Is YOUR career worth the hustle?
Why Senior Executives Struggle to Find Their Next Role (And What to Do About It)
Everyone knows building a brand takes hustle, grind, long days, shameless self-promotion, and showing up everywhere. Finding a job takes the same effort.
Senior leaders in transition need the same mindset. In the current market, expect to spend more time and energy marketing and selling yourself when searching for jobs.
It doesn’t end there.
Once you’re established in your role, turn your attention to building your profile and personal brand by networking and developing a visibility strategy; all of which require effort and hustle alongside the day job.
Finding your next job is likely to take a lot more self-promotion and hustle than it used to...Here’s what I mean.
Why executive job searching has changed
My background is in executive search. I helped companies find and land the best talent by researching the market, assessing candidates, packaging them, introducing them to clients, and handling objections after they left. You didn't see most of that work. You didn't need to.
Over the past few years, we’ve seen a shift in recruitment practices: more companies building in-house talent teams; and more roles advertised, even at senior levels. Search firms are brought in when the role is genuinely hard to fill, high-profile C-Suite or highly sensitive.
So if you're a senior leader looking for a role in the market today, in most cases, nobody is doing that work for you anymore.
You are now doing the heavy lifting as the headhunter, the candidate, and the negotiator, all at once.
Why clarity isn't enough to land a leadership role
This is where most conventional career advice stops short. People get coached on confidence, their story, and how to 'show up as their best self', and then they’re left with a polished, ATS-optimised CV and no idea how to sell themselves on screening calls and interviews.
Clarity is necessary, but it’s not enough.
How to build an executive job search strategy
Most senior leaders aren’t clear about how to scope out their options, and they lack insight into how their skills and experience could transfer or give them a distinct edge. So they end up relying on what’s advertised instead of taking a strategic approach.
That’s why I developed a Strategic Compass as a visual thinking tool. Clients usually arrive with only a vague idea of what they want to do next, often reacting to a previous situation or ill-fitting culture rather than following a solid plan.
The tool forces you to map out your options clearly and creatively. Then, once you’ve got it on paper, you can weigh those options against market conditions and what actually matters to you.
This puts you in control of your career, so you’re not scattergun-responding to job adverts and losing your grounding along the way.
Combine that with proper self-promotion interview coaching, and you walk away with genuine clarity and the confidence to back it.
But clarity and confidence get you to the start line. They don't run the race for you.
Job Search Hustle
Once you know your direction and can articulate your value, the work is still ahead of you.
Someone has to reach out to the right people. Someone has to follow up when there's silence. Someone has to handle the 'we've paused this role' conversation and keep going anyway. Someone has to turn a warm coffee chat into an actual opportunity. It used to be an executive recruiter or headhunter. Now it's you.
This looks a lot like the hustle everyone talks about when they're building a business. Except you're building a career and you're doing it alone, without a team, without a marketing budget, and probably still trying to process the fact that you're job hunting.
The three skills every senior executive needs
Every successful executive job search comes down to three things:
A clear strategic direction so you're not scattergunning applications at every vaguely relevant title.
The ability to promote and sell your own expertise with the confidence and precision a professional headhunter would use.
Sustained, targeted effort: outreach, follow-up, relationship-building, done consistently, not in bursts of panic.
Where I Come In
Executive search has taught me something career coaching alone often can't: how candidates are discussed after they leave the room, what objections clients raise, and what actually gets someone shortlisted.
If reading this feels familiar, the good news is that these skills can be learned. They're practical disciplines that can be developed with the right framework and guidance.
If you know your next role won’t come from simply applying online, book the Career Accelerator. Build the strategy, positioning, and execution you need to create opportunities and land your next role, rather than wait for them.
I built the Accelerator because I got tired of watching brilliant senior people either bypass the strategy stage or struggle with their pitch, lacking confidence in how to get in front of the right people. It’s twelve weeks of 1:1 support. It combines the Strategic Compass work, self-promotion coaching, and go-to-market efforts, including outreach, network activation, and objection handling (basically everything I used to do), now taught to you directly so you can move from preparation to action. If you need that support, join me on the Career Accelerator.
Alternatively, if you want to know exactly where you're strong and where you're exposed, book the Headhunter's Gut Check. One conversation, no fluff, straight assessment, and a clear next-step plan.
Tracy Short, former Head of Fashion & Luxury Brands at The MBS Group and founder of Tracy Short & Co, where she now helps senior executives navigate career transitions with insider intelligence gained on the other side of the table.
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