Ask for What You Want

This framework moves you from “stuckness” and resentment to career fulfillment by treating personal and professional desires as an iterative discovery process. By shifting from people-pleasing or control-seeking to radical integrity, you gather better data and build stronger professional relationships.

Step 1: Articulate the “Dream Behind the Complaint”

Before you can ask, you must know what you actually want. Most people suppress their desires under the guise of being “fine” or vent through unproductive complaints.

• Audit Your Complaints: Identify a recurring frustration at work.
• Find the Dream: Every complaint implies a dream world where that issue is resolved.
  • Complaint: “This meeting is a waste of time and we never decide anything.”
  • Dream: “I want us to make a definitive decision on the product roadmap today so we can stop spinning.”
• Perform an Integrity Check: Ask yourself, “Is there something I’ve been thinking about for 3–4 days that I haven’t said?” If yes, you are out of integrity. State the feeling (boredom, fear, excitement) as data.

Step 2: Ask Intentionally and Humbly

How you ask depends on your default “rut” (People-Pleaser vs. Control-Freak). The goal is to express yourself fully without being attached to a specific outcome.

For Individual Contributors (Low Authority)

Use the Humility + Clarity model. Combine a clear desire with an acknowledgment of the other person’s agency.

• The Script: “I really disagree with this product decision and I would prefer we do [X]. I know it’s not my call and I’m just one opinion, but it’s important to me that you know where I stand. What do you think? Are you willing to reconsider?”

For Leaders (High Authority)

Avoid ordering. Instead, seek Enthusiastic Consent.

• The Script: “I’m hearing you’re lukewarm on the May 1st delivery date. What would it take for this to be a ‘hell yes’ date for you—one where you are 100% confident we can deliver?”

Step 3: Accept the Response (The “Hell Yes” Standard)

Accepting the response is an emotional regulation exercise. Anything short of a “Hell Yes” is a “No.”

• Identify Lukewarm Yeses: If someone says “I’ll try” or “Maybe,” treat it as a “No.” A “Maybe” on a deadline leads to a missed milestone.
• Don’t Over-Accept a No: A “No” today is just data about this person, at this time, with this specific framing. It is not a permanent rejection of your dream.
• Apply Consequences without Coercion: If a teammate says “No” to a deadline, respect it, but follow through with the logical consequence: “Since you can’t commit to May 1st, I’m going to reassign this project to someone who can.” This respects their “No” while honoring your “Dream.”

Examples

Example 1: Disagreeing with a Roadmap

• Context: A PM feels a new feature is a mistake but doesn’t have the “data” to prove it yet.
• Input: Gut feeling that the feature will cannibalize a core product.
• Application: Instead of staying silent, the PM says: “My gut tells me this will hurt our core metrics. I don’t have the SQL data yet, but I wanted to put my opinion on the record because I care about this launch. Can we run a smaller pilot first?”
• Output: The team acknowledges the risk and adjusts the launch plan to a phased rollout.

Example 2: Seeking a Promotion or Role Change

• Context: An employee feels they are being pushed into a “User Research” track when they want to stay in “Product Management.”
• Input: A management directive to change roles.
• Application: Articulate the desire: “I value the company, but I am a Product Manager, not a Researcher.” Ask: “I’ve written a proposal for how I can stay in PM and solve [Problem X]. Are you willing to review it?”
• Output: By asking out loud, the employee moves the conversation from “assignment” to “negotiation.”

Common Pitfalls

• Using Data as a Shield: Waiting for perfect data before speaking up. Your gut feeling and professional opinion are valid data points in a relationship.
• Accepting the “Fine”: Telling yourself “It’s fine” when you are actually frustrated. This leads to burnout and “selling out” on your goals.
• Confusing Discipline with Motivation: Trying to “force” yourself to do things you don’t want to do (e.g., staying in a bad job). Discipline is a short-term tool; long-term success requires following a vision you actually want.
• Ignoring the “Body No”: Accepting a verbal “Yes” when the other person’s body language or tone suggests they aren’t actually committed. This creates “unforced errors” in project execution.