How to Win in Your Job Search
Finding your next career opportunity has become increasingly complex in today's economic climate. Job searches that once took weeks now take several months, requiring more strategy, persistence, and a willingness to adapt your approach.
In this more competitive landscape, many of the best opportunities never make it to public job boards. They're filled through connections, referrals, and networks. As professionals advance in their careers, this trend becomes even more pronounced, with many senior roles being filled before they're ever advertised.
The Counterintuitive Secret to Finding Hidden Opportunities
When faced with a challenging job market, most professionals make a critical mistake. They broaden their search, trying to cast the widest possible net. They position themselves as flexible generalists who can "do anything." They tell everyone they meet: "If you hear of any interesting opportunities, please let me know."
This approach feels intuitive but fails spectacularly in practice.
Andy Mowat, CEO of Whispered, shares a powerful insight: "Every ounce of your intuition will tell you to position yourself broadly to cast a wide net, but the wide net does not catch good possibilities because humans can be expansive, not reductive."
The solution is counterintuitive: You must narrow your focus and be incredibly specific about what you want.
When you tell someone you're looking for "anything interesting," you become instantly forgettable. But when you say you're looking for "a project management role in sustainable construction with companies that value work-life balance," people can remember you and recognize matching opportunities when they arise.
Take Control of Your Job Search Narrative
Many executives approach interviews from a defensive position, focusing on proving they're qualified rather than evaluating whether the opportunity is right for them. This mindset shift is crucial:
From:
Trying to sell yourself
Answering questions passively
Hoping to be chosen
To:
Interviewing the company
Asking thoughtful, challenging questions
Deciding if this opportunity deserves your talent
Master the Interview Dynamic
Andy shares a powerful tactic that immediately shifts the dynamic: "I try to take control over the interview early when I'm the interviewee. Right at the start, I'll say, 'I've got some great questions, but let's start with yours.'"
This simple opener accomplishes several things:
It signals confidence and preparation
It subtly positions you as a peer
It demonstrates that you value the interviewer's time
It sets you up to ask your substantive questions later
Andy notes that interviewers often respond with, "No, no, let's start with yours," which further reinforces your control of the conversation. This approach helps you stand out as someone who approaches leadership opportunities thoughtfully rather than desperately.
Whenever you reach the inevitable "Do you have any questions for us?" portion of the interview, avoid what Andy calls "throwaway questions" like "What's your company vision?" or "Tell me about your culture." Instead, ask specific, thoughtful questions that demonstrate you've done your research and are evaluating fit:
"How are decisions made about resource allocation between departments?"
"What metrics will define success in this role during the first year?"
"How does the executive team handle disagreement during strategic discussions?"
As Andy explains, "I'm not letting them interview me; I'm interviewing them. I want to know if this is going to be a fit, who I work with, how decisions are made, what are the resources." This approach signals a senior mentality that makes hiring managers take notice and demonstrates that you're evaluating them as much as they're evaluating you.
Build a Network That Works For You
For many professionals, "networking" carries negative connotations of transactional relationships and awkward conversations. But effective networking is simply building genuine relationships before you need them.
The most successful executives approach networking with:
Curiosity about others rather than focusing on themselves
Consistent relationship maintenance rather than sporadic outreach
Generosity in making connections without expectation of return
Brief, thoughtful check-ins ("I was walking by your old office building and thought of you")
This approach transforms networking from a dreaded task into a natural extension of professional relationships.
Move Beyond Isolation in Your Search
Perhaps the most challenging aspect of executive job searching is the isolation. The process involves waiting, uncertainty, and often a lack of feedback—all while maintaining the appearance of confidence and success.
Finding community during this process is essential. Whether through formal groups, trusted peers, or platforms specifically designed for executive job seekers, having others who understand the unique challenges provides both practical support and emotional ballast during the search.
Your Path Forward
The most fulfilling career opportunities—those that align with your values, leverage your unique strengths, and offer the impact you seek—are increasingly found through methods that go beyond simply applying to posted positions. They're discovered through clarity, confidence, and connection.
As you navigate your own career transition in today's challenging market, remember:
Clarity trumps flexibility – Define precisely what you want rather than trying to be everything to everyone
Take control of interviews – Approach them as a mutual evaluation rather than an audition
Build relationships continuously – Make networking a consistent practice, not just a job search tactic
Find your community – Connect with others navigating similar transitions to share insights and support
By embracing these principles, you position yourself to discover opportunities that might never appear on a job board—but could be exactly the right next step in your career journey.
Listen to the full discussion on the podcast Do Something Different.
Thanks to Andy Mowat, CEO of Whispered, for his insights.
