team members think differently. Some people love lists. Others need calendars. Some work best with timelines.
Trello's default view is Kanban boards. Trello's greatest feature is its kanban boards, which feel like a digital canvas full of post-it notes. The card-based system lets you organize tasks visually and intuitively.
Want other views? Free users need to stick to the Kanban view since both map and calendar views aren't available without a paid subscription. Premium adds workspace views like Timeline, Calendar, and Dashboard.
The catch? Many views come through Power-Ups rather than native features. Trello's approach to Gantt charts relies on Power-Ups rather than built-in functionality. For teams that live and die by Gantt charts, this feels limiting.
Monday offers 27 different views including Kanban, Gantt chart, Timeline, Map, and Calendar. You can switch between views instantly, seeing your data from different angles. Need to see task dependencies? Use the Gantt chart. Want to see everyone's workload? Check the workload view. Need to see where your field team is located? Use the map view.
This flexibility helps different team roles. Your project manager loves Gantt charts. Your sales team wants a pipeline view. Your content team prefers a calendar. Monday accommodates everyone.
The downside? Gantt view, along with dependency features, is available only in Standard and above plans. Many powerful views sit behind higher pricing tiers, pushing small teams toward more expensive plans.
The Verdict: Monday wins on view variety. If your team needs multiple visualization options, Monday delivers. If Kanban boards work for your workflow, Trello's simplicity shines.
Automation saves time by handling repetitive work. Both platforms offer automation, but with very different approaches.
Trello includes Butler, an automation tool that handles repetitive tasks. You can create rules like "when a card is moved to Done, add a green label and archive it after 24 hours." Butler comes with quotas: free users get 250 command runs per month, Standard users get 1,000.
Butler works through simple, readable statements. You don't need coding skills. The interface guides you through creating rules, buttons, and scheduled commands. For basic automation needs, Butler handles common scenarios well.
The limitation? Complex workflows require multiple rules, eating through your monthly quota faster. Heavy automation users will hit limits regularly.
Monday.com's no-code automation processes use predefined conditions and triggers for routine task management. The platform offers more sophisticated automation options, including integration triggers and complex multi-step workflows.
Standard Plan includes up to 250 automations and integrations per month, which sounds decent but can run out surprisingly fast for automation-heavy teams. Pro plan offers 25,000 monthly automation and integration actions.
Monday's automation feels more powerful but also more complex. You can create sophisticated workflows that span multiple boards and trigger external actions. The trade-off is a steeper learning curve.
The Verdict: For simple automation, Trello wins with its approachable Butler interface. For complex, cross-board workflows, Monday provides more power. Most small teams fall into the simple automation category, making Trello the better fit.
No tool exists in isolation. You need connections to your email, chat, file storage, and other business tools.
Trello integrates with more than 200 third-party tools including Slack, Outlook, Freshdesk, and Evernote. These come through Power-Ups, which extend Trello's base functionality.
The Power-Up system creates both flexibility and limitation. You can add exactly what you need, keeping boards uncluttered. But free users are limited to one Power-Up per board, forcing tough choices. Standard and Premium plans offer unlimited Power-Ups.
Popular integrations work smoothly. Connect Slack to get notifications. Add Google Drive to attach files directly. Include Calendar to see due dates in a monthly view. The Power-Up directory makes finding integrations easy.
Monday.com takes a different approach, building many integrations directly into the platform. You don't need separate add-ons for basic functionality. The free plan has limited integrations, with full integration access requiring paid plans.
Standard Plan includes up to 250 integrations per month. This combined automation-integration quota means heavy users of either feature may hit limits quickly. Monday counts each automated action and each integration sync against this shared pool.
Monday offers deep integrations with enterprise tools. If you use Salesforce, Jira, or Microsoft Teams extensively, Monday's native connections work seamlessly. For small teams using simpler tools, this advantage matters less.
The Verdict: Trello's Power-Up model works better for small teams that need flexibility without complexity. Monday's approach suits teams deeply embedded in specific enterprise ecosystems.
Teams need to communicate about work. Both platforms include collaboration tools, but they take different approaches.
Trello nails the collaboration basics: add team members to projects, assign tasks to them, and follow up. You can comment on cards, mention team members with @, attach files, and have threaded discussions directly on tasks.
Trello enhanced its card detail experience in May 2025 with a new panel view for comments and activity, which can be displayed side-by-side with card details. This makes following conversations easier without losing context.
Trello keeps collaboration simple. You don't need to learn different communication modes. Everything happens on the card where work lives. Team members get notifications when they're mentioned or when cards they follow update.
The limitation? Trello doesn't include native chat or video calls. You'll use Slack, Teams, or email for real-time conversations. Some teams prefer this separation; others find it fragmenting.
Monday includes similar card-level commenting and mentions. You can have conversations on items, share files, and track who did what through activity logs.
Monday also offers WorkCanvas, a digital whiteboard that allows teams to ideate, with built-in two-way sync to monday.com boards. This helps teams brainstorm and plan before creating structured tasks.
Monday.com can generate custom quotes and invoices directly from CRM boards, streamlining client transactions. For teams managing client work, this integration saves time switching between tools.
Monday makes it easy to request status updates on projects without falling back on email and chat. The platform includes update request features that prompt team members for progress reports.
The Verdict: Both platforms handle collaboration well for small teams. Monday includes more advanced features, but Trello's simplicity often proves more practical for daily work.
Understanding how work progresses helps teams improve. Both platforms offer reporting, but at different levels.
Trello's dashboards are clean but show a limited number of simple metrics, such as cards per list and member activity. You can see basic project progress but won't find sophisticated analytics.
For many small teams, simple metrics suffice. You need to know if projects are on track, not complex burndown charts or resource utilization reports. Trello delivers what most small teams actually use.
Power-Ups can extend reporting capabilities. Add cards for charts, statistics, and custom reports. This modular approach lets you add analytics only if your team needs them.
Monday.com excels at reporting and dashboards. Monday's robust task management views and templates make it a superior project management tool for creating dashboards. You can build custom dashboards pulling data from multiple boards, visualizing information with various widgets and charts.
The platform tracks time, budgets, progress, and performance metrics. You can create executive dashboards showing high-level overviews or detailed team dashboards tracking specific metrics.
The free plan allows unlimited dashboards but each can only contain information from 1 board. For cross-project reporting, you'll need paid plans. Standard plan dashboards can pull from up to 5 boards, with higher limits on Pro and Enterprise tiers.
The Verdict: Monday wins on reporting depth. If you need detailed analytics, Monday delivers. For most small teams, Trello's simple metrics prove sufficient.
Understanding how long tasks take helps with planning and billing. Both platforms approach time tracking differently.
Trello's approach to time tracking relies on external integrations through Power-Ups. You can add tools like Toggl, Harvest, or Everhour to track time spent on cards.
This modular approach works if you already use a time tracking tool. Integration connects your existing workflow to Trello boards. The downside? You need a separate subscription to the time tracking service and must manage it as an additional tool.
For teams that don't need detailed time tracking, this poses no problem. For teams that bill by the hour or need accurate time estimates, managing separate tools adds complexity.
Monday.com includes native time tracking, but you must upgrade to the Pro plan to access it. Once available, time tracking integrates directly into the platform. You can track time on tasks, generate time reports, and analyze how your team spends their hours.
The integration means everything lives in one place. No switching between tools. No reconciling data from different sources. But the Pro plan requirement significantly increases costs for small teams.
The Verdict: Neither platform excels at time tracking for small teams. Trello requires additional tools. Monday locks it behind expensive plans. Teams needing serious time tracking should consider specialized tools.
Work doesn't always happen at desks. Both platforms offer mobile apps, but with different strengths.
Trello's mobile app mirrors its desktop simplicity. You see your boards, cards, and lists clearly on small screens. The Kanban layout works naturally on mobile. You can drag cards, add comments, check off checklist items, and update due dates.
The app loads quickly and works offline, syncing changes when you reconnect. For teams with field workers or remote members, Trello's mobile experience keeps everyone connected.
Navigation feels intuitive. You don't need to learn a different interface. Everything works like the web version, just optimized for smaller screens.
Monday.com's mobile app handles the platform's complexity reasonably well. You can switch between views, update items, check dashboards, and communicate with team members. The app includes most desktop features, which is impressive given Monday's extensive capabilities.
The trade-off? More features mean more navigation. Finding specific functions takes longer than on Trello. The learning curve on desktop extends to mobile.
For teams heavily invested in Monday's advanced features, the mobile app provides adequate access. For teams wanting quick updates on the go, it feels heavier than necessary.
The Verdict: Trello's mobile app wins for simplicity and speed. Monday's app impresses with feature parity but sacrifices ease of use.
Even small teams need security. Both platforms provide basic protections, with differences in advanced controls.
Trello upgraded its security infrastructure in April 2025 by implementing OAuth 2.0 with new scopes and token expiry for enhanced protection. This brings Trello in line with industry-standard authorization protocols.
All plans include two-factor authentication and SSL encryption. You can control board visibility (private, team, or public) and manage member permissions at the board level.
Premium versions include priority support and advanced security. Enterprise adds features like single sign-on (SSO), security certifications, and advanced admin controls. For most small teams, Standard or Premium security suffices.
Monday.com provides similar base security features: encryption, two-factor authentication, and permission controls. The platform complies with major security standards and certifications.
Single sign-on requires an Enterprise plan, which is problematic as it's a crucial cybersecurity feature even for small businesses. This pricing strategy pushes small teams needing SSO into expensive tiers.
Higher plans add features like audit logs, advanced permissions, and compliance certifications. Enterprise includes HIPAA compliance and five years of activity logs.
The Verdict: Both platforms provide adequate security for small teams on basic plans. Neither excels at making enterprise security features accessible to smaller organizations.
When problems arise, responsive support matters. Both platforms offer help, but with different levels.
Trello provides email support for all users, with priority support for paid plans. The knowledge base covers common questions and includes video tutorials. Community forums let users help each other and share solutions.
Monday.com extends strong customer support across all paid plans, including 24/7 support via email, live chat, and phone. Trello doesn't match this level of availability. Free users might wait longer for responses, though documentation usually answers common questions.
For most small teams, Trello's support proves adequate. The simple platform generates fewer complex support needs.
Monday.com offers more comprehensive support across paid plans. This extensive support is complemented by detailed knowledge bases, regular webinars, and a vibrant community forum.
The platform's complexity means teams might need support more often. Fortunately, Monday invests heavily in helping users succeed. Enterprise plans include dedicated onboarding and account management.
The Verdict: Monday wins on support depth and availability. For small teams comfortable with self-service help, the difference matters less.
What do actual users say about these platforms?
On G2, Trello rates 4.4/5 from more than 13,000 users. Users consistently praise the intuitive interface and visual task management. User feedback focuses on how easy Trello is to use.
Common complaints mention limited features compared to more comprehensive tools. Power users eventually outgrow Trello's simplicity. Some users mention that the platform has more limited features than other comprehensive tools like time tracking and budgeting.
For small teams and straightforward projects, satisfaction runs high. Teams managing complex workflows often wish for more advanced features.
Monday.com has a rating of 4.7/5 on G2 from more than 12,000 users. Users highlight flexibility, integrations, and the user-friendly interface despite complexity. Users say the platform is super flexible, has great integrations, and amazing customer service.
Complaints often center on cost and the learning curve. Teams appreciate Monday's power but acknowledge the time investment to master it. Some users find the interface overwhelming initially, particularly when configuring complex workflows.
The Verdict: Both platforms receive strong user reviews. Trello wins for simplicity and ease of use. Monday wins for features and flexibility. User satisfaction correlates directly with team needs.
You're a small team (under 10 people). Trello's free plan actually works for teams of this size. You won't feel artificially constrained.
Your projects are straightforward. Task tracking, simple workflows, and visual progress monitoring are Trello's sweet spot.
You value simplicity over features. Teams that want to start working immediately rather than spending time on configuration will appreciate Trello's approach.
Budget is tight. Trello costs significantly less than Monday across all comparable plans.
Your team loves visual organization. If your team thinks visually and appreciates seeing all tasks at once, Kanban boards work brilliantly.
You're managing multiple simple projects. Marketing campaigns, content calendars, event planning, and customer onboarding all work great in Trello.
You need multiple view types. Teams that require Gantt charts, timelines, calendars, and workload views alongside Kanban boards will appreciate Monday's flexibility.
Complex workflows are common. Projects with dependencies, multiple stakeholders, and intricate processes benefit from Monday's customization.
Advanced automation is essential. Teams that automate extensively and need sophisticated triggers and actions will find Monday more capable.
Deep reporting matters. If you need dashboards that pull from multiple projects with various metrics and visualizations, Monday delivers.
You're planning to scale significantly. Monday grows with you more smoothly than Trello if you expect to add many team members or increase project complexity.
Integration with enterprise tools is crucial. Teams embedded in Salesforce, Microsoft, or similar ecosystems will appreciate Monday's native connections.
Choosing between Trello and Monday comes down to three core questions:
How complex are your projects? Simple projects favor Trello. Complex workflows favor Monday.
What's your team's technical comfort level? Less technical teams will succeed faster with Trello. Tech-savvy teams can leverage Monday's power.
What's your budget? Tight budgets strongly favor Trello. Larger budgets can afford Monday's additional costs.
For most small teams, Trello emerges as the better choice. The combination of generous free tier, affordable paid plans, instant usability, and sufficient features for common workflows makes it ideal for teams under 10 people managing straightforward projects.
Monday.com suits small teams with unusual needs: complex dependencies, need for multiple visualization types, or plans to scale rapidly. The higher costs and steeper learning curve pay off only when you truly need the advanced features.
Both platforms offer risk-free trials. Trello's free plan genuinely works for small teams indefinitely. Monday's free plan serves as a test drive rather than a long-term solution, but paid plans include 14-day trials.
The best approach? Start with Trello's free plan. Get your team working. If you find yourself constantly wishing for features Trello lacks, then evaluate whether Monday's additional capabilities justify the extra cost and complexity.
Remember: the best project management tool is the one your team actually uses. A simple tool everyone embraces beats a powerful tool nobody masters. For small teams, simplicity usually wins.
The Bottom Line: Trello wins for most small teams through lower costs, easier adoption, and sufficient features for common workflows. Choose Monday only when specific advanced requirements justify the additional investment. Start simple, scale only when necessary.
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