“It’s been months. I’ve updated my LinkedIn. I’ve applied to dozens of jobs. But I’m still not getting any calls.”
There were tears in her eyes.
Celeste is a seasoned leader who was burned by a toxic boss in her last job. She had excellent experience in operations, commercialization, and sales, but her confidence didn’t match it.
I’ve built multiple teams. One look at her resume told me why.
Celeste doesn’t fit the mold of what people traditionally seek.
She’s a square peg trying to fit into a round-hole market.
The traditional path is the easy path… for recruiters
Senior leaders, even if you’ve built multiple teams, forget that in the search process, the recruiter is just trying to complete a task in the fastest, most frictionless way.
It’s why they look for candidates where the story is obvious and clear. There is a clear progression. Each role should seamlessly lead to the next and the next. In each job, the person grows their scope, their title, and their compensation.
That’s the easiest story to tell. It’s the easiest story to sell.
But most leaders don’t fit that mold.
I’ve worked with many successful leaders who took the path that doesn’t tie neatly into a bow:
Alisa stayed “too long” in one company.
David moved up several levels only to move back down again.
Others, like me, jumped through multiple industries and functions. I started in investment banking, moved into technology and media, and then e-commerce and finally social impact technology.
None of them had the perfect path. Yet all of these leaders found a fulfilling next step.
Help recruiters tell your story
Celeste could do the same. Her mixture of operational and revenue-generating experience was valuable, but she needed to connect the dots and tell a story.
Instead of defaulting to the titles she was given, she needed to translate her roles into a progression and a set of skills and impact that a recruiter could understand.
“Chief Evangelist” became Vice President, Go-to-Market.
“Director of Innovation” became Director, Product.
We revised her titles not to inflate or misrepresent them, but to make them searchable. As my friend and executive recruiter, Kristof Schoenaerts, guides: if you aren’t using the same language as the database, no one can find you.
You aren’t making up a title; you’re taking your custom title and matching it to the industry standard. And don’t worry, doing this doesn’t take away what makes you unique. It’s helping more people find your uniqueness. And in case it isn’t clear, being undiscoverable isn’t integrity, it’s just staying hidden.
For each role, we described her responsibilities and authority to clarify the progression. It wasn’t always growth, but at each step, we showed how she kept adding to her skill set and taking on high-impact roles. We also clarified all of her transitions. She could describe the why and how for each one with specificity and succinctness.
Most importantly, she regained her confidence. By creating a narrative that made more sense to others, she had created a narrative that made more sense to her.
Where your story actually gets told
When Celeste came to me, she was exhausted.
She was a rule follower who had dotted all her i’s and crossed all her t’s to climb in her career. She had followed the steps she had used in the past, over 7 years ago for her last job.
Update her resume. Call a few friends and mentors. Apply to roles. Reach out to recruiters. Wait for calls.
It wasn’t working.
No one had told Celeste, and she didn’t know to ask, that her search process needed to change. That as a senior leader, and as someone whose career path didn’t fit the standard round hole, the classic application path wasn’t going to work.
She knew that networking mattered, but Celeste thought that calling a few friends and mentors was networking.
I’ve hired dozens of executives.
I can count on one hand how many came through the application portal.
When I told her that only networking would maximize her opportunities and increase how often they surfaced, her eyes widened. She took a deep breath.
As a sandwich caregiver, Celeste cared for her father and her children. Her schedule wasn’t predictable, and the work was emotional. But she couldn’t delay her search any longer. She had bills to pay.
Instead of increasing the pressure, we created a process that allowed her to pace herself. We set outreach targets that matched her schedule and created templates to make outreach less stressful.
The hardest part for her? The conversations.
Conversations required preparation, scheduling, real energy, even the virtual ones. The in-person ones were even more taxing. But once the calls and coffees started getting scheduled, Celeste realized something.
The part that had made the conversations difficult — worrying if she had a career that would resonate — wasn’t feeling as hard. The narrative work we had done earlier had helped her go into the conversations with a steadiness that she had lacked in earlier settings.
And once she realized that the conversations were not going to drain her, any remaining resistance she felt about networking faded.
Take action
Celeste is at the tail end of her search, and while she isn’t without stress, she no longer dreads the process, and often enjoys her networking conversations.
Borrow the playbook we created for her. Here are the steps in brief:
Write one sentence per role: A title that’s searchable on LinkedIn. What you were handed. What you changed.
Develop your transition stories. Why did you leave? What drew you to the new role? Naming what matters. If you have a long-tenure stint, explain why you stayed.
Say it out loud to one person you trust. Watch where they get confused. Pay attention to when you felt unsteady. Those are the parts to work on.
The organizations looking for you — and there are many, trust me — can’t find you unless you make yourself discoverable and with a story they can digest.
The steps above aren’t just about finding a job; they are about how you make sense of your past career choices and set yourself up for the next set.
You already did the work. This is about letting people see it.
May you lead without limits,
Kathy
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Such an important thing to remember. I’ve spend my professional life jumping across industries (neuroscience, digital, AI (back in 2015!), pet health, social impact…) When I dedicated some time to crystalise the connecting tissue across all those roles and pull out my superpowers my conversations about who I am and where and how I best add value became a lot easier to navigate. Great piece @Kathy Wu Brady