Why All Businesses Should Help Employees with Career Planning

It’s easy to think career planning is something employees should do on their own and isn’t the domain of HR, especially for smaller companies, but doing so leaves you out of a critical conversation with your most important resource.

June 17, 2025
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2
min read

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Most companies don’t really support employees with their career planning. Some of the biggest ones, typically 10,000 people or more, do. That would make sense since they have decades of rungs on the career ladder all within the company. Startups and small companies rarely do, not only because there aren’t many rungs, but because they often don’t have the resources. (For any startups, the goal is just trying to stay in business another twelve months, let alone think about job titles further down the road.) Even companies that do annual reviews and/or provide some training and development for employees often don’t help employees map out a career plan. They very much should, and failure to do so could be costing them significantly; in 2019 Gallup estimated the cost of replacing a salaried worker is one-half to two times the employee’s annual salary.

Your strongest employees are the ones who are self-directed. This applies not just to their work, but to their careers. They don't simply hope they'll grow in their careers; they plan their growth. If you're not part of the planning conversation, then your company may not be part of their future plans. It’s that simple. So not only will you lose employees but not having this discussion, they’re likely to be your best employees.

Having well defined career paths at your organization allows you to talk to your employees and provide clarity on how your organization can help them on their journey. But even if you're at a smaller organization or startup that doesn't have well defined roles or clarity on org structure in a few years, it's important to have these discussions. Job titles matter, but more important are responsibilities and challenges. Talk to your employees about where they want to be in a few years, even if you don't have higher titles that can be offered, consider expanding their role in the future so they know that they can continue to grow instead of having to find a new job.

If they can't see that path for growth (with or without titles) with you, they'll look for it elsewhere. At a small company that day may come, and that’s just the reality of the labor market. What’s not ok to be caught off guard by it. In my article Let’s Be Honest, This Job Isn’t Going to Last Forever I cover why having frank conversations about a career path that may take someone away from the company is good for the company and the employee. If there will be a time in the future where you can’t support the employee’s career path, it’s better for everyone that the timing is discussed and planned, so a smooth transition can be made. The alternative is just for the employee to quit and his or her manager now has to scramble to deal with an unexpected problem.

This doesn’t have to be a long conversation, and it’s certainly not a costly one. When doing an annual review (or quarterly or whatever schedule you use), take a few minutes to discuss the employee’s longer-term career plans. This is key not only for the insights discussed here, but because ideally the development plan for the employee should be one seen not only to help the employee in her role at the company, but also to help her long-term in her career. If you’re not sure how to start, ask the employee to begin by thinking about these career planning questions: Career plan questions from The Career Toolkit.

This simple conversation can help both sides; the employee gets support and guidance, and the company has visibility into the thinking of the employee. The alternative is more uncertainty, and cost, for both the employee and the company.

By
Mark A. Herschberg
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The Career Toolkit shows you how to design and execute your personal plan to achieve the career you deserve.