Guided Mentorship

• Lead designer providing hands-on work and oversight alongside my report, Sree Rengavasan
• Data analysis showed significant drop-off once mentees and mentors are matched
• User research revealed pain points in the current mentoring experience
• Focused on an improved connection onboarding flow, guided conversation templates, and a completely reimagined video call experience
• ~8x increase in meetings scheduled and tasks created, and ~2.5x increase in participants setting goals

Chronus exists to help organizations run mentoring programs. Our software matches mentees with mentors, and provides features that support those connections. However…

Within 30 days of being matched, 35% of connections had NOT scheduled their first session.

While the problem was clear, we didn’t have a good sense of why it was happening, so we drilled a bit deeper. After speaking with users, program admins, and our customer support team, two key themes emerged:

First: a fair number of our connections were meeting off-platform — either in person, or hopping on whatever video tool their company already had. On the surface, that’s not a failure. NPS stayed consistently high, and by every signal we had, those relationships were going well. But it did mean people were getting matched and then never touching the rest of what we’d built. This was a critical business problem:

If the mentorship happens somewhere we can’t see, the only demonstrable value we are providing is the matching, and, “Are we paying just for matching?” is not a question you want to hear from customers.

Second: both mentees and mentors — especially people mentoring for the first time — told us they weren’t sure how to approach the relationship. They had questions like:

“What am I actually supposed to do here? What do we talk about? Who’s driving? How often should we meet?”

At this point it was pretty clear — we’d done a good job of getting two people matched, but a poor job of helping them progress and get the most out of our platform.

This problem area ended up being the highest priority roadmap item for over a year, spanning multiple work streams that all had to come together to form a seamless mentorship experience. While I was still largely hands-on, contributing design work, a lot of my involvement was also as a mentor (how meta, I know 🤪), helping steer or make decisions when things felt stuck.

To find key opportunities for improvement, we looked at the entire mentorship lifecycle, and explored which areas had the best chance of moving the needle on the problems discussed above. At the same time, I worked closely with a few cross-functional leaders who were helping define, from a program design perspective, what ideal mentorships look like.

A few hypotheses came out of these explorations and discussions:

1. If we can improve clarity at key moments, like product and connection onboarding, users will have a better understanding of what to expect from their connection, and be more likely to engage early
2. If we provide structured conversation templates, users will have a clear starting point instead of starting from a blank canvas, and conversations will be more meaningful
3. If we can make the actual meeting experience more enjoyable and valuable, users will want to stay in the platform, instead of going elsewhere

The solution(s) tackled different aspects of the hypotheses mentioned above. Here’s a glimpse into what we delivered.

Connection onboarding

A quick intro flow that introduces the mentor, confirms what you’re working towards, and nudges you to set up the first conversation.

A focused widget that gives a high-level outline of the connection journey (how many meetings should I expect, etc.) and provides key details about each proposed meeting. Users can always add or skip recommended meetings, and create their own agendas.

Agenda templates & updated meeting experience

Our biggest bet to encourage on-platform meetings was a completely reimagined video-call experience. It brought the meeting guide directly inside the meeting surface, providing specific agenda items so participants can have efficient and meaningful conversations.

AI-powered personalization

Based on your goals, added tasks, and recent meeting notes, AI can personalize the next conversation agenda to keep you on track. And if the recommended guide isn’t quite doing it for you, you can use AI to generate a new one.

The work we did on this project ended up having significant positive impact on our product. We saw about an 8x increase in meetings being scheduled in our product, and a similar increase in the amount of action items created alongside these meetings, proving that more people were coming back and committing to the process. We also saw a 2.5x bump in users who created goals, further showcasing a willingness for people to invest in the experience.

This success certainly didn’t come without challenges, and looking back, there are definitely things I’d do differently. Some quick thoughts:

• I would’ve pushed harder on the note-taking experience within the guided conversations. Because of the structured nature of the agendas, we ended up having individual text fields for each agenda item’s respective notes. I had really hoped for an open canvas kind of approach, like a Notion or Google Doc, but the engineering team wasn’t open to doing that at the time, so I let it go
• I would’ve also encouraged more exploration into integrations with existing video call tools like Google Meet or Zoom. Both had began offering some 3rd party app or plugin support, and I thought it would be awesome if we could bring the guided conversation experience directly in those products. At first that feels counterproductive to the goal of keeping people in platform, but in my mind, the specific video service being used wasn’t all that important so long as they can utilize the conversation guides and then follow up based on the created action items. I think we could’ve easily nudged people back to the product to manage those elements of the experience.