A Roadmap to Making Better Choices: Developing Curiosity, Discernment, and Agency

Over the last couple of years, I've been playing more of a mentorship role in my professional life as I transition into my mid-career. It's been an exciting time and I'm grateful to those that have trusted me to advise them. I've gotten to mentor and peer mentor early-stage professionals in product, yes, but also across many other functions. I've also been able to use my negotiation skills to support these professionals. I typically deploy these skills to support organizational partnership contract formation or management, but I've found I also enjoy supporting negotiated offers, promotions, and exits for employees across these other functions.

Even though I don't have expertise across these functions, I find my conversations look quite similar. My role in the conversations is to act as a honing blade for the other person, pointing them in the right direction by asking questions, clearly expressing my thinking and reasoning (whether I agree with them or not). I also aim to give them permission to come to their own conclusions (not that they need that permission from me). Recently, my mentorship conversations have increasingly required that I also play the role of whetstone, helping the other person to sharpen skills that are atrophying in response to the poor leadership that riddles today's markets.

While there are many skills, both soft and hard, that a professional needs to thrive in today's workforce, I am only qualified to teach people so many. Luckily, just about every one of these particular conversations boils down to the need to sharpen at least one of three specific skills that I'm familiar with: curiosity, discernment, and agency.

I find the best way to encourage these skills is to demonstrate them while in conversation. I start with my own curiosity. Before making any statements, I prefer to ask a ton of questions. Of course, to be effective in this I need to know what questions to ask and how to ask my questions in a way that drives toward the necessary answers.

Though her book is about product discovery, Teresa Torres's Continuous Discovery Habits, particularly the "Continuous Interviewing" chapter, is a great resource for skilling up here for those interested. In this early part of the conversation, I'm trying to understand:

• What is the challenge the person I'm talking with is facing?;
• What important events in their story have happened and what part of the story are they currently in?; and
• What are their motivations?

The hope is that by the mid-point of the conversation, I have a firm enough grasp on the support the person needs that I understand how I can best help them, including understanding where I cannot.

As the conversation begins shifting towards its back half, it starts feeling more strategic and I begin layering in statements. This helps to model the discernment that the person will need to accomplish their goals. The questions never stop, but by this point, they are more specific and I am expressing more of my opinions on the matter at hand.

I make a point of leading with where I am unable to offer the advisement they need – hopefully, I can point them in the right direction of resources, whether that's another person, a book, or something else – so that the remainder of our conversation is laser-focused on areas where I help can get them unstuck more immediately. In trying to understand where I can offer support, I typically ask some variation of the following:

• What are all the possible outcomes?
• What is your ideal outcome?;
• What is the worst possible outcome?;
• What is the most likely outcome?;
• What is the worst possible outcome you will accept?;
• Who has the decision-making power in the situation?; and
• What action will you take for each possible outcome?

Only after these questions have been answered can I ask: Where, specifically, can I offer my skills to assist you? For some, this is legal research to better inform the likelihood of certain outcomes; for others, this is contract review and redlining. And there are plenty of other requests for assistance between the two. I'm also sure to directly offer things I think I could do to help. Some people don't want any further help, but at the very least they walk away from the conversation knowing they have my support.

All of this is the heart of the conversation, where I attempt to use my negotiation skills and experiences to prime the person I'm talking with for the future negotiations that will surely come as they proceed. The critical piece of this, though, is that they understand that the first and last person they must negotiate with is themselves. As such, they need to be absolutely clear on their negotiating power.

Ultimately, I am trying to partner with the person to identify their BATNA (best alternative to a negotiated agreement). This identification process itself is a call to action for them to tap into and leverage their agency. The conversation serves as preparation that helps ready them and put them in an optimal mindset to effectively negotiate the best possible outcome for themselves.

As the conversation wraps up, I start asking the other person questions that boil down to: what are you going to do next? I use my position in the conversation to create a sense of urgency that serves as a call to action. At this stage of the conversation, I want the other person to begin identifying their agency in the situation at hand.

Agency has become a more common word in corporate vernacular over the years. Most of us want it; few of us seem to have it. It's that feeling that one has control over oneself and their actions, particularly within the scope of their role as an employee. A product executive recently told me that she didn't have decision rights over an in-app navigation bar. Her CEO micromanages decisions across their small startup. His overbearing nature creates incredibly low agency for employees throughout the organization, often resulting in missed opportunities for growth and, eventually, less than amicable exits. This is the type of situation most of us want to avoid.

Although it's fallen out of vogue, it used to be said more frequently that product managers are the CEO of their products. I'm not sure that that's ever true, but there are certainly degrees of how false it is. An entry-level employee doesn't expect to drive the entire corporate strategy, but they probably expect to be trusted to respond to an email (or at least to draft one and pass it to a manager for review and approval). In theory, we've all taken the time to demonstrate our skills through a series of interviews. The least we deserve is the trust to perform the core functions of our roles.

In agency law, a principal delegates duties to an agent, creating fiduciary duty, duty of care, and duty of loyalty responsibilities for the agent. In other words, the relationship is one that requires the agent to act in the best interest of the principal. However, the principal does not have the same duties to the agent; in fact, the principal pretty much just has the duty to make agreed-upon payments to the agent and legally protect them from certain claims.

Employees are agents of their employers. And no employee is going to intentionally disregard their duties when payments and legal protection are on the line. This isn't an easy job market. As such, employees need to understand what responsibilities are and are not theirs. This is the bounds of their agency as an employee. As principals, employers typically owe employees very little. But this is merely a contractual limitation.

In the spirit of modern employment, especially regarding knowledge work in tech, employees must remember they are principals of their careers and employers are the agents. Rather than a unidirectional, contractual relationship, the relationship between an employer and employee is one of mutual agency. Employees should recall that they drive the strategy of their careers. Knowing what to say "yes" to and, more importantly, what to say "no" to is critical to executing this strategy and should inform the ongoing negotiations an employee has with their employer, throughout their relationship.

When I talk with people about having agency, they tend to be fixated on crafting this sense within the scope of their role. This fixation causes them to forget to zoom out and harness it in the scope of their careers. In my conversations with people, what I am trying to do is awaken or re-awaken their sense of agency over their careers.

This requires that they are honest enough with themselves to have discernment about their current situation, what they want their situation to be, the delta between the two, and their ability to close that gap. Invariably, their assessment skills are indexed on their privilege. Quite simply, a less privileged person (be that because of race, gender, or other lived experiences) tends to have less of an ability to assess these details.

My hope is that my conversations with these people engender a stronger curiosity that enables them to further develop their discernment and agency. Ultimately, the goal is to encourage people to take back ownership of their lives, something that more of us lose every day as capitalism advances.

The bottom line is this: as people, we always have choices, even when the choices are suboptimal. Sometimes it just takes a conversation (or a few) with a trusted colleague to get clarity on what those choices are that we need to make and to remember that we are the ones with the power to make them. The darker reality is that we are often in positions where the best choice is to walk away, whatever action that requires and whatever risks come with it. Nothing ventured, nothing gained.

If you've read this and think it might be time for you to have a conversation like this with someone, please reach out. I'm just a message away.