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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?


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!

What, you’ve done this before? I really could have used your help…

What, you’ve done this before? I really could have used your help…

I once participated in the design of a new sales process. Our existing process had too many people involved, making prospects confused about who they should be speaking with on our side. It added unnecessary complications to an already challenging process.

After three different experiments, we decided to go with a process that would only involve a sales exec and a sales engineer, cutting out an account manager from the process. While we now know that such a process is quite industry standard in the software world, the majority of our team had no experience with this new structure.

A few weeks later, I had lunch with with a colleague on the sales team and our conversation went along the lines of:

“Hey, how’s the new sales process going for you guys?”

“Oh, it’s going well and we’re learning to collaborate much better. I actually worked under a similar structure at my previous job, and I can tell that this is much better than the model we had before.”

“Wait, what? You’ve worked with a similar sales process before?”

“Yeah, I guess I never brought it up…”

Now to add some context… The team member was still relatively new to the company, having joined us a few months before, and was probably still uncomfortable speaking up and proposing ideas. During team meetings, I had noticed that he only gave his opinion when it was actively sought, but remained silent otherwise. And during the sales process redesign, he wasn’t directly involved with planning and decision making, so didn’t actively provide feedback.

It also never occurred to him that he was the only individuals with experience on the new sales structure. He assumed that the leadership and those involved in the process change knew more than he did.

As result, we failed to leverage a valuable source of insight during the planning stages of our new sales process. It definitely could have helped us avoid some newbie mistakes when we implemented our sales process.

What did I learn? That when implementing new solutions, I need to always proactively ask team members whether they have faced similar situations before. I can’t just assume that people will speak up. Especially with new team members and junior employees, there’s a tendency for them to assume that the leadership knows more than they do, and that they are not in a position to speak up yet (takes a while for some people to understand that startups want people to speak up). I’ve also noticed that for many new employees, their top priority is to learn how to meet expectations of the existing system rather than question the system and improve upon it. We often mis these opportunities to learn from insight rather than trial and error.

So what do I ask people now before designing any new processes or changes?

  • Has anybody faced similar challenges and problems before, maybe at your old job?
  • What were similarities and differences between the situations?
  • Anything we should make sure to do, or avoid doing?

These questions alone won’t guarantee a successful solution, or allow us to skip steps in our innovation process, but they will definitely help us avoid unnecessary mistakes.


Recommended exercise

Next time that we consider changing a process, creating a new role, or even designing a new product, let’s ask everyone on the team: “Does anyone have experience with this?”


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!

I disappointed myself by overestimating an employee’s capabilities

I disappointed myself by overestimating an employee’s capabilities

If there’s one thing that we do well at our startup, it’s hiring smart and ambitious individuals. Those traits are non-negotiable, and we do everything in our power to assess for both during the hiring process.

One realization I recently had about working with such amazing people is that I have a tendency to make inaccurate assumptions about their capabilities, often expecting much more than a person can reasonably accomplish.

In one instance, I asked a team member to give a presentation on a problem that we were trying to solve, and pitch his solution to the team.

I expected the team member to know how to give a powerful and dynamic presentation, assuming that they teach such skills at school. However, the presentation ended up being a reading of the dozens of bullet points found on slides. It was like reading an essay off the projector. The audience was tuned out and bored.

Armed with a better idea on the team member’s presentation skills, I then personally coached him and worked together on another presentation. I pointed him to some presentation best-practices, and also had him practice with me.

He eventually became one of the best presenters on the team, consistently able to capture people’s attention and be effectively heard.

I’ve thus learned the hard way to always start with a diagnosis of an individual’s capability with regard to a specific skill, before setting expectations. Chances are that even the best player on the team can learn a thing or two, and use some practice, when faced with unfamiliar work.

The whole experience also reminded me of three other coaching tactics that I often fail to execute. Often because of a lack of time and mindfulness. So I’m going to list them below, for my own sake:

When people are doing things for the first or second time, let’s show them how it’s done, not just talk about how it’s done. When I learn new physical skills, someone always shows me how to do it before I try on my own. When I first started to rock climb for example, a friend of mine showed me how to belay, tie knots, and climb before letting me try on my own. Nowadays, whenever I want to learn anything, I watch a youtube video of someone doing it first. Yet I tend to forget this coaching approach when it comes to intangible skills. Take project management, public speaking, or time management… I’ve repeatedly assumed, incorrectly, that people could succeed on their own with some verbal tips, but without witnessing how others do it, without doing it together. It usually led to failed attempts until we worked together. So when trying things for the first time, tangible or intangible, let’s make sure to show people how it’s done.

Repeatedly reference best-practices and rules of thumb when practicing a new skill. A couple rules of thumb that I like to reference when coaching people on giving presentations is 1. Let slides complement and emphasize our verbal message, but never become the message; and 2. Answer “So what?” to each slide to ensure that the content is relevant to our overall message. So when I find that the information from a slide repeats our verbal message, or that a slide doesn’t have a clear purpose, I reference either of the pointers above before giving any specific feedback. This helps to imprint the basic rules in the mind of the learner. The goal is for our mentee to have these basic rules imprinted in their brain. Just like we don’t need to think about breathing.

Reference the framework by which we’re doing something while we’re doing it. When someone is learning a skill that has many different milestones and stages over time, I like to remind people of the framework that we’re using before discussing specifics. I want to ensure that the mentee understands the purpose of each step, and that we don’t skip any. For example, when I coach a person to manage innovation projects, I first ask the team member to identify which step of the process we’re currently working on, along with its purpose. Only then do I start discussing specific challenges, status updates, etc. Another popular framework that I reference often is the decision making process.

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!

Why my boss needs and wants my feedback

Why my boss needs and wants my feedback

I want to start this blog post by saying that I love my boss, and almost all past bosses I’ve had. In each case, each job, they taught me invaluable lessons. I’m not trying to kiss ass (ok maybe a little haha), but I’ve honestly been really lucky in meeting awesome bosses and mentors.

Yet once in a while I do get frustrated at my boss (like everyone else in my life).

When that happens, I first keep it to myself, let a good night sleep dissolve my emotions, and move on. I sometimes raise up the matter with them with a clear mind the next day, especially if the issue impact my team, but often not, when it only impacts me.

I never thought to explore why I get frustrated at my boss as compared to other people. That’s until a few days ago, when I was reading The Road to Character (highly recommended), while also being frustrated at my boss for failing to address a situation I raised up weeks ago that has now turned into an urgent fire.

What I realized was that I tend to get frustrated at my boss for failing to be perfect. Being in a position of power (in this case, a VP of our company), being superior to me, and being able to affect our startup’s long-term direction, I expected my boss to know everything I know, take the best decision all the time, and have the answers to everything. How unreasonable, right? Nobody is perfect. Nobody can predict the future accurately. And more importantly, no manager should ever be as technically knowledgeable and experienced as their subordinates (advocated by many top leaders including Andy Grove in  High Output Management).

So why did I expect my boss to never make a mistake? I attribute it to our educational system, where teachers have the answer to everything they teach, and are in a capacity to judge the quality of our work. Especially in STEM programs, there are actually “correct” answers that get perfect scores, and professors whom know the “correct” answers. Our educational system has created the perception that individuals in authority know everything.

This expectation doesn’t stop with bosses. We expect our politicians to be perfect and bark whenever they are less than statesmanlike. We expect our parents to be perfect and get frustrated when they don’t “get us” or don’t understand modern trends. It’s a sign that we simply want people, especially those that have influence over us, to always do what’s best for us.

I personally do not believe that such an expectation is reasonable, for several reasons:

  1. Everyone makes mistakes. As this blog shows, I certainly make a ton of them. And if my boss is anything like me, a human being, they ought to also have emotions, exposure to new situations, and other traits that contribute to a less than perfect response once in awhile.
  2. What’s bad for us may not be bad for others. No other individual in the world has experienced life exactly as I did. Each one of us can only witness life in our own eyes. This leads to various interpretations on the same situation, differing priorities, and diverse goals in mind. This means that what I interpret as a negative outcome may not always be a negative outcome for others. Yet because we think that we’re at the center of the world, we interpret anything that has a negative impact on us as bad. Fact is that a bad decision for us may have been positive one for our boss and the rest of the team.
  3. We don’t share the same responsibilities. As a team, our skills should not overlap, but rather complement each other. Especially in relation to my boss, I’m not supposed to share the same expertise and day-to-day responsibilities. So any expectation that my boss knows what we know perfectly and can do it even better is unreasonable. Personally, I can’t do what many of my team members do technically and that’s great.
  4. Expectations were not communicated. I also notice instances where I expect certain things of my manager, but have never communicated them. How reasonable is that? I once became frustrated at my manager for failing to reprimand a fellow colleague’s manipulative ways, yet I never spoke up about my colleague’s behavior. Without any evidence or insight on the subject, how can I assume that my boss has any idea that my colleague is behaving negatively? When I did bring up the subject, my manager was actually very receptive.

The only element that’s within our control in the above list is the proactive communication of our expectations. Everything else is outside our control, so I’d argue that we need to learn to appreciate them for what they are, rather than complain about any of it.

So if we have any expectations for our superiors, the only thing we can do is to communicate them. Any frustrations that we have in regard to an expectation are only justified if our boss has agreed to that expectation. Just like when we set expectations with our team members.

Let’s also remember that our manager’s goal is to guide our team toward our company goals. This includes making sure that we are happy and successful. Any good manager should thus be trusted with the ability to listen to our expectations of them, along with any constructive feedback.

If by experience, we find that our boss isn’t receptive to feedback, doesn’t have our best intentions in mind, and has a selfish agenda of their own, it’s time to change teams. But let’s make sure we give it a couple of tries and maybe even address the issue with their manager.

Finally, let’s also remember that all of us are in a position of authority to someone else. A team member, a child, a student… The sooner we set the expectation that we’re not perfect, and that we want their feedback, the less frustrations they’ll experience.


Recommended exercise

Let’s sit down with our boss and ask them if they are interested in receiving feedback from time to time. If so, let’s also ask them how to best communicate them.


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!