FAQ's - Rolling out to your team

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

Windmill offers a two-week free for all customers. The process includes picking initial routines, connecting Slack and Google Workspace, and optionally joining a short training session hosted by Windmill. 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.

What drives high engagement with Windy / makes the rollout successful at a company?

Success is primarily driven by clear communication with the team about what Windy will be used for, running a team training session at rollout, and ensuring every team member responds to Windy’s initial message. Engagement remains high when managers use and share the output with employees, demonstrating the value of participating.

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—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? How do you avoid the trap of checking on people constantly or making them feel monitored?

We believe that micromanagement is ineffective and doesn't produce good information. While our system can connect to other tools and show activities such as meetings, we put more emphasis on collecting meaningful context through manager-set routines—prompts tailored to capture relevant feedback, project progress, blockers, and priorities. 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.

What does the onboarding/setup process look like? Do team members have to install anything or take additional actions?

Admins/managers 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.

What are some good sample questions for team alignment checks?

Three recommended questions are: 1) What are you currently working on? 2) How does your work connect to our team's goals? 3) How do you measure success for your work? These prompts provide valuable insight into alignment and productivity.

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, 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 the prompt, explaining its intent, when to expect it, and encouraging responses. This increases transparency and response rates.