Coaching

Career Strategy & Job Search Coaching

James Tomasson

James Tomasson

Career strategist | 2,000+ coaching hours | 250+ coffee chats

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Career transitions get difficult when you are no longer choosing between obvious options.

You may have 10, 15, or 20 years of experience, but still be unsure how to explain what you do, which roles genuinely fit, whether you need to change direction, or why your job search is producing so little traction.

I help experienced professionals work through those questions and build a more deliberate career strategy.

Across more than 2,000 hours of one-to-one career coaching, I have helped professionals clarify career direction, evaluate possible paths, improve resumes and positioning, prepare for interviews, build networking strategies, and navigate difficult labour markets.

My approach is practical and diagnostic. We figure out what is actually getting in the way, then work on that problem rather than following a generic coaching program.

My services are useful if you are...

  • considering a career change but unsure which direction makes sense

  • applying repeatedly without getting enough interviews

  • struggling to explain your transferable value

  • trying to move into a new function or industry

  • unsure how to use networking effectively in your search

  • deciding between several plausible career paths

  • returning to the market after a layoff, career break, or long period in one organization

  • looking for an experienced second opinion on an important career decision

What you will learn...

  • Job-search diagnostics

  • Networking and informational interviewing

  • Resume and LinkedIn positioning

  • Target-company and hidden-job-market strategy

  • Interview preparation

  • Career decision-making

  • Using AI intelligently in your job search

  • Professional positioning and your career story

My approach is...

After 2,000 hours of career coaching, I can confidently say that the most common issue clients face is that they don't really know what they want.

People often come to me asking questions like, “Should I apply for this job?”, “Should I change careers?”, or “What should I do next?” Usually, I am less interested in giving them an immediate answer than in understanding what is sitting underneath that question. What are they trying to get more of, or less of? What assumptions are they making? What do we actually know, and what are we guessing? And, most importantly, I like to ask them why they want that particular thing.

My approach to career development ends up being pretty simple: I help clients figure out what problem they are actually trying to solve before we start throwing solutions at it.

I also don't think people can think their way into perfect career clarity. At some point, you have to go out and collect evidence. That means talking to people, looking closely at roles and organizations, trying different ways of positioning yourself, applying for things and seeing what happens. I tend to think of career development as a series of hypotheses and experiments. You develop a reasonable theory about where you might fit, test it against the real world, learn something, and adjust.

My coaching style is probably a mix of coach, teacher and consultant. I ask a lot of questions, but I'm not completely hands-off. If I think someone is making an assumption that doesn't hold up, I'll challenge it. If there is a framework or tool that will make the problem easier to understand, I'll teach it. And if someone needs to stop endlessly polishing their resume and actually go talk to ten people, I'll probably tell them that too.

Networking plays a big role in how I work because I think conversations are one of the best forms of career research available. They tell you things job postings and websites often don't: how people actually got into the work, what employers care about, what the culture is like, what skills really matter and where the opportunities might be.

I'm not really interested in telling people what they should become. I am, however, much more interested in helping them learn how to investigate their own careers properly, make better decisions with incomplete information and become less dependent on somebody else (i.e. spouse, parent, friend, co-worker) giving them the answer.

Contact

1:1 coaching for career transitions, job-search strategy, networking, positioning, and difficult career decisions.

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