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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.


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