Career Conversations: be the best manager your people have ever had

Let’s say you have 8 direct reports, and while 2 of them don’t seem to be worried about their career development plan or even when their next promotion will happen, the other 6 are on your case about it in every single 1:1. You’re likely ill-equipped to help them with these questions. You don’t even know what you want to be when you grow up – nobody has ever had this conversation with you since kindergarten, and your responses then oscillated between the what-are-the-chances “astronaut” and the really-unhelpful “ice cream truck driver.” Putting your own history aside, you have no clue where to even begin this type of conversation with your reports.

It’s a typical issue in high-growth startups: “I understand what I need to do to develop in my career” ranks smack at the bottom in the employee survey. By the way: congratulations if that’s one of your biggest problems as a company – compared to, say, “I would recommend my company to my friends” or “I approve of our CEO.” ✊ There’s a reason why career development is such a struggle: high-growth, smaller startups need to put basics in place first – things like values, levels, and compensation bands. Career development just doesn’t make the people structures blocking and tackling list. Even in companies that have tried to put career development in place, the effort often produces formulaic CDPs (Career Development Plans) that every manager must fill out for their reports and that go into a mythical “HR file” never to be seen again.

Yet when I ran a pilot of Career Conversations with ~10 managers and ~70 recipients at Segment, managers rated this intense and time-consuming activity 10/10 (median), and recipients gave it 8/10 (median). Here’s what both sides had to say about Career Conversations:

The Career Conversations felt “like my manager really cares about me” and “wants to understand me.” The Conversations were “helpful,” “productive.”


The Career Conversations felt like “impactful,” “helpful,” “like I understand my folks and can help them better now.”


Let me make a bold claim: having high-quality career conversations with your reports guarantees that you’ll build stronger, trust-based relationships with them and will help them in work and life beyond what you both thought possible. Doing so will immediately put you in the rarefied category of “awesome bosses” because it’s so seldom done at all and well, and because it will clearly take time and effort from you, which won’t go unnoticed by your teammates.

The moral imperative for Career Conversations

The reality is that in tech startups and companies, the average tenure today can be as low as 2-3 years (source confirming observed trends). Experience proves that the time a teammate spends working with a given manager is often even shorter.

So let’s say you’re managing a teammate for 1-2 years on average. You’re probably working hard to set them up to be successful in their current role and potentially helping them grow into their next role. But their career will span for up to another 40 years, 99.9% likely not under your leadership. Imagine how much value you could add to this teammate as a person by helping them figure out where it is they ultimately want to go and how to progress on that path!

It turns out that most people need this kind of help – very few of us have a crystal-clear career goal in mind that we’re already following closely. It’s surprisingly hard to figure it out on your own. There’s something about talking about this stuff with another person that adds the last bit of escape velocity needed to get long-term goals formulated. From personal experience, having a well-meaning third-party encourage this type of conversation can make the difference between a person feeling very fuzzy on the topic and the same person achieving some modicum of clarity.

The positive externality of the exercise to the teammate is that they can begin to make strides in the direction of their now-clearer goals and realize how their day-to-day activities help them get closer to their end goal, supplying those activities with more meaning.

The benefits of creating this outcome for your teammates to you as a manager are:

  1. You get meaning from adding a ton of value to your teammates’ long-term success. The extra serotonin kick from getting thanked by the people on your team doesn’t hurt either.
  2. You will undoubtedly get to know your teammates better as people, automatically increasing the likelihood of building better relationships with them, which is a strong predictor of team effectiveness.
  3. Your teammates are likely to be more motivated at work because of the “I see how this task contributes to my long-term goals” effect. Theoretically, you’ll be better able to retain your teammates on your team and/or at your company. Alternatively, in some cases, you may figure out together that another role or opportunity suits them better – which is also a fine, clarifying outcome.

OK, so what are Career Conversations?

Career Conversations are a structured way for a manager to help direct reports define their ultimate career goals and intermediate steps to get there, and hold the direct report accountable for the immediate next steps on the path.

  • Conversation #1: The “Tell me about your life since kindergarten” conversation helps the manager understand the core drives and values of the teammate and – bonus! – plain learn a lot more about them, deepening the personal relationship.
    • Don’t be surprised if your report asks to hear your life story after this exercise. It’s that powerful! It’ll be a good idea to agree to this – remember, you only have to cover the things you’d like to cover. If multiple people are asking for this, you can creatively shortcut through retelling your life multiple times by piloting a 15-min “Life Story” segment in your team meeting. All it takes is a few slides with baby photos and other content of pivotal people and moments in your life for everyone to feel closer. Assuming it goes well, get your teammates to volunteer to do their stories!
  • Conversation #2: Armed with the insights from the above conversation, have the “At the pinnacle of your career, what do you want to be doing?” conversation. After the initial “dream formulation,” it may be useful to talk through “which role at which company you want to hold decades from now.” Here, it may be helpful to run through “what careers and functions are even out there” and do some liberal crossing out (e.g., “I guess I’ll never be a doctor or an artist or a Finance person”). Narrow it down to max 2-3 roles. This is the answer to the G in GROW.
  • Help the teammate to think through what top 10 competencies are required for that dream job and list them out together (e.g., if the goal is to become the CMO of Coca-Cola, then a few of the required skill sets are probably “deep understanding of marketing, especially brand” and “people management”). FYI: For your improvement sort cards can be super helpful here.
    • Once this list is complete, ask the teammate to rate their current ability on each competency. You can definitely also help here because you have information about the competencies the teammate is exhibiting. However, be careful to not overstep – your goal here is not to tell the teammate what they suck at. This is the R in GROW.
    • Next, ask the teammate to pick (they do this, not the manager!) which skill sets they want to develop further now (these could be the low-rated or the high-rated skillsets). This is the O in GROW.
    • Pick one of the long term goals and add it to the leftmost column of the GROW template (see below). From there, ask your teammate to fill out the rest as homework.
  • Conversation #3: Have the teammate describe to you what they’ve put in the GROW and their logic, help them define things better if needed.
    • Help the teammate add opportunities for developing these skill sets into their work at your company – their actual role or a project/team responsibility. For example, if someone wants to start learning about people management while being an individual contributor, perhaps they can help manage the contractors the team works with as the first small step in that direction. Stress-test the number and types of things with the teammate: are these things actually achievable in the next X months? This is the W in GROW.

On a per person basis, the initial three career conversation combo will take a one-time 2.25-3 hours, and the subsequent quarterly check-in will be ~30 min. The three conversations will result in this template filled out once and updated on a quarterly basis:

What follows is a bunch of content on how to roll out and troubleshoot Career Conversations and a word on their methodology, including attribution to original sources/inspiration.

Usage notes for Career Conversations

Before: set it up for success

Following this particular framework is completely voluntary. If you don’t like it or aren’t bought into it, don’t do it. Instead, use a framework you like better! If you go through the motions without believing in them, your reports will feel it, and it’ll defeat the whole purpose of the exercise.

Given how personal the first conversation in the series is, I recommend broaching it only when the manager feels equipped in this regard. If your report doesn’t trust you right now for whatever reason, this isn’t the right conversation to have – first, repair the trust. I also recommend having the whole series and especially the first convo on double-opt-in basis.

Here’s how you can float the idea of Career Conversations by your direct report (aim to do it in real life (vs. over email):

I’ve recently learned about this awesome framework for us to talk about your career development. It’s descriptively called Career Conversations. It’s a series of three conversations that are somewhat structured that are designed to help me help you to define your career goals and the steps to get there. They’ll result in actionable steps that I’ll help hold you accountable for so these important things don’t fall through the cracks. What do you think?

Keep the three conversations as close together for the same report as possible – e.g., get them all done in one month. This keeps the momentum going and prevents both sides from forgetting what was discussed. Schedule all conversations for each direct report ahead of time; you can always move them later.

During: assume a coaching approach

The most productive way for you as the manager to present yourself in career conversations is by taking a coaching approach. Contrast this with mentoring and directing.

According to Coaching for Performance, “coaching is unlocking people’s potential to maximize their own performance. It is helping them to learn rather than teaching them.” Coaching is not dependent on a more experienced person passing down their knowledge. Coaching is about partnership, collaboration, and believing in potential. Coaching is a conversation between equals. See here for concrete examples of questions that work well in the coaching (GROW) framework.

The word “mentoring” originates from Greek mythology, in which it is reported that Odysseus, when setting out for Troy, entrusted his house and the education of his son Telemachus to his friend, Mentor. “Tell him all you know,” Odysseus said. Mentoring is about sharing your experiences for the benefit of your conversation partner.

Directing (a.k.a. teaching) is telling another person what to do, and not very suitable for effective career conversations with your teammates.

You’ll likely find yourself incorporating some mentoring into career conversations with your teammates, which is natural. Just be aware of when you’re switching into the mentor role and ideally delineate it clearly by saying something like, “What worked for me was…” vs. “You know what you should do…” Bonus points for asking permission to mention your own experience before offering it!

After: maintain momentum post the three initial conversations

Credit for this section goes to David Klemenz who was my awesome HR Business Partner at Segment and my partner in crime piloting and rolling out Career Conversations to the company.

You’ve had the 3 conversations. What’s next?

After the initial batch of career conversations with the same report and getting the plan filled out, follow up monthly with an extended conversation at least quarterly. Check-ins can be done monthly as part of your regular one-on-ones and don’t have to take more than 5-10 min. List it as an agenda item and, ideally, don’t save it for last. Are things still according to plan? Cool! Keep checking in monthly. Is there something new to talk about? Also cool! Schedule some time outside your touchbase to chat more.

What happens if my direct constantly wants to have career conversations?

So, the plan is set. But each time you have a touchbase, your direct wants to talk more about career development because something about the plan has changed. There is no hard and fast rule here. You may be working with someone who is a little lost and trying to figure out what’s next, which may mean devoting a little more time than you might usually. Or you may be working with someone who is excited to talk about future plans but who really doesn’t have any updates. Use your best judgment here, remembering that the primary focus is for your direct to perform in the current role.

What happens if my direct’s career plan is on track?

In this scenario, each time you bring up the plan in your touchbase, your direct indicates all is well and there’s no need to chat. If it’s within a month or two of the original conversation, then all’s probably well. If you notice that it has been three to four – or more – months since diving into the plan, feel free to probe a bit more; stay curious just a little bit longer. It may be that all is truly well with the plan. Or it may be that your direct is reluctant to give updates. Again, use your best judgment in this latter case. Feel free to ask if they want to have a separate conversation. If yes, great! And if no, then you might suggest that they reach out to others inside or outside the company to have that conversation. Otherwise, it’s best to respect their wishes; we don’t want to force anyone to have a conversation they don’t want to have.

What happens when my direct gets a new manager?

It’s common for people to have multiple managers during their tenure at any given company for many different reasons. If you have a direct report who is moving to a different manager, chat first with your direct to ensure that they are okay with you sharing the career conversation documentation you have compiled. Then, share the documentation, and schedule time with your direct and the new manager to talk through the ‘in-progress’ plan.

What happens if I’m the new manager for someone who has been at my company for a while and has had Career Conversations already?

After the conversation with the former manager and your new direct, chat with your direct about next steps. You and your direct may agree to have the conversations. Have at it! Or, maybe your direct doesn’t want to spend the time telling their whole life story again, in which case you could plan an abbreviated (60 min) session in which you ask probing questions that help you to understand the highlights of a person’s life and dreams. Or you could simply start working with the plan, checking in monthly, and scheduling career conversations as appropriate.

The Career Conversations methodology

There’s a multitude of effective approaches out there to having career conversations. I’ve had success with the blend presented here. You’re welcome to modify it to your needs. The point, ultimately, is to have career conversations with teammates, not to get stuck on the details. The blend of approaches presented here heavily relies on three inputs:

  1. Russ Laraway’s approach to career conversations
  2. The GROW coaching model
  3. For Your Improvement competencies and sorting cards

I learned about Career Conversations from Russ Laraway. He was a manager of a large Sales team at Google (think 700 people), later went on to run a large portion of Sales at Twitter, and then co-founded Radical Candor the company with Kim Scott, the author of Radical Candor the book. Russ then went on to become a VP of People at Qualtrics. I’ve had the opportunity to meet Russ in person and hear this methodology from him directly. I can’t say enough good things about it. I highly recommend this podcast with Russ, Radical Candor the book, and Radical Candor the podcast.

The GROW coaching model is an established coaching framework used by coaches and leaders. It was first established in the 1980s by a group of British leadership coaches and got its fame when applied by them successfully at McKinsey. See Coaching for Performance.

For Your Improvement is a set of sorting cards and supplementary materials designed by Korn Ferry, an HR consultancy. Korn Ferry catalogued all the possible competencies a human being can exhibit at work. You’d think that these things would be like motherhood and apple pie, but you’d be wrong. The competencies are extremely well thought through, non-trivial definitions. My favorite is “dealing with paradox.” Competencies are super handy in helping your reports understand what skills they want to build to accomplish their career goals. There are many other uses to the competencies, like building job reqs and career ladders and giving feedback in objective terms.

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