FAQ's - Rolling out to your team

What does onboarding and starting a trial with Windmill look like?

Windmill offers a two-week free trial for all customers. The process includes picking initial routines, connecting Slack and Google Workspace to Windmill, and optionally joining a short training session hosted by our team. Set-up takes less than 10 minutes for experienced teams. After the trial, the cost is $500/month for up to 50 employees, month-to-month, with cancellation any time.

In terms of specific trial frameworks, we'll work with you to find a Routine configuration that makes sense for your team.

What drives high engagement with Windy and makes the rollout successful?

Engagement remains high when managers use and share Windmill's output with employees, demonstrating the value of participating. Thus, success is primarily driven by clear communication with your team about what Windy will be used for. This might mean hosting a team training session at rollout, ensuring that every team member responds to Windy’s initial message. We can also provide materials for managers and employees to better understand how Windmill works prior to their first interaction with Windy.

How do you avoid overwhelming employees with too many prompts or Routines?

We recommend a balanced approach: for every new Routine implemented, remove an equivalent process (like eliminating a standup if you’re using a Priorities Routine). The goal is to integrate seamlessly and reduce—not increase—your team's workload. During any transition, there may be a brief overlap, but once new Routines are established, legacy processes should be phased out to avoid duplication and fatigue.

How do you prevent your tool from becoming a micromanagement system that makes employees feel monitored?

We believe that micromanagement is ineffective and simply doesn't produce good information. While Windmill can integrate with business tools and show activities (like meetings, code activity, etc.), we put more emphasis on collecting meaningful context through manager-set Routines. These routines are meant for high-value check-ins, not granular oversight, and can be fully customized (including anonymity and frequency) to align with your team's culture. The main idea is to provide actionable insights without hovering or adding unnecessary surveillance.

Do team members have to install anything or take additional actions during onboarding?

Admins connect Windmill to their Slack workspace as part of setup. Team members do not need to install anything. Once Routines are created, Windy will appear in Slack and team members will receive prompts directly.

How can we improve response rates to Windy’s prompts or notifications, and what happens if we miss responding within the window?

Response rates improve significantly when Windy Reports are used as the basis for actual team meetings, providing visible accountability. Windy sends reminders for Routines (which are configurable), but if prompts go unanswered within a set period (e.g., 24 hours), users may miss the loop for that cycle.

How should we notify the team about these recurring prompts?

It's important to communicate via a general channel (such as Slack) before sending your first prompt with Windmill. Explain its intent, when to expect it, and encouraging responses. This increases transparency and response rates.