From an anxious, entry-level employee to Google executive and now New York Times bestselling author, I'm passionate about helping you achieve your personal
& professional goals, unapologetically.
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You want to grow in your career.
Maybe it’s a raise, a promotion, or just more opportunities to work on projects you’re passionate about.
The Problem
Too many people wait for their manager to initiate career conversations.
The result? You might be working hard, but no one knows where you want to go—or how to support you.
It’s time for a career development conversation.
The Big Small Thing
Have a simple, structured career conversation every 6 months with your boss.
Here’s the step-by-step guide:
Step 1: Use These Scripts to Ask for the Meeting.
Employees:
“Hi [manager], I’d love to schedule a 30-minute career conversation with you. I’m having such a great time on this team, and it’s always nice to carve out time to talk big-picture! I’ve retitled next week’s standing one-on-one to ‘Career Development Conversation.’ If that doesn’t work, please let me know.
I’ll plan to send you my answers to the below questions ahead of time so we can prioritize what matters most to me right now.”
Managers:
“Hi [employee], as you know, career development is important to me, and I like to do a check-in every six months. I’m excited to hear how you’re feeling on the team, what projects you’re enjoying, and how I can best support your 6-month to 2-year goals. I’ve retitled next week’s standing one-on-one to ‘Career Development Conversation.’ If that doesn’t work, just let me know.
Below are some questions that will get us started. If you share your answers beforehand, we can prioritize what matters most to you and how I can immediately support you.”
Step 2: Take 20 Minutes to Answer These 5 Questions:
#1: What’s one skill you’re most proud of?
Highlighting your strengths helps your manager understand what you excel at and enjoy.
#2: What’s one skill you’d like to improve with your manager’s support?
Flagging an area for development shows self-awareness and opens the door for coaching. By asking for help directly, you turn potential weaknesses into growth opportunities.
#3: What 2-3 people do you want to set up time with in the next 4 weeks?
Be specific! For example: “I’d love an introduction to [Name/Title] to learn about [specific area].” Make these choices count. Aim high. Write down people who are senior and matter for your career.
#4: What project could better set you up for career success?
For example: “I’d love to take the lead on [Project X] to expand my skills, work with senior stakeholders, and prepare for [specific career milestone].”
#5: What’s one goal outside of work you’re excited about in the next six months?
Sharing a personal goal reminds your manager that you’re more than just your job. It’s a fun way to spark connection and share what lights you up.
Quick Story:
When I was a Google exec, career conversations often unlocked hidden potential—for both the employee and the team.
Take Doug, for example. During one of our conversations, I asked, “What’s a skill you’d like to do more of?”
He surprised me by saying, “I feel like I’m not innovating enough.”
I’d always seen Doug as an amazing people leader and stakeholder manager—someone everyone loved. But when he shared this, I realized I had no idea he enjoyed innovation or was good at it. That skill wasn’t being tapped.
I started assigning him innovation-driven projects, not just people-focused ones.
The result? Doug thrived, delivered incredible results, and got promoted. It was a win for him, our team, and the company.
If Doug hadn’t spoken up, I never would’ve seen that side of him—or given him those opportunities.
Step 3: Send Your Answers 24 Hours Before the Meeting.
Sharing your responses in advance gives your manager time to reflect and come prepared to support your goals.
Step 4: Make the Meeting Count
Use the full 30 minutes (or better yet, 45!) to focus entirely on your career development.
If you try to squeeze “Career Development” into the last 5 minutes of a full meeting agenda, it ain’t gonna happen. (Hence why the meeting title should be “Career Dev Conversation” vs “Weekly One-on-One.”)
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How This Helps You Chase What You Want
Regular career development conversations put your growth on the radar.
By taking charge, you show initiative, build trust with your manager, and create opportunities for meaningful feedback and support.
Your goals matter. Start advocating for them today.
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