The obvious questions: What about work? What about friends?

Sachin and I are fully remote—we’ll continue running Notejoy, Sachin is creating courses on Reforge, and I’ll continue my work coaching founders. As for friends, Monterey is only 90 minutes south. Come visit!

We’ve debated this move endlessly, and I want to share our thought process as well as the three factors that drove the decision.

Relationships Matter

Our biggest fear: Losing our Bay Area friends. The people and conversations here are a treasure—the smartest people I know who always leave me energized and buzzing with ideas.

The reality: We rarely see them. Between work, traffic, and young kids, finding time together is #scheduleJenga. A decent amount of my relationships have already shifted to calls and occasional meetups.

Our plan: Proactively build community in Monterey. The people we’ve met are friendly, interesting, and less hurried. Plus, we can maintain existing friendships digitally and through visits.

Following Our Values

My core values haven’t changed (relationships, growth, achievement), but how we spend time has shifted:

• Personal health is now a priority
• Time with our daughter Zoe is a priority
• Career is a steady drumbeat, important but less all-consuming

The move to Monterey is a way to design our life around these changes. Our happy place is next to the ocean on hiking trails.

Why Monterey fits:

• Daily access to Big Sur hikes and ocean runs
• Less hurried, friendlier community
• Bay Area and airports are still accessible (90 minutes away)

Silicon Valley Parenting Is Intense

Prior to this, we’re resigned ourselves to the thought that while Monterey is our happy place, this would be a retirement move because we couldn’t uproot our daughter Zoe. The Bay Area’s educational seemed too rich and valuable, why would you raise a child anywhere else?

What changed our minds: After touring schools and talking to parents in both areas, we realized Bay Area parenting is really intense. Even in kindergarten, there’s underlying paranoia about kids falling behind. Did you know that Susie is already reading chapter books? Billy goes to jujitsu for an hour every day! Parents are hiring tutors, booking extracurricular classes, and constantly pushing the envelope to keep up.

Our philosophy: While some kids attend summer academic camps, we don’t want to pursue supplementation from a place of fear and competitiveness. Rather, our philosophy is to invest in academics and activities aligned with Zoe’s interests. We would love to raise a high-performing, compassionate human who is pursuing her passions.

The breakthrough: We found a school aligned with our priorities—fostering curiosity, maintaining academic rigor, and building character. We also verified Monterey has a rich ecosystem of extracurriculars.

Living Life Intentionally

Unlike many moves driven by external factors, we’re making an intentional choice. There’s risk, but I’m guided by two questions:

• What’s the worst thing that could happen? We could move back after a few years.
• What’s the best thing that could happen? We could be in a more optimized, happy place aligned with our values.

I’m excited for the chapter ahead!

The post Leaving Silicon Valley After 18+ Years first appeared on Ada Chen Rekhi.

Charlie Munger, Warren Buffett’s late business partner, was often quoted saying “It is remarkable how much long-term advantage people like us have gotten by trying to be consistently not stupid, instead of trying to be very intelligent.”

What he’s referencing is the power of inversion thinking, where you can look at a problem or situation differently by turning it upside down and sideways. Instead of trying to map out a very aggressive plan relying on smarts to win, also map out a defensive one guarding against obvious stupid mistakes.

This is especially valuable for startups because not only are you solving difficult and challenging problems, but you’re also doing it in situations of high ambiguity. Even if you execute flawlessly, will it work? While there’s a certain amount of blind faith and optimism required to chart a path in a new market, it’s also helpful to avoid the obvious pitfalls.

Thinking forwards

Often, the common and most straightforward way of thinking through a startup problem is looking forwards. This ethos aligns with the idea that “execution is everything” and emphasizes preparing roadmap to pursue your goals.

The question asked here is, “How do I reach my goal?”

For example, if I’m trying to build a successful company, a forward-looking path is to map out the steps to achieve it.

• identifying a clear pain point that customers face
• building a product to solve it
• crafting a hypothesis of how to distribute the product to these customers
• scaling the team to address the problem

The problem with this approach is sometimes we get a little too focused on reaching that happy outcome. Our thinking then runs the risk of being too optimistic and simplistic: if I check the following boxes, then I’ll achieve my goals.

Thinking backward

This is where inverse thinking comes into play.

The question asked here is, “What would cause my plan to fail?”

Many startup founders are reluctant to think backward due to conditioning to avoid ‘negative thinking,’ the idea here being that it’s important to keep our spirits and optimism high in order to keep working. Unfortunately, this misses the reality that we need to clearly map out potential risks in order to plan against them. It’s like entering a swamp without an idea of where the monsters lie.

To continue on the SaaS productivity company, here are some of the obvious monsters for what would cause this company to fail.

• building something that isn’t differentiated from existing competition
• not adequately solving the pain point customers face
• solving the problem upfront but not providing enough value for ongoing renewals
• needing a sales team for distribution, but not being able to charge enough for the channel to be cost-effective

Building this list often comes easier than you think, because these are the sorts of issues and questions that keep many of us up at night. However, having a documented list can make these fears addressable. If I know that there’s a risk that we aren’t differentiated, then I can start incorporating contingencies against this problem into my go to market.

While the example above is company-centric, the genius behind inversion is that you can apply this to all kinds of situations.

For hiring, ask: What support does my new hire need to be effective? Why would my new hire fail?

For sales, ask: How do we drive sales? What’s the fastest way to lower our sales?

Mapping the happy path

The value of thinking backwards and forwards is straightforward: you put together a plan of attack, while avoiding the obstacles that might be in your way. Or to borrow from Munger, executing while trying not to be stupid about it. This is the happy path where you can execute an ideal strategy without any faults.

The post The power of avoiding stupidity for startups first appeared on Ada Chen Rekhi.

What am I afraid of as a parent? When I think about how we could screw up, I’m afraid of raising a child who is ungrateful, entitled, and lacking in motivation because we provided her with an environment of too much.

The definition of Spoiled

According to psychologist James Fogarty, the clinical definition of spoiled comes in four parts. Spoiled kids have these 4 attributes, but all don’t have to be present:

1. Living a life with few chores and responsibilities
2. There aren’t many rules to govern their behaviors and schedules
3. Parents and others lavish them with time and assistance
4. They have a lot of material possessions and extravagant experiences

He goes so far as to say that parents who overindulge their children can hinder their development into an adult.

At our current pace, our 4 year old daughter is trending toward spoiled. No chores, ample time, and lots of material possessions. The only redeeming quality I had is that we are fairly structured about our schedule and boundaries.

The rise of the fully provisioned child

There’s a modern trend in parenting which Lieber calls full provisioning. A fully provisioned child receives everything they could ask for in their parent’s power, the full kit of toys, enrichment, experiences, and clothes.

I see a lot of fully provisioned kids in the Bay Area (and we are guilty ourselves) and this book makes me wonder whether this is ultimately a harmful act. Seeking to shield them from the discomfort of being a “have not” in some cases is actually a healthy thing.

According to Lieber, we’ve shifted from seeing our children as “future workers” to the other extreme of “no expectation of usefulness.” In 1998, 45% of kids 16-19 had some part-time job and in 2023 that number has shrunk to 20%.

This is harmful because doing a job is what teaches grit and a work ethic. Kids like to work and seek it out. I wouldn’t want to rob my child of the experience of earning something through hard work. Moreover, if I’m so afraid of raising a kid lacking motivation, work is exactly how you learn it. How else will the incentives and mindset line up that work translates into results?

Helpfully, Lieber provides a number of suggested actions we can take to address this.

How and why to give your child an allowance

Lieber is a financial columnist, so naturally his lens on this is through money. He believes that teaching personal finance is a critical path for children to stay grounded in their adult lives. One of the first tools is an allowance, which he wants parents to start as early as children begin to ask questions about money. It’s his belief that allowances are a critical tool to learn patience and decision-making while stakes are low. He also strongly believes that allowances should not be tied to the completion of chores, which should not be compensated.

Here’s his allowance system:

• Start 1st grade at the latest, though there is no harm in sooner.
• Give $0.50-$1/week per year of age. So a 4-year old would receive $2-4/week.
• For younger kids, divide the money into 3 clear bins labeled Spend, Give, and Save.
• Give young kids an achievable savings goal and tape a picture of the item.
• As kids are older, the bins can become a virtual debit card. It’s also possible to add interest rates, matching, and other incentives.
• He discourages credit cards and instead suggests cash for younger kids and debit cards for older.

Having tangible money to hold and clearly divided bins begins to introduce the idea of a simple budget, while allowing them to make their own decisions. Then with the allowance system is in place, he introduces the concept of needs and wants.

Teaching Needs vs. Wants

The idea of teaching needs and wants is teaching kids about the tradeoffs of how they can choose to spend money. I particularly like the exercise he describes because it’s easier to explain to a child. Here’s my own take with a winter jacket example –

Winter jacket example

Let’s imagine we are trying to buy a new winter jacket. Draw a horizontal line, labeling one side “Need” and the other side “Want”.

On the Need side, you can have a perfectly serviceable $15 jacket from Old Navy which will satisfy the need. On the Want side, you can have a $870 jacket from Moncler.

The next step is you draw a line on what your willingness to pay is. In his case, Lieber uses his “Land’s End line” which is the price equivalent of a Land’s End, which represents mid-range decent-quality article of clothing. This would be around $65.

The difference between the $65 and their wanted item must be funded from their Spend or Save budget.

By middle school, you can sit down with your child to create a budget of clothing items they need for the school year. After it’s priced out according to your willingness to pay, they receive a debit card with the amount pre-loaded to spend as they see fit.

While this creates some massive risk of blowing it all on a few items, he argues that giving them the power to make decisions is one of the most effective ways to learn.

Takeaways

Overall I think this book has been a reminder of how much influence we can have in our child’s development. Previously my mentality was a mix of helplessness and hopefulness that we’d manage to avoid spoiling our child, and there are so many great ideas in this book on how to actively foster life lessons.

What am I going to do differently because of it? Here is how I’m implementing this:

1. Give her chores to do. I have now explained to her that now that she is 4, she has chores and a job to do just like we do. Her job right now is to clean up and put away her toys and books every night.
2. Add an allowance sometime in the next year, most likely $1 per year of age per week following something similar to Lieber’s model.
3. Determine where our own “Land’s End line” falls and be more intentional about not fully-provisioning.

In short, recommend this book if you’re a parent thinking through some of these questions yourself. The landscape of parenting has changed a lot since we were kids, and a lot of the valuable lessons I learned from watching my immigrant parents labor to make a life in America aren’t accessible to my daughter today. We need more tools, and this book offers many specific and interesting ideas on what to do.

The post How to Not Spoil a Child first appeared on Ada Chen Rekhi.

It’s a great practice which I would highly recommend. I have year in reviews going back to 2011 and paging through them helps me appreciate how far I’ve come. Depending on the year I’ll spend anywhere from an hour to half a day’s worth of time putting together my review. While the format has changed over the years, I want to share my current approach.

My Year in Review Format

I start my year in review by outlining my doc into six sections.

1. Big events of the year
2. What I learned
3. Where I am (Work, Play, Love, Health)
4. What to keep doing? What to add or subtract?
5. Review last year’s intentions
6. Set next year’s intentions

Start by writing down the main points

I recommend filling out each section with bullet points or key ideas first, rather than tackling this section by section. This is because diving right in and writing out the section can easily suck up a lot of mental energy and it’s helpful to capture the main points first.

After I’ve captured the main content in each section, I’ll go back in and write more in-depth reflections into each section.

The Six Sections

Big Events of the Year

Big Events of the Year is a great opportunity to look back at the big picture of the year. I’ll pull open my calendar and create a bulleted list of the major events of the year, like travel, occasions, big milestones. Sometimes I’ll even look at other respositories of data (like sorting my purchase or order history, book lists, emails) to try to pull out themes. In addition to dated events, I’ll also add in big themes or ideas that have been part of the year.

For example, last year my list included:

• Zoe enters daycare (February 14)
• Publicly launching my executive coaching practice
• Dexter gets hit by a car during Thanksgiving
• Community: joining Leaders In Tech Board, Menlo Park Library Commission
• Seattle trip with family
• New York for Thanksgiving
• The great debate on how to splitting holidays with family
• COVID and its impact

What I Learned

What I Learned is an opportunity to reflect on new ideas and lessons learned for the year.

Another way to frame this: If you had an opportunity to go back and give yourself advice at the start of the year now that you are at the end, what would you tell yourself?

Where I Am

Where I am is a recent add borrowed from the book Designing Your Life which I’ve previously written about. It’s basically a pulse check on how I’m doing holistically. I particularly like how intentional they’ve been about creating categories distinct from work because it’s easy for me to get caught up in that category.

Here’s how they define their categories

• Work — not just what you’re paid to do, but also include other duties such as second jobs, consulting, advising, volunteering, home-making, houseworking.
• Play — any activity that brings joy just for the sake of doing it, which can include organized activities or productive endeavors so long as they’re done for fun and not merit.
• Love — the health of your primary relationship, children, pets, community, or anything else tied to affection. Where is the love flowing in your life, from you or from others?
• Health — not just physical health, but an engaged mind and satisfied spirit.

For each of these categories, I give myself a percentage score that reflects how full my tank is in that area. Sometimes I’ll add bullets in to help myself understand how I’m doing in those categories. The goal is not to be FULL on every category (that sounds overwhelming) but to reflect on if those levels are where you’d like them to be.

What to keep doing? What to add and subtract?

This section flows naturally from the Where I Am section. I’ll look at my current state and think about how I’d want to adjust it to meet my needs.

Often this space will become a repository for my ideas on what I could add or subtract to my life. For example, last year I noticed that I’m very low in the category of Play. I haven’t been doing much for the sheer joy of doing it. I brainstormed a list of activities that fall into this category. When I think about what to subtract, sometimes it’s an exercise of what I actively didn’t enjoy from the year but often it’s considering what I wouldn’t miss doing.

Review Last Year’s Intentions

Review Last Year’s Intentions is an opportunity to look at what you set out to do in the past year and reflect on what worked and what didn’t and why. If I had resolutions from last year, I’ll write about how I did against them and what I learned. If I didn’t, then I might take some time and reflect on how I entered the past year and if I am where I thought I’d be.

Set next year’s intentions

After thinking about the past year, it’s time to turn our gaze toward the future. This section provides a space for planning the year ahead.

• Resolutions – writing down a list of measurable goals/areas where I want to improve for the next year and thinking about how I can set up my environment today to achieve them.
• Wishes – what do I wish for myself by the end of next year? writing down a list of wishes that I have for my future self at the rest of the year
• Intentions – how do I want to approach the coming year and what are my intentions on where I want to focus my time and energy?

Want to try this for yourself?

If you’d like to try this for yourself, here’s a template that I’ve created with the prompts and examples.

Click here for the template

If you tried this or found it helpful, please support me by letting me know and sharing with others!

The post How to Write Your ‘Year in Review’ first appeared on Ada Chen Rekhi.

Who is Frank Slootman?

Frank Slootman is a serial CEO who has consistently delivered massive business outcomes in the enterprise software space. He was CEO of enterprise data storage startup Data Domain and grew it to a $2.4 billion acquisition. After that, he led ServiceNow, growing it from $93 million in 2011 to $1.4 billion in 2016 to IPO. He is now the CEO of Snowflake, which was the biggest IPO of 2020.

In addition to delivering results, he’s notable for known for creating some of the most intense work environments out there, teams that drive drive hard and throw work-life balance out the window. He’s also come under fire in the past for comments about prioritizing merit over diversity.

Frank is not a nice guy

If I had to describe Frank’s leadership style, I would say blunt, demanding, and results-oriented. This shows up in the book itself, which is slim and spare on filler content. It is not an autobiography capturing the glory of his previous wins but rather an operating manual on how he runs teams. It’s clear throughout the book that he’s not focused on being liked but on achieving the mission.

One area that really exemplifies this is his talent management approach.

Topgrade your talent

Frank advocates for “topgrading,” a strategy developed by hiring expert Brad Smart. Topgrading is the process of systematically upgrading talent in key roles. Rather than doing what most companies do and replacing people as they begin to fail at their roles, Frank replaces people when it’s known there are higher caliber people available. In this way, your team’s talent bar is constantly being upgraded.

Hire drivers, not passengers, and get the wrong people off the bus

“If you don’t act quickly to get the wrong people off the bus, you have no prayer of changing the overall trajectory. We often believe, naively, that we can coach struggling teammates to a better place. And sometimes we can, but those cases are rarer than we imagine. At a struggling company, you need to change things fast, which can only happen by switching out the people whose skills no longer fit the mission or perhaps never really did in the first place.”

Frank defines two categories of people: drivers, who have ownership and a strong satisfaction from making things happen, and passengers, who are carried along by the company’s momentum but don’t take strong positions to improve outcomes. He advocates for ruthlessness in getting passengers out of the company as quickly as possible.

Solving for the revolving door of talent

Topgrading and kicking people off the bus are controversial ideas. Most leaders would blanch at the idea of firing loyal people to topgrade talent. Or proactively firing people who are performing in their roles, but not exemplifying an appropriately go-getter attitude. I would be the first to admit that I’d struggle with putting this into action because I care a lot about the people around me. Not to mention the business implications. What about the cycles it takes to hire new people? What if you get a bad reputation? What if you don’t have the brand to attract great talent and this is the best you’re able to get?

The lesson I took away is that this type of strong, contrarian position takes special qualities and self-awareness to work. Fundamentally, you must have a thick skin and deep conviction. Frank’s special sauce is that he’s acting in alignment with his temperament and beliefs. Judging from the leadership conversations I’ve had in my exec coaching work, this is something that doesn’t feel natural to many. In addition to this, you must have the strong self-awareness that firing quickly means you must build the skill to hire quickly. Frank builds in three strategies to offset the talent drain:

• Hire for aptitude over experience. Frank learned quickly that it can be difficult for a struggling company to hire people with a lot of experience. Furthermore, optimizing for experienced hires often results in people who lack hunger and drive. He prioritizes aptitude (hunger, curiosity, career-frustration) over experience in filling roles.
• Set the bar high and make expectations clear. By giving clear expectations and feedback, Frank solves for the risk that people will live in fear of being fired. High performers have security with clear feedback.
• Make hiring everyone’s job. Managers throughout the company are expected to leverage their networks to hire great talent. That way, there’s always someone waiting in the wings when a role is open.

If he had taken the stance of firing quickly without putting these other practices in place, it would have failed catastrophically as unfilled roles languished and created bigger workloads for others. It snowballs after that, as the mounting workload creates a further reluctance to fire. However, if everything works as it should, Frank’s ability to create an organization that both hires and fires quickly becomes a superpower.

Conclusion

I would not give anyone reading this book the advice to adopt Frank’s operating manual and try to run with it. Frank himself even writes in the book, “There are many different paths to superior outcomes in business. You will have to find your own path, one that suits your temperament, disposition, and natural aptitudes. Therefore, don’t try to copy or emulate other leaders–including me.”

Frank is passionate about fighting mediocrity, relentless focus, and high performance, and he’s willing to engage in the conflict necessary to make it happen. The rest of his management approach falls out accordingly. In other words, he’s operating in complete alignment with his values.

One of the most common conversations I have in executive coaching is discussions about underperforming team members, and how and where you draw the line in supporting them vs. firing them. Does this mean that you’re going to fail because you aren’t hardcore about firing fast like Frank? No, not at all. Frank is just one leadership style among many and there are so many paths to success. Whatever your approach is, it should be aligned with your values and play to your strengths.

The post Frank Slootman on creating a high-performing culture first appeared on Ada Chen Rekhi.

“If you want a thing done well, do it yourself”

If you, like Napoleon Bonaparte, have ever reached this conclusion, you are not alone. Delegating effectively is a struggle and it often feels faster and better to do it yourself.

The challenge is the devil is in the details on how to effectively delegate.

Make your expectations clear

Failure point one: it’s not clear what you expect, or context is lacking to execute. Delegating is like outlining a box for someone else to fill in. In order for delegation to be effective, it must be clear:

• goal – the problem you’re solving
• context – the relevant information or skills they need to complete the task
• metric – how you evaluate whether the goal is met
• timeframe – when you need the task complete

What you can do to check this: It’s a great idea to ask after you’ve shared a request if your expectations are clear.

• Validate clarity: Does it make sense what I’m asking you for?
• Check on next steps: Let’s talk through how to get this done. What do you think the next steps are?

Match the level of structure to the recipient

Failure point two is that you’re providing too much or too little structure to get the task done.

I define structure here as the level of specific detail and open-endedness you’re providing with the task. Here are some examples of delegating an international payments project at different levels of structure.

As the ability of your recipient goes up, the level of structure should go down. When level and ability don’t match, failure ensues. Another way to think about this is spelling out a highly structured task to VP should be very different from your college intern!

If you provide too much structure to someone of high ability (e.g., an expert in the area), you’re missing out:

• there may be more optimal ways to achieve the spirit of your ask that you’re not even aware of
• you’re perceived as micro-manager

If you draw too little structure to someone (e.g., a new college grad), you’re missing out:

• they deliver the wrong product or miss a deadline because they’re missing information or ability
• you’re perceived as handwavey/confusing

One particular challenge at startups is managers often have teams at all levels of ability. In corporate teams where VPs manage Directors, Directors manage Managers, etc., it’s usually much easier to master one mode of delegation and stick with it. When you are managing a diverse team, it’s especially important to consider how you’re structuring your asks to get the results you’re hoping for.

What you can do to check this: The resentment of being too vague or micro-managing can build up over time, so it’s helpful to talk through tasks after they’ve been completed. Some tactics that may be helpful:

• Sharing feedback: “I want to give you some feedback on this… ” and discuss how any expectations were not met, and ask what you could have done to help.
• Mine for ideas: My goal with this project was X. Do you have any ideas on how we could have done this differently?

The takeaway? Make sure you’re setting clear expectations when you ask others to do things and tailor your ask to the recipient’s ability.

The post How to Delegate Without Being a Micro-Manager first appeared on Ada Chen Rekhi.

What is Leaders in Tech? LIT is an organization that provides personal development programs for founders and leaders at tech companies. Their flagship experience is called a a T-group session, and it is based on Stanford’s well-known Interpersonal Dynamics course (aka “Touchy Feely” to GSB crowd).

The Fellows experience

Let me walk through the mechanics of the LIT experience first, before speaking to the impact. The weekend was a fully immersive experience and structured as bringing together roughly a dozen leaders at a hotel for four days. Over the course of the retreat, the facilitators regularly introduced teach pieces that introduced content/frameworks to the group. The teach pieces provided scaffolding for the conversation by giving the group concepts and vocabulary to use. However, the experience was largely experiential, unstructured, and didn’t follow a set curriculum. On some level, you can describe it as we had a schedule with large blocks of time with no agenda where we sat in a circle and talked. This is the opposite of a programmed course with lectures and topics. As the group spent time together, I got to know them better and better as people, and we built up a shocking amount of trust and disclosure.

It’s hard to describe the experience and almost easier to describe what it was NOT:

• a curriculum to learn a structured set of skills
• a forum to bring business-oriented challenges to a set of peers to find advice and solutions
• a networking opportunity to meet other people

It’s actually something else. The LIT website describes it as “an experiential learning format focused on discovering when and how you are most influential, how others really think and feel about how you act, and how you lead” but I don’t feel that it captures all of what it is. In effect, it’s a shared group conversation where the group sets the content and agenda and you learn from each other. The quality of the group I suspect makes a big difference, and I was impressed by how curated and high-quality the group was.

Overall the experience was super impactful to me personally and professionally, and also hard to describe. So I’ll try to explain that more below.

The power of the T-group

As someone who works with others in a 1:1 way, I’ve been reflecting a lot about the power of the group experience. There is unique benefit from learning from others’ experiences that is hard to capture through individual work. Whenever someone else describes a problem or situation they are facing, as an observer, it can feel so clear what the solution should be. However, as they unpack the considerations and feelings that go into their situation, it’s always more complex than that. In the T-group, there’s space to describe a situation in detail and for the group to ask follow-up questions.

I got just as much if not more value from participating in someone else’s experience as I did in sharing my own. T-group is unique because it’s possible to get the reactions of everyone participating and hear how it’s landing. This opportunity to hear the other side is like a supercharge to understanding interpersonal dynamics.

What I learned from Leaders In Tech

I will be the first to admit that I came into my LIT retreat extremely skeptical about whether it was a good use of my time. Since then I’ve talked to many others who shared the same skepticism and came out as a believer. It takes a glance at the quotes people have left to see the impact of the experience.

LIT shattered some long-held stories that I had in my head about how the world works. The opportunity to get real-time feedback from someone else (their story, their reactions, their thought process) was a game-changing opportunity for me to break down these beliefs. I have an entire single spaced page of notes and feedback jotted down, and here are my top 3 takeaways.

Relationships are not a function of time or luck, they can be actively sought out and nurtured. After spending 4 days with my T-group, I came away feeling a closeness and connection to them that surpassed many of my long-standing friendships. I had been under the impression that sometimes I get lucky with someone and “click” or friendships are built on time spent together, which means it’s hard to create deep friendships in our time-starved world. However, LIT taught me that there are steps we can take to improve the quality of time spent and build relationships intentionally.

The flawless leader is not the one people love to follow. Growing up in an appearance-oriented Asian culture, I held the belief that the winning strategy is to put your best foot forward and downplay the challenges (this concept is also known as “saving face”). This makes it hard to admit mistakes or discuss problems. As I watched others share their challenges, I became aware that the feelings it evoked were not loss of respect but the exact opposite. These are the kind of people I wanted to follow! It occurred to me that maybe some of the things I’ve crammed down as shameful, boring, and unliked, are actually sources of strength and connection. This has translated into a more positive, proactive way of tackling difficult conversations and driving a result.

There’s always another side to the story. As I shared my own thoughts or listened to others, it was striking to me how often my initial impression could be way off by what was actually going on. In T-group, sometimes we’d take a pause and ask someone, how did you react to what was just said to you? and the answers were fascinating. My favorite framework from LIT is the idea of The Net which has made it far easier to constructively give and receive feedback.

LIT created an opportunity for me to get some honest feedback on the impressions others had of me good and bad. And many of the foundational challenges of being a leader lie in exactly this realm, which is how this stuff translates into the business world. How can you get really good at identifying and addressing conflicts as they arise in your team? Can you get faster at admitting problems and fixing them? While the tactical and operational work of building companies is often what gets the focus, these intangibles are just as important.

LIT is enacting change, one human at a time

I see LIT is an antidote to the cultural problem that many founders and leaders are facing in their work today. It was originally founded during the time of the #metoo movement rising and a lot of articles about toxic workplaces, with the belief that a small group of committed leaders can set the standard for what it looks like to build a successful AND culturally healthy company.

Many leaders feel an intense pressure to posture and say everything is great when it’s not. There’s an idea that we must wear “The Mask” that is our public face, when inside we may be stewing with inner turmoil. Founders already have one of the most difficult jobs out there, and struggling in isolation shouldn’t be yet another burden. This pressure at the top magnifies inside companies as well. If the fearless leader is working around the clock and admitting no difficulty, what kind of norm does that establish within the team? These are the challenges that compound to create unhealthy workplaces.

I don’t see the output of this work as encouraging leaders to be bleeding hearts that are in touch with their feelings and mentally healthy at the cost of their business execution. I see it as a win-win to unlock the possibility of a better way. There is a better way to build a resilient organization that executes faster. Or to retain and engage employees. Or to keep leaders saner and more compassionate. The more conversations we have on this, the better off we are. This is part of why I’m so excited to be on their board helping them do this great work in the community.

If this resonates with you and you’re interested in learning more about Leaders in Tech, visit their website here. Applications for Fellows are also open through May 4 and you can apply here.

The post My Fellows Retreat with Leaders in Tech first appeared on Ada Chen Rekhi.

Listen: Apple Podcasts | Spotify | YouTube
Transcript: Lenny’s Podcast

I was recently invited onto Lenny’s Podcast and had so much fun there talking about how to make better decisions, career strategy, and living a life aligned with our values.

Topics covered:

• Curiosity loops to make better decisions
• Values and how to map them
• “Explore and exploit” strategy for careers
• “Eating your vegetables”
• and more!

Have a listen and hope you enjoy it!

The post Podcast: How to make better decisions and build a joyful career first appeared on Ada Chen Rekhi.

I use something I call a curiosity loop to systematically extract wisdom from my network.

Curiosity Loops in Action

To get you inspired, here are some examples of curiosity loops I’ve run

• I’ve been struggling to manage a never-ending to-do list. Can you share what you do personally and what lessons you’ve taken along the way?
• I have someone on my team who is obviously very talented but can be unreliable. I have given them feedback in the past, but it doesn’t seem to stick. Any advice on what I could be trying?
• We’re getting ready for a new baby. I imagine there are some surprises in store for us. What are the biggest lessons learned that you wish you’d known as a parent?
• You’re someone I admire who wears multiple hats professionally. How do you juggle and prioritize across having multiple jobs pulling at your time?

How to Run a Curiosity Loop

Step 1. Come up with a good question

A good question has to be specific and meaty to get a good response. This gives them something to hang on to, and solicits their rationale.

An example of a bad question: what should I do with my career?

An example of a good question: I’m thinking about doing a dev boot camp and changing professions to be an engineer. Do you think it’s a good fit for me and why?

Step 2. Curate your list of people

Think about who would be helpful for you to answer this question. It isn’t necessarily always just people who know something about the topic area, but could also be someone who knows you very well.

Step 3. Ask them for their feedback

I use curiosity loops to answer everything from life questions to business questions, so depending on the context I’ll adapt the way that I ask it.

If it’s a loose personal question where I’m just trying to get a diversity of inputs, it becomes a question I ask in all my meetings during the week.

• Example ask: Can I ask you a parenting question? We’ve been having a debate on the value of extracurriculars for our 2 year old daughter. She gets a lot of activities through her preschool, and we regularly take her out to hikes, shopping, and restaurants. We’ve also read about the value of unscheduled time. What’s been your take on things like swim and dance classes and how much to fit them in?

If it’s a professional question, I might frame it as a short, targeted request for feedback which they can respond to over email.

• Example ask: Hi. A quick favor to ask from you — I’ve been invited to join Lenny’s podcast and am preparing some potential topic ideas for his audience. I wanted to ask for your help because with your xyz background. My ask: Take a few minutes and review the list below. What are the top 2-3 topics that you personally would be most interested in hearing about and why?

Step 4. Assess their feedback

After every piece of feedback arrives, ask yourself if there are any surprises? If they disagree with what you would have wanted to do, look at it closer.

Step 5. Close the loop

Instead of a generic thank you, close the loop by sharing some of what you’ve learned.

The post Make Better Decisions with Curiosity Loops first appeared on Ada Chen Rekhi.

My belief is that it’s important to operate our lives by an Inner Scorecard. While an Outer Scorecard is based on how the external world sees you, judges you, and stacks you up in comparison to others, an Inner Scorecard is something based on what you truly want without thinking too much about what other people think of you*.

Like many people I know, I’m at base an Outer Scorecard person. I’m always worrying about what other people think, making comparisons, and choosing paths based on how it looks. This was not necessarily a bad strategy, despite not knowing what I wanted out of life: it drove me to attend a top university, maximize my career and finances, and have a lot of fun along the way. I consoled myself that this is a path that preserves optionality. While I honestly didn’t know what I wanted to do, it is hard to go wrong doing what was expected of me. I was envious of others who seemed to have conviction and confidence about what they wanted out of their lives.

However, there are some challenges with this approach. A common problem that Outer Scorecard people often have is they don’t know what they want! So how do you work toward a goal if it’s undefined? It’s a good investment to work on figuring that out, and below I’ll share a tool I recommend to do so. Furthermore, while this initially seemed like a good strategy, following a life based on what others wanted is suboptimal for your happiness. It’s easy to get trapped along the way: a joyless but prestigious job, unfulfilling relationships, mismatched expectations, etc. If I continued on my path, I worried that I would wake up one day and see an overworked and unfulfilled person in the mirror spending my days in the exact opposite way that I actually wanted to spend them.

The Values Exercise

Doing this Values Exercise, adapted from Taproot Foundation, is one of the most useful tools that I’ve ever had in defining what I want.

It takes a short 10-15 minutes to complete and has helped me build my own Inner Scorecard.

Click here to get the exercise.

The output at the end of the exercise is a stack-ranked list of core values that define what you care about.

The beauty of the values exercise to build an Inner Scorecard is that it’s not a structured plan but more like a rubric. It’s not a life plan or charted path. Instead, it’s more like a compass that helps name elements that you care about so they can be considered in an explicit and intentional way.

As an example, here’s a list of my output:

1. Build strong bonds with my chosen family
2. Nurture happiness
3. Seek growth opportunities
4. Grow in wisdom
5. Realize meaningful achievements

How to Apply the Values Exercise

Once you have your results, consider these questions:

How well are you living your values? If this is a scorecard for your life, how are you doing against them? It’s helpful to take a look at your past week’s calendar from this lens. When I’ve done this in the past, I’ve noticed points where I’ve needed to course-correct from workaholism to ensure I’m spending time and energy on key relationships and learning new skills.

How well does your decision align with your values? When considering big life decisions, how do the choices stack up? I’ve used this for decisions from career opportunities, relocation, and managing friendships. It’s been very helpful as a counterpoint to decisions that have very clear outer scorecards like career ($ or prestige) or social expectations (what you’re expected to do). Having the clarity of an alternative values scorecard exposes the happiness tradeoffs more clearly.

There are other ways to use this, as well! I asked some of my closest relationships to take this and in the process of talking through the words they chose I learned a lot more about what they care about. It’s also been an interesting insight into how I view others – whenever I run into anyone who is the opposite of those values, I’ve noticed that I have a stronger reaction.

Where paths diverge

More than social approval, more fame, more wealth, we need a life with less stress, more connection, and more meaningfulness. What that looks like is different for everyone. We’ll only have this if we are successful by our own scorecard.

*If you’re interested in hearing more about scorecards, this isn’t an original concept. The first time I ran into this concept was in Alice Schroeder’s biography of Warren Buffett and the concept has stuck.

The post Build Your Inner Scorecard: A 10-Minute Exercise for Better Decisions first appeared on Ada Chen Rekhi.