Quick note before we get into this week’s newsletter: if you want a more structured way to strengthen your coaching practice, my Confident Career Coach System course walks you through the tools, frameworks, and skills I use with coaches. You’ll also earn 10 Continuing Education Units (CEUs) when you complete the course.
I’ve spent years teaching people about careers, job searches, and hiring.
And lately, I’ve had one of those humbling experiences where you realize that knowing something and actually doing it are two very different things.
I’m hiring for my own business right now.
I know I need support, actually in several areas, not just one.
And that’s the problem.
I’ve found it surprisingly difficult to get really specific about the person I need, what I want them to own, and which needs matter most.
There are projects I could hand off and parts of the business where I’m slowing things down. But turning all of that into one clear role? That’s harder than it looks.
I’ve caught myself doing something I’ve seen employers do for years.
Trying to put several different people into one job.
You know those job descriptions where you get halfway through and think, “Wait. Are they hiring one person or four?”
I have a lot more empathy for those now.
Because when you’re sitting on the employer side, you realize how easily it happens.
The organization has 10 different needs, but there’s budget for one hire.
Everything feels important, so everything ends up in the job description.
I think there’s an important lesson in that for us as career coaches.
A messy job description may tell you something about what’s happening inside the organization.
Maybe they’re growing quickly. Maybe priorities keep changing. Maybe the team is stretched. Maybe leadership itself hasn’t fully decided which problem this person needs to solve first.
That doesn’t make a chaotic hiring process a good one, but it gives us a different way to coach clients through it.
When a client brings you a job description that feels all over the place, we don’t have to help them prove that they can somehow do every single thing listed.
We can help them get curious.
What does this company actually need?
Where is the pressure?
Which responsibilities are truly central to the role?
And then, instead of saving five generic interview questions from Google or asking AI to generate something that sounds polished, they can use the interview to find out.
They might ask:
“What are the 2 or 3 things you most need this person to solve in the first 6 months?”
Or:
“Of everything listed in the job description, where is the team feeling the most pressure right now?”
Or even:
“If I started tomorrow, what would you most want taken off your plate?”
Those questions help your client understand the role, but they can do something else too.
They can help the recruiter or hiring manager clarify what they actually need.
That’s where the candidate starts demonstrating value before they even have the job.
They’re listening.
They’re identifying the real problem.
They’re helping someone prioritize.
They’re showing how they think.
That stands out far more than another perfectly polished question about company culture.
I still believe employers have a responsibility to create thoughtful, realistic job descriptions.
But going through hiring myself has made me realize that sometimes the confusion starts long before the job ever gets posted.
And if we can help our clients see that, they can do more than decode a messy job description.
They can use it to have a much better conversation.
Heather
The Coach for Career Coaches