The year Ben learned to stop forcing his next move
When experienced leaders feel stuck in a job search, the issue is often not effort but misalignment. Clarity on where and how you create value changes how you show up, making networking, interviews and negotiation feel natural instead of forced.
Ben came to a point many experienced leaders reach quietly.
He wasn’t struggling because he lacked ambition or results. He had built strong teams, delivered meaningful work and knew he wanted to return to a high growth tech company. What surprised him was how stuck he felt despite all of that experience.
The harder he pushed himself to network and “sell” his background, the more misaligned the process felt. Asking for conversations felt uncomfortable. Talking about compensation felt even worse. He worried that advocating for himself would come across as transactional or inauthentic.
So we didn’t start with tactics.
We started with reflection.
Clarity before strategy
Before Ben spoke to a new contact, we spent time clarifying the environments where his work creates the most value. Not just company names, but moments in specific initiatives. The kinds of problems that energized him. The leadership contexts where he did his best work.
That clarity changed how he showed up.
Instead of trying to impress people with a long list of accomplishments, Ben began to speak clearly about the problems he’s solved and the value he brings when organizations are scaling quickly. Networking stopped being about asking for something and became about exchanging insight.
When alignment changes the process
Once that mindset shift was in place, he was off and running.
His conversations became more intentional. He activated his powerful network, skillfully guided the conversations and assessed whether an opportunity was truly aligned before investing time and energy. Even negotiation felt different because it was grounded in shared value rather than fear of asking for too much.
That approach led him to HubSpot, one of the companies he had identified early on as a strong fit.
He secured interviews through his network, joined the team in a job aligned with his strengths and increased his compensation by over 40%.
A year and a half later, he was promoted to lead a team in a key area of the business.
Why forcing your job search doesn’t work
What stands out about Ben’s story isn’t just the outcome. It’s how much lighter the process felt once alignment came first.
The effort didn’t disappear, but it stopped feeling forced.
As you think about your own career, consider this:
Where are you pushing harder than necessary because the path itself isn’t aligned with who you are or how you do your best work?
