This Practical Planner Could Change Your Career Conversations
Let’s talk career converations—and how to get the support you need to make them more meaningful.
Your manager can be one of your most powerful career allies. They can open doors, connect you with opportunities, and help you build the skills and relationships you need for what’s next. But even the most well-intentioned manager can’t read your mind. So the question becomes: How can you help your manager help you?
One tool that works brilliantly—whether you’re in-person or remote—is something we call the Development Discussion Planner. It’s straightforward, easy to use, and, more importantly, it works.
This is a tool you can use for yourself, and once you know how it works, you can also use it with your team members. It’s designed to bring clarity, structure, and momentum to career conversations that often feel fuzzy or awkward.
Start with a Role You Aspire To
Before you talk with your manager, take a few minutes on your own. Think about a role you might want in the future—maybe it’s your manager’s role, something more senior, or a lateral move to a different department. You’re not locking yourself in. You’re simply creating a target to guide your learning and growth.
Once you’ve identified that future role, you’re ready to walk through five questions—first, for your current role, and then again for your aspired future role.
When you show up with these answers in hand, you’ve done the heavy lifting. You’ve given your manager a starting point and something concrete to respond to. That’s the magic of this planner: it makes it easier for your manager to truly support you.
The 5 Questions That Unlock Growth
Note: This video is part of our online human-centered leadership development video series. Learn more here.
1. What strengths would you like to leverage and grow?
We always recommend starting with strengths. Where do you shine today? How might those talents apply to the role you want next? If they don’t align, that’s good information too—it might help you rethink what you’re aiming for. And your manager may see strengths you’ve overlooked.
2. In what strategic relationships would you like to invest?
Growth isn’t just about skills—it’s about people. Who do you need to know to get ready for that next role? Who could champion your work, give you feedback, or help you learn what it takes? Relationships are often the bridge to opportunity.
3. What challenges do you want to overcome?
This is a moment for honest reflection—and a chance to compare notes with your manager. What do you see as your biggest growth areas? Do they agree? You go first, then ask for their perspective. This builds trust and creates clarity.
4. What skills would you like to learn or improve?
Think through what you’ll need to succeed in your desired role. What gaps do you see? What new skills could help you be more effective in your current job, too? Your manager might suggest additional skills or offer opportunities you hadn’t considered.
5. What support do you need?
This is where it all comes together. When you ask for something specific—coaching, visibility, a project stretch—it’s far easier for your manager to say yes (or help you find the next best thing). Vague requests rarely move the needle. Specific ones? That’s where momentum lives.
You’re Not Just Asking—You’re Leading
When you walk into a conversation with this kind of clarity, it shows. You’re not just hoping to grow—you’re leading your development. You’ve done your homework. You’ve made it easier for your manager to say, “Yes, let’s do this.”
We’ve seen countless professionals and leaders use the Development Discussion Planner to spark powerful career conversations—and create real momentum. And once you’ve used it for yourself, you’ll find it’s just as effective when used with your team.
Q&A: Let’s Talk Career Conversations (Employee Perspective)
Here are some of the most frequent questions we hear as our clients consider using the development discussion planner for career conversations.
Q: What if I don’t know what role I want next?
A: You don’t need to have it all figured out to get started. Think of choosing a future role less like declaring a life path and more like picking a direction to explore. It’s just a tool to help you uncover your growth opportunities and start a meaningful conversation. Ask yourself: What kind of work lights me up? What problems do I love solving? Who do I admire—and why? You can also talk with your manager about a few possible paths and use the planner to test-drive more than one. Clarity often comes through conversation, not before it.
Q: What if my manager doesn’t seem interested in my career development?
A: First—take a breath. This doesn’t mean you’re stuck or that your growth is on hold. Some managers just haven’t been trained to have these conversations, or they’re overwhelmed and don’t know how to support you. That’s where the Development Discussion Planner shines. It gives you the structure. You’ve done the thinking, you’re coming in prepared, and all they have to do is react. You might open with:
“I’ve been thinking about my growth and filled this out to help us have a focused conversation. I’d really value your perspective.”
If they still don’t engage? That’s useful data. Look for mentors or sponsors elsewhere in the organization who do care about development—and let this be your cue to build relationships that support your goals. Growth doesn’t have to come from just one person.
See Also: How to Warm Up Your Relationship with an Icy Boss
Q: What if my career goals don’t align with what my manager needs right now?
A: That’s a great place for dialogue. If your aspirations don’t line up perfectly with the team’s current needs, talk about it. That doesn’t mean it’s a no—it just means you might need a longer runway or a creative path forward. Ask:
“How can I contribute in a way that supports our goals and also helps me build toward where I want to go?”
Alignment doesn’t always mean immediate action. Sometimes it means a shared plan and a little patience.
Q: What if I’ve had this conversation before… and nothing happened?
A: Oof. That’s frustrating—and also a reason to try again, this time with a bit more structure. Use the Development Discussion Planner to bring specificity and momentum. Say,
“I know we’ve talked about development before. I put together some thoughts using a tool I found helpful—can we revisit the conversation with this as a guide?”
And if things still stall? You may need to explore other growth channels—mentors, special projects, lateral moves—or take an honest look at whether your current role supports your future goals.
Q&A for Managers: Leading Career Growth Conversations that Stick
And, here are a few questions we hear from managers in our leadership development programs as they prepare to have these conversations with their teams.
Q: How can I use this tool to guide conversations with each person on my team?
A: Once you’ve experienced the Development Discussion Planner for yourself, you can flip the script and offer it to your team. Have your team fill it out first, just like you did. That way, they come into the conversation with clarity and ownership. Then your role becomes about listening, exploring, and helping them connect dots—not pulling ideas out of them in real time. Bonus: It helps you calibrate your development plans across your team without falling into one-size-fits-all thinking.
Q: How do I introduce this tool to my team without making it feel like extra work?
A: Lead with purpose, not paperwork. Let your team know you want to support their growth—but you also know career conversations can get vague or stuck. This tool makes it easier for both of you. Try:
“I’d love to have more focused development conversations with each of you. This tool helps you think through your goals and gives me a clearer way to support you. Take a look, reflect, and we’ll schedule time to talk through it together.”
Framing it as a shared investment in their future makes all the difference.
Q: What if a team member doesn’t know what they want next?
A: That’s okay—it’s part of the process. Encourage exploration over certainty. You might say:
“You don’t have to have it all figured out. Let’s use this as a way to uncover what energizes you and where your strengths could lead.”
Be curious. Ask about the types of work they enjoy, challenges they want more of, or people in the organization they admire. Sometimes clarity starts with conversation, not conclusions.
Q: How do I follow up without micromanaging?
A: Easy—be supportive, not suffocating. Follow-through builds trust, and it doesn’t have to be heavy. After the conversation, ask:
“What’s one small step you’d like to take in the next month? How can I help?”
Then, schedule a lightweight check-in to revisit progress. Even 10–15 minutes makes a big impact. It’s not about tracking—they just need to know you’re still in their corner.
Q: What if I’m not sure how to guide them in their goals?
A: You don’t need to have all the answers—you just need to ask great questions and connect them to people or resources who might. You can say:
“That’s a great goal, and I want to help. Let’s explore what support looks like. I may not have all the steps, but I’ll help you figure them out.”
Think of yourself less as the expert and more as the connector and advocate.
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