Crossposted from my blog.

I’m going to first describe a leader’s responsibility to their team because I don’t think it’s possible to develop good principles for working and communicating effectively with individuals without understanding the broader environment that the leader-individual relationship exists within.

Leaders have the following responsibilities towards their teams:

1. Identify your team's purpose — leaders must know their team's role in the success of the broader organization. A clear purpose helps the team adopt habits and actions essential for success, growth, and survival.
2. Identify the resources available to the team — this essentially is just the skills, talents, and attitudes of the individuals on the team, but it also includes material resources like tools, software, etc. The key recognition here is that individuals are, for lack of better words, dynamic resources - they perform at an extremely variable level depending on the context that they’re placed within. This means that leaders must not only learn individual talents but also the contexts in which those talents manifest most fully for everyone on the team.
3. Figure out how your team can best leverage the resources available to fulfill its purpose — this involves building a set of structures for the team that gives the team its best chance to fulfill its purpose properly given its resources.

The biggest challenge is that all of these are so dynamic. Unless you’re in a large and bureaucratic organization, things change all the time - reorganizations happen, people can join or leave, priorities shift, and so, so much more. It’s a constant challenge for leaders to stay on top of these changes and adapt the structures that their teams operate within.

The leader-individual relationship is extremely tough to manage within this context, especially given that the leader’s responsibility to the team and the organization as a whole must come ahead of their responsibility to each individual on their team^[1]. Despite this challenge, there is a set of principles leaders can adopt to not only help individuals navigate the changes and continue contributing effectively but also bring the best out of individuals and help them grow:

1. Make them feel seen
2. Help them understand what is happening
3. Provide meaning to their work

make them feel seen

There are two critical questions that every effective leader must help individuals they’re working with answer:

1. Where are you right now? — This question helps individuals understand the current context that they’re operating within, and how their strengths and weaknesses manifest within the outcomes that they’re currently experiencing.
2. Where do you want to go? — This question helps individuals create an aspirational model of themselves that they can work towards which excites them and provides additional meaning to the work that they’re currently engaged in.

I think the foundation of the best leader-individual relationship is alignment on the answers to these two questions and a constant intention to revisit and update them based on changing circumstances, goals, etc. The key thing is that these questions can’t be bounded within the context that your team is working in. In other words, they can’t solely focus on work and the specific responsibilities each of you has to the team and organization. It must be boundless, even if many of those answers aren’t directly relevant to the tasks at hand.

Essentially, in answering these two questions, you’re creating two models: one model that represents who they are right now, and another model that represents what they could be. As a leader, you need the person you’re working with to know that they’re seen for what they could be, but you need to manage them or lead them as the person that they’ve shown they are. Your leadership, feedback, and guidance help individuals bridge the gap between who they are and who they could be^[2].

The aspirational model is crucial. As a leader, if you’re invested in learning about each person and really care about helping them become the best versions of themselves, you’ll make them feel seen and cared for as complete individuals and not just as a means to an end for the organization. And this makes all the difference in the world^[3]. This model must be honest as well; you can’t just be lavishing praise and positivity that isn’t rooted in something you’ve honestly observed.

However, I’ve noticed that rarely do leaders give people too high of an opinion of themselves by heaping too much positivity or praise. The biggest challenge is that typically the aspirational model that leaders build is only tied to helping individuals best fulfill the current responsibilities tied to their current role^[4]. They’re not helping individuals feel seen as something larger than their job title or function, and I’ve never seen a situation where people are fully content with just getting better at their current role. Everyone has dreams and ambitions, and they won’t feel seen unless those ambitions are recognized^[5].

Doing the work of answering these questions not only makes people more engaged in the work that they’re doing, but it also makes it dramatically easier to share honest feedback. Praise feels less hollow because it will reinforce the potential that each person has and the effort they’re making in walking that path; it’s directly tied to their aspirations. Constructive criticism feels compassionate because people know the feedback is being shared not as a power move meant to belittle, but as truth meant to facilitate growth.

I’ve found that feedback is best shared in an action → impact approach. Instead of making normative judgments on others (i.e. saying something like “you’re really bad at making presentations), I prefer just sharing the actions I observed they took and the impact I observed their actions had on me, their teammates, and the organization. I use that as a starting point for discussion and seek to understand their perspective so that we can both arrive at a more contextually honest assessment of what happened. From there, we can work together to decide what to take from it.

I think this works well for both positive feedback and constructive criticism. It makes both feel more substantial and honest, and it ensures they’re not just passively receiving feedback, but are actively engaged in the process of extracting something meaningful from what happened before.

help them understand what is happening

A lot of the friction that I’ve seen occur between leaders and individuals can be attributed to the lack of transparency for no reason. Individuals and teams experience so much frustration when they don’t understand the broader context that they’re working in and the rationale for why certain decisions are being made.

As mentioned above, leaders have a lot of different responsibilities that aren’t directly visible to teams. They have to continuously update their team’s purpose amidst shifting organizational dynamics and refine the structures their team is operating within to ensure their team can best function in a way that serves the organization. All of this typically happens in the background.

The question I’m always left with is why does this happen in the background? Why aren’t teams and individuals given more context about what is happening in the background? While they may not be the decision-makers, they’re certainly important stakeholders in the outcome of whatever ends up happening. There are a few reasons that I’ve seen, but I don’t find them too compelling in most cases:

1. People will talk and misconstrue what is happening, and we don’t want to deal with that — this just means that you don’t really trust your team, and this lack of trust is probably manifesting in a lot of sub-optimal outcomes throughout the organization which is much more costly than “people talking”. And even if people do talk and you have to spend time telling them what is actually happening, I’d argue that’s a much better problem than dealing with an environment in which trust is low and information flow is halted.
2. “They don’t need to know” or “It’s not worth my time to share” — I completely disagree! Sidestepping the question of whether or not the content that’s shared is relevant/helpful or not, the intention is impactful itself. It makes teammates feel valued and appreciated, and it makes a big difference in their level of engagement and trust in you and the team since they’ll feel more ownership over the full outcomes of the organization instead of just their individual outputs. I think the content itself is also really helpful; it helps team members build a level of empathy and understanding for leaders and the organization and prevents a lot of miscommunication.
3. Information is confidential — this is fair in certain cases, but I generally think that more things are labeled “confidential” than need to be. Instead of the default being confidentiality, I think the default should be open sharing of information. Nothing should be confidential unless there is a strong, affirmative case for confidentiality (i.e. a reason that impacts the survival or success of the organization itself).

There are two additional caveats to this.

First, when I talk about helping build an understanding of the broader context they’re working in, I mean helping them understand all the systems that are in place in the organization, the various motivations and incentives of each, and how it all works together to fulfill the organization’s purpose here. A lot of the individual details can (and probably should) be abstracted out. Your teammates don’t need to know that you think the CEO is an idiot, but they’d probably benefit by knowing how the team’s roadmap is being impacted by the CEO’s new goals.

Second, information sharing should be bi-directional. In the same way that leaders should be transparent and forthright in sharing their understanding of the broader org, they should also be inquisitive about the observations and experiences of the team members. This will help leaders build a better understanding of whether the systems they’ve built are achieving their desired purpose^[6].

provide meaning to their work

There’s rarely going to be complete alignment between an individual’s dreams in terms of what they want to work on and dedicate their time and energy towards and the current reality of the role that they’re in. It’s still possible for leaders to help individuals find meaning and purpose in those roles. I think there are two ways to do so:

1. Find resonance in terms of actions performed — it’s possible to find elements of a current role or an opportunity presented to the team that aligns with the types of things that someone may want to do in their dream role in the future. For example, someone who dreams of being an entrepreneur may not have the ability to do that fully in their current role, but can still find entrepreneurial elements within their job; they might find an opportunity to pitch an operational improvement the team can make.
2. Find resonance in terms of skill development — if someone’s ambition includes the expression of certain skills (for example, writing and communicating), it’s possible to find ways to develop those skills in line with their goals in their current role. In a sense, change, growth, and skill development become the focus, while the specific work responsibilities are the substrate through which the change occurs. For example, if someone aspires to be an independent writer someday, they can develop their skills and flex their writing muscle by adding documentation in their current role.

In my experience, I’ve found that even if leaders can’t find perfect fits for either, the attempt to do so itself is meaningful and generates loyalty, trust, and engagement from team members, at least in the short term. In the long run, it’s very hard to keep people from churning from teams if they can’t find some resonance in at least one of the ways above.

I’m still learning how to implement all of this fully and properly. It takes a certain level of vulnerability to tell other people that you’re interested in learning about at a deeper level than is normal; it feels risky to cross the artificial boundary of only interacting with their “work self” and trying to see them as a complete individual. In many cases, I’ve let fear and discomfort stop me from getting to know people as well as I wanted to. On the flip side, even when I develop a great relationship with the people I work with, I have a hard time fully trusting it and feeling comfortable sharing honest feedback and observations that I know will be well-received and beneficial for everyone.

I fully believe in these principles and their ability to transform not only relationships and organizational outcomes, but individuals. It may be impossible to implement or embody these fully, but I think they present a powerful ideal to strive towards.

1. ^{^}

   It has to — even if you’re a “people-first” leader, it hardly does the people you’re leading a service if you put their wishes above your responsibilities to the team. This is because you’re threatening the team's survival by putting other things first — if your team fails to fulfill its purpose to the organization, it will either be disbanded or replaced, or you’ll be removed as its leader. In either of those cases, you won’t be able to do much for the individuals you are (or were) leading. I know this from my personal experience of messing this up many, many times. I’ve taken stands in organizations I’ve been in where I’ve criticized organizational structures and the impacts they’ve had on the people I’m leading. I prioritized changing those structures over the work that we were doing as an organization and as a team. Instead of increasing the chances of change happening, my fellow leaders typically just stopped working with me and eventually removed me from the organization. Looking back, I wouldn’t change my impulse or instinct, but I would certainly change my strategy. The chance to do something meaningful for people is better than the guarantee of being able to do nothing.

2. ^{^}

   This is something I’ve messed up so, so many times before. I fall into the trap of thinking the aspirational model is enough, and that making other people feel seen and appreciated will be sufficient to get them to act in ways that will be beneficial for themselves and the team. I have led by assuming that just by showing people the aspirational view I have for them, they’ll automatically fill that vacuum and become that. I’m only now learning to take the responsibility of helping them bridge the gap by providing both structure and honest feedback that helps them achieve that transformation.

3. ^{^}

   In my current role, just knowing that my manager sees me as a great communicator and problem-solver is enough to motivate me to continue voicing my thoughts and proposing ideas and solutions. There was a night and day difference in my energy level at work after he shared those observations with me. I know I’m not alone in responding this way to genuine and honest positive feedback.

4. ^{^}

   It’s so bad that you can almost feel like you’re betraying your manager or mentor by saying that you don’t actually want to be a banker or consultant your whole life because that’s all they’ve been grooming you to do.

5. ^{^}

   This is a huge reason why I never connected with one of my previous managers. All of our feedback sessions and 1:1s were related to me strictly improving as a software engineer and my potential as an IC, but that was never my goal. I have always had much larger dreams, and none of them involve me coding for more than a few more years. I was always like thanks for the feedback, I guess, but I’m not going to dedicate much of my energy towards this. I’ll be good enough to fulfill my responsibilities but I’ll invest all of my learning and growth potential in other areas that I’m more excited about (like writing and communicating).

6. ^{^}

   There have been so many instances where leaders in organizations I’ve worked in have implemented changes designed to improve the experiences of everyone on the team, but have completely fallen flat. Usually, it’s because they either 1) fail to communicate the rationale of the change (i.e. don’t communicate the problem they’re trying to fix), or 2) fail to ask sufficient people about what they’re experiencing, making them tone-deaf and blind about the problems they’re trying to solve.