There are a variety of contexts in which these conversations can be helpful. Maybe roles have shifted after a reorg, and you want to make sure that all of your team members are set up for success. Or maybe you just have a sense that certain of your direct reports don't have a vision of where they want their career to go. Whatever the case, having a clear structure to these discussions will ensure that they're as productive as possible and provide both you and your reports with a clear view of where they're headed.

While you don't necessarily want to get too personal, starting with a broader discussion around your employee's background will help you better understand how they got to where they are today, as well as how they approach making decisions about their career.

I've found that people often learn all sorts of things they weren't expecting in the course of these conversations. Even if something funny or tragic or surprising might not seem like it immediately reflects their day-to-day work life, having this full picture of how a person thinks and responds to a variety of different situations is so helpful in setting them up for success.

It's always possible that, in the course of these conversations, you learn that a person's long-term future isn't with your org. Especially when it comes to working at startups, that's no surprise. While it might seem counterintuitive, that's just as important a potential learning as any other here: the sooner you know where someone's career is headed, the sooner you can start taking that information into account when you're doing things like org design and hiring. The sweet spot of an employee's development is when you can match the needs of the organization to the employee's desired growth.

Crystal Proenza

Having a clear vision of where your direct reports see their careers’ heading is key to success at both the individual and business levels.

Career Conversations Approach to Development Plans

This is an approach to development plans that focuses on connecting a team member’s long term goals to their short term commitments, keeping in mind their strengths and unique experience.

The 3-meeting structure suggested was developed by Kim Scott from her book Radical Candor. You can read a post that details the format 

. The original structure calls for three 45-minute conversations. The format can be adapted to three 30-minute conversations, with another hour of the manager’s time utilized to synthesize the most important parts of the conversation and create a starting draft of the development plan. The end result is a written development plan that can be revisited and tracked.

The other amazing thing about these conversations is that they have a way of making your relationship with your direct report stronger.

The best approach to start is to give a high level overview of each step with a team member in advance so that they know what to expect.

The ‘What Brought you Here’ Conversation

Schedule and hold a 30 minute conversation focused on your direct reports’ “What Brought You Here Story” or as I like to call it - The Journey To INSERT COMPANY NAME HERE. No phones and no interruptions, you will ask your direct to outline what brought them to the position they hold at the company right now. This is purposely vague. 

What you’re looking for is to understand your direct’s career moves and major life transitions.

 As they tell you about their lives, you are going to stop and ask questions at points when they made major decisions (where they went to school, what they majored in, the first place they worked). 

Below is a list of questions to help spark conversation and get to the “heart” of the journey

Start with high school and bring me to today

What drove your decision to choose X major or X career path?

What was your thinking behind that decision or pivot?

When were their major pivots and/or transitions in your career?

What were you up against in your career? (family pressure, financial pressures)

What was your thinking behind making that decision or choice?

What did those transitions teach you about what motivates you or demotivates you about your work?

What experiences were most formative in your life from high school to now? What did you learn about yourself?

What did you love or hate about your work? (at a particular company/moment in time)

At the end of the conversation, thank your direct for sharing so much about themselves and tell them you look forward to the next conversation. At this point it’s good to take your notes and bold the pivots/reactions/values that stand out to you. Think about what this journey tells you about how this person likes to make decisions, or is driven to make decisions, and if you can, their strengths. Later on, when you’re creating the development plan, you will want to point to one of their strengths or habits to attach to an area of development.

Schedule and hold a 30-minute conversation that again is an open conversation, purposely unstructured. I like to begin this meeting by pointing out the bolded observations that I made from the first conversations (ie. It seems that many of your decisions as it relates to your career were based around your love of collaboration or working with friends or your desire to utilize your strength in math, etc.) and ask “Does that resonate with you?” These few points, even if they are not 100% accurate in the way YOU state them, encourages the person to think through any trends / strengths / underlying motivations that led them to this point in their career.

Next it’s time to move on to talk about dreams. This is often the most difficult part for direct reports to get started on. There is often a question of - “are we talking about our careers or our lives?” I have found that encouraging them to blend the two and being open to talking about both / all is often the most valuable. As their manager, you are looking for both where they consider the pinnacle of their career, and what other aspects of their lives they envision for the future around their career. It’s hard for people to talk about their dreams out loud. You are trying to figure out what paths will help them to get to their dreams. Below is a list of questions to help spark conversation during the Dreams conversation:

What were your dreams when you were younger?

When you imagine the pinnacle of your career, what does it look like?

Who are the people that have been most impactful in your career progression? What do they do? What have they achieved?

When you look back at your career, what would you like to say are your biggest achievements?

Where do you see yourself living in the future?

What kind of team do you see yourself working on? What size company?

The final conversation is about (loosely) connecting the dots from today to some of the aspirational images of the future for the team member, keeping the idea of the trends / motivations that got them to this place in their career in mind. I developed this document as an actionable follow up plan. It’s a basic format for a development plan.

Before the meeting I usually take a few minutes and fill in one or two lines, and then talk through the rest with the team member. I like to tell them that this is their document to own. Even though you may help them by making suggestions about how their development areas attach to their dreams and even relate them to how they’ve made decisions in the past about where they would work/what they would study, etc., most of the document should be filled out with their thoughts.

Like most development conversations, there usually isn’t enough time to finish. Encouraging them to continue building out the document, and then offering to revisit it with them at a cadence of their choosing is what I find most helpful. Some will want to show it to you when they complete it. Some will ask to review it on a quarterly cadence. Let them own those calendar invites. And in those conversations do your best to be focused on their development vs. talking about ongoing projects/status updates. You want to be a resource and advocate for their development in this area.

As a leader, one of the most beneficial aspects of this set of conversations is that now you know more about where your team member wants to develop. This will help you delegate work to them to have them test areas that they’re interested in, encourage them to pursue projects that might be outside of their current scope, and generally find ways to invest in their future. Generally, the conversations also create stronger bonds between manager / team member because they create space to focus solely on an employee.

It should also be noted that there are times when the conversations spark introspection that could lead to a team member discovering they are not in the right role or that they are not fulfilled in their current role. How a manager handles those revelations or conversations matters - remember that the purpose of these conversations is to invest in the growth of your team members. That investment is meant to equate to more productivity for your team and the company as a whole, whether that is moving a team member up the ladder, respecting their desire to be a “rock” star in a consistent position or helping them move on to another role or company.

Career Conversations Guide and Next Steps Template by Crystal Proenza

Career Conversations Approach to Development Plans

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