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5 Ways yoga makes me a mindful leader

5 Ways yoga makes me a mindful leader

There was a time when a day never had enough hours.

I’d start work at 7 or 8 in the morning, checking emails right after waking up. I’d either skip lunch, have it at my desk, or have it during a meeting. By the time I realized it’s already 7pm, I’d have gotten to less than half of my day’s to-do list.

And I loved it. Working gave me purpose. A busy day like that made me feel important and valuable.

Until it didn’t.

My family life hit many challenges. I was never present with them. On vacation, I’d get bored at anything we did, finding little value in spending time “unproductively.” I went in and out of top restaurants at the same speed as drive-thrus. And worst, I neglected my partner in life, my best friend, the love of my life. I spent very little time acknowledging her needs, often failing to listen… thinking that my life was more important.

That’s when I knew I needed to stop and smell the roses. I hadn’t been able to enjoy the moment for years… always preoccupied with the next step.

So I picked up yoga. I chose it because I wanted to take on an activity that I perceived as “useless” professionally, that would snap me out of my daily routine, and that would take me out of my comfort zone. And if I got a good stretch out of it, why not?

I thus signed up for a Groupon at a local yoga studio. It became the best thing that ever happened to me all year.

It was everything I expected, and more. It did take me over six months to start feeling what it’s like to live in the moment, to focus on what I’m doing. I still struggle at it. Yoga also made it apparent when I failed to be present: I simply fell from my poses. Falling helps me recognize my mind has gone astray, subconsciously. And that’s when I actively bring my mind back to the moment.

Ironically, taking the time to be away from work has also allowed me to reflect more comprehensively about work. That’s right, I owe to yoga many important lessons in leadership. Here are five of them:

“It’s ok to fall, it shows that you’re trying.”

My yoga teacher said this to me a lot when I first started.

I’d be falling left and right when trying to balance my poses. Her words encouraged me to keep trying and to push myself.

The same can be said of innovation. If we truly want to do something new, may it be a new product, new process, or new business model… we have to be OK with mistakes. We have to create an environment where team members are comfortable trying new things. It’s when we make a stretch mistake that we know we’re trying, that we’re pushing ourselves into unknown territory, that we’re growing.

“Observe differences, don’t judge.”

As a decision maker, it can be difficult to not judge everything around me.

Everyday, I have to judge individual team members’ performance, the team’s progress, the company’s culture, among other things. And it rarely stops when I go home. I keep judging my friends’ behavior, my spouse’s thoughts, and even strangers’ actions. I once judged a mother who seemingly was neglecting her child in a park… Yet fact is, I don’t even have a kid. Who am I to judge?

My constant need to judge also affected my objectivity. I’d often base judgements, and even take action, on unconfirmed assumptions and preconceptions. At work and at home. This hurt the people around me.

In one instance, I received note that a team member said something inappropriate. Without fact checking and without asking for that team member’s version of events, I proceeded to reprimand him. It fired back once we discovered that the person reporting the event misheard the conversation and took things out of context. The damage was done.

Then one day at yoga, we were doing a pigeon pose where we stretch our hips. After stretching the right hip, we proceeded to the left one, and the teacher said “Observe differences, don’t judge. Notice how the left one feels compares to the right.”

That’s when something clicked in my mind.

Being so quick to judge, I had forgotten the importance of observing things as they are. It impaired my objectiveness.

Slowly, with the help of yoga, I learned to simply observe. At work, this translated into spending more time assessing the facts before jumping to a conclusion. Instead of starting conversations with “I think that…,” I asked “Why is it that…” or “What’s the background on…” I became more confident in my decisions, but more importantly, team members trusted my decisions more.

“Practice non-attachment”

As I made my way to yoga class one day, I found myself with a substitute teacher instead of the usual teacher. I really enjoyed my usual teacher and reacted with some disappointment. Yet when class started, the substitute teacher said “I know that many of you didn’t expect me to teach your class today. It’s thus a good opportunity to practice the concept of non-attachment. To be OK when things don’t go as planned. To not be attached to a certain idea or desire.”

She was brilliant. Not only was it one of the best yoga classes I’ve attended, she also reminded me of the importance of being OK with not getting what I want. To simply go with the flow, react accordingly, and not be emotionally disturbed by surprises. Fact is, nobody can predict the future, so why get upset at something that was never certain in the first place?

At work, I applied this mindset when planning for the future. I favored scenario planning as opposed to forecasting when it came to strategic planning. I wanted the team to be ready if things went wrong, and not to be upset by surprises. We continued to try our best in achieving the best case scenario, but we were also much better prepared to face the worst case scenarios.

“Let the teacher and student in me honor the teacher and student in you.”

My yoga teacher ends her practice with this line every single class. At first, I thought to myself “I don’t get it… there’s nothing that I can teach her about yoga.”

Yet one day, while having a random conversation with my teacher, she asked for my advice on something about online marketing. It finally occurred to me that each and single one of us knows something that another individual doesn’t.

Armed with this mindset, I saw my team members in a new light. I perceived their diverse background and experiences as sources of learnings for me and for everyone around them. I actually went back and looked at each individual’s resume to see if I had missed anything about them. I also became a lot more active in asking whether anybody has had previous experiences when it came to implementing a new change or a new process.

Needless to say, I’ve learned a lot more from my team and my colleagues after seeing everyone as a teacher.

“Dedicate your practice”

At the beginning of class, my teacher often starts by asking us to dedicate our practice. I usually go to yoga without much planning, so that question always catches me by surprise. It forces me to ask myself “Why am I here?”

To which I’d respond with: To learn to live in the present, to avoid conflict with so and so, or to stop hating inconsiderate drivers. That question helped give meaning to the time I spend at yoga.

Then one day, I started asking myself that question at work as well: “Why am I at work today? How should I dedicate my work?”

To which I’d respond with: To help solve XYZ, to feed my family, to make a positive impact on…

On good days, asking myself these questions boosts my motivation. And on bad days, they remind me of the bigger mission I’m pursuing, helping to smooth out any temporary bumps in the road.

I can confidently say that dedicating my practice, and my work, helps to remind me of my life’s purpose.

I’ve been much happier since that first day of yoga. It helped me make some good headway in being mindful, in appreciating the time I spend with my family. And in addition to yoga, I also discovered a book that helped me reflect and practice mindfulness: Wherever you go, there you are. Highly recommended to all those that are always thinking about the next thing in line…


Recommended exercise

Let’s ask ourselves: “When’s the last time I didn’t try to get somewhere else?”


Are you leading a startup team? Get started on the right foot with the Start-up Manager Handbook. And subscribe on the right for new insights every week!

When is it time to move on, change job, switch career?

When is it time to move on, change job, switch career?

I acknowledge we all share different priorities, backgrounds, and ambitions, leading to very different career outlooks. I’m thus not going to answer the above question for anyone else but myself.

I do find it important to address this topic in the context of startup leadership. Moving on opens up an opportunity for others, while allowing ourselves to tackle new challenges. It helps everyone realize more of their potential.

What I’ve realized in asking myself this question is that there’s never just one motive. Deciding to move on from one role to another is the result of many variables. I’m thus going to share a set of questions that have helped me make such a decision:

“Am I the best player in the band?”

Learning new things every day is important to me. Therefore, if I’m the best person at doing XYZ at my organization, chances are I’m not learning about XYZ anymore.

To quote, Louis Armstrong (I believe he said this): “If you’re the best player in your band, it’s time to look for a new band.”

This can however be a tricky question to answer, since learning to teach XYZ to another individual is also appealing to me.  It’s not always about learning in the context of gaining new knowledge, but also giving new knowledge to someone else (especially as a leader).

In the end, it comes down to what my motives and goals are.

“Do I agree with where we’re going?”

It doesn’t matter if the company is heading toward a guaranteed gold mine or working on the trendiest technology. If the destination or strategic goals don’t jive with my personal interest, it’s a waste of time to me. I view the opportunity cost of not pursuing something I enjoy as extremely high.

For example, many people would jump at the chance of working on a space vehicle that goes to Mars, yet personally, I couldn’t care less. I am much more interested in solving problems with an impact here on earth.

“Am I more frustrated than I am happy?”

If I experience more anger, frustration, and sadness at work than I experience excitement, joy, and hope, it’s a sign I need to ask myself some serious questions.

My take on the goal of life is to be happy. If I am not happy now, I need to identify why, and do something about it. Yet sometimes, the negative emotions experienced at work can be r of issues outside of work. I thus need to be careful in finding the root cause of my negative feelings.

For example, I once experienced a period of frustration at work, getting upset at anything that didn’t go perfectly. I knew it was not related to work, but rather caused by an issue with my family. It was unacceptable and I needed to do something about it… So I worked to resolve my personal problem, which also made my days at work much more joyful.

“Do I trust the leadership?”

I need to trust that my leaders know where we are going, know why we’re going there, and are capable of taking us there. That they have an explicit strategy.

My trust for the leadership team tends to erode every time they say one thing and do another (words mean nothing anymore), don’t follow up on an ask of mine without explanation (don’t value my thoughts), or ignore concerns I bring up (don’t listen to what I have to say). At a minimum, I need to trust that they have the team’s well-being at heart. If they don’t, then there exists irreconcilable differences between my values and their. It would indicate that it’s time to move on.

A special case with inexperienced leaders / founders is their inability to act on their intentions. They will have the best intentions, but fail to execute. They lack skills, experience and knowledge. In that case, even though I trust their intentions, I do not trust their ability to lead. That’s a sign I need to advocate for more experienced leaders to take over, or move on as well.

“Am I excited to go to work?”

In one of my previous jobs, the first thing I thought about in the morning was leaving work and how I could shorten my day. I clearly didn’t enjoy what I was doing, wasting both my time and the company’s time.

“Is the culture toxic?”

Luckily, I haven’t experienced this first hand. But a friend of mine did.

His manager was verbally and emotionally abusive, often publicly blaming, shaming and yelling at my friend in public.

My friend didn’t fully recognize that his boss was wrong until he quit. The whole time this was happening, he felt responsible for the mistakes and problems blamed on him. It’s only when he compared his new job’s culture with his old one that he realized his manager’s behavior was abusive and discriminatory. To assess whether there exists an abusive relationship with our manager, I recommend reading the signs of abusive romantic relationships and replace “partner” with “manager.”

Beyond bad bosses, a company’s overall cultures can also affect our well being. Perhaps we’re selling products that hurt people more than they help, perhaps we’re deceiving our investors, or perhaps the culture simply doesn’t allow us to be honest with ourselves. If the culture is making me unhappy, it’s time to change culture.

Deciding to move on is difficult. It destabilizes our routine. Plus, we all have to pay bills, support our families, and respond to social pressures. Sometimes, no matter how unhappy we are, we stick with our job, thinking that it’s the best worst thing for us. I get that, it’s hard.

Yes, it does take courage to say no to a steady paycheck and look for a new job (which may not be any better), pursue a passion, travel the world, or found a company. But to make the switch easier, we can start by drafting a plan. Things suddenly get easier and look plausible once we identify small steps that we can take immediately, over the next weeks, and next months, to eventually achieve our goals.

We can work on our personal goals in the same way we helped our company achieve its goals. We can apply the concepts of scenario planning, market research, idealized design, and competitive strategy to our personal objectives. Don’t believe me? Many have done it… Check out “No fear no excuses” by Larry Smith.


Recommended exercise

Let’s ask ourselves: “Am I doing exactly what I want to be doing, and making progress toward my goals?”


Are you leading a startup team? Get started on the right foot with the Start-up Manager Handbook. And subscribe on the right for new insights every week!

Top 6 business intelligence mistakes

Top 6 business intelligence mistakes

These days, companies large and small have an insane amount of data to help with decision making.

A small mom and pop restaurant with a cloud based reservation system can forecast how much ingredients to order for the week. Yet we all still make bad decisions. Why?

First of all, let’s not blame the data. By itself, data can’t do anything.

If there’s anyone to blame, it’s us. That’s right: the human beings behind the data.

We are the ones that decide what data to record, how to record it, how to analyze it, and how to look at it. Between the moment we have a question and the moment we make a decision, there are numerous chances of misusing data and arriving at the wrong conclusion. It’s like walking through a minefield.

Working in the analytics field, I’ve seen hundreds of data analyses go nowhere, wasting thousands of hours of effort. So I’m going to share five of the most prevalent mistakes I’ve seen.

“What’s the actual problem?”

I once helped an e-commerce company analyze their top 10 sources of new visitors. After seeing the results, they were ecstatic to find that both their paid campaigns and their blog were top sources of new visitors. These were channels that they could actively control and scale. So they did just that: They invested more money in their paid campaigns and kept their blog active.

Yet a few weeks in, they started to complain that their effort didn’t translate into higher revenue. A lot of new people were visiting the site, but not buying. Why is that?

The simple answer is that the analysis they wanted answered a specific question: Which sources brought the highest number of new visitors? It did not answer which sources brought the highest number of new paying customers, or high lifetime revenue customers, which would both have been more helpful to their actual problem of growing new revenue. So to avoid wasting time, effort, and money, let’s ask the right questions to begin with.

“Is the sample statistically significant?”

I once observed a sales team cancel a process change after 10 prospects failed to convert under a new process (they handled on average 200 prospects a month). By no means was that sample size significant enough to draw any conclusions yet, scientifically speaking. It was not a data-driven decision. It was an emotional decision.

I’ve also witnessed a case where a company made product decisions based on half-a-dozen phone interviews with select clients that they had good relationships with. This particular company had 500+ clients. Half-a-dozen people among a population of 500+ clients does not represent an accurate view of growth opportunities. In addition, the quality of the sample was also questionable. All clients interviewed had good relationships with the company, which indicates that the opinion of unhappy customers and churned customers were not acknowledged.

Sampling problems, including selection bias and lower than optimal sample size, abound in business intelligence. Startups are especially prone to taking shortcuts and use poor samples. Sometimes, it’s because there is simply not enough data… If a company just started acquiring customers, there may not be enough customers to make the analysis statistically significant. Other times, it’s because of pure impatience… Teams want to take decisions now, not in two weeks, so they often fail to wait for their experiments to fully complete.

The result is a decision based on poor data.

“Are the numbers relevant?

I’ve also witnessed many companies set future sales goals based on historical trends, but then change their entire sales process and expect the same goals to be hit. How can one expect the the same forecast when all input variables have changed?

It’s like expecting to fly from New York to Los Angeles in 6 hours, but then change our plane for a car and still expect to get there in 6 hours.

Let’s recognize that the analysis or forecast that we do is only good for the scenario that we considered. Should we decide to tweak or change our scenario, a new analysis needs to be performed.

“Are you sure the numbers are right?”

NASA once lost a $328 million satellite in space because one of its components failed to use the same measurement units as the rest of the machine. Target lost $5.4 billion in Canada partially because its inventory system had incorrect data.

Time and again, huge mistakes were made because the underlying data fueling these projects was bad to begin with.

So to make sure that my analysis is accurate, I often ask a second party to check the numbers. One should never review their own essay. The rule applies to analyses as well.

“What does this mean?”

Having access to information doesn’t mean that we know what to do with it. I’ve seen many people confused by data reports and unsure of what decision to take.

I once helped a B2B company evaluate which customer group to target for an advertising campaign. Their product was used by customers from three different industries, but they didn’t have the resources to tailor their sales processes and marketing content to all three groups yet.

So they began by looking at revenue generated by the three industries. Then they looked at revenue growth over time, profitability, and lifetime revenue. The results showed that 50% of their revenue came consistently from one industry, but that another industry was the fastest growing, going from 10% to 35% of their revenue over the past year. Both were potentially good choices to target and they didn’t know which one to pick.

I thus asked them to divide the total revenue by the number of clients/companies in each industry, effectively giving us the average revenue per client. My logic was that their sales and marketing efforts were going to be spent on a select number of prospects, so targeting prospects with higher individual revenue may yield a better ROI (e.g. between a $500/year client and a $5,000/year client, I’d advise to choose the $5,000/year client assuming that cost of support is similar). Based on the analysis, we saw that the fastest growing industry was also the one with the highest paying clients. This thus made the decision easier.

The point is that looking at the right information is important, not just information. This requires people that can interpret data, explain caveats, and tell a story. I thus highly recommend for all managers, data analysts, and data scientists to read Cole Nussbaumer’s Storytelling with Data book.

“We deleted what?

I once tried to help a SaaS company understand their user churn trends, only to discover that they delete customer account information 3 months after a user deactivates their account. This meant that there was only data on recently churned clients. The sample proved to be too small and biased to draw any useful conclusions.

Developers may delete data because they are running out of room on their hard disk, or because they think that a certain piece of data is unimportant. Regardless of what developers think, from an analytical perspective, we should never ever ever delete data.

Are you leading a startup team? Get started on the right foot with the Start-up Manager Handbook. Subscribe on the left!

Checking our blind spot when making a decision

Checking our blind spot when making a decision

In a previous post, I discussed a tendency for startup teams to be blindly optimistic.

So today I’m going to share a simple exercise to help check our blind spots when taking decisions.

We start by asking ourselves…

… how do we tend to react by default?

Understanding our default behavior provides critical details on who we are, what we stand for, and how we behave in our job.

It helps us acknowledge where we stand, and whether we’re going in the desired direction. By reflecting upon our natural tendencies, we shine a light onto behaviors that we don’t usually notice. It allows us to make corrections to subconscious actions.

For example, I once asked my team: “what is the first thing that you do when you get to work and why?” 

To which a team member responded: “I check my emails to check for any fires to fight, but I really should review and adjust my to-do list before reacting to anything…” Simply thinking about something that is more or less a habit can trigger a correction.

To paraphrase famed author David Foster Wallace, a fish may not even know what water is, being surrounded by it since birth. Similarly, there are so many elements in our day-to-day that require our active focus that we may not know how our subconscious is behaving. Personally, I had a tendency to hyper-focus on my work and neglect chats I receive throughout the day, leading some people to think that I don’t care about them. I only realized it after a team member joked about the situation over lunch, after which I became more aware of my chats throughout the day.

In the context of an organization (or a team), default tendencies act as a reflection of its culture. A proactive diagnosis thus helps to ensure that the team’s culture is aligned with its desired culture.

To diagnose my team’s tendencies, I like to first recognize three entities including:

  1. The team;
  2. The team leadership; and
  3. The team’s relation with other teams.

Next, I ask each team member to reflect on the tendencies and behaviors from these three perspectives. Specifically, I ask: “In your perception, what does the team or the team leadership…” OR “In your perception, when collaborating and working with other teams, what do we…”

  • “…enjoy spending their time on?”
  • “…don’t enjoy spending time on?”
  • “…excel in?”
  • “…repeatedly fails to achieve?”
  • “…never get the time to do?”
  • “…usually ask about?”
  • “…not ask about?”
  • “…forget about?”
  • “…get confused by?”

Compiling results from all team members provides us with a comprehensive picture of our tendencies, our blind spots, and our culture in general. Our goal is not to judge, but to effectively observe differences.

Next, we need to ensure that our culture is moving in the right direction. I thus pull all team members together and review whether each trait is desirable or not. In the case that it is not, we try and identify ways to actively remind ourselves of our bias and compensate for it. For example, if we have a tendency to avoid working with other teams, we could compensate by first asking “Does any other team need to be involved?” before kicking off any new projects.

How often should we assess our tendencies? I recommend performing this exercise every quarter or two. Culture is slow to change.

I do advocate for someone to act as a culture champion to hold people accountable to any tweaks and changes we decide to pursue. In the example above, a champion would praise people when they remember to consider whether other teams need to be involved in a project, and reprimand when we fail to do so.

In my opinion, success does not translate into achieving our dream culture, but very much being conscious of our existing culture. Simply being aware our biases, weaknesses, and tendencies helps to avoid taking decisions blindly.


Recommended exercise

The next time that we’re faced with a decision, let’s analyze our immediate response (default tendency) and then take a day to think and see if we change our opinion. Is our default state of mind limiting our abilities?


Are you leading a startup team? Get started on the right foot with the Start-up Manager Handbook. And subscribe on the right for new insights every week!

How to not let failure hurt morale and diminish ambition

How to not let failure hurt morale and diminish ambition

We had missed our quarterly sales target. Again.

The news was given during a company all-hands. All over the room, I saw people staring at our CEO, not sure how to react. Frustrated, confused, and scared.

We had extremely ambitious targets to begin with, as is the case with most VC backed companies. Most individuals knew we’d be lucky to meet them. Yet as results were announced, we all felt like failures.

In the following weeks, the mood in the house was grimmer than usual. People were doubting the company’s ability to succeed, ever. Many feared losing their job as this downtrend continued.

Personally, the bad news didn’t surprise me, nor did it hurt my optimism. I never expected to hit those numbers, knowing full well they were best-case scenarios. They were not set based on what we could realistically achieve, but rather on numbers investors wanted to see (~somewhat imaginary). So it didn’t affect my outlook of the future. I knew we had a strong team and we did the best we could.

To help my team get back on track, I set up a meeting and said something along the lines of:

“Team, I know that some of you are feeling grim about the fact that we missed our sales targets again. I’m not going tell you that things will be better in the future or that the sales team will do better next quarter. I can’t predict the future.

However, I will remind you of the reason all of us are here for. Every single one of you told me that you wanted to join a startup to make an impact and to learn by doing. And the only promise that I ever made to you is that you’ll be able to do both. Does anyone in this room feel cheated by my promise?

Nobody ever promised you that it’d be an easy ride. In fact, you knew from the beginning that it was going to be a challenging and chaotic ride. Yet you still joined.

Many of us are doing things for the first time. It’s my first time leading a team. It’s our founders’ first company. For many of you, it’s your first job. So I don’t expect us to always get things right.

What I do expect of all of us is to work hard and work smart. To never let bad news and missed results beat us down. To always get back up and continue our journey.

We’re all here to do one thing and one thing only: Give out best shot. So I don’t care if we missed our targets. Let’s focus on the day-to-day and do our best.”

My point isn’t that a pep talk will fix things. Rather, it’s that people are too emotionally and mentally attached to results. So much so that when they fail to achieve their goals, regardless of how realistic it was, they lose confidence. I needed to remind my team that hitting targets, winning deals, and achieving milestones only play a small part in our overall success. It’s our day-to-day work, the time that we spend grinding and planning, that matters.

We missed our targets. So what?

I attribute our team’s grim reaction to prevalence of a fixed mindset in our culture.

[To quickly remind readers of the meaning of a fixed mindset versus a growth mindset, allow me to quote Carol Dweck (top researcher on the subject): “Individuals who believe their talents can be developed (through hard work, good strategies, and input from others) have a growth mindset. They tend to achieve more than those with a more fixed mindset (those who believe their talents are innate gifts).” I find it fascinating how these two mindsets affect how we approach life. To learn more, I highly recommend readers to checkout Mrs. Dweck’s book: Mindset.]

In my opinion, people with a growth mindset would look at the missed targets and say to themselves: “Well, looks like there’s more work to do and things to learn. Let’s try harder.” On the other hand, a person with a fixed mindset would say: “Shit. Maybe we’re just not cut for this.”

I like to think I have a growth mindset, and that my team does as well. Yet fact is many of my colleagues have quite fixed mindsets. I don’t blame them for it. It’s my opinion they’ve received too many praises supporting a fixed mindset.

Allow me to elaborate… Every time that we compliment someone with “Wow, you’re so good at…” or “You were really born to do…,” it gives the impression that success is tied to who that individual is. Their genetics. How they’re wired. It couldn’t be more wrong. Ask anyone successful and they’ll tell you that success comes from thousands of hours of practice, bouncing back from failure, and many iterations. To quote Thomas Edison: “Success is 99% perspiration.” If that’s not enough evidence, I highly recommend Malcolm Gladwell’s book Outliers, which argues that it takes 10,000 hours to master anything. I believe that. I also acknowledge that some people are better positioned to achieve those 10,000 hours faster than others, but nobody said that life was fair. The point being that success is correlated to work and effort, not simply our genes.

Are targets detrimental to the team’s motivation?

No. Targets are absolutely necessary.

Targets and goals provide direction to our teams and help gauge our progress. Without them, we’d be all running in different directions and without a clue about whether or not we’re successful.

But hitting our targets is not the only thing form of success out there. People need to feel good for having tried really hard and giving their best.

How do we prevent missed expectations from de-motivating our team?

In my opinion, it comes down to setting realistic goals, having an underdog mindset, and rewarding a growth mindset. Let’s explore each in detail:

Set realistic targets

Set targets too high and we’re bound to miss them. Team members will feel like we’re asking the impossible. Set targets too low and the team loses the ambition to achieve more (they’re already there, why try harder?). I thus recommend to set targets slightly higher than what we can achieve today.

For example, if we forecast $100 in revenue based on historical performance, and $150 in revenue under a best-case scenario, I’d set our target as a range between $120 and $150. I’d proportionally increase the reward should we hit higher than $120. This challenges the team to do more than they have done historically, while incentivising even better results should they actually hit the lower goal.

If the team fails to meet the target in their first try, I’d keep the target unchanged until we achieve it. The goal is to keep learning and iterating until we succeed. The critical part of this approach is learning how to leverage scenario planning to set targets, instead of forecasting based on the best possible outcome. I thus recommend checking out author and VC Guy Kawasaki’s Art of the Start, which has a great section on how to set realistic goals from the bottom up.

Maintain an underdog culture

The moment that we think we’re successful is the moment that we stop trying.

I therefore believe we need to support an underdog mindset. We need to feel like we’re always chasing a bigger fish with limited resources. We cannot be too positive in our assessment of the company – the best underdogs feel that they’re behind and need to work harder.

For example, we need to avoid saying things like: “We have a ton of money in the bank from our investors;” or “We’re growing faster than any competitor in the field, ahead of the game by a good margin.” Even if these statements were true, it creates the perception that we’re successful and can relax a bit.

In addition to saying the right things, we also have to act like underdogs. Buying $2,500 Macbooks for everyone, giving free lunches and craft beers, and stocking the office with $1,000 chairs and standing desks does not paint the picture of an underdog company. These “perks” create a culture of entitlement, where people fail to value what they have, and perceive that they are in a pretty comfortable spot.

We don’t want our people to feel comfortable. We want our teams to feel like their survival is at risk. We need people to work hard to win. If we’re going to give perks, people need to earn it: e.g. Food should only be offered when there’s progress to celebrate, like when the team pulled an all nighter, or made an awesome attempt at hitting their goals.

We can’t give anything for free.

Praise effort and progress

Creating a growth mindset culture starts by praising team members’ daily effort. As leaders, we need to make the time to observe team members regularly.

A couple years ago, I’d only high five people when they hit their targets (which meant rarely), and had 0 hours dedicated to observe and praise people. Little did I know that I was actually supporting a fixed mindset.

Nowadays, I spend at least 30min to an hour every day to see if team members are trying harder than usual, and praise people’s efforts. For example, if I see someone is practicing ahead of a presentation, I’d stop by and say “Hey, I see that you’re working hard on the presentation. Feel confident yet?” Or if I see team members brainstorming solutions to a problem, I’d approach them before the end of day and say “I saw you spending a good amount of time brainstorming in that room with so and so. Looked like there were some good ideas on the whiteboard. How are you feeling?”


Recommended exercise

Let’s observe team members when they fail to achieve a goal. Are they optimistic and already thinking about how to improve, or are they simply feeling down?


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