How To Discuss Career Development Plans With Your Team

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Career growth and development are crucial aspects often neglected by startups, small companies, and first-time managers. They want to celebrate milestones, little victories, and big wins from their team, but without giving a second thought to effective career development plans and long-term career goals.

According to a report from the American Psychological Association, this perceived lack of personal and professional development is one of the foremost reasons for poor employee retention — with some figures showing as much as two-thirds of the workforce quitting.

When everything is smooth sailing, finding the downside to certain situations is always taxing. That’s why open conversation and a roadmap to career development plans are vital to future success — for everyone involved.

How To Have a Great Discussion on Career Development Plans

Manager: “So, I was thinking — should we talk about your career goals and career development plans?”

Employee: “Erm…ok...”

Many of us have been in a situation where either we’ve said those words or been on the receiving end of them. Often, it doesn’t go that well.

It’s a great shame because, in theory, conversations like these should be some of the most valuable that a manager has with their team members. Only by knowing what your team members really want from their careers can you begin to help them plot a way to success. Discussing career development plans is key to being a great manager — and an even better leader.

So why do these conversations often feel artificial, difficult, and worthless?

If we break down that first sentence on how we talk about goals, seeing where these conversations go wrong and what we can do to improve them becomes more apparent. In this article, we will tear down “We should talk about your career goals and career development plans” and give you some practical tips on what to do instead.

Part 1: The “We” of the Equation

Boss and employee having a conversation at a cafe with brick walls

This is the first potential problem. Using the phrases “career goals” or “career development plans” makes the discussion sound straight from the human resources office — (which it often is, just see Part 2). But we’re really talking about someone’s plans for the future. When discussed fully, professional development is a very personal question.

It might involve a number of deliberations:

  • How their personal life interacts with their work
  • Whether their career path is on the right track
  • How they have no particular roadmap, short-term goals, or long-term goals, and how it affects them
  • Whether they enjoy their current job or see career growth opportunities in their current position
  • How they’re worried they’re not able to do enough of what interests them in your team
  • Whether they have the current skills or have developed new skills in their current role that can propel them to the next level
  • Perhaps they are thinking of leaving your company
  • Maybe they’re thinking about leaving the company because they’ve been badly managed

The list could go on.

Behind the banality of “career goals” and "career development plans” sits endless questions, many of which your team member might typically only discuss with a trusted friend.  

So the “we” in this situation really matters. Have you established the right relationship and context with your team members for this discussion?

If you’re a new manager who has only been working with someone for a short period of time, asking them to discuss these topics is inevitably going to be difficult - particularly if it’s phrased as we’ve described.  

The trust just isn’t there yet. That’s not to say you can’t talk about these topics, but you have to consider your relationship and consider easing your way into it.

Part 2: The “Should”

Assuming you have the right relationship to discuss some of these topics, why “should” you discuss career development plans or development opportunities?  This has two aspects:

What Is the Motivation?

There is a clear wrong answer to the first question, but unfortunately it’s often the truth. Evelyn Kim, Director of Product Design at Uber Eats, tells a story on this topic which probably sounds familiar. She speaks about how every quarter she had to fill out a form with her manager on:

  • What are your strengths and weaknesses?
  • What are your one-year, two-year, and five-year career development goals?
  • Where do you want to grow in your skill sets?
  • How will you get there?

Understandably she was skeptical:

“I never liked this format. It felt like I had to boil down my life and professional career into a 45-minute conversation, and somehow, this document was going to help me reach five-year goals.”

Spoiler: It’s not.

But these are the kinds of discussions that happen when managers feel they “should” be talking about these topics — often because HR has instructed them, not because they genuinely want to develop the careers of their team members.

Maybe you’re in a situation like Evelyn, and your company has a structured goal-setting program that requires your engagement. This may be formalized into an OKR-type structure and/or tied to compensation.

We’ll discuss how to align these with a discussion of fulfilling career goals. But suffice to say the starting point should always be a genuine desire to help, and then alignment, rather than using an HR process as a prompt for opening the discussion.

Why Is the Conversation Worth Having?

The second aspect of “should” relates to the impact of the conversation.

The scenario goes like this: “OK, I trust you, and I know you’ve got my best interests at heart, but why bother discussing goals and career development plans? Either nothing will change, or everything will change — in which case my goals, self-assessment, and action plan will be irrelevant in three months anyway.”

It’s up to you as a manager to demonstrate that this conversation can actually make a difference, and how you can positively impact their career. You can’t assume that they will think it’s a worthwhile discussion.

To some degree, you turn from manager to career coach. Your focus shifts from required HR discussions and team/project management to a focused approach to improving your team. The conversation acts as a firestarter — not only to career development plans and goals — but also an approach to personal development and full potential.

Part 3: “Career Goals” and “Career Development Plans”

Outside of a contrived HR process, have you ever paused to consider your own “career goals” Probably not. You’re a human being after all.

You might have stopped to consider whether you’re happy at work, your dream job, the projects you’d like to work on, or what you enjoy most — but rarely, “career goals” or “career development plans.”  

This jargony phrasing has hindered positive conversations about employee engagement and development for years. It’s not a phrase people recognize, so unsurprisingly, they struggle to respond.  

You might also get some pretty blunt answers depending on who you ask. Oftentimes, this wording leads to individuals narrowing their ambitions to the scope of your organization rather than their career aspirations.

“What are your genuine ambitions for the future?”

“Gee, I’d love to be a Senior Sales Manager one day at this firm.”

Said no one ever — except when asked about “career goals” or “career development plans” in a contrived meeting or a performance review with a manager they don’t necessarily trust.

So if we talk about professional goals and planning processes to get there, let’s at least make the discussion more human. When we say “career goals,” we’re really talking about the specific skills people would like to learn, the relationships they’d like to build, the work they’d like to do, and the life they want to lead. Let’s talk more in those terms.

A Better Way to Talk About Career Development Plans

Employee and a boss at a table having a discussion

Ok, so we’ve established that to discuss career development programs/plans and career goals well as a manager you need to:

  • Be mindful of the personal nature of the question and assess the degree of trust with your team members in how you ask about these topics.
  • Make clear that you’re asking because you genuinely want to help progress their careers, create accessible and achievable professional development plans, provide learning opportunities, and believe you can have an impact as their manager.
  • Avoid discussing career goals or using HR-based career plan templates and talk more broadly about their future plans, ambitions, strengths, and what makes them happy.

If that sounds difficult to pull off, that’s because it is. Management can be hard. But you’re halfway there by acknowledging that, rather than just plowing ahead and asking mundane questions about goals employee career development plans.

Fortunately, to get the rest of the way there, we think there’s a framework that can help.

You may already know Russ Laraway, the former Chief People Officer at Qualtrics. Several jobs prior, while he worked at Google, he developed a new way of discussing career development with his team. After he implemented it, a subsequent employee satisfaction survey found a degree of improvement that the HR department had never seen before.

He taught every manager on his team to have three 45-minute conversations with their individual team members over the course of three to six weeks. We will summarize them here, but they’re discussed in more detail in Chapter 7 of Kim Scott’s Radical Candor.

Career Conversation One: Life Story

In the first conversation, you’re trying to understand how team members got to where they are today. Russ suggests beginning this with “Starting with kindergarten, tell me about your life.”

Though it’s a personal question, it’s very open, and your colleagues can choose how they want to approach it. You’re also not going to have the “career development plans” problem of people not having anything to say, because the question is on everyone’s specialist subject: themselves!

Use active listening to pay particular attention to where transitions occurred in the person’s life or where they had significant decisions to make. At these points, an individual’s motivations can tell you a lot about what they might want in their future career and what they care about. For example, why they applied for a new job, left a certain job, moved to a different city, or prioritized their family or mental health, etc.

You shouldn’t be afraid to ask questions.  It’s meant to be a conversation, not an information download. However, if you feel you’ve pressed on a too personal subject, back away, particularly if you don’t know the person well. You’ll be able to get all the context you need without it getting awkward.

Career Conversation Two: Dreams

Remember to leave a one- to two-week conversation gap. Forcing the issue only pushes the concept toward one of those outdated, overused, HR template conversations.

By now, you should have some context about what motivates the person and what they care about. By discussing these things, you’ve demonstrated that you care about them and have started to build some trust.

Now you can talk about the future.

Calling this conversation “Dreams” can make it seem ephemeral, but the word choice is very important. The point is to discuss what someone sees as the apex of their career.

It’s not the promotion they’re hoping for on your team nor where they want to be in five years, but what they would see as the best possible outcome for their career.

You’re not just looking for job titles or positions. You’re also trying to get a feel for what pattern of life they’d ideally like. That might mean

  • Being financially secure for the first time
  • Being home in time to pick up their kids three days a week
  • Working remotely from a certain country over the course of their lives.
  • Becoming an expert in a particular field.

The answer to this question shouldn’t just be one thing. Ultimately, Russ advises team members to develop three to five dreams for the future.

The final step in this conversation is mapping out what skills the employee feels they’ll need to fulfill their dreams. Then — and only then — can you start making career development plans catered to the individual.

Career Conversation Three: Make a Career Development Plan

For each of those skill areas, you can brainstorm answers to these questions:

  • Which projects should they work on to improve?
  • Which people should they spend time with?
  • What training should they do? Do they need to upskill?
  • How should they prioritize their time?

If you convert those into to-dos, for want of a better word, your career development plan begins to come full circle. For once, the plan and goals align with what a person wants to achieve and come from a place of care and trust.

At this point, you can align them with any internal processes. Revisit the plan in your monthly one-on-one meetings to check progress and update it.

But look — you don’t just get career development plans out of this process. You’ve learned so much about your team members at the same time. Armed with this understanding, you have innumerable, intangible ways to steer opportunities and progress their careers — simply because you know what they want.

The Downside to Career Development Planning

Sometimes, someone’s personal aims will not precisely match the work you can offer them at your company. But hopefully, most of the time, you can offer them opportunities to develop their skills while providing value to your firm. When that stops being possible, it’s probably time to move on.  

In many ways, the worst thing a manager can do is ask a candidate or team member to pursue meaningful work that will advance their interests when it doesn’t exist at their firm. At this point, a good discussion about career development should involve advice about opportunities beyond your company.

How To Talk About Career Development Plans in 7 Easy Steps

woman creating a roadmap for career development
  1. Don't talk about “career development”: The term and its sibling term — career development plans — are too formal and corporate. It will put off those who have less firm (but no less valuable) ideas about the future direction of their careers.
  2. Talk about their lives, dreams, and aspirations: Instead of talking about “career goals,” talk about subjects that everyone has opinions and thoughts on: Where they came from, where they'd like to go next, and the work they'd like to do to get there.
  3. Make a career development plan — without using the corporate name: Once you've established some future aspirations, make a plan for how you're going to get there. It provides a source of accountability and gives you a reference point for future career discussions as you check in on progress.
  4. Explain the approach: Before having any of these discussions, explain to your team why you’re holding a conversation and the general framework. It will give them time to think about their answers, which should make for a better quality of discussion — although they shouldn’t feel any pressure to prepare ahead of time.  
  5. Give examples of our own: Give your team members examples of relevant moments in your career that have influenced you, your dreams, and your plans, to help them understand the benefits of these conversations. At this juncture, it’s about the people and the process.
  6. Practice if you want: If you feel apprehensive about any of these conversations, practice with other managers before talking to your team.
  7. Don't be afraid to take notes: Jot down the important aspects of the conversation. If you’re unsure whether you have something correct, you can always send it to your team member to check your understanding. They’ll appreciate you taking the time.

Career Development Plans and the Penultimate Step of Great Management

Discussing career goals, career progression, and career development plans is just a part of the equation that creates a superb manager and leader. However, what’s contained within these plans and the conversation surrounding them makes you a better leader.

You have your own career goals and career aspirations, but those are a side note. When you take time to improve the lives of your team members with goal creation, discussion of personal and professional development, and ultimately, the urge to see their goals fulfilled, you’ve transcended from mere manager to leader.

Creating career development plans for your team members is one of the final stepping stones before realizing your leadership abilities. You only need to take that penultimate stride.

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