Letter to a mid level designer

Originally published to my substack here.

A few years ago I wrote a Letter to a junior designer. I figure it’s time to write an open letter to all the folks still in the middle ground between junior and senior. You’re a few years in, definitely not the junior designer you used to be, and looking for the path to the next level. To get to the next level you’re often asked to “be more strategic” but still expected to execute the day-to-day tactical tasks. These are the things I wished I had known earlier in my career.

The following applies to many roles outside of design as well.

Your manager isn’t planning your career

Ideally your manager should support you in this process but they can’t tell you what you want. Getting clear about the experiences you want to have in your career will help you to form your goals, areas for growth, and determine your next steps. It’s also totally okay to admit that you don’t know what you want and focus your goals around exploring. What you put into your career planning is what you get out of it. This clarity will allow you to be more decisive around what kind of projects to take, when to switch teams, or change jobs.

Your manager is a great partner in helping you think through opportunities that will align with your goals but they aren’t the only resource you have. Discussing your goals and growth areas with your peers can help uncover unique opportunities as well. For example letting your team know that you want to grow as a public speaker/presenter makes room for you to take more ownership in that realm. Your team is now able to cheer you on and give you considerate feedback while you step out of your comfort zone. As you share your intentions, others will be more open to sharing theirs as well.

Creating a document like David Hoang’s career hype doc is a great way to get started in cataloging where you’ve been so you can best determine where to go next.

Earn respect

If you started out as the intern who was still learning the basics, how will your coworkers ever see you as the senior designer you are today? Whether you’re starting at a new company or trying to get noticed for that next promotion at your current company, covering the basics of rapport building can go a long ways to earning respect. Here are a few key elements of building rapport with your colleagues.

• Deliver: When you agree to do a thing do you deliver it on time in its entirety? If you’re not going to be on time do you communicate updates early and often?
• Consistency: Can you deliver on your commitments consistently? Sometimes things slip, it happens. But when it does, do you take the steps to ensure it won’t happen again in the same way?
• Team player: When was the last time you asked “How can I support you?” to one of your coworkers? If they need your support do you show up for them and deliver on time? Do you share in the successes and failures of your team?
• Stay engaged: One way to lean in is to take notes during meetings. It can help you both build context and guide the team to the next steps.I’ll never forget when a new (more senior) designer joined my team and very quickly started calling the shots and being the go to person for context. His trick was to take notes in every meeting we were in, capture action items, and send out the follow up message after the meeting. It kept him engaged in the conversation and holding the keys for what we did next. Taking notes in meetings is not a chore. It’s a position of power.

These are just a few elements of your performance that can hold back an otherwise talented performer. Folks who nail these four things are also the people that are enjoyable to work with and get the glowing reference calls when interviewing for a new job.

Commit thoughtfully

People will ask you to do all sorts of things as your skillset grows and if you’re anything like me it’s easy to get excited and say yes to all of them. However, keep in mind that folks often remember what you didn’t deliver more than what you did. Specifically, committing yourself and delivering all of it is better than stretching yourself and having to explain why a few commitments couldn’t be met. Put simply, commit to 80% of your realistic output so when you come through with the extra 20% it’s a nice surprise. Under promise and over deliver.

When considering taking on an additional project or effort here is the checklist I run through in the conversation:

• What does success look like? Clarify that you are both aligned on what you are going to deliver by when and how. For example, how you want to run a team meeting and how your manager runs a team meeting can look very different. What are the key outcomes of that meeting that determine success? Be okay with saying no to a request with unclear success criteria because if this request is too difficult to define it will often be difficult to satisfy all of the requirements.
• Do I have everything I need? Ensure that you have the resources and support from the folks you need to deliver this commitment on time. Consider making your commitment dependent on other key resources. For example don’t take on this extra project unless the requestor agrees to spend an additional hour per week answering questions and giving you feedback.
• What is the priority of this? Ask folks to prioritize this new task against your current work. Forcing the requestor to think about the larger implications can help you both align on an appropriate delivery time and sequence. Keep in mind that the more things you simultaneously commit to, the more context switching, the slower everything will go.

Seek feedback

The HR team at Patagonia found that employees who requested feedback were more likely to receive a higher bonus. By requesting feedback you’re lowering the awkward barriers for the other person to be honest about how you can improve. Here are a few actionable tips to gather more feedback:

• Timely: Directly after you give a presentation, run a meeting, have a hard discussion, ask for feedback while the experience is still fresh in the minds of others.
• Specific: Frame feedback in a way to learn something specific. Not “have any feedback?” Try “What do you think about my framing of the problem? Any advice on how I could make it more clear?”. The difference between good and great lives in the details.
• Curious humility: You will definitely get a wide range of feedback if you’re asking enough people. Not everything will be helpful and not everything will be easy to hear. Be curious and ask for clarity. Take what insights you can act on and leave behind what doesn’t fit. Remember you are not your job or even your performance at a single point in time.

Ask better questions

The night before I interviewed for my position at Lattice I debated trying to build another portfolio piece or planning questions for them. I chose to prepare questions specific for each person I was interviewing with and printed out pages to bring with me. I doubt anyone remembers what my portfolio looked like but they definitely remembered me as the guy with all the questions. Their answers to my thoughtfully crafted questions unlocked new insights about the company and gave me a greater confidence in my decision to join. Looking back my questions were definitely not perfect but the effort showed how much I cared about the opportunity and it allowed me to flip the table on the person interviewing me.

Taking the time to think about those incisive questions will help you understand a situation from all angles. You’ll use these skills of curiosity to learn from your mentors, assess candidates, grill future employers, and cultivate deeper personal relationships. Here are a few of my favorite question tips and techniques:

• Prepare ahead of time: Bring a cheat sheet. Life isn’t a math test. For some reason in modern society we think that smart people are supposed to be able to recall everything off the top of their head including impactful questions. I love breaking this unwritten expectation. I’ll bring out my notebook or phone filled with questions and start rattling them off in job interviews, dentist offices, first dates, or The Home Depot.
• There are no stupid questions: Being thoughtful enough to ask the same question from multiple angles to ensure your understanding is a powerful skill. I once participated in a whiteboard exercise where the candidate asked the panel so many questions about the exercise, the expectations, our perspectives that we essentially handed her the framework for success without fully realizing it until after the exercise. She got the job.
• Follow ups: Active listening and asking follow up questions will take the conversations to new levels. This is a skillset that takes practice but the CAR framework is a great way to keep yourself on track. CAR stands for Context, Action, Result — these are the key elements of a story you’ll watch out for and then inquire about if something is missing.

“Everyone has something to teach you, you just have to ask the right question.”
Alex Stupakov

Look for levers

In every situation you find yourself in you have a series of levers to pull that represent actions within your control that can affect the outcome. As you learn more and increase your skillset the number of levers available to you will increase. When things get tough, keep asking yourself what levers you have available. Whether it’s a people or design challenge, keep focused on what you can control and look for opportunities versus seeing everything as a problem. The words you choose to describe your current situation are important.

• Avoid this: Fixed mindset — I either have the skill or I don’t. I don’t want feedback. I have it all figured out already.
• Practice this: Growth mindset — I can improve. I benefit from feedback. I am constantly learning new things.

What challenge are you facing today that could use a reset? What would it be like to look again and describe the challenge from a growth mindset perspective? Read Mindset by Carol S. Dweck

To the next level

All of the above are things I’m still practicing and learning more about each day. These skills will be applied to everything that comes next in your career. Keep in mind that your journey will be as unique as you are. You’ll see people appear to pass you by or get left behind in the scramble to climb the achievements ladder. Trying to follow someone else’s path for the wrong reasons will leave you lost and frustrated. Figure out what the next level looks like to you, set your goals, and find a little joy in the journey.

What advice would you share with your younger-designer self? Reach out and share: Twitter(X) | Threads | Linkedin