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Don’t let instincts get in the way of doing the right thing

Don’t let instincts get in the way of doing the right thing

I like to believe that I am an objective being, actively in control of my decisions and actions, especially at work.

Yet time and again, I find myself less than proud of some of my past behaviors. I’ve had demographic biases toward people; I’ve opposed arguments without assessing their basis; and I’ve agreed to ideas that are against my personal values.

Fact is, I am often a slave of my subconscious, of my brain running on cruise control. And I’m starting to recognize that like animals, I have instincts that are challenging to overpower.

Why is this a problem? It’s a problem if our actions differ from our desired actions. If our brain on autopilot takes decisions that go against those we’d take consciously. It’s especially a problem if our instincts get in the way of creating a fair, transparent, and innovative workplace. The type that startup companies in this globalized world need.

So let’s take a moment to recognize our instincts. Allow me to share three instinctual behaviors that get in the way of…

… debating with the boss

I can recall numerous occasions where I’ve disagreed with my boss and yet didn’t try to voice or argue the matter. I’ve disagreed over the team’s compensation plan, our holiday policy, and even our company strategy. Yet on many of these issues, I’ve kept my thoughts to myself.

Why?

Well, to survive of course. Self-preservation is the need to keep myself alive and economically healthy. It is also the reason I will avoid arguing with my boss. Fact is, I see my boss as the hand that feeds me, so the last thing I want to do is to create conflict and paint myself as an enemy. I simply don’t want to get fired.

How can I become more vocal with my thoughts?

Everytime that I disagree with my boss nowadays, I first note it down in my journal to first avoid losing that thought. I then let it sit for 24 hours to ensure that my reactionary emotions are gone. If I still disagree after that, I will start to work on a way to introduce my disagreement, gathering evidence to support my thoughts, and planning for the right time to speak up. I also find it helpful to state my goals (why I’m of this different opinion), because they are often the same as my boss’s goals, so it helps us start the conversation from the same footing.

… being excited about changes

Most people I know react to a new proposed change with skepticism. Not many individuals react to a surprise change with a “Hooray!” Ok, maybe extreme sport athletes do. But for most of us commoners, we love a good old routine.

Why?

For the simple reason that we are creatures of habit and routine. As explored by NPR and Psychology Today, our habits and routines help us navigate our days with greater ease, greater comfort. As I’m typing this blog post, I am not actively thinking about which letter to press on my keyboard, my brain has made typing a habit, and I only have to think about what I want to say. There are dozens and dozens of tools that each of us depend on to do our work. To become more productive, we make a habit of using all these tools.

Yet when things change, our habits and routines have to be reset. We thus are naturally upset by change. If someone was to change the letter placement of my laptop keyboard, I’d be frustrated regardless of whether it’s better for my health or not. It simply takes me outside my comfort zone and I have to re-learn basics of typing again. We thus dislike it when people change the tools or processes we’ve grown accustomed to.

Being skeptical of change is in my opinion a good thing – it ensures that we take the time to properly review any proposed change’s potential impact, and take the necessary precautions. Yet this instinct can also backfire when people are stubbornly opposed to change without reason. According to some studies, 70% of change management initiatives fail. I’m willing to bet that people’s instinctive opposition to change has something to do with that.

How can a workplace assess changes objectively?

On our team, we first make sure that there are no surprises. No changes are made or even proposed before we first accurately pinpoint the problem at hand. We then work to ensure that all stakeholders agree on the problem. Only then do we start working to find a solution to the problem. Since all impacted parties are already involved and have agreed to participate in solving the problem, there is usually little to no opposition to any proposed changes. They architected it together.

… objectively judging people, especially individuals that are different

When I interview candidates, I often find myself asking more questions to people that did not come from a background (education, experience) similar to those of existing team members. In a way, we could call it playing it safe, but on another level, I’m simply judging people differently because they come from different walks of life.

As I consulted colleagues from other companies and startups on how they handled these situations, it became clear that this problem exists across industries, and in companies large and small. Age, gender, education, ethnicity, and even fashion discriminations were rampant. My colleagues and I both suffered such discriminations as well as contributed to them. We realized that most of the time, people were not even aware that they were discriminating. We’re talking about really smart, often Ivy league educated managers that would fight for feminist causes or march with Martin Luther King should he still be with us.

Why?

In my opinion, it comes down to the fact that we fear the unknown. We are afraid of things we are not familiar with: Foreign cultures, people, ideas. Here, foreign can take the form of a different neighborhood in the same city, not just another country. In its worst form, our fear morphs into Xenophobia, as witnessed in the recent Brexit. Day-to-day, we avoid certain parts of the city, sit with colleagues that are similar to us at the cafeteria, or ask some people more questions than others at interviews.

Again, why?

The question then begs… Why in our multicultural society (at least in much of the western world), are we still so afraid? Haven’t we been exposed to enough different people, cultures, and ideas that we can comfortably shed away our biases?

Well, fact is that even though there are multiple cultures found near each other geographically, there are limited interactions between them. Cultures are not mixing.

Simply glossing over a demographic map of the USA will expose the fact that most neighborhoods in cities are segmented demographically. African Americans, White Americans, Asian Americans, and Hispanic Americans can all be found living apart from each other, in different neighborhoods. How do we expect to really understand other cultures if we are never exposed to them? Do we really understand their differing values and cultures? The situation is even worse in rural areas and smaller cities.

So this leaves us popular culture to educate us on the values and lives of foreign cultures. Yet no luck there either. According to research from USC, 73% of actors in Hollywood are white, 13% black, 5% Asian, and 5% Hispanic. That means that we are all overwhelmingly educated on white American culture, but little else.

All these stats are further augmented by the fact that 75% of white Americans do not have non-white friends. White Americans thus have no clue about the values, culture, and ideologies of the ~70 million non-white neighbors they share their land with.

This problem persists in the startup ecosystem and Silicon Valley, where most people are White or Asian. It reflects the demographic of university populations.

So how can I avoid being biased toward foreign people / cultures?

Simply being aware that we feel safer around people like us, and less so around those that look and think differently is a good start. Acknowledging we need people who think differently for innovation may be the next step. Let’s not fear our differences, but embrace them. We are all different, not better or worse.

The next time that candidates are being interviewed, perhaps we should take cues from musical orchestras and do it behind a curtain with voices masked. I’m kidding. Let’s all start with being more aware of how our brain operates on cruise control.


Recommended exercise

The next time that someone proposes a change, at work or at home, on how we do things, take note of our initial reaction. Did we oppose it instinctively, or did we keep our mind open and curious?


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!

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!

What we should never say to a new hire

What we should never say to a new hire

A relatively new team member (let’s call her Taylor) caught me out of the blue and said “Hey Blake, thank you.”

For what?” I asked Taylor, with a confused face.

For telling me that you don’t expect anything of me on my first day.”

Turns out, Taylor was at a leadership conference and one of the sessions focused on imposter syndrome. The session described how feeling like an imposter starts when we perceive what is expected of us to be more than what we think we can deliver. For example, we may feel like an imposter when we’re expected to cook Thanksgiving dinner when we can barely make a salad.

By communicating that I expected nothing from Taylor on day one, it eliminated any potential for imposter syndrome to develop. In turn, most team members are quite confident in their roles.

I wasn’t always this clear with new team members. Quite the opposite actually. I used to get so excited about finding someone that was a good fit that I expected them to solve all my problems right away. It didn’t help that we hired really smart, hard working, and ambitious people.

I’d often delegate work that required knowledge that nobody outside the company would have, and a lot of it. I would also fail to clarify whether they should be getting help on certain topics. New team members would then spend many more hours than veterans in the office, trying to make sense of the tasks by themselves. They thought that they were expected to do everything on their own, and that this was a test of their abilities. Most were too intimidated to ask questions.

While all team members successfully ramped up by themselves (speaks to their intellect and resilience), it wasn’t without stress. In 360 reviews, team members would communicate that I was demanding, intimidating, and impatient. Not traits that I want to be associated with when I’m trying to build long-lasting, transparent, and trusting relationships.

My goal has always been to create an environment where people feel comfortable asking questions and sharing their thoughts, so this was definitely a problem. What led to this?

In retrospect, these feelings likely started to develop from things I’d say to team members in their early days on the job, such as:

  • I saw that you’re working on a request for client X. They’re really important to us. I know that you will wow them.
  • So and so is dealing with a pretty tough request, can you help them since you have experience in Y?
  • I can’t wait to see the results from your work on project Z tomorrow. A lot of people are waiting on it.

What do these sayings have in common? They assume that the individual can independently complete the task with flying colors, and set the expectation that they are fully responsible for its success. Wouldn’t anyone be intimidated by these words, let alone new hires?

Fact is, even if new team members have performed similar tasks before, they’re now in a new organization that requires new knowledge and skills. Every workplace have unique processes, culture, and people that make them different from other workplaces. It’s thus unreasonable to expect anyone to be able to run at full speed without a ramp up period.

Let’s also remember that for some people, it’s their first time working with a start-up team. It’s their first time coping with an unstructured and chaotic environment. It’s thus our job as leaders to ease them into it.

The only thing we can expect of new team members is for them to ask a ton of questions. We need them to avoid making assumptions, and to never fear speaking up.

Based on the questions asked, and the speed at which they learn the job, it also gives us an opportunity to diagnose the type of coaching that they need.

So instead of saying “I know that you have experience with X, can you help…,” it’s much more fair to simply ask “What’s your experience with X? Could you tell me more about it?”

What does success look like? Success translates into a new hire that has the confidence to attack challenges we throw at them without feeling like an imposter. They should know that as a team, we help each other and face challenges together.

I don’t expect anything from you, except that you ask a ton of questions.

Related reading: Presence: Bringing Your Boldest Self to Your Biggest Challenges


Recommended exercise

Let’s include a new step on orientation checklist for new hires: Communicate that we expect nothing from them, simply that they become the best students ever and ask a ton of questions.


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