The Blank Stare: Why Career Conversations Are Failing (And What We're Doing About It)

You know how sometimes you ask what feels like a simple question, and the response tells you everything you need to know about a much bigger problem?

"Tell me about your career goals."

I've asked this question dozens of times over the years — to team members, to colleagues I'm mentoring, to people in our Bootcamp program. And you know what I get back more often than I'd like to admit? A blank stare. Sometimes followed by an uncomfortable laugh or a hesitant "I'm not really sure."

It's not because people don't care about their futures. It's because somewhere along the way, we've failed to create environments where career growth feels accessible, visible, and achievable.

The Career Dissatisfaction Crisis Nobody's Talking About

Here's a stat that stopped me in my tracks: according to CEB's 2015 employee survey, 70% of employees across industries reported being dissatisfied with career opportunities at their company. Seventy percent. That's not a small pocket of disengagement — that's a systemic problem.

And here's the kicker: career development is one of the biggest drivers of engagement and retention. When people can't see a path forward, they start looking for the exit.

At the same time, 75% of organizations said they expected to face a shortage of necessary skills and knowledge. So we have employees who want to grow, and companies that desperately need them to grow, but somehow the two aren't connecting.

Something's broken.

Why the Blank Stare Happens

When someone gives you that blank stare after you ask about their career goals, it's usually not about lack of ambition. It's about lack of clarity. They might be thinking:

• What opportunities even exist here?

• Am I allowed to want more than what I'm doing now?

• What if my goals don't fit into a neat box?

• Will I be judged for wanting something different?

And honestly? Those are fair questions. Too many workplaces treat career development as a once-a-year checkbox during performance reviews rather than an ongoing conversation. We expect people to have fully formed career plans without giving them the tools, visibility, or support to create them.

Doing Things Differently

At Cloud Business Services, we've decided to approach this differently. Career development isn't a separate initiative — it's woven into how we operate.

Here's what that looks like in practice:

We talk about growth regularly, not annually. Career conversations happen during regular check-ins, not just during formal reviews. It's normalized, not intimidating.

We invest in professional development. Real investment — not just lip service. We budget for training, certifications, and programs that help our team members grow in meaningful ways.

We create visibility. Our team knows what skills matter, what growth looks like, and how their development ties into our business goals. We've seen team members grow into leadership roles over the years because we've been intentional about creating those paths.

We make space for different kinds of growth. Not everyone wants to climb a traditional ladder. Some people want to deepen their expertise. Others want to pivot. We support both.

What You Can Do as a Leader

If you're getting blank stares when you ask about career goals, here's where to start:

1. Make career conversations regular and low-stakes. Don't wait for the annual review. Ask about growth during one-on-ones. Make it normal.

2. Share what's possible. People can't aspire to what they can't see. Talk about career paths, skills that matter, and examples of growth within your organization.

3. Listen without judgment. Someone might want to grow in a direction you didn't expect. That's okay. Your job is to support, not dictate.

4. Invest in development. Training, certifications, mentorship, conferences — these aren't nice-to-haves. They're how you show people you're serious about their growth.

5. Be honest about opportunities. If there's limited room for advancement, say so. But also get creative. Growth doesn't always mean promotion. It can mean new responsibilities, cross-training, or leadership opportunities.

The Bottom Line

Career dissatisfaction isn't just an HR problem — it's a business problem. When 70% of employees feel stuck, you're not just risking turnover. You're losing engagement, innovation, and momentum.

But here's the good news: this is fixable. It starts with asking the right questions, creating the right environment, and being willing to do things differently.

So the next time you ask someone about their career goals, pay attention to their response. If you're getting blank stares, that's not a reflection on them. It's feedback about the environment you've created — and an opportunity to do better.

Until Next Time,