How to Talk About Career Goals (so it's not Forced and Awkward)

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Article Summary

  • Why should you read this:  discussing a team member’s career should be a valuable conversation which gives managers the context they need to set someone up for success.  Instead, when a manager says, ‘we should talk about your career goals’, the subsequent discussion is often awkward and difficult.  It doesn’t have to be this way. We break down why these conversations go so badly, and propose a different approach. 
  • ‘We’: it might not seem this way if you’re just told by HR to ‘talk to people about their goals’, but this can be a very personal topic.  It touches on people’s future plans, their lives and their priorities. In this context, the ‘we’ in this situation really matters.  Often managers haven’t established the right relationship and trust to have a substantive conversation.  That’s not to say you can’t talk about these topics, but you have to consider your relationship and think sensitively about how to approach it. 
  • ‘Should’: it can often be easy for team members to question the motivation and impact of these discussions.  Often they’re held because of internal processes - e.g. a quarterly HR form to fill out - and they have negligible impact on individuals’ careers.  This doesn’t encourage engagement with the conversation from either side.  These discussions only work if employees feel that their manager genuinely cares about their progression and can help.
  • ‘Career goals’: outside of the world of HR jargon, this phrase is barely used - it’s no surprise that when people are asked about them, they struggle to answer.  When we say ‘career goals’ what we’re really talking about are the 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: you may already see ways in which you can improve the quality of these discussions with your team.  If you want some further inspiration though, there’s a framework we think you can use from Russ Laraway, former Chief People Officer at Qualtrics.  It spreads the discussion across three conversations, over three to six weeks, and helps build the trust, understanding, and structure to really develop someone’s career.  It’s tricky to summarise but it comprises the final section of this article. 


‘So, I was thinking we should talk about your career goals?’


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

Last week, Cynthia Chen, a product designer at Stripe, posed exactly this question.  You can see from the number of likes and replies that she’s not alone.

Cynthia Chen Tweet

It’s a great shame, because (in theory) these conversations should be some of the most valuable that a manager has with their team members.  It’s only by knowing what your team members really want from their careers that you can begin to help them plot a way to success.  In many ways, it’s the key to being a good manager.

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

If we break down that first sentence on how we talk about goals, it becomes easier to see where these conversations go wrong and what we can do to make them better.  So in this article we’re going to tear down ‘we should talk about your career goals’ and give you some practical tips on what to do instead.

Let’s get started.

Part 1: ‘We’

This is the first potential problem.

Describing them as ‘Career goals’ makes it all sound like a bullshit HR discussion (which it often is - see Part 2), but what we’re really talking about here are someone’s plans for the future.  When discussed fully, this is actually a very personal question. 

It might involve deliberations of how their personal life interacts with their work.  Or whether they enjoy their current job.  Or how they’re worried they’re not able to do enough of what interests them in your team.  Or perhaps they are thinking of leaving your company.  Maybe they’re thinking of leaving the company because they’ve been badly managed.  The list could go on.

Behind the banality of ‘career goals’ sits endless possible 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 member for this kind of 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.  

Career discussion tweet

That’s not to say you can’t talk about these topics, but you have to consider your relationship and think about easing your way into it.  More on that later on. 

Part 2: ‘Should’

Assuming that you have the right relationship to discuss some of these topics, why ‘should’ you?  This has two aspects: 

  • What is the motivation behind the conversation?
  • Why is it worth having at all?

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 1 year, 2 year, 5 year goals?
  • Where do you want to grow in your skill sets?
  • How will you get there?

Understandably she was sceptical:

“I never liked this format. It felt like I had to boil down my life and professional career into a 45 min conversation and somehow this document was going to help me reach 5-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 because they’ve been told to (often for HR process), not because they genuinely want to  develop the careers of their team members.

Cynthia Chen again:

Career discussion tweet

When you tell your team members that you ‘should’ or ‘need’ to discuss their career goals with them, you will only have a meaningful discussion if they know it’s motivated by a genuine desire to help them progress.  

Now, it may be that you’re in a situation like Evelyn and your company has a structured goal-setting program which you have to engage with.  This may even be formalised into an OKR-type structure and/or tied to compensation.  We’ll get onto how to align these with a fulfilling career goals discussion later on.  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 it worth having?

The second aspect to ‘Should’ relates to the impact of the conversation.  

The scenario goes something like this: ‘Ok so I trust you, and I know you’ve got my best interests at heart, but why bother talking about goals? Either nothing’s going to change, or everything’s going to change, in which case my goals will be irrelevant in three months anyway.’

Career discussion tweet

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.

Part 3: ‘Career Goals’

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

You might have stopped to think about whether you’re happy at work.  Or types of projects you’d like to work on.  Or what you enjoy doing most.  But rarely ‘career goals’.  

This jargony phrasing has been hindering positive conversations about employee development for years.  It’s not a phrase people recognise, so unsurprisingly, they struggle to respond.  

Career discussion tweet

Depending on who you ask, you might also get some pretty blunt answers. 

Career discussion tweet

Often these wording also leads to individuals narrowing their ambitions to the scope of your organisation, rather than what they genuinely want to achieve.  

‘What are your genuine ambitions for the future?’ ‘Gee, I’d just love to be a Senior Sales Manager one day at this firm’.  Said no one ever.  Except when they’re asked about ‘career goals’ in a contrived meeting with a manager they don’t trust, which they just want to end as soon as possible.

So if we are going to talk about career goals, let’s at least make the discussion more human.  When we say ‘career goals’ what we’re really talking about are the 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 Goals

Ok so we’ve established that to do this 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 member in how you ask about these topics.
  • Make clear that you’re asking because you genuinely want to help progress their careers, and believe you can have an impact as their manager.
  • Get away from talking about ‘career goals’ 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 just by acknowledging that, rather than just ploughing ahead and asking shitty questions about goals.  

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

Some of you may already be familiar with 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 which 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’re going to summarise them here but they’re discussed in more detail in Chapter 7 of Kim Scott’s Radical Candor and here in an interview.

Whilst there’s no silver bullet for these conversations, this is as close a universal tool as we know to helping you have them in a constructive and engaging way.

Three conversations

Conversation One: Life Story

In the first conversation, you’re trying to get a better feel for how the team member got to where they are today.  Russ suggests beginning this one with ‘Starting with kindergarten, tell me about your life.’

It’s a great start, because whilst it’s a personal question, it’s very open and your colleague can choose how they want to approach it.  You’re also not going to have the ‘career goals’ problem of people not having anything to say, because the question is on everyone’s specialist subject: themselves!

The areas you should pay particular attention to are 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 the things they care about.  For example, why they left a certain job, or 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 subject that’s too personal, you should also back away.  Particularly if you don’t know the person that well.  You’ll be able to get all the context you need without it getting awkward.  

Conversation Two: Dreams

Remember to leave one to two weeks’ gap, no need to force it.  Then you’re ready for the next conversation.  

By now you should have some context about what motivates the person and what they care about, and crucially 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 choice of word is very important (you may want to explain this to your team).  The point is to discuss what someone sees as the very apex of their career.  Not the promotion they’re hoping for on your team, not where they want to be in 5 years, but what they would see as the best possible outcome for their career. As Russ says, when he spoke to one Google employee, he was surprised to hear her dream was to run a Spirulina farm!  

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.  With reference to one of the tweets above, that might mean being financial secure for the first time.  It might mean being home in time to pick up their kids 3 days a week.  Or working remotely from a certain country over the course of their lives. Or ultimately becoming an expert in a particular field.  The answer to this question shouldn’t just be one thing.  Ultimately Russ advises team members to come up with 3-5 dreams for the future.

The final step in this conversation is mapping out what skills the employee feels they’ll need to ultimately fulfil their dreams, and their current competency level.  Then you can start making a plan.

Conversation Three: Eighteen-Month Plan

For each of those skill areas, you can then work out:

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

If you convert those into to-dos, for want of a better word, there’s your ‘career goals.’  And for once, they actually align with what a person wants to achieve, and they come from a place of care and trust.  It’s at this point that you can look to align them with any internal processes.  You can revisit the plan in your 1:1s, probably on a monthly basis, to check progress and update it.  

As you can probably see, you don’t just get a plan out of this process. You’ve learned so much about your team members.  Armed with this understanding, there will be innumerable intangible ways that you’ll be able to steer opportunities their way and progress their careers, because you know what they want.

It should be said that it is almost certain that someone’s personal aims will not precisely match up with the work you can offer them at your company.  Russ was not able to offer that person a Spirulina opportunity at Google.  But hopefully most of the time you can offer them opportunities to develop their skills whilst providing value to your firm.  At the point where that stops being possible, it’s probably time to move on.  

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

Some Final Notes

As you can hopefully see, this three step framework beats ‘We should talk about your career goals’ hands down.  It doesn’t rush, lets you take the time to get to know your team member, and helps you draw out some of the key motivations and ambitions that you’ll need to understand to really plan their careers.

A few final points.  First, before having each one of these discussions, make sure to explain to your team why you’re having them 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’).  

Second, to illustrate the value of the conversations it can help to give examples of how you’ve applied it to your own career.  Give your team members examples of relevant moments in your career that have influenced you, your dreams, and your plans to get there.

Third, if you feel apprehensive about any of these conversations, you can always try practicing with other managers before actually talking to your team. 

And finally, don’t be afraid to take notes.  Some of what you’ll be told will be really important, and if you think there’s a danger you’ll forget something, write it down.  If you’re unsure whether you have something correct, you can always send it over to your team member to check your understanding.  They’ll appreciate you taking the time.

Good luck!

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