Should I Include My Resume When Sending a Boss-Hunting Message?

Key Concepts

• Boss Hunting: A proactive job-seeking strategy where a candidate directly targets a specific manager or decision-maker rather than applying through general HR channels.
• Direct Outreach: The act of initiating contact with a potential employer or manager without a formal job posting.
• Strategic Communication: Tailoring the content and intent of an outreach message based on the recipient's role (e.g., potential boss vs. potential peer).

Strategic Outreach: When to Send a CV

The core argument presented is that the decision to include a Curriculum Vitae (CV) in an initial outreach message depends entirely on the professional relationship and the hierarchy of the recipient.

1. The "Boss Hunting" Strategy

When the objective is to secure a position under a specific leader, the speaker advocates for a direct and transparent approach.

• The Methodology: Send the resume immediately in the first outreach.
• The Rationale: By sending a CV, the candidate is explicitly stating, "I want to work for you." This removes ambiguity and signals professional intent.
• Key Perspective: The speaker emphasizes that for senior roles or specific target managers, hesitation is unnecessary. The CV serves as a tangible proof of value and a clear call to action.

2. Peer-to-Peer Networking

The speaker distinguishes between "boss hunting" and networking with potential teammates.

• The Methodology: Do not send a CV in the first outreach when contacting a peer or a potential teammate.
• The Rationale: The goal when contacting a peer is to build a relationship, gather information, or understand the company culture. Sending a resume prematurely can be perceived as transactional or overly aggressive, potentially hindering the development of a genuine professional connection.

Logical Framework for Outreach

The speaker provides a binary framework for determining the inclusion of a CV:

| Recipient Role | Action | Primary Goal | | :--- | :--- | :--- | | Potential Boss | Send CV immediately | Expressing intent to work for them | | Potential Teammate | Do not send CV | Building a relationship/networking |

Synthesis and Conclusion

The primary takeaway is that intent dictates the strategy. When targeting a decision-maker (a boss), the outreach should be direct and resume-forward to establish a clear professional proposition. Conversely, when engaging with peers, the focus should shift toward relationship-building, where the immediate presentation of a CV may be counterproductive. The speaker’s definitive stance—"100% final answer, always"—underscores the importance of clarity and confidence when pursuing a specific leadership target.