Zen and the Art of Designing Career Conversations
I now pronounce you Growth Goals and Opportunities
The most energizing part of my job as a manager is facilitating the development of my designers as they continue on their career journey. This is a journey with no bookends and in fairness, “development” is a loaded term that captures a lot to be excited about. It incorporates:
- Discovery and exploration of what energizes or depletes them
- Identifying and pursuing skillsets they’d like to invest time in deepening.
- Professionally maturing to accomplish wins and lead in ways they’ve never done before.
Part of what challenges and excites me about guiding designers on their career journey is the duality of development.
On one hand, we need a high degree of intentionality when covering the above areas, in order to make measurable progress in the right direction. On the other, the journey is not linear nor is the destination constant. Our desires and strengths change as we mature as people and professionals.
In both theory and practice, the art of designing career conversations lies in the balance of guiding designers towards intentional decisions, while maintaining the space to marry evolving growth goals with real world opportunities.
Theory: Career Thinking Process
Just like the products we launch, career conversations can benefit from the design thinking process. After all, our career and growth aspirations don’t stay stagnant so the conversations you have with your team should flex to reflect this. Though staying agile might seem like additional work at face value, it has the beneficial implicit acknowledgement that career development is iterative and that it’s okay to experiment! This is how you can approach the “career thinking” process:
Consolidate any past and new resources related to career conversations. Hopefully you have a wealth of artifacts to leverage from past conversations you’ve had with your managers and if not, there are plenty of resources out there! Have an understanding of the type of career conversation you’d like to design and identify the resources that might be most helpful for you. Don’t forget what Pablo Picasso once allegedly said “Good artists (read: designers) copy. Great artists (read: designers) steal.”
Empathize and understand where your designer currently is in their thinking. Also, identify what they’re looking to get out of the career conversation. This can be done by having them answer some baseline questions asynchronously or in-person. Here is a template I often use.
Ideate different ways you can approach the conversation using the artifacts and context you gathered prior. Some questions you might want to ask yourself are:
- How do they typically like to collaborate? Is it through white boarding? Reviewing prepared material? Talking through major themes?
- How will the questions asked be used to help craft a path forward for the designer? If the answer to the question won’t be leveraged, avoid asking the question. This is so that a focused conversation can be had.
- How might you take what has worked well in the past to create something better and more tailored to this designer?
Prototype a template to use to facilitate the career conversation. It can come in the form of a document, virtual whiteboard (my latest favorite being FigJam), or anything else you can use to create structured and sustained dialogue.
Test the prototype with the designer. Okay, so this is actually the career conversation but I’ll say “test” to double down on the fact that it is experimental and iterative! Once you’ve had the discussion with the designer, make sure to invite feedback. Some questions I ask are:
- Was this useful to you? How so?
- How could this have gone even better?
- Do you feel as though you have measurable action items to track against your growth goals?
Monitor their progress against the goals created. Just like a product release to customers, the work is not done when it is launched. Now is the time to make sure there’s a plan that will create visibility into the leading indicators of the aligned success metrics or in this case — growth goals. This might look like reserving time every other 1:1 to check-in on progress or having shared documentation that can be viewed asynchronously.
And that is the career thinking process! Feel free to read on if you’d like to see one of many ways it can manifest in practice.
Practice: Career Convo in Action
Below is the latest version of my career conversation. It is not the first version and certainly will not be my last.
Pre-populate
Before conducting the career conversation, I pre-populate my FigJam template with the answers from the pre-work the designer completed and my own resources. I’ve divided my template into four sections that are framed from the perspective of the designer: (1) Where I am, (2) Where I can go, (3) How I can get there, and (4) My Action Plan.
Leveraging the pre-work, I fill out all of ‘Where I am’ as well as the dream roles they have in ‘Where I can go’. I also tap into my network of amazing designers and researchers to identify a handful of potential mentors that could provide additional guidance on their career journeys. My objective here is to find mentors that have a similar background, career aspirations, or demographics so that they may provide mentorship that I may not be able to fully realize. If you want to expand your network of mentors, there are great services like ADPList that you can leverage. Lastly, I like to include books they should expense that I think would align with their growth goals.
Important note: I may not always have the luxury to receive firsthand guidance around the nuances that a black man may personally face in the professional world. Similarly, I may not be able to provide designers of different backgrounds and identities, like maybe the female designers on my team, with the comprehensive support they need to navigate and thrive in the workplace. So as I continue to empathize with my incredibly diverse team of designers, it’s amazing to have a network of mentors that have lived similar experiences or paths to supplement my guidance. The career conversation — Where I am
For the first part of the conversation, we focus on their reflection of what work has been energizing, depleting, and most challenging for them. We go through each item and they provide additional color if necessary. I might ask some prompting questions so that we get to the ‘Why’ behind each but I also make sure to bring, when I can, any related experience I have to that energizer, depleter, or challenge. It’s always nice to know you’re not alone in a particular area and even better if you can hear a firsthand account of how that has evolved for someone else.
The career conversation — Where I can go
Next is where we start putting pen to paper. I start by asking about the people with dream roles they provided and what about their role or company attracts them. After, I ask them to identify 1–3 career destinations they’d like to grow towards. The obvious is usually the next level on the career ladder but I encourage them to think past that and even past our company. That said, it can be as concrete as “Senior Product Designer” or as broad as “Management in some capacity”. (My favorite so far has been “A distinct, strong, and fun-filled legacy of design leadership”)
Now that we have a few headliners, I set five minutes on the clock and together we brainstorm competencies and activities for that career destination.
Under Senior Product Designers, you may have:
- Helps craft and lead vision in product area
- Co-owns quarterly planning with product vertical with Product Managers and Engineering partners
Management in some capacity can look like:
- Support designers in navigating pillar level initiatives
- Mentor junior designers
Once we have exhausted all the competencies and activities that come to mind, I ask them to vote on the top 6–8 they’d like to work on in the next quarter. The top competencies and activities move to the next column: How Can I Get There.
The career conversation — How I can get there
Time to bring more specificity to the process. Using the top voted items from the previous ‘Where I can go’ column as our anchor, we brainstorm what internal and external opportunities there are to develop the competency or get exposure to the activity. The more concrete and specific the opportunity, the better. Some examples:
- Be the source of support and mentorship for [designer’s name] through check-ins and regular one-on-one’s.
- Design a vision creation workshop for X team in the next quarter
- Increase confidence of X team roadmap by planning and driving customer research on Y
- Co-develop what a summer internship program can look like
Once all of the opportunities are noted, you are ready to create an action plan for the next quarter.
The career conversation — My Action Plan
With so many great opportunities mapped out, it is easy to want to overcommit to pursuing them all. However, just like prioritizing feature work, creating a focused action plan that is both achievable but challenging is critical to setting yourself up for success. To do this, I create four sections under ‘My Action Plan’:
- One opportunity within [product team name]
- One horizontal opportunity across product teams
- One opportunity within the design org
- One opportunity on my own
This typically covers various scopes and altitudes that will allow my design team to grow holistically. I ask the designer to bring the top two opportunities for each section and then vote between the two on their top priority. This allows us to have a clear priority while also having a stretch goal in case they accomplish the first one earlier than expected.
Follow-up
Once this action plan is created, the real work starts. It is important to revisit these goals to track progress but also see if there are any adjustments needed. Changes to our development plan is just a reflection of self-reflection! Be flexible if a designer understands more about where they’d like to grow or if an exciting opportunity surfaces that wasn’t there before. Just document it and continue to monitor their progress over time. Our plan should flex to reflect our changing aspirations so that we appropriately invest the time and resources towards our north star.
In the spirit of being iterative, I’d love to hear your feedback on this approach or methods you’ve used to have productive career conversations! Here is the template I used above. Feel free to comment below, reach out on Twitter @KwasiTwumA, or message me on LinkedIn.
