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3 career development questions to stop asking employees

We need better questions about employees' career development if we want to help them grow in this modern work environment. Here are 3 questions for leaders to change.

6 min read


3 career development questions to stop asking employees


This time of transition between the restrictions imposed by the global pandemic and a return to business as usual (or as usual as it’s ever going to be) has been a renaissance for many organizations. It’s been an opportunity to reimagine core value propositions. To innovate. To leverage technology in new ways that serve customers better. To rethink how work gets done.

This time of transition and today’s tighter labor market have also inspired many organizations to reconceive the employee experience — everything from where and when work gets done to a range of innovative benefits to meet the needs of the current talent pool.

So this is an ideal time to also consider making the changes required to one of the most fundamental and intimate dimensions of the employee/employer relationship: career development. For many organizations, career development has been frozen in time – a time long past when:

  • Cradle-to-grave employment was a common experience. Employees could be hired into and get their gold retirement watch from the same organization decades later.
  • “Up or out” was a common refrain, forcing those who were perfectly happy (and productive) in their current roles to take on positions that they were less interested in or leave the organization altogether.
  • Organizations were committed to systematizing development with a focus on forms, processes and 100% compliance.

As we rationalize, update and enhance other dimensions of the business and the employee experience, let’s do the same with career development.

Fortunately, bringing career development into the 21st century may be easier than one might think. Certainly, organizationwide changes would have an enormous effect upon how career development operates. But leaders have tremendous influence as well. How leaders talk about it sets the stage, establishes employee expectations and determines whether career development remains stuck in a limited past or becomes part of a possibility-filled future.

And in many cases, it comes down to what leaders ask. Changing the questions can change an employees’ understanding of and relationship with development.

Here are the three most problematic probes leaders tend to ask — old-fashioned questions that reinforce old-fashioned expectations. Consider the challenges associated with each, as well as alternative questions designed to launch a more contemporary, productive, expansive and satisfying career conversation.

1. Do you see a path for career advancement here?

There are two problems with this question. First, career paths may not be agile enough to meet the changing needs of today’s workforce and marketplace. Customer expectations are morphing fast. Innovation is spawning unexpected opportunities. The jobs of the future will be different from the jobs of today. As a result, blindly following career pathways could lead to dead ends rather than opportunities.

And second, advancement is just a drop in the ocean of what’s possible for employees who are looking for development. This narrow definition invites dissatisfaction because, in most organizations, promotions and moves are limited. De-emphasizing the illusive and amorphous concept of advancement allows you to focus on what is more plentiful and well within the sphere of influence of leaders and employees: meaningful challenges and development experiences.

So instead, begin asking: Can you access the challenges and experiences required for your continued development and growth? This opens the door to exploring stretch assignments, opportunities for greater visibility, strategic networking and more. It allows leaders and employees to jointly find dynamic possibilities beyond static and dated pathways of the past.

2. Do you have access to the training you need to develop your career?

This is another way leaders simultaneously set limited and unreasonable expectations with employees — expectations that lead to dissatisfaction. Development happens day in and day out through countless formal (and more frequently) informal ways.

Training, while important, is a relatively small element of the ecosystem of activities to drive development. Questions like this focus on areas over which leaders may have little control rather than those that are squarely within their spheres of influence.

So instead, begin asking: Do you have opportunities to learn and grow on a regular basis – through others or through experiences, allowing you to develop in ways that are meaningful to you?

Tap the full range of opportunities to develop informally — organic activities within the workflow, peers, coaching and more. Set the expectation that learning isn’t dispensed by the organization, rather sought out by the employee.

3. Do you have a documented development plan with concrete steps you need to take to reach your career goal within the next year?

Given the speed of business and the speed of change within business, annual plans are quickly becoming a thing of the past. Organizations and individuals must be more agile and nimble. This means shorter windows, incremental goals, development sprints and ongoing dialogue that takes advantage of ever-evolving opportunities in the moment.

So instead, begin asking: Do you routinely engage in discussions with others (leaders, peers, etc.) about ways to learn, stretch yourself, build new skills and/or grow in your current role?

Help employees understand that career development is a team sport versus an exclusive relationship with you, the leader. Encourage them to dialogue with and learn from others. And while your organization may require that a formal plan be tucked away somewhere, make sure that you and the employee are routinely talking about how their interests are evolving, how skill gaps are showing up and the learning that’s most necessary and appetizing now.

Peter McWilliams wrote: “Our thoughts create our reality — where we put our focus is the direction we tend to go.” And I’d suggest that the questions leaders ask can also change thoughts. Imagine the power we have through these simple alternate questions to create a new and more satisfying career development reality for employees.


Employee engagement will be key in the months to come – to retain the employees you have and to build an employment brand that will attract top talent. And career development is a primary driver to make both happen. If you’re looking for actionable strategies for growing and retaining employees, download our latest complimentary e-guide, “Looking to Improve Engagement? Look No Further than Career Development.”

Julie Winkle Giulioni is a champion of growth and development in the workplace, helping leaders and organizations optimize the potential of their people. Named one of Inc. Magazine’s top 100 leadership speakers, she’s the co-author of the international bestseller, “Help Them Grow or Watch Them Go: Career Conversations Organizations Need and Employees Want,” and a forthcoming book that ATD Press will publish in spring 2021. Learn more about her work at

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