Transition Team Recap 6/3

• The Ambitious Exec program
• AI Interview Prep Strategy
• Provocative Self-Assessment Qs (To Ask Yourself)
• Strategic Networking & Follow-Up
• Conference Strategy for Industry Transition
• Red Flags & Toxic Environment Prevention
• The Confidence Multiplier

The Ambitious Exec Program

• One Huddler has joined The Ambitious Exec program ($7,500)
• Their friend used them and within a few months was fielding multiple offers
• Ambitious Exec helps set up campaigns, update your resume, have pre-interview coaching sessions, build lists on LinkedIn Navigator, +++
• Huddler is seeing initial traction with meetings from campaigns, expecting results after 2-3 months of effort
• We’ll keep an eye on this and report on findings!

AI Interview Prep Strategy

• Before: Practice orally with AI tools, ask them to be harsh and grade responses
• Don't ask AI for answers - give YOUR answers and have AI analyze them
• After: Dictate questions and your responses to build a database of improving answers
• Deep Research advantage: Do complete competitive analysis — interviewers don’t have time for this level of prep
• Pro tip: Create a dedicated "Interviews" project in ChatGPT to track everything

Provocative Self-Assessment Qs (To Ask Yourself)

• "What would the best CMO version of you be doing this week?"
• "If your career were a brand, what's the tagline?"
• "What's the boldest thing you've done in your search? What would 10x bolder look like?"

Strategic Networking & Follow-Up

• Asking “How can I help you?” reverses typical job-seeker dynamic (even if they don’t take you up on it)
• Real example: One Huddler connected interviewer's son with job opportunities through personal network
• "If you ask for advice, you get a job. If you ask for a job, you get advice."
• Don't just remind people you exist—bring something useful
• Use AI to research their challenges and find relevant content
• Timing: Initial thank you, then meaningful contact after 3-4 weeks

Conference Strategy for Industry Transition

• "Act like a journalist, go to a conference, then meet as many people and capture as much content as possible.”
• The goal: Create content that connects the dots between your last position and where you want to go next
• Take photos of speakers and detailed Q&A notes, try to meet them in person at the event, then reach out later: "I have a photo of you at the event and your Q&A notes - can I share them?"
• Use alumni databases for warm introductions

Red Flags & Toxic Environment Prevention

• Even perfect due diligence can't prevent reorgs that change your boss post-hire.
• Due diligence essentials:
• • Talk to person who held your role previously
  • Go beyond Glassdoor - use Fishbowl, Blind for real insider perspective
  • Ask provocative questions: "When was the last promotion on your team and why?"
• Leadership mindset shift: Instead of being victim to "toxic bosses," develop skills to manage up and help flawed CEOs grow. Every CEO is human with weaknesses - successful CMOs learn to guide and coach upward.

The Confidence Multiplier

• "Even if you don't want the job, get the offer."
• This mindset shift from scarcity to abundance changes how you show up in interviews and positions you as the #1 choice rather than #2.
• The most successful job seekers are treating this transition as an opportunity to level up their personal brand, thought leadership, and strategic approach - not just "finding the next job."