Nalani's Blog

The How & Why of Development Conversations

Written by Nalani Rodriguez | Oct 9, 2025 5:28:06 PM

The How & Why of Development Conversations

The goal of development conversations between you and each of your team members is to create a trusting relationship that demonstrates your care and commitment to their growth as a human, not just in the company’s benefit. 

This approach to employee development is more than helping them reach a promotion or build the skills they need to keep growing in their role. Regular development conversations can lead to trust enough that they can feel safe to say something as bold as a dream unrelated to their current role. 

*Cue the skepticism*

I’ve seen this happen, it IS possible. 

Imagine you’ve built this trust and your team member tells you they want to be an astronaut one day. Or a winemaker. Or a chef. 

Now imagine replying to them with something like: 

AWESOME! Let’s talk about how I can support you in preparing for that path while you’re here on my team even though those aspirations might not seem related to your current role.

Are there skills you want to develop that we could work on together that would support both this path and your current scope of work? (think: project management, people management, negotiation, public speaking, proposal writing, etc.)

Why would I even entertain this idea?

Assuming (or pretending) that everyone on your team wants to grow in their current role long term is a recipe for disengagement when inevitably some of them move into a quiet quitting mindset out of lack of interest, then at some point quit unexpectedly. 

The real test of your commitment to their growth would be your willingness to support them in growing in a direction that will take them away from the organization in the short or medium term. This can no doubt be scary. What if you asking them about their aspirations prompts them to think about leaving because their dreams don’t align with their role or what is available at the company?

It’s possible this happens, but if you know ahead of time you have a higher likelihood of working with them on timelines and transitions so you don’t experience an unexpected departure. 

Yes, it’s much easier to find ways to support your team members in staying on your team if they want to grow toward related industries or roles. If their aspirations feel so unrelated it doesn’t seem possible, remember that your care and commitment to them could simply look like periodically asking about how they are feeling about moving toward that dream. There may be nothing you change in their day to day role or tactically help with, but even just this can build immense trust and engagement for the time they are on your team (for some, a prolonged tenure). 

Preparing for a Development Conversation

  1. Initiate a dedicated time for a development conversation, at least 30 min every 6 months
  2. Clarify ahead of time that during this conversation you will:
    • Talk about how they want to be growing in their career, regardless of the scope of their role or what the company might want from them 
    • Not be discussing their performance, projects or task updates
    • Not be talking about the growth path you think they should want
  3. Ask them to prepare reflections ahead of time
    • Consider asking your team member to start and own a document where they capture their aspirations along with goals they set to help them progress in that direction (see sample questions below if they need inspiration) 
    • This document is then an easy starting place for development conversations (ask them to update it ahead of the next conversation)
    • Note: Many people have never been asked what THEY want before. This will be new to many, especially those earlier in their career. Some team members may struggle with these open-ended questions about aspirations. That is normal. Your job is to communicate and re-communicate that it’s okay to dream, and not abandon these questions just because they don’t know right now. 

 

Having a Development Conversation

There are three goals of development conversations: 

  • Communicate care and commitment to them as a human, not just as a member of your team
  • Check-in on what the vision of their professional growth path is
  • Discuss ways you as their manager can support them toward their vision

 

Tips & Tricks

  • Let your team member lead
  • Listen more. Give less advice and ask more questions. Lots of questions!  
  • Identify their next steps for their development
    • If their aspirations are in line with the linear growth path of your team/their role:
      • Together, identify areas for development that they are excited about
      • Set development goals that you will check in on together at your next development conversation
    • If their aspirations are beyond your team or even your company:
      • Re-communicate your support of their growth
      • Ask them what areas for growth would be meaningful focus areas in the short term both that could overlap with their current role, and goals that may be unrelated
      • Ask how you can best support them
      • Offer any introductions if you are willing and able 
  • At the end, make sure to set expectations about when the next development conversation will happen

 

Sample Questions for Development Conversations

 

When a team member isn’t clear on their aspirations

  • If you could choose without financial or structural barriers, in the long term of your career how would you love to be spending your time?
  • What would you like to be different in your work life 1 year from now? (a different type of role, having new skills, becoming a manager, etc)
  • If time and money wasn’t a factor, what would you do?
  • What types of work energize/drain you?
  • What parts of the business would you like to be more involved in or learn about? What interests you about that?
  • What would you say your biggest skill / super-strength is? What % of the time do you get to use it? How can we increase it?

 

General Questions

  • Has your aspirational path changed since we last talked about your development?
  • What is one professional goal and personal goal you have right now?
  • What do you most want to be learning over the next quarter? What support do you need in that?
  • What qualities/resources do you have to help you achieve this aspiration? What might you need?
  • What are the internal/external obstacles? How would you tackle this goal if those weren’t factors?
  • What will you do now? When will you do it?
  • How will we know when you were successful?

After a Development Conversation

  • Find ways to incorporate their development goals into the type of project work you give them wherever possible
  • Make introductions to other people in the company (or in your network if you are comfortable) that might support them in further exploring 
  • Check-in periodically on how they are progressing (and feeling) about their development goals