How monday sidekick is Changing Work Management with AI

Meet Your New AI Teammate!

Understanding monday sidekick and What It Means for Work Management

In July 2025, monday.com launched its newest AI feature: monday sidekick, an intelligent, context-aware digital worker designed to proactively support teams across industries. As the name suggests, sidekick is here to assist - not replace - humans, by handling repetitive tasks, prompting action, and generating insights in real time, directly from within the monday.com Work OS.

But what exactly does this mean for your team, and how can it enhance your monday.com instance?

Let’s break it down.

What is monday sidekick?

At its core, monday sidekick is an AI-powered assistant designed to act within your existing monday.com workflows. It’s not just a chatbot or a passive recommendation engine. It’s a digital worker that understands:

• Your role within the organisation
• The projects you're working on
• The outcomes your team is trying to drive

With this awareness, sidekick can do things like:

• Suggest actions to move projects forward
• Generate reports based on real-time data
• Summarise customer feedback into product roadmap items
• Provide insights into sales strategy or competitor activity
• Book meetings and venues from within your workflows

It’s a leap from rule-based automation into intelligent collaboration.

Why It Matters: AI That Works With You, Not Around You

Many organisations have dabbled in AI tools only to find them disconnected from their day-to-day work. The power of monday sidekick lies in how deeply it’s embedded into the fabric of monday.com’s Work OS.

Because monday.com already structures data around boards, tasks, owners, and timelines, sidekick can "see" and understand this structured context. That means:

• Less time spent chasing updates
• Fewer clicks to get the answers you need
• Automated, reliable support that scales with your team

Rather than simply answering questions, sidekick can take initiative - providing nudges to complete tasks, flagging anomalies in project timelines, or preparing materials before you even think to ask.

Real-World Applications

Whether you're in sales, operations, product development, or marketing, monday sidekick is designed to support a wide range of use cases. Here are a few examples of how it can be applied:

🧠 Strategic Planning

Generate executive-level reports with just a few prompts. sidekick can pull relevant KPIs, summarise progress across initiatives, and format the data into presentation-ready summaries.

📈 Sales Enablement

Need help decoding a competitor's positioning or creating an account-based strategy? sidekick can gather signals from CRM boards, communication logs, and more to build a clearer picture of your pipeline or market.

🎯 Product Feedback

Got a flood of feedback from customers? sidekick can analyse qualitative input and group it into actionable feature requests or product themes - helping you inform the roadmap without manual tagging.

🛠️ Task Automation

From booking venues for events to organising files for onboarding, sidekick’s one-click actions reduce friction, freeing your team to focus on higher-value work.

How Is This Different From Existing Automation?

monday.com has long offered powerful automation capabilities, but those automations are based on “if-this-then-that” logic. They’re great for recurring workflows, like sending reminders or moving tasks between groups.

sidekick takes it further with:

• Natural language processing: You can ask sidekick to perform tasks in plain English.
• Contextual understanding: It considers your team, your current projects, and your history when suggesting actions.
• Proactive assistance: Rather than waiting for input, sidekick can recommend what to do next.

In short, it’s no longer just automating the known - it’s helping you discover what needs to be done.

What Are the Limitations?

While sidekick is a major step forward, it’s important to have realistic expectations:

• It’s still in early access and will evolve as monday gathers user feedback.
• Human oversight is essential - especially in strategic or customer-facing outputs.
• Its effectiveness relies on how well your monday instance is set up (clean structures = better AI support).

If your boards are cluttered, under-utilised, or inconsistently configured, you may not get the full benefit.

Preparing for AI in monday.com

To make the most of sidekick, your monday.com setup should support clarity and structure. That means:

• Clear naming conventions
• Consistent use of columns and statuses
• Defined owners and deadlines
• Well-structured dashboards and automations

Not only does this make work easier for humans, it also ensures that AI features like sidekick can interpret and act on your data effectively.

Final Thoughts: AI as a Team Player

monday sidekick represents a broader shift toward embedded AI in work management platforms. Instead of jumping between tools to get AI help, you’ll increasingly see intelligent features emerge inside the systems your teams already use.

The value is in turning everyday workflows into intelligent, insight-driven actions - without disrupting your team’s rhythm.

Whether you're managing product backlogs, launching marketing campaigns, or coordinating support requests, sidekick can help you work smarter and faster - provided your foundation is ready for it.

For more information on monday AI, please see this monday.com news article →