3 Questions You Need to Ask for Deeper Career Conversations

Lack of career development is the #1 reason people leave a job, and meaningful work is the #1 reason they stay. But most managers don’t know how to talk about what makes work meaningful to each individual. Without getting to know each person’s strengths, interests, values, and dreams for the future, managers will find it challenging to engage and retain their employees.

Here are a few questions I often start with when I’m doing career coaching. Whether you’re a manager or an employee, feel free to use these questions to help yourself or your team start having deeper career conversations.

1. If you had a magic wand, and money was no object, what work would you love to do?

Too often we start by asking “what do you want to next?” But what really drives meaningful career development is discovering what matters to someone, and asking about their dream job is a great way to get at that. This question isn’t meant to be solely pragmatic — if the answer is “I’d love to be a gardener,” you don’t necessarily need to start brainstorming development goals for a gardening career path. Instead, talking about someone’s dream job can help you to get clues about someone’s sense of purpose in life and their ultimate vision for their career.

Becoming a gardener may not be a realistic career path, but you may learn that the person is really passionate about “growing” people, programs, or teams. Asking about specific elements of that dream job could lead to valuable brainstorming about how to translate it into practical actions. And you might even want to ask if that dream something they might actually want to pursue as part of a future career path. For managers, this means going beyond the desire to keep someone on your team and avoid the hassle of re-hiring and re-training for that position, but who knows — you could be the catalyst for helping them to make a career change that fulfills their true potential!

2. What do you love doing the most in your work?

This question is pretty straightforward, but it can take a bit of digging to get the full benefit. For example, if someone says they like working directly with customers, it helps to ask what they like about it. You might also ask for specific examples of instances where they felt really happy with what they were doing — you could discover that they really love working with a certain type of customer, or that they’re really talented at solving a certain type of problem. These are insights about someone’s strengths and values that you can use not only in helping them map out potential career paths, but also in deploying your team members more effectively in their current roles. I’m also a big fan of the StrengthsFinder assessment in helping to identify strengths.

As with all of these questions, it’s important for a manager to foster trust and create a safe space for open conversations before asking some of these deeper questions. If someone fears retaliation from their manager if they share their honest thoughts about what parts of their current job they like or dislike, they won’t share their authentic perspectives.

3. What would you like to learn more about?

Answers to this question can vary widely. Someone may want to learn more about an existing aspect of their job, to do it better. They may want to learn how to use a new system or software program, either one that they use now but want to get better at, or one that they’d need to know in a future career role. They may want to learn more about their manager’s role, or to connect with someone in a different team or department to learn more about what that individual or team does. Or they may want to work on improving soft skills such as public speaking, communication, leadership, or emotional intelligence.

I encourage you to keep this question as broad as possible. It’s tempting to restrict it to what someone would like to learn “in their current job” or “related to our work in this organization,” but at this early phase of the conversation that could limit your discovery of what really matters to the person. You don’t necessarily have to agree to support their efforts to learn something unrelated to their work, but keeping the door open to unexpected areas they might be interested can result in valuable insights — and it may also surface opportunities for them to pursue additional learning outside their job that benefits their work.

Asking these questions can be a powerful way to ground your career conversations in discovering what really matters to someone, so that you can work on exploring career paths that are truly meaningful. But remember that these questions are just a starting point — once you’ve gained a greater sense of what’s important to someone, what their strengths and values and interests are, you’ll still need to have a more practical conversation about what opportunities exist and what development activities to set goals around. However, starting with these deeper questions will ensure that practical goal-setting is much more meaningful — and much more effective.

For more help with deeper career conversations, download my free Coaching Questions for Managers tool. More resources at www.DeeperEngagement.com.

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