When Your Team Has No Clue What They Want (And How to Help Them Figure It Out)

Let me paint you a picture that's probably all too familiar:

You're sitting across from someone on your team—maybe during a performance review, maybe over coffee—and you ask that well-intentioned question: "So, tell me about your career goals."

And then? Crickets. Or worse, a deer-in-headlights stare that tells you everything you need to know.

Maybe they mumble something about "not really knowing" what their goals should be. Or they confide that they're not even sure if there are opportunities to grow at your firm. And suddenly, you're left wondering: How on earth do I help this person when they can't even articulate what they want?

Here's the Thing: You're Not Alone

Career dissatisfaction isn't just a "your firm" problem—it's an industry-wide epidemic. And honestly? It's getting worse.

Get this: A 2015 CEB employee survey found that 70% of employees (across multiple industries) reported being dissatisfied with career opportunities at their company. Seventy percent! That's not a small pocket of disgruntled folks—that's the majority of your team potentially feeling stuck, uninspired, or just plain lost.

And here's the kicker: Career development is one of the biggest drivers of engagement and retention. So when your people feel like they're going nowhere, they're probably already mentally halfway out the door.

But wait, there's more (and it's not good news). At the same time that employees are feeling stuck, 75% of organizations said they expected to face a shortage of necessary skills and knowledge. So we've got a perfect storm: people who want to grow but don't know how, and companies desperately needing skilled talent but not knowing how to develop it internally.

Why This Matters in Accounting and Bookkeeping

In our world—accounting, bookkeeping, tax prep—this problem hits differently. We're not just dealing with generic "career ladder" issues. We're talking about:

• Bookkeepers who don't see a path beyond data entry

• Team members who don't realize they could become trusted advisors

• Talented people who leave because they think "bookkeeping" is all there is

• Firms struggling to retain good people because growth paths aren't clear

And here's what I've learned after years of working with bookkeepers and accounting professionals: Most people aren't lacking ambition—they're lacking clarity.

So What Do We Do About It?

First, let's acknowledge that this isn't a quick fix. You can't just hand someone a career ladder poster and call it a day. Real career development requires intentionality, regular conversations, and a willingness to meet people where they are.

Here are some practical ways to start:

1. Make Career Conversations Regular, Not Annual

Don't wait for the annual review to ask about goals. Make it part of your regular check-ins. Even a simple "What are you enjoying most right now?" or "What would you like to learn next?" can open doors.

2. Help Them See What's Possible

Sometimes people don't have goals because they literally don't know what options exist. Share stories of others in your firm or industry who've grown. Introduce them to advisory services, process improvement, team leadership, or specialized niches they might not have considered.

3. Create Micro-Opportunities

Not everyone needs a promotion to feel growth. Can they lead a client presentation? Mentor a newer team member? Implement a new process? These small wins build confidence and clarity.

4. Be Honest About What You Can (and Can't) Offer

If your firm genuinely doesn't have room for upward movement right now, say so—but then get creative. Can you support lateral growth? Skill development? Flexible work arrangements? Sometimes honesty about limitations, paired with genuine support, builds more trust than empty promises.

5. Invest in Their Development (Even If It Scares You)

Yes, there's always that fear: "What if I train them and they leave?" But here's the scarier question: "What if I don't train them and they stay?" Investing in your team's growth—whether through courses, certifications, conferences, or mentorship—pays dividends in engagement, loyalty, and capability.

The Bottom Line

When someone on your team gives you that blank stare after you ask about their career goals, resist the urge to move on quickly or assume they're not ambitious. Instead, see it as an opportunity—a chance to help them discover possibilities they didn't know existed.

Because here's what I truly believe: Every person on your team has potential. Sometimes they just need someone to help them see it.

And when you create a culture where growth is expected, supported, and celebrated? You don't just retain good people—you develop great ones.

So the next time you get that blank stare, don't panic. Lean in. Ask better questions. Share possibilities. And watch what happens when people start to believe that their career—and their future—actually matters to you.

Because it does. And they should know it.

Until next time,