Written By Cari Borden

How to Get the Conversation Flowing With Your Manager (Without Getting Laughed Out of the Room)
You know the drill.
Numbers go up → leadership gets nervous → morale drops → cue the pizza party.
But guess what?
People don’t stay for pepperoni. They stay for possibility.
If you’re ready to stop being pacified with perks and start building a career with purpose, it’s time to get serious about the conversations you’re not having with your manager.
Here’s how to get that conversation flowing—without it turning awkward or adversarial:
🍕 1. Come With the Receipts, Not the Rage
Don’t just vent. Bring facts, wins, and a clear picture of your current performance. If you’ve exceeded expectations, show it. If you’ve grown, prove it. Your path starts with proof, not pizza.
🧭 2. Ask, Don’t Assume
Instead of, “Why haven’t I been promoted?” try:
“What specific skills or behaviors would I need to demonstrate to be considered for [next role] in the next 3-6 months?”
That shows initiative and invites guidance.
👂 3. Listen Like a Leader (Even If You’re Not One Yet)
Your manager’s responses are data. Listen for patterns. Are they avoiding commitment? Giving vague answers? Or are they genuinely supportive but unaware of your ambition? Each of these tells you where the real blockage might be, and it’s not always you.
🛠️ 4. Propose a Path, Not Just a Problem
Managers are more likely to invest when they see you investing too. Ask to shadow other teams, take on a stretch project, or develop a skill relevant to your next role. Make it easy for them to say yes.
🔄 5. Make It Ongoing, Not One-Off
Development shouldn’t be an annual performance review surprise. Set the tone with:
“I’d love to check in on progress toward my development goals regularly. Could we touch base monthly?”
This builds rhythm and accountability (for both of you).
Because if they can order pizza, they can support your path. One costs $10. The other? A little effort and some decent leadership.
🔥 CTA:
If you’ve ever felt like your hard work was rewarded with a slice and a thank-you, let’s talk. I help professionals find their voice, build their plan, and navigate these conversations with confidence.
📥 Message me or find me on Fiverr for mentorship and strategy sessions.
📚 Subscribe for more workplace wisdom, coaching tips, and a little sarcastic sass.
Leave a comment