How to Talk to Your Employees About Their Careers


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What do your employees actually want out of their careers? What do they enjoy, excel at, aspire to, dream of? What skills are they lacking to actually achieve their long-term career goals, or do they even have career goals?

This article is designed to present a framework for considering career conversations, and offer a few ideas on techniques that can help you be supportive while talking honestly about an employee’s future career. As always, I’d love your feedback and suggestions, either over email or in the comments.

Why Bother Talking to Your Employees About Their Careers?

Having regular conversations about your team members’ career goals can have long-term, positive consequences for your relationships with your employees, employee retention, and job satisfaction.

Let’s start with the most basic, but perhaps least comfortable idea for many managers: your employees will probably leave you. Sooner or later, most of your employees will eventually find a different job. Some of them will move to a different role within the same organization, but many will leave your organization completely. A few will stick with you for years, and—rarely—others will stay for a lifetime.

And that’s OK. In fact, it’s totally expected. There are reasons to check in about career goals regardless of whether someone is going to be with you for one year or twenty.

For employees who will be transitioning in 0-5 years, career conversations can help you get the most out of the time you’ll have together. You can help them gain insight into their potential career opportunities, reflect back to them where you see their greatest potential, and offer them chances to improve the skills they’ll need as they head toward their ideal career. You’ll also benefit: employees that are gaining valuable experience and skills will have ample reason to stick around longer and, when they do decide to leave, it can be something discussed more openly and supportively, so you aren’t blindsided.

For longer term employees, career conversations can help ensure that they are regularly given new ways to sharpen and improve their skills, as well as transition in roles and responsibility in ways that make sense for both the employee and the organization. Together, you can craft a win-win situation, where they are gaining fulfillment from their careers over many years and the organization continues to benefit from their continued enthusiastic engagement.

Career conversations aren’t just for your strongest employees. Honest career conversations can help employees who are under-performing understand what opportunities are and aren’t available within your organization, and can help them learn what skills and insight they need to develop for the future, whether they stay at your organization or go elsewhere.

How to Frame a Career Conversation

I think good career conversations have three characteristics:

  1. Entered into without expectations. We are no longer living in an era where people climb a single career ladder within an organization. Many employees make lateral leaps in their career, or “step down” in order to maximize flexibility or satisfaction in their jobs. When setting up a conversation with an employee, let go of preconceived ideas about what “growth” must look like. It may not mean a new title, a bigger office, or more direct reports. Does your employee want to increase her interactions with the public? Does your employee want to pick up a new skill set that the organization needs and wants? Were certain projects especially fulfilling to her? Or maybe she’s serving as a caretaker for a relative and career “growth” right now means transitioning to work that allows her a flexible work schedule. Try to step into a career conversation without baggage about what career advancement looks like, and try to notice if you tend to think that “success” for someone else needs to mimic how you perceive success.
  2. Iterative. Some employees know exactly what they want their future to be and exactly how they want to get there. But for the rest of us, the future is a roiling mass of possibilities, uncertainties, and fears. The ideal future today may look wildly different from what it looked like two years ago. Career conversations can be iterative in a few ways. First, because your employee and you slowly gain more insight into what career path is truly the best match for her skills and passions. Second, because career paths can change. This can happen because of a serious life event—such as a health scare or change in family situation—or just because time and experience has impacted an employee’s goals and job satisfaction. It’s totally normal for someone to feel different about their career at 30 than they do at 55. Rather than lock an employee into a single path for “success,” offer flexibility for the career plan to change over months and years. Don’t be surprised if it evolves in ways neither of you were expecting.
  3. Collaborative.  You and your employee aren’t trying to simply come up with the best career path for her as an individual. Rather, you’re trying to find that perfect mix of what she wants to do, what the organization needs, and what she is good at. She may have more insight into the first, but as a manager you’ll have a lot of insight into the second and third. Reflect honestly where you see her skills and what brings the most value to the organization. As you continue to develop your relationship, search for ways that you can construct win-win scenarios, where your employee taps into her passion and skillset in a way that benefits the organization. Be willing to be active and engaged in helping show the employee ways she can contribute to the organization’s success.

Practical Career Conversations

Ready to actually try a career conversation? The first step is letting your employee know you’re up for it. Many people make the annual review process a place to check in on career development. I think there’s no harm in that as long as both you and your employee know that’s the plan. You might also decide you want to carve out time during your one-to-one meetings, or set up a dedicated meeting just to talk about career growth. Regardless of how or where you structure it, I’d suggest you tell your employee it’s coming.

When you’re scheduling the conversation, you might say something like, “I’d love to set up a time to talk about your career more generally. I know we can get stuck in focusing on day-to-day tasks, but I’d like to step back and talk about the future of your career. How about two weeks from now?”

That may feel very stilted to you, or not the kind of language you normally use with your team. Adapt the language to find something that does work. The key factors are that you signal that this will be a conversation at which you talk about their careers specifically and that you schedule it a little bit out. That ensures your employees have time to think about it, and hopefully they’ll be able to step back from their day-to-day work and think more generally about their career as a whole.

Once it’s been scheduled, I’d suggest that you as the manager take the lead in the conversation. I suggest you let them know why you’re having the conversation and what outcomes you are hoping to achieve.

Examples for why you’re having the conversation:

  • “I want to talk about your long term career goals so we can make sure you’re developing the skills you need over the next few years to achieve those goals.”
  • “I realize we’re always heads-down focused on the task at hand. I want to talk about your career more generally so that we can make sure you’re heading down a path that you find fulfilling that also helps the organization.”
  • “I really value you as an employee, and I want to make sure you’re fulfilled. I want to hear if you have thoughts about your career over the next few years, and talk about where I see you shine, so that we can keep an eye toward the future.”

What outcomes you expect:

  • “I don’t expect to figure everything out today. But I want you to know that I’m open to these conversations. I value your work, and I want you to start thinking about where you’d like your career to head.”
  • “This isn’t going to be a conversation where you come up with a finalized plan and present it and then I say yes or no. I want to collaborate on this, and give you a chance to think things through openly. Maybe you have a firm idea of where you’d like to be in 10 years, maybe not. Either way, I want to be able to start talking about it.”
  • “I know that people define success in many different ways, and I don’t want to presume what career growth looks like for you. I want to hear what matters most to you in your career.”
  • “By the end of this conversation, I’d like a better understanding of what work you find most fulfilling. And I’d like you to know where I am seeing a lot of potential for your growth.”

During the conversation, you can ask guiding questions to try to solicit information from the employee on what she finds most fulfilling and engaging, as well as offer your reflections on where you see the greatest potential for growth. Some guiding questions could be:

  • What projects did you most enjoy in the last year or two? Why?
  • You took on a new set of responsibilities with X project. Is that something you’d like to do more of in the coming years?
  • Are you enjoying collaborative work or have you been enjoying the solo projects?
  • What aspects of your work are you finding especially uninspiring? Why?
  • Have you seen other folks with career paths you find especially inspiring? What factors do you notice in those?
  • What are you looking for in your career?
  • What would you hope to change about your career in the coming years?
  • What skills do you want to develop in the coming years?

I also think it’s important that you reflect back to the employee the skills and experiences that are most beneficial to the organization. You might say things like:

  • I’ve been extremely impressed by X, and I was wondering if you had interest in doing more of that.
  • Your experience in X is a fantastic asset to the organization.
  • I appreciate X in your work.
  • You are very skilled at X.

When Passion and Skills Don’t Align

If you have enough of these conversations, you’ll notice that what an employee most wants to do doesn’t always align with what the organization needs or even with what she’s good at.

At a recent retreat, I heard other nonprofit leaders discussing the problem of “the firefighter who wants to be a ballerina.” I think of this as a metaphor for the nonprofit employee who is skilled at what she does now and fulfills a vital need for the organization, but her career goals are pointed at something else. Maybe she’s great at handling a crisis and keeping the organization afloat during even the most difficult of times, but during a career conversation she confesses that she wants to step away from the fray and focus on long-term projects. Or perhaps she’s part of your support team, but longs to move into programmatic work. Unfortunately, this firefighter has no experience being a ballerina. Even if you could shift her to a different role, the learning curve would be painfully high, and you’d have to replace her with someone who is less talented at firefighting.

Some people avoid having career conversations because they’re afraid this exact situation will arise, and their best people will ask to shift to roles where they aren’t qualified and aren’t helpful to the organization.

If you find yourself in this situation, know that you aren’t alone. Many managers have been where you are. Here are a few concepts you might consider if you find yourself in this spot. First, consider whether you can appreciate that at least this conversation is happening openly and with trust, instead of having your best firefighters secretly applying to ballerina roles at other organizations after hours. Second, if someone is expressing frustration with their current firefighter role, are there changes that can be made to make them feel more fulfilled in it? Third, are there small aspects of the ballerina role that could be integrated into her current firefighter work, so that she can continue firefighting most of the time but spend a percentage of her work on the ballerina tasks? (Though be careful about this one: you don’t want to end up with someone who works 20% more to try to add in extra ballerina hours while still holding down a full-time firefighter job!)

Fourth, remember that career goals change. Someone coming to you with dreams of being a ballerina today might find they’re less interested in that work in six months or two years, especially if they had a chance to dip a toe into it and found the waters less glamorous than they expected. So even if your very best people are in the firefighter/ballerina dilemma, remember to take a few deep breaths, be a little flexible, and give it some time. Maybe they’ll eventually leave you to pursue that ballerina life full time, but there’s a good chance that if they feel supported, heard, and appreciated and can integrate a touch of ballerina in their current roles, they may remember what drew them to firefighting in the first place.

Finally, remember that the worst case isn’t that bad. If your very best firefighters are hell-bent on becoming ballerinas, and they are terrible ballerinas, and your organization doesn’t need ballerinas, it’s actually OK. You can still acknowledge their interests and your limitations clearly and empathetically. That acknowledgement might sound something like: “I hear you’d like to work on more long term projects, which you have less experience with. Right now, you are doing fantastic work on the quick-response projects, and I want to keep you there for as long as you’re willing. I’m not sure that there’s ever going to be a full time role for you in the long-term project department. But I’m glad we’ve started discussing it. I’ll keep my eyes open over the next year for opportunities to help you build those skills while keeping you in your current department. I’d like you to think about it more, and let’s keep this discussion going. I’d like you to find fulfillment in your career, even if that might mean you go to another organization one day.”

Your firefighters may not want to hear that, but at least they’ll know where they stand. Even better, you’ll have created a relationship built on honesty.

Uncertainty is Fine

If you start chatting with your employees about their careers, don’t be surprised if a few of them are a bit mystified at the idea of a career trajectory. You may find the conversation stilted, uncertain, or even a bit suspicious. Such a conversation can also be successful. You’ll still have an opportunity to flag your investment in your employee as well as talk to her about what skills she’s bringing to the organization. Knowing that your employee is uncertain about her career goals is also useful for you; it can prevent you from making unnecessary assumptions about where she’d like her career to head.

Try to take the pressure off and acknowledge that uncertainty is fine. You might try starting smaller: what are a few tasks or projects she enjoys? What skills does she want to develop? It doesn’t necessarily have to lead anywhere right away.

Don’t Drop the Conversation

If you’ve had an initial conversation with an employee and established a good dialogue, then try to keep it going. Schedule a time later in the year to discuss it more. Look for key take aways from your early career conversations. Were there skills your employees hoped to develop? Projects that would give them valuable experiences? Remember to keep that career discussion in the back of your mind and remember it when you prioritize projects, responsibilities and opportunities. When you schedule your next check in, talk about those choices.

Want to discuss this more? I’d love to hear about your career conversations. Please shoot me an email and let’s start a discussion.


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