Experimenting with Identity and Personality

The most important technique I’ve learned in the last year is how to run an identity/personality experiment. It’s unlocked an ability to intentionally learn and grow far greater than any reading, conversation, class, or singular experience. It’s the only way I’ve found to create lasting changes at a core, underlying level to my personality. Many resources I’ve read talk about specific experiments to run, but almost nothing I’ve read talks about how to develop this muscle so you can see it, train it, and use it on your own. This, to me, is the key to unlocking the wisdom well-known in history; it’s how we can speed up the process of learning from our experiences.

So, what exactly is an experiment? Let me give you an example. Earlier last year, I didn’t give my team members concrete feedback if I thought they were doing great work, but could do exceptional work. I wanted to be a “good” manager — kind, supportive, and responsible — and I told myself I’d be irresponsible if I gave someone feedback without 100% conviction in the criticism. I was making two assumptions: (1) if I gave a high-performer feedback, they would be upset and therefore less productive, and (2) if I gave them imperfect feedback, they might adapt to a behavior that I didn’t actually desire. Reading this now, my reaction is “of course that’s not true!” but to actually internalize that, I had to run a series of experiments to test those assumptions. To start, I just gave a specific, concrete piece of feedback to a team member (let’s call them David) on how they might communicate more effectively — sharing my observations of the impact of their current communication style, and how they might be more effective at achieving their goals with some small modifications. My first assumption was challenged nearly immediately: David was extremely grateful and energized to receive the feedback! Because I shared it with compassion and care, not blame, David received the feedback as a gift and as a challenge. With a couple more of these experiments, I mapped out a pattern: high performers want to improve, and receiving feedback (even when they’re doing a good job) is received as an extremely rare gift. Challenging my second assumption took some more time and some more experiments. With David, over the span of several months, he incorporated the feedback in his own way — taking the parts of what I said that were good, and bringing new parts from his own identity and experience — avoiding any harmful consequence. On the other hand, in certain experiments when I shared feedback, I learned why someone was making the tradeoffs and decisions they were — helping me learn how to work more effectively with them without them having to change what they were doing in a counterproductive way.

I call these actions “experiments” for several reasons: I’m testing a hypothesis/assumption, I’m deviating from my default identity and its ensuing default behaviors, I’m often nervous doing them, and I’m creating space for failure or unexpected outcomes. Experiments are bite-sized chunks of things I would not normally do, because of some long-standing assumption or belief that’s holding me back. By making them small enough, I’m able to test whether those assumptions come true without bringing too much risk to myself. At the same time, they’re very intentional and deliberate: I know the outcome I’m worried about, I have an expectation of what might happen instead, and I can check to see what actually happened.

Experiments are effective because they help build wisdom, not knowledge, by challenging assumptions and rewiring your brain. If you’re like me, there are probably lots of things that you “know” to be true, but don’t necessarily believe deep down. I’ve certainly felt this way about many sources of deep wisdom (religious teachings, Buddhism, spirituality, mindfulness) and even self-help resources. They all tell us very similar facts and observations that we might know to be true, but we still have a hard time bringing into our identities and actions. It’s why people often feel a spurt of change as they read a self-help book, acting better for the week they are reading it, and quickly revert back to normal afterwards. The key question is how we internalize that knowledge and turn it into wisdom.

Big assumptions are what get in the way of turning that knowledge into wisdom, because you can cognitively “know” they are not true, but you are likely to take them as true in your actions (and especially non-actions). Based on our many years of lived experience, we’ve told ourselves stories about how the world works - what might happen if we do one thing versus another. Those assumptions, even if we “think” they’re wrong and can reject them on face value, hold us back from internalizing new ways of seeing the world, from turning our knowledge into wisdom.

The standard way people turn knowledge into wisdom is through experience and age; experiments are merely a way to shortcut that. As we live, we experience many data points that tell us what happens when we act in different ways. If we’re observant, we can gradually build a better and better mental model of the world. It’s why we use the word “wise” to generally refer to someone older - like an old, wise grandparent. The goal of experiments is to find a way to build this wisdom actively, instead of passively through experience. Instead of waiting for a data point that challenges our assumptions, we can recognize our agency and take actions that might challenge our assumptions! This creates the opportunity to rapidly rewire your brain.

Experiments can take many shapes and forms: I’ve run experiments to become more assertive, and to find ways to lead from emotion and not just thoughts, among others. For example: I’m naturally inclined to make consensus driven decisions and convince others of my reasoning so I can get buy in. However, sometimes people need to disagree and commit. A deep discomfort would “hold” me whenever I asked someone to disagree and commit to my perspective — especially if they had many years more experience than me. I worried that I might be wrong and they might resent me for it; I worried that they wouldn’t effectively execute those decisions. When framed like this, the experiment became obvious: I could run a test to disagree and commit once or twice, and see what happened. It was surprisingly effective!

In another experiment, I tested alternatives to my conventional leadership style — logical and analytical. I’ve run a series of experiments where I lead from emotion instead: when I’m experiencing a strong feeling, instead of voicing my opinion, I voice my feeling and its source. For example: “I’m feeling scared that we won’t hit X target because of Y reason.” I had never tried expressing this feeling; my default was to focus on the problem or solution. Expressing those feelings was an experiment with no known outcome: I was uncomfortable doing it purely because I had no idea what would happen! It has turned out to be extremely effective: either I learned that I didn’t need to hold the worry (and was able to avoid sending people off working on an unnecessary solution), or others proposed a solution that was even more effective than what I had in mind, with 100% buy-in.

A tremendous challenge to running experiments is finding opportunities for them. That’s hard because some of our assumptions and behaviors are so ingrained that we don’t even see them, and because experiments often require a situation or context involving other people. I’ve found a number of shortcuts to identify experiments to run “in the moment” — then there’s hardly enough time to even worry about running them! I use one key rule of thumb: never avoid something out of fear or hesitation. There’s plenty of reasons not to do something, but I strive for fear or hesitation to rarely be the reason I avoid an action. Whenever I sense that little nagging thought: “oh no - what will happen if I do X,” I lean in and ask myself, “do I actually want to do it, and what’s the consequence I’m afraid of?” I’ve found many variants of this rule to be effective in helping me recognize potential experiments. I often refer to Claire Hughes Johnston’s operating principle of “say the thing you think you cannot say” as a specific type of fear. The number of times that’s come in handy has been unbelievable! One example is when I’ve noticed a presenter wondering why they’re doing the work they’re doing - calling that out, however uncomfortable it feels - has been extremely effective.

In addition to noticing situations as they arise, it’s also possible to plan for experiments by leaning into your agency. If there’s something I want to happen as a leader that’s not actually happening, I figure out experiments to see how to make that possible (or, of course, recalibrate my expectations). Being high agency and knowing what you want, especially when that’s lingered for some time, is a great way to identify experiments.

Experiments are naturally scary. It’s normal to wonder “what if they don’t work?” or “what if I mess up everything?” The key to avoiding big risks is to make small experiments — for example, try making one or two different comments in a conversation. If you do that, with genuine intentions to help yourself and those around you, the worst that happens is a need for repair if the experiment goes poorly. Typically a genuine apology with an expression of your intentions will be more than enough. In other cases, people around you might need some time to adjust to your new way of acting. Take it easy, take small steps, and they will accommodate over time.

The biggest risk to experiments is actually with yourself: by making too big of an experiment, by stepping out too far over your skis, it’s easy to fall flat on your face and reinforce the fear you already had. With all experiments and new approaches, there’s effective and ineffective ways to go about them. If you try to make too big of a change too fast, you could easily make it in an ineffective way, or the people around you (especially longstanding, close relationships), could completely reject it. That can reinforce a fear of running experiments themselves, completely stunting growth. Remember to take it easy and start small.

Keeping experiments small has many other benefits: the risk is low, the frequency of experiments can be higher, the growth compounds, and others can slowly adapt to your changes. Opportunities for small experiments show up all the time – basically whenever we slightly hesitate – which for me happens many times a day. If we can take tiny steps that help us change by 1% every day, without taking a large step and being set back, compound growth can lead to tremendous change in just weeks! On top of it, it’s challenging to experiment with big changes around people we already know well. Others have expectations for how we act, and inhabiting another identity altogether can place too much strain on the relationship. Small changes, compounded over time, are much less risky for long-standing relationships.

With that, the most effective lesson that I’ve learned is that experiments are highly effective and not that risky! Initially, I worried with each experiment about the possibility of it going wrong. Now I rarely worry about running experiments. Sure, some of them might not have the intended outcome, but it’s almost always fixable, and I always learn something. This meta-lesson has been transformative for me: it’s what enables me to continue running more and more experiments as I discover more of the things holding me back. Getting comfortable with running experiments has been more valuable than any individual experiment itself; it’s a muscle I’ve been able to repeatedly exercise. Now, I have the opportunity to run multiple experiments every day!

These experiments have produced tremendous value for me. They’ve enabled me to see multiple perspectives simultaneously. They’ve let me build deeper connections with the people I care about most. They’ve helped create an incredible sense of humility as I’ve realized how often I’m wrong about the world.

Mentors are a critical part of this journey — it wouldn’t be possible to do it otherwise. They’ve helped me see the blind spots that I wouldn’t have known to experiment with, given me the tools to actually run experiments, and the feedback to be able to more accurately see whether experiments are going well or not. I’ve found this valuable in the form of regular cadence professional coaching, leadership programs such as Leaders in Tech, and of course, weekly confrontations with my very perceptive wife :). While these aren’t necessary to learn from experiments, they can significantly accelerate the process, and give you wonderful company along the lonely and bumpy ride!

As I’ve come to use this tool more and more, I’ve started to wonder if there are more effective ways to do it. Experiments are slow, stressful, and time consuming. How can we make them faster? I’ve found three shortcuts that help. First is the observation of others. When I hold an assumption about how things work, I can often identify several people I know who challenge that assumption and live a perfectly effective life. (An extreme example: “if I don’t exactly follow some very specific religious custom, I won’t be able to live a good life” – notice there are plenty of counter examples!) I can use those observations as case studies to challenge my own assumptions. Second is through simulation: once I’ve built a good enough mental model, I can predict what might happen with no intervention or several different possible experiments, and predict what to choose. And finally, there’s empathy: I ask myself how I would react if someone ran that experiment on me. Would I be appreciative? Angry? This was most useful when creating spaces for vulnerability at work — I was scared to do so because of fear of judgment, but on the flip side I’ve always appreciated whenever people have made space for that!

Of Observational, Simulation, Thought, and Behavior experiments, the Behavior ones have been the most effective of these techniques - they’ve helped rewire my brain in a way that no amount of reading, simulation, or empathy can substitute. Real, lived experience is what changes how you see the world. Self-help books and other resources tell you specific experiments to run, but I’ve found that learning how to run experiments myself is far more effective. I look forward to the many more years of learning that it can bring!

Acknowledgements

I’d like to thank my coach, David Zeitler, for teaching me how to run the Immunity to Change version of behavioral experiments, question my identity, and change in a persistent way. I couldn’t ask for a better mentor along this journey. I’d also like to thank Tony and Terra, the facilitators of the Leaders in Tech retreat I attended, who’ve helped shape many of my perspectives. Finally, Shruti, my wife, and Tanay, my co-founder, have been incredible resources in giving me feedback through all my experiments and being patient with all my mistakes.