UX Career Strategizer: Boost Your UX Career With This 4-Hour Workshop

Have you ever found yourself struggling with your career choices? Would you like to be more strategic about them? Then the UX Career Strategizer is just what you need. This 8-step workshop will help you figure out the best direction for your career, and plan strategic activities to reach your goals.

Have you ever found yourself struggling with your career choices? Would you like to be more strategic about them? Do you spend long hours while making decisions on job changes because you are unsure of them? How often do you map & analyze your career as thoroughly as you do it with the products or services you design?

We’ve been there too. Making thoughtful trade-offs about your UX career can be a hard nut to crack. Sometimes even harder than all those design decisions you arrive at daily to help products grow and companies thrive.

The UX Career Strategizer is an 8-step workshop that will help you embrace all the possible ways to grow, figure out the best direction for your career, and plan strategic activities to reach your goals. The good news is that, as a UX designer, you already have the perfect skills and methods to map, ideate, and create your career!
So get comfy, open up the UX Career Strategizer Miro board to follow the steps, and let’s get the ball rolling.

What is Career Strategy?  

Career Strategy is all decisions about things you will do and things you will not do to achieve your goals. Specifically, what efforts you need to make, what activities you should undertake, and what to reduce or resign from to be fulfilled and happy with your work life. What’s crucial in being strategic about your career is making thoughtful trade-offs and acknowledging that in most cases we can’t be superhero-unicorns who can be the best at everything. 

Not sure what your career goal is at this point? Not to worry, that’s exactly what we’ll be starting with.

Who is the UX Career Strategizer Workshop for?

You'll benefit from this workshop if:

  • You are a UX Designer (and you still want to be one in the future)
  • You’d like to set some goals regarding the future of your role and skills you’ll be using then
  • You need a framework to realistically plan strategic activities aiming at fulfilling your objectives

Moreover, this framework can help any UX leader or manager to support other designers in defining their growth trajectory. 

How it works

Before diving into the workshop details, you might want to decide how to organize your UX strategizing session. 

How long will it take me to complete it?

Based on the feedback from 12 designers this workshop was initially tested with, it should take you ~3–5hrs to finish all the steps. As a rule of thumb, it’s good to break it into two sessions on separate days to keep the energy levels high.

Should I do all the exercises in the predefined order?

UX Career Strategizer was designed as a complete journey. However, we’ve learned that some exercises work well for some people and some others are extremely valuable for other designers. There is no recipe for success, it all depends on your needs and wants regarding career planning. Therefore, you can go from step 1 to 8, but you can also pick some activities that resonate with you the most. 

Can I run it with a team?

Yes, absolutely! UX Career Strategizer is primarily designed as an individual activity. However, you can run it with a team. Here are some tips if you want to run the UX Career Strategizer in a group:

  • Keep the group relatively small (6-8 people) and make sure that there is a high level of mutual trust between the participants. 
  • At the beginning of the workshop make the agreement that all that happened in the session is fully confidential to create a more safe space for sharing. 
  • Work together alone. Let the participants work on their boards and then share the outcomes. 
  • Some people might not be eager to share all their plans and thoughts, especially if they made some surprising breakthroughs, and that’s okay.
  • Certain exercises will work well in pairs. For example, doing the Skills Matrix with a partner can be a great way to see how other members of the team perceive the level of your competencies (see more in the description of the exercise).

Learn to confidently facilitate any meeting or workshop

Should I run it in a digital or a physical space?

If you decide to use a fully digital workspace, we recommend using this Miro template. However, we’ve also tried strategizing in a fully analog way, with pen, paper (or whiteboard) plus some printed materials, and it’s as effective as the digital version and maybe even more fun. 

UX Career Strategizer workshop in action

Without further ado, let’s get to it!

Step 1/8: Define your values (15min)

 When thinking of your future path, the values you’re driven by at work count as one of the crucial elements that guide your career choices. Discovering your values is not only about exploring what you enjoy and like, but it’s primarily about defining what is meaningful for you even when time gets hard. 

Outcome of the exercise:

You will have your North Star, a collection of work-related values that will help you set the goals and make further choices.

Your task:

Think about what makes your day meaningful at work. What is important for you? In the good times and when you are trying not to choke under pressure or when you feel insecure or stressed.

Look at the list of values and start crossing them one by one to eliminate the ones that are less vital for your happiness and satisfaction.  When there are 5 values left, you are finished. Some tips and questions to get you started:

  1. Accept that it might feel uncomfortable to cross out “stability” or “success”, but your goal here is to define your core values, not a finite set you are driven by. 
  2. How do you decide how to behave at work? What motives drive your choices in case of some dilemmas? If let’s say, you accept a job offer from a company known for its environmental sustainability but offering a bit less salary than the other one, how does this choice reflect your values? 
  3. Who do you admire and why? What values do they embody? 
  4. Look at the peak powerful and bitter moments in your life, as they can reveal your values. Have you recently been happy about winning a peer award? Maybe your value is “helping others” or “leadership”?
An example of defining your career values

Step 2/8: Outline your strategic career goal (15min)

As you’ve just defined your core values, you are ready to create a draft of your goal. Yes, just a draft! Just as you create a sketch before you are ready to build a high-resolution prototype, let’s first define your high-level career goal.

Outcome of the exercise:

  • You will have a general direction for your career that you’ll make more specific in the following steps.

Your task:

Draft your goal by completing the sentences in the template. Make sure your objectives are linked to the values you’ve just defined.  For instance, if your core value is “open communication” and “work-life balance”, your goal might be to “work in the culture of regular, honest feedback” and “work from home 80% FTE to spend a bigger portion of my day with family”. Alternatively, jot down your goal and then verify each part of it asking “which of my core values does it reflect and how?”. 

Remember that this goal outline is something to keep moving you forward. You can tweak it later when you get more insights while strategizing.

An example of outlining your strategic career goal

Step 3/8: Map your Org & Role (40min)

It can be a challenge to embrace all the possible facets of the organizations and design roles and achieve clarity regarding your preferences in this matter. Especially if you are under pressure of deciding on any job changes. 

That’s why it might be a worthwhile idea to understand what your must-haves and nice-to-haves are in advance. What are the qualities of your perfect organization? To what extent is this place similar or different from where you are now? What is your dream role like? What product do you design? Who are your teammates?

Learn to confidently facilitate any meeting or workshop

We identified some possible answers to those questions (and some more!) so that you don’t need to worry about coming up with ideas but simply mark your choices on the map.

Outcome of the exercise:

  • You’ll gain clarity about where you are now and where you want to be in terms of the company and role. You might note some discrepancies between the current and future state. 
  • You’ll pinpoint which qualities of organizations and roles are crucial for you. They will act as guidance for your further decisions.

Your task:

Take a glance at the map of predefined qualities, or rather choices you make each time you decide to change your job or something about it. 

First, think of the current situation and mark where you are now. Then review all the qualities of organizations and roles again and signify where you want to be. 

We’ve learned that people often have intermediate and more far-fetched goals. Therefore, you can also mark your ultimate goals and wishes.

Last but not least, prioritize the main categories (tier 1). Mark them as very important, somewhat important, and not important to reflect how strongly they should guide your choices.

An example of mapping your role and organisation

Step 4/8: Assess the gap between your current vs. desired skills level (40min)

After you mapped your org & role, you might find yourself either seeing overlaps or discrepancies between the current and the desired state. No matter what result you ended up with, you need to now identify the skills you need to brush up on to either thrive in your current workplace or to be successful in that role and org you envision yourself at.

Note that this set of UX skills we propose here is probably not a one-size-fits-all collection (looking for more UX skills to add to your toolbox, you can get some inspiration from the articles here or here)  You might want to add or replace some UX superpowers so that it better fits your needs. We know that some designers tend to add some product management skills, some others tweak the settings so that they add coding or to the wheel. Remember: this workshop is for you so make it work for you. 

Outcome of the exercise:

  • You will gain a profound insight into your current skills.
  • You will know which skills you need to upgrade and to what extent
  • You might also be able to make your skills assessments more realistic if you’re doing this activity with a trusted colleague or manager.


Your task:

Start with indicating the skills you truly like using, no matter how good you are at them.

Get familiar with the skills levels on the top of the canvas. Now start assessing the level of each skill as of now. Stay down-to-earth and close to facts. Refrain from diminishing or overestimating your skills. Try to recall specific situations that reveal your true skill level. Think of some feedback you got from your colleagues. Does your company provide job descriptions? If so, what are the requirements you already meet? If you provide mentoring on UX Writing, you probably score 8 as the scale suggests. If you’ve just read a few articles or a book on Workshop Facilitation, you might score 1, as you haven’t practiced yet. 

Next, keeping in mind your goal and desired org & role, draw your desired skill levels. Think of the superpowers that would bring you closer to where you want to be.

Pro Tip: Team up with a  trusted colleague or leader and ask them to assess your skills in the same manner. Compare your self-assessment and the perspective of another person. Can you see anything to tweak in your map?

skill assessment matrix

Step 5/8: Allocate your time & energy (10min)

Time, energy, money, ability to focus and learn, and so on - all those resources are limited. That’s why we NEED to make strategic trade-offs. Otherwise, you won’t be able to keep up the consistency, especially when your time and energy budgets will be challenged.

Outcomes of the exercise

  • You will have a more realistic outlook on spending time on taking your skills to the next level.
  • You will get yourself ready for defining specific actions that will eventually make your high-priority skills shine like diamonds.

Your task:

Copy-paste the skills you decided to elevate from the Skills Matrix. 

All the time and energy you can invest in developing your skillset equals 100%. Allocate the percentage of your time & energy budget you want to invest in certain skills. 

Pro Tip: You can invest 100% of your time & energy budget in a single skill or you might want to distribute it between several of them. Just make sure the sum of your % equals 100. 

Example of prioritising time and energy

Step 6/8: Plan Strategic Activities (40min)

Congrats on being strategic about your skills! You’ve already made thoughtful trade-offs and now it’s time to dive into details of what specific and tangible actions you will take to master your competencies. 

Pro Tip: if you invested in more than 4 skills, consider doing this exercise with breaks and start from the 3-4 top-invested ones. 

Outcomes of the exercise:

  • You will end up with a series of concrete activities that will boost your skill levels.
  • You will have a clear recipe to address the skills shortcomings that might be experiencing.
  • You will be able to monitor and measure your progress.

Your Task:

For each skill you decided to invest in the previous exercise, run the same sequence of steps. Let’s say that you committed to working on the “Workshop Facilitation”.

  1. First, think about any struggles you might experience due to some shortages in this skill. Maybe you observed that people are not super-engaged in the sessions you moderate? Or you feel anxious while speaking in front of a crowd? Note each problem on a separate post-it.
  1. Now think of what you can do to address your struggles. Naturally, one solution can eliminate one or a few issues. 
  1. Add some ideas on how you can simply elevate the skill you are focusing on. Ultimately, you need to both defeat your pains and create pure gains.

Pro tip: Quantity over quality! The more ideas you produce now the better - we aim at ending up with a comprehensive menu of actions to choose from.   

  1. Find out the metrics that will help you monitor your progress. Supposing your issue was related to the lack of self-confidence while facilitating. Ask yourself: How will I know, how can I recognize that I am more self-confident? How will I feel and behave? It could be for instance ‘I am confident enough to be flexible and change the activities if needed during the workshop itself”.
Template for Plan Strategic Activities

Step 7/8: Make last strategic trade-offs (15min)

Once you know what to do, the question remains: what not to do.

UX career strategy is not only about things we get involved in but also about activities we choose to reduce or eliminate to make room for what’s critical for our goals. Eventually (almost) none of us is capable of practicing UX research, reading about UX leadership, doing some cute animations, and mastering understanding of business at the very same time, right?

Let’s now eliminate and reduce some activities that you engage in to make more time and save more energy for what is strategically important for you.

Outcome of the exercise:

  • You will free up some time and energy for doing your strategic activities
  • You will know how to use your resources even more thoughtfully. 

Your task:

The CREATE and RAISE quarters represent the strategic activities you’ve planned to engage in. You can copy them to the canvas if you like.

The REDUCE and ELIMINATE quarters represent all things you choose to consciously refrain from to make more room for what’s important for you. Think of your days. Observe what potentially drains your energy and what you are willing to give up or decrease. Maybe you need to participate in fewer meetings? Maybe multitasking makes you tired? Or too much UI-related work hangs on your task list although you wanted to do more research. What’s not productive or simply not in line with your objectives?  

Pro Tip: It can be work-related and it can be very personal. Be honest with yourself. List small things and those big beasts too.

Example of making strategic career trade-offs

Step 8/8: WOOP Your Career (15min)

Did you know that thinking about the obstacles in the path to achieving your career goals can increase the chances of success? That’s what 20 years of research shows and that’s exactly what we will use to increase the likelihood of a positive scenario happening. 

A well-documented mental strategy, WOOP, is a set of simple thought triggers that can be used to find and fulfill your wishes. The main premise is that while we engage in daydreaming, we should incorporate imagining the obstacles that jeopardize our dreams and wishes.

Outcomes of the exercise:

You will have an actionable ‘rescue plan’ that will help you deal with the obstacles that can stand in the way to achieving the career goals you’ve just strategized.

Your task:

  1. Write down your key wish or ambition regarding your career. 
  2. What would be the best scenario? Imagine the best possible outcome and write it down.
  3. Now take a while and think of any obstacles, especially internal ones, that could prevent this scenario from happening. Note it down.
  4. Then make a plan. Name one specific action you will take if the obstacle steps in your way. How would you overcome it? 
  5. Make an If-Then plan. If I meet this obstacle, I will do this and that. Repeat it and keep it in mind in case you face the problem.
WOOP strategy matrix

Design your career

Companies use strategy to reach their goals even when conditions are uncertain. Strategy acts as a North Star. It guides decisions so that they are more optimal and consistent over time. As individuals, we can use similar principles for our careers - get strategic by thoughtfully engaging in certain activities and intentionally ditching some others. 

Becoming more strategic is a never-ending journey in search of feeling fulfilled at work. Yet, it’s certainly worth the effort. We hope that the UX Career Strategizer workshop can make this path a tiny less twisty and bumpy for you.    

Keep up with what the Strategizer workshop team is up to:

Kasia is here

Wojtek is here


Katarzyna Małkiewicz & Wojciech Zasina

We're two designers based in Wrocław, Poland. Passionate about workshops, strategy, and mapping experiences. Constantly in search of new ways to change and grow. ‍