I am stuck in my career. How can coaching help?

"I am stuck in my career" is the most popular issue clients bring to coaching. Clients say that they don't understand why everyone around them is getting promoted before them and wonder how to make their manager notice their value. So, how does coaching help with this request? It helps in a few different ways:

• Strategy & analysis: the coach becomes the client's thinking partner in defining a strategy for getting promoted.

• Feedback loop: the coach constantly requests the client to take small steps forward and then encourages him/her to asses results and harvest the learning.

• Holding the big picture: most notably, coaching helps stay on track by connecting the immediate issue ("I am stuck in my career") to the big picture of the client's fulfillment. Although it sounds fuzzy, that is what makes coaching different from a frustrating to-do list.

Now, let's look at each of these aspects in more detail.

Strategy & analysis

One would think that a person can use their own brainpower to analyze what it takes to get promoted. Not to mention, every manager responds to this question by pulling up a massive spreadsheet with leveling criteria. Yet, people get stuck and genuinely don't know what to do. It often happens because one is too busy "doing the work" and finds no time to lift his/her head to choose the work that would result in promotion. It may also be that one has a blind spot in some areas.

The coach's job here is not only to bring back that annoying spreadsheet but to introduce additional ways of thinking about the problem. For example, looking at people in your organization who are one step above you in their careers and analyzing what differentiates them. There is that saying that a promotion is just a formal recognition of the competencies one already demonstrates day to day. This saying is frustrating because managers most often use it to justify why one won't be promoted in this cycle. Yet, in coaching, the client will use this principle to their benefit: analyzing the competencies of the people one step above gives the client an idea of behaviors and skills they need to demonstrate. The coach will also help think through how to learn these skills — but more on that later.

Another obvious source of information that people somehow overlook is the manager's direct feedback. Sounds trivial, right? Well, it's not uncommon for people to expect a promotion while completely ignoring what their manager said. The reasons for that can include busy schedules, cognitive overload, a strained relationship with the manager, and more. That is exactly why it is helpful to have a coach who will shed light on one's blind spots.

In the end, the list of competencies or focus areas will be specific to the client, but here is a list of usual areas:

1. Excellent execution in your current product areas. That makes sense, right? Turns out, not always and not to everyone — perhaps, again, because people are often too busy to step back and assess how they are doing.

2. Demonstrated ability to take on more strategic work. Notice that this is not just about your ability to do more. It is about showing that you can think more strategically. This may include proposing changes to a broader product portfolio, identifying overlooked business problems of your business unit, proposals on how to make your product area more impactful, and more.

3. Leadership skills. Now, that's broad; I get it. As a coach, I would suggest defining this in more concrete terms by observing other leaders: how do they show leadership; what makes them stand out? Some common answers include confidence, expertise in their area, and the ability to help and mentor others. Yet again, a good coach would analyze what leadership means to an individual coachee.

4. Helping one's manager. One's promotion ultimately depends on their manager's perception, not on that spreadsheet with defined criteria. So, an employee seeking promotion needs to ask themselves how they can help their manager. It may involve proposing process changes to make the team more effective, taking over some mundane work the manager currently carries, and more. A good start would be to ask the manager what they struggle the most with.

5. Strong relationships with the manager's peers. Yes, the manager will be the ultimate decision maker on one's promotion, but in many organizations, the manager will ask around before finalizing that decision. Hence, it is wise to build strong relationships with other stakeholders (e.g., engineering, sales, marketing, etc.).
   

Frankly, there is no rocket science in creating a list like this. Yet, what is surprisingly rare is being intentional and following through on your plans. That is what our next discussion is about.

Continuous Action & Feedback Loop

Now the real work begins. This is where a surprising number of people need the most help: taking continuous incremental actions in the areas defined above, learning from the outcomes, and planning the next action. Sounds simple, right? At the end of the day, that is the core of product management. Yet, most people do not apply these principles to their lives and careers.

What does this work look like in coaching? First, the coach will encourage the client to look at every area they defined above and reflect on what success would look like in that area. E.g., what would it look like for this specific client to demonstrate their ability to take on more strategic work? Maybe it means presenting to the manager three strategic ideas that span beyond the scope of one's product; perhaps it means proposing new solutions to known business problems that are top of mind for the manager. The client needs to define what success can look like and how it can be measured; the coach is there to help by asking clarifying questions.

Now every area in the overall plan has a more specific definition. But it's not yet time to celebrate. Nothing will change until the client takes action in their actual workplace. The coach's job here is to help the client define a specific action that the client will commit to doing before the next session. The step can be small, but it needs to propel the client toward their goals and stretch the client.

Every next session will start with the coach checking in on the client's last taken action. But the coaching is not exactly like a nagging parent. The focus of this check-in is always on learning. What did the client learn from taking action? What did they learn from the outcome of their action? What did they learn about themselves from not taking action? Coaching is a no-judgment zone; as long as the client is learning and moving forward. This is at the core of coaching: learning through action. Not through dwelling on the problem for hours; not through talking oneself out of action— but through action. Again, this principle should be familiar to all PMs: we all preach the good ol' lean feedback loop. Now we just have to walk the walk.

Holding the big picture

Okay, so we figured out a strategy and followed through by taking incremental actions. What else is left to do? Well, not much—except that all of this work would be exhausting if it were not clearly connected to the client's values and broader goals.

The deal is, getting promoted is a goal with limited power on its own. There is something behind it that really matters to the client, and it is different for everyone. For someone, getting promoted means getting access to more creative work; for someone else, the end goal is to make more money to save up for starting a business; for someone else, it is about being able to impact more people positively. That vision and the values behind it have a lot more power in driving our behavior than the mid-term goal of getting promoted.

Having the vision doesn't take away the work, but it puts immediate obstacles in a different perspective. Sounds fuzzy? Well, remember that one guy at work who is always grumpy, no matter what he does? He sees every project as a hopeless mess—and indeed, he gets stuck repeatedly. But then there is this other person who is always enthusiastic. They see those same projects as a fun puzzle—and somehow, they get things done (and piss fewer people off, I might add). Who is right? They both are: one's perspective changes one's possibilities. And a perspective lit by one's vision and values opens way more options than a dark fight for a promotion.

The coach's job here is to help one hold that vision front and center. Without that extra help, people tend to fall back on being reactive and solving immediate problems. While being a problem-solver is good for a lot of things, there are two issues with that. First, some of these problems need not be solved to reach one's long-term vision. And second — it is just exhausting and demotivating to solve problems that have no clear connection to one's vision and values. Hence, people quit.

After 1500 words, a summary is in order. An observant reader must have noticed that coaching works in trivial ways—which does not take away its power. Most of the time, we get stuck in our careers for trivial reasons, so no wonder the remedy for that looks straightforward too:

• A good coach helps the client analyze their current situation, identify competency gaps, and define a strategy for bridging them;

• The coach helps the client take continuous action and learn from the outcomes.

• A great coach ensures this journey doesn't turn into torture by helping the client connect daily actions to their values and vision.

From Design to Product Management

Coaching designers, I noticed that the desire to switch from Design to Product Management is common. After spending several years in UX, it is natural to become curious about the phases that precede design: market analysis, ideation, customer validation, prioritization, etc. Some of this interest comes from frustration with existing product managers, while another part stems from the desire to grow and evolve. But the path to making this transition is unclear. What courses to take? What to read? How to find the first product job? Although this transition can feel uncertain, moving from Design to Product Management is attainable: many of your skills will transfer to the new role and give you a competitive advantage, while other skills can be learned on the job—as long as you carefully pick your first products and find a supportive manager.

Many design skills are transferable to product management.

Although product management and design are different disciplines, many of your skills will be transferable. Most importantly, your ability to think about user problems will remain a critical asset. While it is so natural for designers to think about the user, not everyone can do it: others (even other PMs!) may jump to discussing the technology, specific features, or messaging around the product. But you know from your design experience that jumping to tactics is counterproductive until you completely understand your customer's problem. Your experience will serve the team by keeping everybody focused on the right questions at the right time. Hence, your ability to hold the user front and center will remain essential and help you stand out in your new role.

Another valuable skill easily transferable to the new job is your ability to visualize ideas. This skill will allow you to communicate your vision to the team effectively. While most PMs solve this problem by creating PowerPoint slides with some diagrams and lots of text, this artifact only gets the team so far. Such vision presentations leave much room for interpretation and often fail to inspire the team. Luckily, you can do more: create vision prototypes and videos to convey what you have in mind and set the direction for the team. Your stakeholders and your scrum team will appreciate the added clarity. Thus, your ability to visualize ideas effectively will help create alignment.

Your third valuable asset may seem trivial, but it's not: it is your knowledge of how to work with designers! Remember how frustrated you would sometimes get when a PM was being way too vague or, on the contrary, too specific in their request? Remember how you would spend extra cycles trying to agree on what is needed? Well, as a PM, you will do better. You know how to present your asks in a way that gives designers room for creativity and exploration but defines clear boundaries around the task. This will eliminate extra cycles and allow designers on your team to do their best work. Your experience being a designer will inform your way of working with your design team.

Finally, another transferable skill you possess is ensuring the quality of UX implementation. Unlike other PMs who might miss UX defects at the end of a sprint (or worse yet—a release), you will not let that happen because these details have always been important to you. After each engineering sprint, you will be able to see how your product is shaping up and catch any deviations from the design. Moreover, if you find any discrepancies, you will now be able to have them fixed — unlike before when you had to negotiate priorities with your product manager first. Now it will be all within your control, and you will b able to achieve flawless design implementation.

In summary, after transitioning to the new role, you will find that many of your design skills are still relevant and give you a competitive advantage over other PMs. Your abilities to think about user problems, visualize your ideas, work with other designers and catch minor UI defects will help you in your new role.

You will be able to learn other skills on the job.

While many of your existing skills will remain relevant, you will be able to acquire the rest on the job. Of course, product management takes more than good design, and it will be essential to learn the core of this role. Luckily, it is not rocket science, and it is entirely possible to learn it as you go by being reflective and seeking mentorship. The most critical competency you will need to acquire is business acumen. Indeed, this is the core of the product management job, which is why there is a saying that a product manager is the CEO of one product. You will need to learn how to find product-market fit, test your ideas as cheaply as possible, measure everything you do in terms of business value, and much more. Yet, while it may sound intimidating, you can figure it all out by reading good books, thinking through the work at hand, and asking your manager for guidance.

Another skill that will be critical to learn is managing customer relationships. Although you probably have other people in the company that focus solely on customer relations, you will need to master this skill too. As part of your work, you will be interviewing customers to learn their problems, presenting solutions to get their feedback, holding their hands to adopt your product, and maintaining relationships with them to be seen as a trusted partner. This part of the job may be pretty uncomfortable because it requires much more social exposure than the job of a designer. Yet, you will be able to develop the necessary soft skills with time; if an impossible introvert like me has been able to do it, you will also be able to.

Finally, one more skill you will master on the job is consensus-building. As a product manager, you will not have any direct reports, but you will need to influence many people to follow your vision. This will require more than excellent communication skills. Apart from being a good communicator, you will need to learn how to manage the requests, desires, and expectations of numerous stakeholders, such as your engineering, sales, marketing, product success, and many more. Sometimes these people's opinions will contradict each other; sometimes, they will be far from your own. While these people do not own the product roadmap, you will not be able to ignore their views; you will need to bring them on board to succeed. Luckily, this skill will also come naturally with practice. In fact, practice is the only way to learn it, and your mastery will grow continuously over time.

All in all, although there will be a lot to learn in the new role, and you should be ready to be a beginner again, it will be possible to learn new skills while working on your first few products. Competencies like business acumen, customer relations, and stakeholder management will come over time if you regularly reflect on what you do, think critically about your next steps, and learn from your actions.

Remember to find suitable first products and a supportive manager.

Although this role change will require you to learn some new competencies on the job, you can smoothen the transition by carefully choosing the first few products you own. First, it may be helpful to start with products that require a lot of design work (as opposed to, say, a change of data model or building new integrations). This type of work will allow you to fully leverage your existing skills while adding a few new responsibilities at a time (e.g., writing user stories and working with engineering). Thus, you will be able to remain confident even though you have a lot to learn. The second tactic to help you make this transition easy is to continue designing — for now. Although you can delegate it to a designer immediately, keeping this responsibility with you for some time can be more comfortable. Holding on to your design responsibilities can give you more confidence: even though there may be gaps in your product management skillset, you are still delivering tremendous value. Not to mention, your engineering team will appreciate the quick turnaround from having one person play the roles of a PM and a designer. In short, choosing frontend-heavy products and using your design skills fully will help you feel more confident while changing positions.

Another way to smoothen this transition immensely is by working with a manager who is willing to help you fill the gaps. I cannot stress enough how important it is to find a good leader—it is critical for any tech career, but especially so when you are in a vulnerable position of learning a new role. So find a leader who sees value in what you bring to the table and wants to invest in your growth. In contrast, a manager who is hypercritical and controlling would make this transition near impossible (they can make your life miserable without any transition, too, so why work for them, to begin with?). So choose your manager wisely.

In summary

It is quite natural for a designer to want to move to product management after some time. A product management role gives one a broader range of responsibilities, more visibility, and a higher impact on the success of the product. In addition, stepping into this role gives one a shot at fixing what often appears to be broken: unclear prioritization, poor front-end execution, and constant descoping decisions. While this opportunity is appealing, many designers don't know where to start and feel intimidated by the journey ahead. Yet, while there will be bumps along the way, moving from Design to Product Management is attainable. As you start this transition, you will find that many of your design skills are still relevant and give you a competitive advantage. Although you will be missing some core product management skills, you will find ways to learn them on the job. Finally, you can make this whole journey smoother by choosing products that allow you to leverage your existing skills and relying on a supportive manager who can help you grow in the remaining areas.

Promotion to a manager

As you think about your career in product or design, you see two options: further growth as an individual contributor or a transition to management. Many people choose the management route: the individual contributor path tends to be shorter and does not promise the same level of visibility. As a result, competition for management positions tends to be high. While the field is so competitive, you can maximize your chances of promotion by purposefully demonstrating relevant competencies, such as your understanding of the business, leadership skills, and the ability to run large-scale projects.

Being a leader means thinking about your product in the context of the business and helping others do the same, and it requires that you understand the business better than anyone else.

• What problems does our product solve?

• Who are your customers?

• Who are your competitors?

• How is your product different?

• What industry trends are relevant to your business?

• Who sells your product and how? When do your sellers win, and when do they lose?

• What are the biggest threats and opportunities for your product?

Understanding the answers to these questions will not only help you make wise roadmap decisions; it will also allow you competently represent your product in leadership and analyst discussions and help other team members be effective at their jobs. Luckily, you definitely have coworkers who would be happy to share their knowledge. Ask your peers, your manager, and that guy who has been in the company for 15 years. Save any materials they share with you and add your own research. Knowing the business will be tremendously helpful in positioning yourself for a promotion.

Apart from business acumen, another critical competency you will need to demonstrate is leadership skills. Even though you are not a manager yet, start acting as a leader, and promotion will follow. One of the ways to do it is by helping strengthen the team. For example, you can propose and implement improvements for some of the team processes (e.g., competitive analysis, release management, design reviews, etc.). Another way to act as a leader is by helping your manager with some of their responsibilities. For instance, delivering some presentations in cross-functional forums, managing a specific client relationship, or keeping the team on track with critical deliverables—there can be many options, so ask your manager what would be the most helpful. Finally, another way to be recognized as a leader is by becoming an expert that other team members want to reach out to for help and advice. So if you already have unique expertise, make sure others on the team know about it and feel welcome to leverage it. In short, demonstrating your leadership skills will position you perfectly for the manager role.

One final way to secure your promotion is to choose impactful projects that let your skill set shine. You can be a fantastic PM or a kick-ass designer, but it won't get you the role you want unless others see your impact. So, given an opportunity, choose the projects of high visibility and the highest impact on the business. In addition, make sure that what you work on allows you to demonstrate your best skills; choose projects that require innovation, strategic thinking, and creativity. One added benefit of impactful products is that they tend to grow, opening up opportunities to form a team under you. Thus, be purposeful in choosing your products.

To summarize, although there is a lot of competition for management roles, you can increase your chances for that promotion by acquiring and demonstrating relevant skills. First, understanding the business will allow you to make wiser product decisions and help your team do the same. Second, acting as a leader by strengthening the team will demonstrate your abilities to perform in a management role. Finally, choosing impactful large-scale projects will ensure that your talent will get recognized.