Key insight: Learn how AI coaching is reframing frontline leadership development and daily managerial workflows.
What's at stake: Under-supported managers risk productivity loss, higher turnover, and weaker execution across teams.
Supporting data: 51% of managers with <3 years feel unprepared; 74% report burnout (Insperity).
Source: Bullets generated by AI with editorial review
As companies continue the trend of scaling back on management positions in 2026, those remaining or moving into these roles still need support to
Only 51% of managers with "less than three years of leadership experience feel prepared to manage people," and 74% report
"We haven't given managers the tools to be effective," said Doug Dennerline, CEO of employee performance management software platform Betterworks. People in this position need "tools that let you manage more proactively by understanding when you need to reach out, what you need to say, what you need to do and at what point in time."
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How AI can help
Structured training models, development opportunities, goal setting and continuous performance evaluation are
This month, Betterworks acquired Rypple, a native AI platform that offers coaching and mentoring assistance to managers with the goal of making them better leaders. People going into manager roles are being asked to take on more diverse responsibilities than ever, said Ian Gover, Rypple's CEO and co-founder, and they shouldn't be expected to automatically have mastery of everything involved.
"For example, if you're an engineer, you're really good at creating rock-solid code. Then you get promoted, and over the course of a weekend it's expected that you're going to develop this whole new set of organizational leadership and a complex set of new skills, and the reality is most managers go into that sort of transition point without clarity on how to do even the basics," he said.
For now, Rypple continues to operate independently business-to-consumer, and offers a free version of its AI features as well as a premium version for $12.99 per month. Its feedback is based on any user-uploaded management competency models, leveling rubrics, and culture and values documents from their company, along with hundreds of management frameworks, Gover said.
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The platform can help managers prepare for and conduct one-on-ones and other team conversations, construct feedback, navigate challenges like employee conflicts, lay out performance improvement plans and conduct meeting practice runs. The tool's ability to connect to multiple company communication and organization tools like Slack and employee calendars enables it to search for relevant management moments with team members, summarize and schedule meetings, and offer input on potential next steps.
"It's facilitating the parts of us coming together that don't really require human connection, like calendaring and scheduling and receiving raw feedback from people," Gover said. "Those are not the things that require the uniquely human element, but as a manager, you get stuck doing all of that stuff as the lead up to what's most important. By the time I get to walk into that room, I'm burnt out from all of the things I needed to do in order to get us there."
The idea is to demystify management tasks and integrate into the daily responsibilities and needs of these leaders, Gover said.
"An example would be if two employees are butting heads, and I need to figure out how to resolve conflict, [the AI coach] is still going to give me advice and counsel, but it's also going to say … 'The best way to do this is get feedback and input from [them], then the three of you sit down and have that conversation. Do you want me to collect that feedback, merge it together, and identify the themes? I'll also set up that meeting for you,'" he explained.
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As AI's impact on work continues to cause trepidation among workers, Gover emphasizes its ability, when used the right way, to make them more efficient at their job.
"The true unlock is when AI allows us to become more human in those moments, because it's resolved all the busy stuff, all the grunt work that was needed in order to get there," he said.
