How to empower a friend to make a career decision

Aligning values for success: A roadmap for helping a friend, mentee, or team member make fulfilling career choices

👋 Hi there, it’s Adam here with a special announcement: This week is our first post written by a guest author on Mind The Beet!   Arwa presented to my team recently her strategy for discovering your career values and using them to make pivotal decisions.   This post is a distillation of the advice, and it was so much fun collaborating with her on it.  You can follow her on LinkedIn. - Adam

By Arwa Tyebkhan, Group Product Manager for Microsoft OneDrive  

Have you ever found yourself or those around you asking questions like “What should I focus on in my role?” or “What should I spend my time building to set myself up for future success?” These big career questions can be overwhelming. Approaching these questions by leaning into how your choices align (or don’t align) with your own personal values can help you move forward with clarity.  

I’ve certainly faced these difficult questions several times in my career of 15 years (thus far). While I consider myself to be incredibly fortunate to have found my dream career path as a Product Manager in my first full-time role after school - there are so many choices and tradeoffs I've since navigated to find my daily joy. Five years into my career, I found myself wondering if I was stagnating when it came to building the PM-craft and I explored opportunities that would connect me with a team and culture that aimed to modernize the PM discipline in a way that I wanted to achieve for myself. Over the years, I’ve faced several moments of self-doubt as I watched many in my network make big career moves, wondering if I should follow their path. And whenever I’d find myself happy and fulfilled in my role, I would get in my own way by wondering if that fulfillment made me complacent.  

Over time, I have built an approach through countless conversations with mentors and mentees, managers and direct reports, friends and allies, that guides me through these moments. I have since regularly leveraged this for myself and for the many people I aim to support. This post describes this approach, and I hope you find value in it as well. 

The big (or small) pivotal moments in our careers 

Consider any of these life moments that one may be exploring. Each provides them an opportunity to think intentionally about their career choices:  

• Getting started: You may be talking with a new hire on the team to build a common understanding about the kind of work that best maps to their passions and skills.  

• Building forward: You may be discussing the kind of projects and challenges a direct report wants to take on as they work towards the next stage of their career. 

• Picking between jobs: You could be chatting with a mentee who is trying to decide which of three offers they should take.  

• Deciding on industry trends: You could be chatting with a friend who is looking at others making career moves and is wondering whether they should follow suit.  

• Regular reflection: Or you could be pondering your own next steps as you try to be intentional about your career. 

I call these "pivotal moments" and the goal of this post is to give you the tools to help a friend, mentee, or team member navigate and make the most of them. 

The big (and difficult) questions 

Pivotal moments in our careers often come with daunting questions that can feel like looking into a vast and unknown void. At their core, these questions come down to the thought, “How can I be happy/successful/fulfilled/<your choice of attribute here>?” Whether pondering which project to take on next, which company’s offer to accept, or how to make a career pivot, these kinds of decisions are not only important, but they come with some big feelings as well: fear, overwhelm, stress, pressure, and hope. 

Here’s the deal: when we approach these decisions with a broad goal like wanting to be “happy/successful/fulfilled,” we allow the ambiguity of that notion to create stress. Yet, while so many of us may yearn for those things, we are unique beings with our own blend of strengths, areas of growth, life circumstances, and energizers. Naturally, our path to get there needs to be individualized for us as well. 

Instead of focusing on broad goals like happiness or success, let’s dig deeper to understand the foundation of what would make one feel like they are progressing on a path that is true to them. 

What do you truly value? 

As with any big problem, we must break it into smaller pieces to help reason over it. Here, I’ll share an exercise you can leverage to empower others to do just that. It will enable them to navigate the question of “what do you really want?” by focusing on their values to get closer to that truth.  

First, let’s start with the list of values that I use for this exercise. These include elements about a role, team culture, people, incentives, product space, compensation, potential for learning, and several other attributes of one’s work experience. There may be others that are relevant to them as well - this is not a static list and please feel free to add any that should be considered. 

Unless one is being careful, it’s easy to aspire to “all the things” and decide that they want to have *all* the attributes of work that are important to them. Heads up - this is a trap! This is how one can end up with decision fatigue and lack of clarity. 

The challenge and the work lies in stack ranking the values to indicate what they truly value over something else. The tradeoffs they make are where the insights lie. 

Let’s dig into the exercise next. It will take some pre-work by your friend, one 60-min career values discission between the both of you, and a big dose of trust and curiosity. 

Prior to the discussion: Ask to prepare 

If someone approaches you with one of the big questions, suggest this exercise to them. Then, I’d highly recommend asking them to do the exercise of stack-ranking their values prior to your discussion together. This allows for a high-bandwidth discussion that can focus on many layers of the “why” behind the priorities and tradeoffs that the exercise uncovers. 

During the discussion: Enable deep reflection 

Your most important role as a manager, mentor, or friend having this conversation with someone is in creating a safe space that allows for self-reflection: to listen, understand deeply, and to ask great questions. Here are the three questions I’d recommend:  

Question 1: “How did you feel while you were doing this exercise?” 

Begin the exercise from a place of empathy. Your friend may respond by sharing a few feelings they experienced (fun, insightful, challenging, stressful), and this will give you some early insight into where they are.  

Question 2: “Let’s talk about this value. What does it mean to you? How do you think about it?” 

For each career value, ask them what it means to them. The words they use to describe each value, as well as body language and facial expression cues, all hold much insight. Try to understand how your friend relates to each value since their interpretation is an early lens on what matters to them. This is also a moment to consider sharing your own experience as well. For example, someone early in their career may not be thinking about culture deeply, and I’ve been able to add perspective on how I have seen team culture impact people’s career. 

Question 3: “Why did you stack rank this value over the next one?” for as many of the choices as time allows. 

Asking this question for every respective pair of career values in the list is key. This forces an articulation of the choices they have made - the “why” behind them - and gets to the heart of how they would make a choice. Put another way, what would they sacrifice in order to get something else? This is where the magic lies in determining the path that is right for them. The answers to the big questions lie in the articulation of the tradeoffs they would make to get closer to what they desire.  

There are some traps that are easy to fall into during this exercise as well, and you’ll want to be mindful to avoid them.  

• There is no “right” or “wrong” answer, just the “truthful” answer. Be careful to not implicitly or explicitly judge a person’s prioritized values, as they may pick up on your bias and feel the need to protect themselves by sharing less or amending their answers based on what they think you would approve of.  

• This session is about them, not you. While it's great to share some of your own experiences and perspectives, be clear about how your insights may be relevant to them. Avoid projecting your own values on them or taking up disproportional space through your own monologue.  

• It’s all about the journey, not the destination. The value from this discussion truly is in the process that identifies *how* one can make a good decision, now and in the future. Give this process all the time it needs to flourish, and as tempting as it may be - be careful not to jump to solutioning through it.   

After the discussion: Offer a follow up 

As a closing and optional step, offer to discuss any particularly challenging areas in depth as a focused discussion next. Additionally, there is value in doing this exercise on a semi-regular basis (every year or so) – offer that as an option to your friend. As our lives evolve, our circumstances change, and we grow as people, it’s not surprising that our stack-rank of values changes over time as well. 

I hope you found this approach helpful. Good luck on your journey as you work to empower those around you to define their paths based on their values and their truth. 💘