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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!

How to fire an employee without bad feelings

How to fire an employee without bad feelings

Who we hire, who we promote, and who we let go defines our team culture.

If we hire and promote hard working, ambitious individuals, while letting go of lazy people, we incentivize and maintain a productive culture.

Reality is not that simple. Many of us managers struggle to let go of underperforming team members. I find that this can be caused by a lack evidence on these individuals’ unproductivity, a hope that things will improve, or bureaucracy and politics that make the matter overly complicated to deal with.

In one instance on my team, the decision on whether to let go of an underperforming team member dragged on for almost a year. During that time, we provided weekly one-on-one coaching sessions, mentoring from three different leaders around the company, and even made changes to the person’s work responsibilities to better match their perceived strengths. 

Because the individual tried so hard to make it work, we were OK to go all out to help.

Yet improvements we saw were always temporary. As soon as we let go of the training wheels, things would go sour again. In the end, it was clear that the position was simply not a good fit for the individual.

The whole experience was a costly lesson. Much time was wasted as we failed to improve the individual’s performance, or to let go of the individual early on. I spent upward 40% of my energy on an underperforming team member, among a team of 20 people. Instead of leading our top performers to new heights, I tried to rid the team of a drag. It’s like trying to build a faster car by reducing its weight, but failing at it, while not trying to improve the engine’s performance.

As result, the team didn’t innovate, nor grow as fast as we hoped for.

What would I do differently today? Two things: 1. Have a clear deadline in mind when deciding to let go of a team member or not; and 2. Never spend more than 10% of my energy and time to help an under-performer improve.

That said, I may have a different opinion if I worked at an established company. I do believe that training a hardworking and passionate, yet currently underperforming individual, can translate into an A-player down the line. So if our company’s survival wasn’t at risk, spending a little more time on training could be OK. Yet in the context of our startup team, we have limited time and resources, and each individual has a strong impact on our collective success, so we cannot waste time on people that can’t independently add value to our mission.

Now, having this clarity doesn’t make it easier for me to let go of people. Every time I have to make a firing decision, I’m reminded of the impact that I have on people’s lives, not just at work, but outside. People have family obligations, bills to pay, and careers to grow. So to help, I have created a checklist of questions to help me assess whether I’ve done everything I could, and that letting go of a team member is the best outcome for both the team and the individual team member.

Have I given the team member a fair chance?

To have a clear conscience in letting go of a team member, I personally need to make sure that the individual has had a fair chance of meeting my expectations. I thus ask myself:

Have expectations been clearly set? It’s unfair to judge an individual’s performance if we’ve never communicated what is expected of them. I often resort to clear metrics to assess whether an individual is meeting expectations. For example, if I need a team member to participate more in meetings, I may set the expectation for them to speak up at least once at each group meeting, and use that count as a gauge. If there are no quantitative measures available to evaluate one’s performance, we can set SMART qualitative expectations. In my experience, setting a clear expectation with team members resolves 50%+ of performance related issues.

Do I give feedback and direction? To further clarify my expectations, I try to provide active feedback. Taking our example from above, as we try to get a team member to participate more in meetings, I would praise the team member when he or she speaks up during a meeting, and reprimand when they don’t. Feedback reinforces the importance of the expectations we set.

Have I provided adequate training? If someone is underperforming because they lack the necessary skills, then it’s my duty to provide that training. I may perform the training myself or enlist the help of a colleague with more experience. If we lack the experience inhouse, then we need to seek training externally.

If the above steps have all been taken and the individual is still not meeting my expectations, I’d seek to let them go as soon as possible. I do usually give a final warning, where I restate my expectations, where they stand in relation to that, along with a clear timeframe on when I expect to see progress. In my opinion, this helps avoid any surprises if we let go of any individual – they may be upset, but not surprised.

In the end, we need to recognize that letting go of an individual is a win-win scenario. Our team gains the opportunity to find someone new that can add value instead of being a drag. And on the other hand, the team member being let go gets a chance to find work that suits them better. It’s clearly that they are not doing something that they thrive at right now, or doing it in an environment they thrive in, so why drag it out? Nobody likes doing something they fail at. I’ve witnessed several cases where an individual becomes an A-player at a different company or another field of work after being let go. So let’s waste our time, nor other people’s time. Let’s everyone’s full potential sooner.

[NOTE: Your legal jurisdiction may have specific laws on employee termination, please consult an HR lawyer for specific advice. The content exposed in this article is only an opinion.]

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 working at a startup makes me happy

Why working at a startup makes me happy

When I joined a startup straight out of college, I had 3 goals in mind: 1. To help people make data-driven decisions; 2. To learn how to lead and grow a team without risking my own dollars; and 3. To make a positive impact on the world.

So when I found work at a 12 people strong business intelligence start-up that just raised a seed round, the fit couldn’t have been better. Throughout this adventure, I had the chance to work with tons of talented and ambitious individuals, who instead of taking a well paying job at an established company, also decided to join an unproven startup.

I always asked myself why these other people took the plunge… So I started asking them and documenting their motives. In this blog post, I’ll be sharing the top reasons behind why people take startup jobs. This insight has been crucial in helping our team retain talent.

Why do we join startups? Because we want…

“… to have an impact”

During job interviews, I always ask candidates why they want to join a startup. And I can’t remember the number of times that people respond with: “I want to have an impact.

Many of these candidates have worked at larger and more established organizations where their ideas weren’t listened to, or just graduated from PHD programs where they grew frustrated of academic politics. And they’ve definitely come to the right place.

Because startup companies lack proven business models, functional processes, and sometimes experienced leadership, opportunities for each single individual to make an impact are found everywhere.

Let’s however recognize that as our organization grows, there are high chances that structure, processes, and politics affect our team members’ ability to voice their ideas and have an impact.

So what can we do to maintain our innovative culture? Here’s what I think: 1. Never lose trust of team members; 2. Strive to coach and delegate, not micro-manage; and 3. Involve team members in decision making and be transparent about our choices. In the wise words of my boss: “Just do the right thing.

Team members will be happy as long as they can influence decisions. It won’t matter how large our organization grows.

… to learn”

Another recurring theme when I probe team members about their motivations is the desire to learn. To learn new technical skills, lead projects, and how to manage people. To learn in an environment where making mistakes is OK, even rewarded.

Sounds familiar? That’s right, startup team members aren’t that different from founders: We all want to push ourselves to the limit, get out of our comfort zones.

That said, learning also happens at established organizations, not just startups. It takes the form of observing senior people do things “right” and receiving some kind of structured education. However, the missing piece is the opportunity to learn by trial and error.

Ambitious (and sometimes impatient) people want to learn by doing. And because established companies usually have proven business models and functional processes, they have little incentive to let inexperienced people try things and make mistakes. They are simply more conservative and risk averse.

However, I do want to share a word of caution. Completely learning by trial and error can be taxing on a startup’s growth. It takes a lot more time to get things right. So I personally like to adopt a hybrid model, where we have experienced managers and senior technical people available that can coach younger team members while they try things for themselves. This allows our younger team members to learn by doing, but also leverage the experience and insights of those that have already made mistakes. As result, the number of mistakes made before getting it right and chances of making the same mistakes are greatly minimized.

“… to have a quick win”

Another trend that I’ve noticed among startup employees is the desire to have a quick win. To become successful now, not when we hit 40 or 50. Some people want this more than others, but we all hope for a successful exit.

Why do I think that this mindset is prominent among startup employees?

For one, I don’t notice people joining social or non-profit startups as much as I notice people joining for profit companies, especially well funded and fast-growth ones. How many social entrepreneurs or startup companies can we actually name? We’re lucky if we know one. Fact is, society and media outlets find for-profit ventures that receive billion dollar valuations much more sexy than non-profits. Our goal is therefore to flip those stock options of ours and make a quick dollar.

Second, startup team members have extremely high, sometimes unrealistic, expectations for their companies to succeed. I witnessed this after our startup, unfortunately, had to perform a strategic layoff. While most individuals took the news with maturity, there was a good number of individuals that were extremely upset at the company’s failure to hit its goals. What I realized was that these individuals expected the company to succeed. Even when the chances of a startup making it to an IPO or getting acquired is only 1 in 10, some team members expect success as an outcome. They expected a quick win.

So how can we satisfy our team’s thirst for quick wins without promising IPOs? By accelerating other aspects of their careers, which gets to the next point…

“… to accelerate our career and be valued”

Media outlets continuously report on stories of people straight out of college making millions. While most of us know that the chances of actually becoming millionaires is slim, we’re still attracted to the thought. And by joining startups, we’re hoping to jumpstart our careers.

We want to do meaningful work, to lead, to get big titles, and to get big money.

So in my opinion, in order to retain talent, startups need to delegate responsibilities and promote employees at a faster pace than established companies do. If banks promote an engineer to senior engineer in 3 years, startups need to do so in 2 years or less.

I’d also argue that we need to promote in the form of added responsibilities, titles, and leadership opportunities, rather than a high salary. We care about comparing our career progress against their friends, and salary is hard to compare, so we value it slightly less.

“… to work with smart people”

During interviews, job candidates often ask my team “what is the best part of working here?”

To my great pleasure, all our team members tend to respond with “the people here.”

So number four on the list: Startup employees want to work with talented and ambitious people like themselves.

When I took on my job, I also moved to a new city. And because most of my colleagues shared similar interest, outlook on life, and values as myself, they also became my social circle. Even when we hired new team members, it felt like we were hiring friends. We had people of all backgrounds, demographics, and ages, but all shared the same drive to create something great.

This culture is very hard to create at established companies, where some employees have been there for ages, may not prioritize their professional life as much, or simply don’t have the same amount of energy anymore.

So one simple thing we can all do to keep ourselves happy is to continue hiring top talent, and never be OK with mediocrity.

“… to be cared for”

I’m going to bring up benefits for a moment. I’m currently witnessing a trend where startups promise unlimited vacation, free lunches, beer… thinking that it motivates people and that these things are the basis of a good culture. Yet nothing could be further from the truth (this Bloomberg article supports my argument).

Honestly, I believe that much of these material perks are unnecessary and unproductive. If we do everything mentioned in the points above, our team members will be motivated by what they do, not what they have. Free food and material perks such as the latest Macbooks may actually set the expectation that our unproven startup is already successful. That we’ve got so much cash in the bank that we can afford these perks.

Yet what we actually need is for team members to feel that we’ve yet to achieve success, and that we have to continue working hard and smart. Perks work against that perception.

And regarding unlimited vacation days, I’ve always found that policy confusing. In my opinion, it sets unclear expectations around what is a reasonable amount of time off. Some individuals will take 5 weeks off, yet their managers will complain about it – the policy clears states unlimited, so why are we making the individual feel bad? On the other hand, some individuals will only take a couple weeks off every year, the norm in the USA, but envy colleagues that take more time off – as if others were abusing the system.

The problem is that everyone interprets “unlimited” differently. Some judge unlimited to be 2 weeks, while others judge it to be 5 weeks. It all comes down to what individual managers agree to, but whatever they decide, it’s unlikely to be anywhere close to unlimited. So to set clear expectations for everyone, I strongly advocate for an absolute amount of vacation time every year (e.g. 4 weeks).

The one element of a compensation package that we should not neglect is a fair market rate salary. Many startups underpay their workforce and compensate by giving titles and perks. However, we need to realize that it’s not a replacement for salary. As our team members age, they start having family and kids. This changes their priorities.

I’ve witnessed many talented colleagues leave the organization because of undermarket pay, joining organizations that can afford to pay them more. They also tend to be our A players, individuals that acquired a ton of experience and knowledge through trial and error training. Quite valuable assets that we lose to established firms…

So forget the material perks. We want market rate compensation and a clear amount of vacation time. We want to feel cared for.

“… and to work for a visionary leader”

Startups are a chaotic affair. Our priorities change month to month, and sometimes even our business models pivot.

Among all these changes, I’ve found that team members often find comfort in a visionary leader. An individual that knows exactly where we are going, why, and how. By believing in their leader, team members don’t doubt their eventual success.

So how can we, as leaders, create the perception that we know where we’re going, why, and how? Well, for one, we need to know these things. I thus find it helpful to:

  • Make sure to have a competitive strategy;
  • Explain why before implementing any changes;
  • Care honestly about team members’ well being and personal growth;
  • Be around the team, experience their daily work, and empathize with their daily challenges;
  • Facilitate problem solving and provide active guidance on what solutions are aligned with our company strategy (know what not to do prioritize and undertake); and
  • Avoid micro-managing as it undermines the team’s ability to execute.

Ultimately, we all want to feel important. As long as we feel purpose in our work and have the means to live comfortably, we will fight ferociously to achieve our team goals.

Recommended exercise

Let’s conduct a survey with our team members and ask them: “Why did you choose to work with us? What is important to you in your time here and what is not?”

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!

Should I speak up and voice my thought?

Should I speak up and voice my thought?

I’ve definitely had strong thoughts about things at work, and yet kept them to myself.

In many instances, it was absolutely the right thing to do (e.g. when I’m frustrated at a client), but in other cases, it was most likely counter-productive. Especially in a startup environment, it’s my opinion that ideas need to flow freely. 

So in this blog post, I’m going to explore a few situations where not voicing our thought can be detrimental to the company:

“That’s a good point… now I don’t need to bring it up anymore.”

My process for reviewing product plans goes something like this: 1. Review the entire plan; and 2. Give feedback that others haven’t given yet (e.g. ask about how my team will be impacted).

What I fail to do is show support for other people’s thoughts and feedback with +1’s.

That hurt us bad one time:

After reviewing the plan for a new product feature, I noticed a comment that a colleague put in: “The design team failed to gather input from the customer success team, which would eventually have to use and educate our clients on the new feature.”

I agreed entirely with that comment, but didn’t show my support. My colleague ended up being the only one that voiced that concern.

So guess what happened… They designed and launched the feature without input from customer success. It resulted in flaws that caused some frustrations among users at launch. There’s a high chance that it could have been avoided by simply including the CS team in the product design process. That wasn’t the only negative outcome either. By neglecting their input, the customer success team had also lost a good amount of trust in the design team.

Speaking with the design team leader over the issue, it became clear that they didn’t get feedback from customer success because they thought that it wasn’t as important as some other issues. Afterall, only one person voiced the opinion that CS feedback was warranted.

So what did I learn? That +1s are important. People gauge the priority of issues by evaluating how much support it has.

“I don’t think they’d listen to me…”

I have dozens of conversations each month listening to colleagues’ frustrations about their managers and other team members. Most of the time, they’re simply venting sessions and I sit there listening. Yet on more than one occasion, people also shared with me thoughtful and well researched ideas that they didn’t share with their managers.

And when I ask them: “That’s a really good idea. Have you shared it with [manager name]?”

The answer is almost always: “No, I don’t think they’d listen to me.”

This clearly indicates that the individual lost some trust in their managerI therefore spend time helping individuals gain the confidence to voice their thought, and formulate a pitch that properly communicates their idea. We then rehearse it together and prepare against potential rebuttals.

In most instances, I’m happy to report that people find the confidence to effectively communicate their idea to their boss. Their ideas aren’t always adopted, but they always feel acknowledged and listened to. And more importantly, they learn a crucial lesson in how to influence leaders.

So if they don’t listen to us, let’s find a way to make the message more appealing and manage up.

“There’s nothing we can do about that…”

When discussing long-term or low-priority issues, I noticed a tendency for me to end a discussion with “Yeah, oh well, there’s nothing we can do about that.”

And right after, I’d feel like a naysayer rather than a problem solver. Why did I even spend time talking about the issue if there’s nothing we can do about it? Clearly I care enough and want to do something.

Yet fact is, there are situations where I’ve heard “no” to an idea so much, or witnessed the de-prioritization of an idea so often, that I think nobody cares anymore.

So how do I deal with that? With time, I’ve learned to stop complaining and take action instead. I actively discard ideas that I also feel are low-priority, but re-work how I pitch an idea that I believe is important. I may gather further evidence to support my viewpoint, or assess if other individuals and teams in the organization feel similarly to gain additional support.

This helps me avoid feeling bleak about the future, and continue fighting for ideas that matter to me.

When should I not voice my thought?

In my experience, there’s only one scenario under which an individual should not voice their thought and that’s when our emotions control the best of us.

Too often, I’ve reacted emotionally to frustrations and concerns I have with a team member. It’d usually put the individual in an awkward spot. Even if the concerns were valid, I always regretted my reaction. It’s simply unprofessional and demeaning to others, and fails to demonstrate that I can keep my cool under pressure.

How do I deal with my emotions now? I have a 24-hour rule. I don’t react for 24 hours and let a good night sleep help me think about the situation. It helps me take the emotions out of the situation, so that I can think and act rationally the next day.

Recommended exercise

Let’s identify one thought that we failed to voice this past week and find a way to communicate it.

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!

Do I care about my team more than my company?

Do I care about my team more than my company?

When a start-up company scales from a core team of 10-20 team members to 100+ people, I’ve witnessed a tendency for departments to lose touch with one another. Thats when we become hyper-focused on scaling our own individual team.

This often results in the loss of cross-team communication, break-downs in collaboration, along with other inter-department conflicts.

In this blog post, I’m going to share one exercise that will help our teams avoid conflicts and stay cohesive. It starts by seeing the organization as one entity, rather than a group of separate teams.

Do I see the company as one?

Adopting this perception is critical to the success of an organization, because the alternative, to see the company as parts that work separately, will never grow the company as a whole. Allow me to elaborate:

In our day-to-day, we often view ourselves as part of one specific team, one group. In turn, we subconsciously view the organization as a group of separate entities such as marketing, sales, customer success, product management, engineering, R&D, finance, etc.

The danger of this perception is that it can create inter-team conflicts: e.g. when goals are missed, we tend to blame it on other teams; when budgets are planned, we tend to fight each other for a bigger piece of the pie.

As we don’t emotionally relate to other teams as much as we do with our own team, we focus on improving only one team: Our team. This can be detrimental. Improving only one segment of the company will not result in a better company: e.g. Hitting our sales goals may not result in higher revenue if the sales team is not collaborating with customer success on retention goals.

A company thus needs all teams to be aligned on a single strategy for it to grow. It becomes clear that improving how teams interact and work with each other is more important than improving the team itself.

In one case, I was helping a clothing retailer’s merchandising team identify product trends. The goal was to find characteristics of clothing items that people would buy as part of repeat purchases, then advertise them as part of newsletters. However, because the marketing team had differing priorities, the products we identified as leading to a higher chance of repeat purchases failed to be advertised. Instead, newsletters featured customer stories in an effort to connect emotionally with users. This is not to say that the marketing team’s tactic wasn’t effective, but because both teams failed to coordinate, time and resources were wasted. The merchandising team’s effort was in vain.

The good news is that everyone is capable of seeing the company as one. We do this every day when we look at other companies.

For example, we don’t react to news on Google’s self-driving cars and say: “Wow, the marketing team on Google’s self-driving car project is really effective at …” Instead, we say: “Wow, Google is really catching a lot of eyeballs with their cars.”

Now we only have to see our own company as a unit.

Does my team see the company as one?


To help our team members see the company as one entity, we can perform a diagnosis of the company’s traits. This translates into the creation of a profile that defines our organization and exposes our group dynamics.

Having team members evaluate the organization as one re-enforces the mindset that we are all on the same boat, regardless of what teams we work with.

One approach is to survey all team members’ perception of the organization, asking the following questions:

  • What is your perception of our company’s current vision and strategy? How do we hope to impact the world, why, and how do we plan to achieve that?
  • What are natural tendencies and behaviors that you notice of your team, other teams, and the company as a whole? What are some biases that you observe, what do we enjoy/don’t enjoy doing, what mistakes do we repeat, and what do we prioritize and de-prioritize?
  • What frustrations do you experience that gets in the way of our company achieving its strategic goals? What are you repeatedly frustrated by?
  • What do you feel are our company’s strengths and weaknesses? What helps us achieve our goals and what drags the team back?
  • What values do we live by? Based actions and behavior observed, what values do you think we stand by?

Assembling a company profile based on every team member’s perception allows for the entire company to actively reflect on what type of animal it has become. This awareness alone will make team members more empathetic to other teams. Should we take it a step further and incentivize changes while praising improvements, teams will also implement changes to eliminate behaviors they perceive as negative or unproductive.

How often should we do this and why?

I recommend for this exercise to be performed at least twice a year for a couple reasons:

  1. Start-up companies tend to get distracted by new ideas that pull teams off alignment from the company strategy, so regular assessment helps to diagnose whether any team is going off-course, and to actively re-align them;
  2. Similarly, as a company evolves, its traits change. It’s thus important to regularly assess whether the company’s behavior is evolving in the direction that we want, creating the culture that we desire.

Let’s explore these two points in more detail.

1- Aligning teams to the company strategy

one team

In my opinion, it is easier for top leadership to set a competitive strategy than it is for them to keep all teams aligned to the strategy.

Especially at start-ups, individual teams tend to get distracted by new ideas and initiatives that fall outside of the company strategy. This is caused by a combination of factors including:

  • Ambitions and smart team members that want to change the world, but are easily distracted;
  • Ineffective communication from senior leadership about the actual strategy; and
  • Lackluster enforcement of the strategic plan.

The result is that actions across teams and individuals are misaligned and the company is pulled in all directions.

For example, a payment solution provider’s competitive strategy may be to focus on providing payment systems for large hotel management businesses, offering industry-specific solutions.

If that strategy is ineffectively communicated and ill-enforced, teams may take actions and decisions that are counter-productive. Marketing may run campaigns that attract all hotel operators, large and small, to get as many leads as possible. On the other hand, customer success may adopt a low cost strategy to boost profit margin rather than offering enterprise level support for clients.

The result will be that marketing money is wasted on attracting the attention of small and medium hotel companies we don’t want. And down the line, customer success will have a hard time retaining large clients without proper resources to create deep relationships.

Misaligned goals across an organization will thus slow down the company’s growth, if not reverse it.

To avoid such a fate, it’s critical to first decide and agree on a competitive strategy among the senior leadership team. Each department head should have a clear idea of their role as part of the strategy and who they need to collaborate with. Afterward, leaders will need to design and communicate the strategic plan to all their team members.

Results from the company profile survey will reveal whether everyone understands the strategy. Should there be confusion, misalignment, or lack of information on what team members believe the company strategy to be, we’ll need to clarify the strategy (i.e. highlight decisions and initiatives that are aligned or misaligned), actively refuse resources to misaligned initiatives, and review team goals for strategic alignment.

With limited resource, there’s no time to waste on misaligned initiatives.

Following up on our example above, the payment solution provider’s marketing goal should be to attract as many large hotel operators as leads as possible, and to neglect any small and medium size operators. On the other hand, customer success needs to provide enterprise level support with an appropriate budget.

2- Is the company maturing as desired?


Keeping an eye on the company’s behavioral tendencies, strengths, and weaknesses helps leaders acknowledge the company position, and whether we need to change course to stay relevant.

As teams gain experience tackling their problem, and as new individuals join the team, a company’s strengths will evolve and new skills will be added. On the other hand, a larger team will also bring new organizational challenges (e.g. bureaucracy, processes, politics) that may add to the company’s weaknesses and frustrations. Externally, competition and changing customer expectations will often redefine whether a company trait has become a new strength or a new weakness.

Blockbuster‘s rise and fall is a great example of a company that failed to understand itself, and its position within a rapidly changing market. With the introduction of Netflix type services and changing customer expectations, Blockbuster’s competitive advantage evaporated. What were once strengths (e.g. a lot of physical stores and access to customers) became weaknesses (e.g. too much overhead cost), while existing weaknesses grew in impact (e.g. limited stock and selection). Should they have acknowledged these market changes early, there was certainly a chance to stay relevant.

Since a start-up’s operating environment can change month-to-month, it’s critical that we regularly evaluate its evolution and position within the market.

Are we too optimistic?


It takes a healthy dose of self-belief, courage, and optimism to found a start-up company. This positive outlook on the future is foundational to the culture of most start-up companies, shared by almost all team members that decide to join a start-up and forego a safe job.

I, for one, certainly believe in my company’s eventual success, even though we’ve yet to make $1 of profit.

Fact is, a positive mindset is necessary to pursue dreams and work on unproven solutions. If we had any doubt in our success, we wouldn’t be pursuing this venture. We know that the odds are stacked against us, and yet, we decide to put up a good fight.

The upside of having an optimistic mindset is clear: We always have the energy to get back up after experiencing failure, and keep moving forward.

Yet, there is also a danger to our optimism: It can make us blind to our weaknesses. At start-ups, we have a tendency to turn a blind eye to our company’s structural problems, strategic threats, and other long-term issues. These issues tend to be ones that we can’t solve right away and necessitate company-wide collaboration. And because there’s always more urgent short-term issues to solve at a start-up, we tend to ignore our long-term challenges. With time, the team learns to turn a blind eye to structural problems and let their optimism take over.

What’s the result? Blind optimism can cloud the evaluation of a company’s true situation. And slowly, it can become culturally unacceptable to voice negative thoughts. Team members may not raise or report their frustrations and challenges, for fear of being perceived as pessimists or even worse, not believing in the company’s future success. Complaints and frustrations will often follow with someone saying “Yeah, but we work with really smart people. We’ll figure it out.” Like that adds any value to the conversation…

The leadership team is certainly not immune to blind optimism (they need it most!), so they may become unreceptive to team members’ concerns, shielded by ego and by the fear that there’s nothing they can do about the issue.

At that point, the entire company is no longer capable of objectively assessing itself. Everyone drank the cool-aid. As it is no longer looking to improve itself, the company will slowly become unable to face changing market forces, to resolve internal challenges, and ultimately, to hit its goals.

So allow me to share a word of advice: When assessing the company’s profile, ask team members to be brutally honest. In the wise words of my yoga teacher: “Observe differences, don’t judge.”

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