Bonus Episode — Starting the Right Conversation: How to Approach Your Job Search with Strategy and Intention

Welcome back to Your Path to Career Success - the podcast that helps you build the skills, confidence, and strategies to thrive in your career.

In this special bonus episode, inspired by listener Andrew Malinow, we explore a question that sits at the heart of every successful career transition:

“How do you ensure job seeking starts with the right conversation, rather than just hoping one happens?”

Too often, job searching becomes a waiting game - updating CVs, refreshing LinkedIn profiles, sending applications and crossing your fingers. But at senior and executive levels, your next opportunity rarely appears in a job advert. It begins with an intentional conversation you initiate, one rooted in clarity, curiosity and strategic connection.

This episode reframes job seeking from a passive process to an active, conversation-driven strategy so you can stop waiting for doors to open and start opening them with purpose.

What You’ll Learn in This Episode

• The mindset shift from “applicant” to strategic conversationalist
• How to start the right conversations that uncover real, unadvertised opportunities
• Practical ways to network with confidence, authenticity, and value
• Common conversational traps that slow down a job search (and how to avoid them)
• A guided reflection exercise to help you build your own conversation strategy for career transitions

At every level, but especially in senior leadership, the most meaningful opportunities emerge not from applications but from conversations. When you lead with clarity, curiosity and value, you become someone people want to refer, recommend and open doors for.

What Next?

Thank you for tuning into this bonus episode of Your Path to Career Success — where ambition meets actionable advice.

🦉 Ready to start more intentional career conversations and transition into your next role with confidence? Book a free discovery call to explore how my Unlock Your Career Potential coaching programme or my 1-2-1 ad hoc support can help you turn conversations into opportunities: 👉 https://calendly.com/thecareerowl

🦉 If this episode helped you rethink your job search strategy, subscribe, leave a review and share it with someone navigating a career transition.

🦉 Connect with me on LinkedIn for daily insights on career strategy, leadership development, and intentional networking.

Useful Resources

📘 The 20-Minute Networking Meeting by Marcia Ballinger & Nathan Perez — a practical guide to mastering purposeful career conversations
📘 Designing Your Life by Bill Burnett & Dave Evans — tools for prototyping career possibilities through conversation and exploration
📘 The Startup of You by Reid Hoffman & Ben Casnocha — strategies for building career opportunities through networks and continual reinvention

Next Steps

Your challenge this week:
 Choose one person whether that is a peer, mentor, former colleague, or leader you admire and start a curiosity-led career conversation. Don’t wait for the “right moment.” Create it with intention, insight and authenticity.

And remember, opportunities rarely arrive fully formed. They begin with a single, well-crafted conversation.

Career success doesn’t start with luck. It starts with the right conversation.

Transcript

Bonus Episode – Starting the Right Conversation: How to Approach Your Job Search with Strategy and Intention

Inspired by listener Andrew Malinow

Welcome back to Your Path to Career Success—the podcast that helps you build the skills, confidence, and strategies to thrive in your career.

I’m your host, Kathryn, and today’s episode is a little special.
 
 

It’s our Bonus Episode, inspired by one of our listeners, Andrew Malinow, who asked a thoughtful question:

“How do you ensure job seeking starts with the right conversation, rather than just hoping one happens?”

It’s such a powerful insight—because so often, job seeking becomes a waiting game. We update our CVs, tweak our LinkedIn profiles, send applications… and then we wait for someone else to start the conversation.
 
 

But at senior levels—especially for executive and leadership roles—your next opportunity rarely comes from an advert. It comes from a conversation you initiate with clarity, confidence, and purpose.

So today, we’ll explore how to approach job seeking as a series of intentional conversations, not random opportunities—so you can move from hoping for a door to open, to strategically opening it yourself.

What I’ll Share in This Episode

In this conversation, I’ll walk you through:

• The mindset shift from applicant to strategic conversationalist
• How to start the right conversations that uncover real opportunities
• Practical ways to approach networking with confidence and authenticity
• A reflection exercise to help you build your own conversation strategy

Reframing the Job Search: From Applying to Engaging

At senior levels, your value isn’t captured in a CV—it’s revealed in conversation.
 
 

The people who find the best-fit roles don’t chase openings; they create them by connecting their strengths to organisational needs through meaningful dialogue.

Below are three mindset and action shifts to help you lead those conversations effectively.

1. Start with Clarity, Not Desperation

When people start job hunting, the first question they often ask is “Who’s hiring?”
 
 

But the more strategic question is: “What kind of impact do I want to make next?”

Example:
A senior HR leader told me she was “open to anything.” Yet when she tried to network, her vagueness made it hard for others to help. Once she refined her story along with me in terms of—“I’m passionate about leading transformation in purpose-led organisations”—people immediately started connecting her to the right conversations.

Practical approach:

• Define your value proposition: what unique results or transformation do you deliver?
• Identify the types of organisations, cultures, or challenges that excite you.
• Craft a concise narrative that connects your strengths to what the market needs.

Stretch exercise:
Write your “career headline” in one line. Example: “I help complex organisations transform culture through people and performance strategy.”

Reflection prompt:
Could someone else easily introduce me based on how I’ve described what I do?

2. Lead with Curiosity, Not a Pitch

The most productive job search conversations aren’t sales calls—they’re learning conversations.
 
 

Your goal is to understand where the organisation or industry is heading, what challenges exist, and how your expertise might be relevant.

Example:
A marketing executive approached a potential employer not by asking about vacancies, but by saying, “I’ve been following your expansion into new markets—how are you approaching brand localisation?” That one question turned into an hour-long discussion that later led to a role being created for her.

Practical approach:

• Do your research before reaching out.
• Ask thoughtful questions that show insight, not need.
• Frame the discussion as exploration: “I’d love to understand your priorities in this space.”
• Share a perspective or observation that demonstrates your value without pitching yourself.

Stretch exercise:
List three organisations or leaders you’d like to connect with. Write one curiosity-based question for each that would spark a meaningful conversation.

Reflection prompt:
Am I approaching people to ask for something—or to understand something?

3. Build Momentum Through Relationships, Not Rejections

At executive level, success in job seeking is rarely about one “yes.” It’s about building momentum through consistent, quality relationships. Every conversation plants a seed—even if it doesn’t lead to an immediate opportunity.

Example:
A CFO I coached spoke to over 20 leaders during his transition. Only two conversations were directly about roles. But one of those early chats turned into a referral six months later—and that referral became his next position.

Practical approach:

• Focus on building relationship capital, not just collecting contacts.
• After each conversation, follow up with gratitude and a relevant insight or article.
• Stay visible by sharing thoughtful content or updates aligned with your expertise.
• Track connections using a simple spreadsheet or CRM—treat it like a pipeline of relationships, not transactions.

Stretch exercise:
Reach out to three contacts this week—no asks, no agenda. Simply check in, share something useful, or express appreciation.

Reflection prompt:
Am I nurturing relationships consistently—or only when I need something?

Common Traps to Avoid in Job-Seeking Conversations

Job-seeking is less about luck and more about intentionality. Many professionals stall not because they lack skill or experience, but because they fall into predictable conversational traps. Recognizing these pitfalls and adjusting your approach can turn networking from a passive activity into a strategic engine for opportunity.

Trap 1: Waiting to Be Discovered

What it is:
Believing that opportunities will appear simply because your LinkedIn profile is polished or your résumé or CV is online. Visibility alone doesn’t create meaningful conversations; opportunity emerges when you proactively engage with the right people.

Why it happens:
Job-seekers often overestimate the power of passive visibility, assuming that recruiters or hiring managers will find them without outreach. This mindset fosters inaction and delays momentum.

Story example:
A senior manager spent months “optimising” her LinkedIn profile—headline, summary, recommendations—but didn’t reach out to anyone. Once she began initiating targeted conversations with peers and alumni, she received two interviews within weeks. Action, not visibility alone, unlocked opportunity.

How to counter it:

• Be proactive. Schedule informational conversations, reach out to peers, and engage with industry forums.
• Treat visibility as a complement, not a substitute. Profiles attract attention; conversations convert it into opportunity.
• Create momentum. Consistent outreach builds relationships, insights, and trust.

Reflection prompt:

Am I being strategic—or just hoping to be found?

Trap 2: Leading with Need, Not Value

What it is:
Opening conversations by emphasizing that you’re “looking” or “available.” This frames you as needy rather than capable, and puts the other person in a pressured position.

Why it happens:
It’s natural to want immediate results, but leading with need weakens your positioning. People respond better when you highlight what you bring to the table, not what you want.

Story example:
A leader reached out with, “I’m job hunting—do you know of anything?” Doors closed quickly. When she reframed her approach to, “I’m exploring how my experience in transformation could support growing businesses,” curiosity and engagement increased. Conversations became about contribution rather than desperation.

How to counter it:

• Lead with capability. Position yourself as someone who can create impact.
• Use curiosity and exploration. Ask questions that invite insight rather than asking for favours.
• Focus on contribution, not need. Be the person others want to help because you offer value.

Reflection prompt:

Do my conversations highlight my expertise—or my availability?

Trap 3: Treating Networking as Transactional

What it is:
Reaching out only when you need something, rather than building ongoing, mutually beneficial relationships. Transactional networking feels opportunistic and rarely generates sustainable support.

Why it happens:
Job-seekers often underestimate the power of long-term relationships. They focus on immediate returns, missing the cumulative benefits of consistent engagement.

Story example:
A director admitted, “I only message people when I need help.” She started reaching out year-round—celebrating others’ achievements, sharing insights, and offering help. Over time, her network transformed from a list of acquaintances into advocates who proactively shared opportunities and guidance.

How to counter it:

• Shift from networking to relationship-building. Focus on reciprocity and connection, not transactions.
• Add value first. Share insights, congratulate successes, or connect others to opportunities.
• Invest consistently. Small gestures over time compound into trust, influence, and advocacy.

Reflection prompt:

How often do I add value before asking for it?

Reflection Exercise: Designing Your Conversation Strategy

Transition from a passive job search to a proactive conversation plan with this structured approach.

Step 1 – Define Your Direction

Clarify your target:

• What role, impact, or environment are you seeking?
• What kind of work energizes you?
• Write an impact statement that communicates your focus and intent.

Step 2 – Identify Your Network

List 10 people who can offer insights—not necessarily jobs:

• Peers, mentors, industry contacts, alumni.
• Think beyond immediate opportunity; aim for perspective, guidance, and connections.

Step 3 – Prepare Your Narrative

Craft a concise introduction that highlights:

• Who you are.
• What you do best.
• What you’re exploring next.
   Keep it confident, positive, and curiosity-driven.

Step 4 – Plan Three Conversations

Reach out with personalised messages rooted in curiosity:

• Example: “I’d love your perspective on how [industry/organization] is evolving in [area].”
• Focus on insight, not immediate requests.
• Be intentional: schedule, prepare, and follow up.

Step 5 – Reflect and Repeat

After each conversation, reflect on:

• What did I learn?
• Who else could I engage next?
• How can I add value in return?

Iterate this process consistently to build both insight and relationships.

Final Thought:

Opportunities rarely appear fully formed—they often begin as conversations. By being proactive, leading with value, and nurturing genuine relationships, you create the conditions for doors to open. 

Courage, clarity, and consistency in your conversations are what transform potential into opportunity.

Closing

Today we explored how to shift your job search from waiting to initiating—how to start the right conversations that lead to meaningful opportunities.

Thank you to Andrew Malinow for inspiring this bonus episode. Your question captures something many professionals experience but rarely articulate—and it’s exactly the kind of insight that helps others grow.

Your challenge this week: identify one person you could start a meaningful career conversation with. Don’t wait for the “perfect” opening—create it with curiosity and purpose.

If this episode resonated, share it with someone navigating a career transition, and let them know they’re not alone.

Connect with me on LinkedIn—search Kathryn Hall, The Career Owl—and visit www.thecareerowl.co.uk for more tools, courses, and career insights.

And remember—career success doesn’t start with luck. It starts with the right conversation.