When you bring a new team member on board, you’re making a fundamental decision—you trust them. You believe in their capabilities, their intent, and their potential to contribute. That’s why I’ve always believed that trust should be the starting point, not something earned over time.

Too often, leaders hold back, waiting for proof that a new hire will deliver. But imagine starting a new job with the underlying message: “We’ll see if you’re good enough.” It creates hesitation instead of ownership. On the other hand, when a leader communicates trust from day one, it signals confidence and accountability.

Many years back, I had a very high-potential team member join me. He had offers from multiple companies, but something clicked about the mission of the company I was working at, and he decided to join us. A few days later, when I checked in with him, he said he was doing okay. But then, interestingly, when I checked in again a few days later, he said, “Ishan, I have seen you in action, and I don't trust you a lot.” I was surprised, but I immediately responded, “That's okay. I don’t expect you to trust me. I would love to earn your trust as we work together. But at the same time, I want to let you know that I trust you.” Over the next few months, we worked on many projects together, building trust through actions, not just words. Fast forward to today, and this person remains one of my most trusted professional relationships.

Trust is not static. It’s a bank account that gets built up with every credible delivery or eroded with each misstep. Some employees will continually reinforce that trust, showing reliability, ownership, and growth. Others may struggle, and over time, that trust can fade. But the key is to start from a place of trust rather than skepticism.

Think of your own career—when did you do your best work? Likely when someone believed in you, gave you space to execute, and supported your growth. As a leader, that’s the culture you need to build. Trust isn’t just a nice-to-have—it’s the most important currency in building high-performing teams.

So, next time a new hire joins, let them know: “I trust you.” Then, see how they rise to the challenge.

Culture isn’t shaped by grand speeches or company-wide memos. It’s built in micro-moments—the countless small interactions that, over time, create an environment where people feel connected, valued, and safe.

I learned this firsthand when I inherited a team that had gone through multiple rounds of layoffs. The team was exhausted, disengaged, and disconnected from the company. There was a clear lack of psychological safety, and as a result, people weren’t sure if they should give their best. It was one of the most challenging situations I had ever faced as a leader.

At first, I did what most leaders do—I met with people, listened, set a vision, and established team values. We even brought people together in person after long stretches of remote work. But while these were important steps, they were big, structural changes. They weren’t the micro-moments that truly shift culture.

So, I shifted my focus. I started building trust one person at a time.

I remember one team member who was hesitant to let me join a client meeting. They were worried I might form a negative opinion about their work. Instead of insisting, I asked questions, reassured them, and showed up consistently. Over time, they saw that I was there to support, not judge. Eventually, I earned their trust, and they started inviting me to meetings on their own.

Another time, I noticed conversations would stop when I entered the room. Instead of ignoring it, I acknowledged it—sometimes with humor, sometimes with vulnerability. Slowly, people realized I wasn’t there to micromanage, but to be part of the team.

These micro-moments—small conversations, gestures of trust, and follow-through on commitments—stacked up. Over time, the team’s culture shifted. People started feeling safer, more engaged, and more willing to contribute.

If you’re leading cultural change, know this: You have to show up every day. It’s exhausting at times, but stopping isn’t an option. Change happens through relentless commitment to the little things—because in the end, culture is built in the micro-moments.

Hiring top performers is the goal of every leader. And once we hire a person who we think is going to be a top performer, there is a natural excitement because these individuals are seen as the driving force behind success- possessing the skills, experience, and motivation to excel in their roles. 

However, what happens when you 'think' you've hired a top performer, only to discover later that the reality may be different? We all make mistakes, particularly when it comes to hiring. When it comes to me, I have made my share of mistakes where I have thought of a person to be a high performer only to realize later on that I was wrong.

Let’s explore how to check your intuition whether a person is really a high performer or not and delve into the potential challenges that arise when expectations don't align with actual performance.

Align Expectations by Judging Competency:

When you believe you've found a top performer, you naturally have high expectations for their performance. However, if those expectations are based on inaccurate or incomplete information, it can lead to disappointment and frustration. Unrealistic expectations may put undue pressure on the employee and can create a negative work environment. It's crucial to evaluate candidates objectively and establish realistic expectations to ensure a smoother transition into their role.

So for judging whether the person has a competency problem or not give tight projects. Lay down KPIs and timelines and evaluate them to judge competency and skills.

Sometimes, candidates may appear to be top performers during the hiring process due to a lack of comprehensive evaluation or misleading information on their resume. This can result in skill gaps becoming evident once the individual starts working in their role. Identifying these gaps is crucial to ensure the employee receives the necessary training and support to bridge the gaps . 

Check for cultural fitment:

Another reason for disappointment could be them being a cultural misfit. Hiring a top performer goes beyond their technical skills and qualifications. Cultural fit plays a vital role in an employee's long-term success within an organization. If the individual doesn't align with the company's values, work culture, or team dynamics, it can lead to conflict and disengagement. A mismatch in cultural fit may result in decreased motivation, a lack of collaboration, and difficulties integrating into the team, ultimately affecting overall performance.

Talk to them to evaluate if they are feeling settled. Check with peers to evaluate if the employee is feeling overwhelmed in the organization.

Evaluate if the attitude is in the right place:

The third reason for someone turning out to be unfit for your company could be attitude problems. When a top performer joins the organization they might come with a sense of entitlement. They might ignore feedback and not value team's opinions. Evaluate and address it if you find this is what is hampering the performance.

My framework: For me, I want at least 2 out of these 3 to be in favor of the company. If during my evaluation, I find that the new hire is failing in 2 or more areas and if I can’t address it then I start the process of letting the employee go.

Thinking you've hired a top performer and later realizing the reality doesn't match your expectations can be challenging for any leader. To mitigate this challenge, it is important to have a robust and thorough hiring process which includes comprehensive skills and cultural fit assessments.

Regular performance feedback and ongoing development opportunities can help bridge skill gaps and support employee growth. By acknowledging and addressing any misjudgments early on, companies can strive to create a more effective and successful workforce. But if nothing works then you need to respectfully let the person go, so they can succeed in a place where they fit, while you can find a person who can help to scale it up!

In this uncertain global economic climate companies are forced to make tough decisions to stay afloat, including layoffs. As someone who has witnessed layoffs firsthand, it's clear that there is no easy way or right time to do it, and the consequences affect not only outgoing employees but also those who remain.

After a layoff, attention understandably turns to the departing employees, but the remaining employees are often overlooked. Those who remain may feel a mix of emotions, including anxiety about their own roles and sadness for their former colleagues. They may also be concerned about the stability of the company and its organizational structure.

Studies have shown that productivity can decline among retained employees after a layoff, and they may also lose trust in the company. However, employees who have access to senior leadership or their managers tend to experience less anxiety, guilt, and anger, and their productivity remains stable.

Therefore, it's crucial for leaders to step up and help employees deal with survivor guilt and maintain productivity.

Here's how

• Acknowledge and communicate the truth as much as possible

Avoid sugarcoating during a crisis. If you don't know if there will be more layoffs, don't make promises. Keep it real.

• Encourage proactive communication

Prevent rumors from spreading by communicating regularly with your employees. Be transparent about the reasons for downsizing and the steps being taken to support outgoing employees. When employees are confident about the company's future, they are more likely to remain productive.

• Encourage two-way communication

Provide a safe space for employees to ask questions and share concerns. Address ambiguities honestly and transparently. Open discussions help employees feel more confident about the company's and their own future.

• Ensure outgoing employees are treated with respect

Treat departing employees with dignity and respect. Fulfill commitments, such as severance packages and references, to mitigate survivor guilt among retained employees.

• Respect outgoing employees

Avoid speaking negatively about former colleagues. Show that the company values all employees, and that they will be treated fairly if they were ever laid off.

In summary, communicate proactively and honestly during a crisis, create a safe space for retained employees, and treat them with empathy and respect. By taking these steps, leaders can help retain employees' trust, confidence, and productivity during difficult times.

In my previous newsletters in the #ScaleItUpIn2023 series, I spoke about the importance of a leadership memo and decision making. In this newsletter, I am going to focus on year end conversations. 

Year end conversations are great for giving and receiving feedback. I am not talking about just a performance review but a deeper and more vulnerable conversation around what matters to your team members and what matters to the organization. 

I have seen that more often than not these conversations turn into year-end performance reviews. As someone driving these conversations, try to put them in the right direction. Being clear in your head and setting the agenda straight for the team helps in driving them in the right direction. Some of the questions that I usually ask in these conversations with my directs are:

• What does your dream job look like?

• What will help you to make this your dream job?

• What do you think about me as a leader? What did I do well, what could have been better?

• What matters to you the most at work? Do you have it here?

Talk to them about,

• the organization’s goals and vision in the coming year

• where do they fit in

In fact, I suggest all my directs and leaders to also hold these conversations with their teams. It gives them a clear sense of what their teams expect from the organization and from their jobs.

Tips to Hold Year-End Conversations Effectively

If you’re planning on having these conversations any time soon with your teams then keep in mind that:

• Conversation is about the employee and not you: Focus more on the expectations of the team member and less on the organization’s and your own expectations. This will help them have a more honest conversation.

• Don’t make any promises or commitments: Don’t make any promises like potential increments or promotions. You should only commit about how you, as a leader, will implement the given feedback.

• Create a safe place for discussion: Listen and listen more. Be honest and vulnerable. Make your team trust you that the conversation will not impact their performance reviews. This will help them open up and trust you more. 

All in all, I suggest you to be genuine and transparent during these conversations to make the chats more effective. Ask as many questions as you want but understand where they want to go next. How would they carve their dream role and also what do they look out for in their dream manager.

The first step to scaling up an organization is to scale up the team and these conversations really help. 

Have you set time with your team yet? How do you plan to hold these conversations?

One of my previous newsletters talked about the importance of building relationships with your skip-level reportees. While it is absolutely gold for leaders to build skip-level relationships, the opposite is also true. As leaders or emerging leaders, maintaining relationships with your skip-level managers is equally important because you can get both mentors and sponsors in them.

A major part of how you develop and manage this relationship depends on your organization's culture. While some organization’s encourage skip-level relationships, others might not. But in the end, it’s always going to be helpful for you to build these connections. 

Here are some tips that have helped me in the past to build rewarding relationships with my skip-level leaders and might be helpful for you too.

• Find a Purpose: Before you start to forge this connection, you must know why you want to do it. Your purpose could be anything, right from you expecting your skip-level manager to be your mentor or you wanting to share feedback about your direct manager or maybe also discuss the organization’s goals. Clarity about what you want from this relationship will help you structure your approach better.

• Evaluate if Your Organization Encourages Skip-Level Relationships: Ask around if it is ok for you to reach out to your skip-level leaders. I have been fortunate enough to have always worked at organizations where everyone has been super approachable and in fact, always encouraged to reach out to leaders irrespective of the hierarchy. 

• Reach Out to Your Skip Leaders: The next step is to reach out to the leader you want to connect with and set up a meeting with them. I would suggest not to schedule a recurring meeting in the beginning. Show that you are mindful of the other person’s time. 

  In one of my previous organizations, my skip-level leader flatly refused my request to set up recurring meetings! He insisted that we keep these meetings open in terms of the schedule. This meant that I could schedule them whenever there was a requirement. We started with this arrangement but eventually these meetings became recurring (how? - see below!). 

• Prepare Well: Once your meeting is set up, the next step is to prepare well for it. Have a structured agenda so you can manage the flow of the meeting and get the maximum out of it. Also, think about your intentions. For instance if this meeting is supposed to be for providing feedback about your manager, then go with the right intent and make sure to communicate your intent.

• Think About What’s In It For Your Leader: These meetings shouldn’t only be about you. Think of ways in which these meetings can benefit your skip-level managers also. So go in with insights, learnings and feedback that you think could be of interest to your skip-level leader. In the example I shared earlier, once my skip-level manager found value in the meetings, he proposed to make them recurring.

These are just some ways that have helped me build long-lasting relationships with my skip-level leaders. 

Skip-level relationships always help to develop leaders on both sides, bring alignment across the organization and ultimately help to scale up the company. 

How do you think about these relationships? Do share what has and hasn’t worked for you to build these connections!

Bringing a co-founder to your start up is a super high stakes decision.

Over the years as an entrepreneur, I have realized that many founders make mistakes while bringing on a co-founder. One of the reasons is that many times this decision becomes a choice between the skills needed by the company and whom you see fit as a partner. But it need not be a choice if you are intentional about whom you bring on. While you may know what you want in a co-founder, there are areas to really watch out for. There are some big NOs for me if the areas below are not clear before you bring a co-founder in-

• Core values alignment

If you can’t be on the same page when it comes to your core ethical or business values then it’s going to be tough to work together in the long run. Now it’s very difficult to find this in the beginning but I would encourage you to ask tough questions and see how close or far both of you are on values that matter to you.. 

• Vision & purpose alignment

There should be alignment in your vision for the business as a shared vision certainly makes it easier to function together. 

You should also watch out for the purpose—why they want to be part of this journey and more importantly, why do it with you. Their reasons might be different than yours but both of you should be able to appreciate each other’s purpose and respect it. Tread cautiously if you feel otherwise. 

• Clarity of the co-founder role

Hiring a co-founder has merit only when you know what skills are needed in the company. A co-founder should ideally bring complementary skills to the team. For example, if you are a technologist, then your co-founder could be great at business. 

This not only helps to add different skill sets to the organization, but also helps to set clear operational boundaries for both of you. It is critical to discuss this with your potential co-founder and evaluate where they see themselves in the organization. Define their role or at least principally align on what it should be.  

You might have to revisit the responsibilities in the future but that should not mean that you will start with ambiguity. Renegotiating the role again and again will turn out to be harmful for both the business and your relationship, especially in the early days of working together. 

• Clarity of organizational hierarchy

As much as it is important to define clear roles and responsibilities for your co-founder, it is also important to lay down the hierarchy between co-founders. 

Of course, titles change all the time and being the CEO might not matter to you now but evaluate if you can at least have these discussions about reporting structures with your prospective co-founder at the beginning. There are some examples of successful co-CEOs but setting functional boundaries is important. 

Remember, that there will be times during the co-founder search when you will want to put the company interests above your relationship with the co-founder. But I believe unless you can see yourself working together in the tough times (not just good times), don't commit to someone. Search hard and ask the tough questions needed to be asked to find the right co-founder for yourself!

Managing organizational culture is always challenging. As the organization grows, the layers increase & communication gaps widen. In such situations, I always find skip-level meetings to be a crucial communication strategy that helps in the flow of ideas, increases organizational transparency, drives leadership development, and frankly, teaches me a lot!

Skip-level meetings are beneficial in a number of ways

• Avenue to give team members insights into leadership expectations

As an organization grows, the sharing of vision and values becomes more difficult than you can imagine. Skip-meetings provide me a platform to share expectations with the team. At the same time, I can get genuine feedback on the team’s direction, and that forces me to think more. Truly a win-win!

• Opportunity to become aware of challenges

Often times the challenges being faced at the ground level don’t reach the leaders in the company. Hearing about the team’s challenges directly from the ones who are facing them on a day-to-day basis, is a great way to understand what is truly going on in the team.

• Ability to collect actionable feedback for my directs

In these meetings, having frank conversations about what they think is affecting their performance and how it can be improved is important. Make them feel heard and note down details of their problems. 

When you aware of the issues affecting your employees’ performances, you will have actionable feedback for their managers (your directs) instead of just high-level feedback.

• Actionable feedback for myself

The skip-level conversations help me to understand and evolve my own leadership style. I receive direct and helpful feedback on what I can do better as a leader and how I could contribute more effectively to the company.

The correct way of doing skip-level meetings

These meetings can be tricky to conduct. Here are some tips to conduct them in the correct way.

• Focus on building a connection

I always think of my skip-level managers as the bench strength for my team. I would start with informal sessions, but with a disciplined cadence. These meetings are a great way to build deeper connections with your skip-levels. Some questions that I often ask are - 

“How are you doing?”

“What are you most excited about?”

“What’s bothering you?”

 “How can I help?”

Maybe even consider spending some time talking about their families, their aspirations and share yours as well.  

• Don’t make it about others; no politics

A skip-level meeting shouldn’t be about the person in-between or about their peers. Always make the expectation clear that these skip-level meetings are about feedback and increasing transparency for each other. It is not the chance to gossip about the person getting skipped i.e. your direct. Hence, ensuring no politics is critical in this skip-level relationship.

• Stay away from giving directives

Skip-level meetings should be more about brainstorming, ideation and providing transparent feedback.

• Don’t make any promises

It is important to not make any promises in skip-level meetings like a new project, a promotion or an increment, without the manager being a part of the conversation. 

• Don’t act like their manager

Identify what you can help solve but never override the manager, unless you see clear wrong doings. Instead, partner with your directs to solve issues.

Skip-level meetings are time-consuming. But they are a fun and effective way to connect with your team members. They teach you about your leadership style and also help to drive alignment at the same time. 

Let me know if you find skip-level meetings useful and how you have been doing these in your teams.

I consider leading teams as one of the greatest privileges of my professional career. However, the teams may come to you in a different manner - there are teams that you build from scratch and there are teams you inherit from other leaders. As an entrepreneur, for most part of my early career I always built teams from scratch. However, over the last few years, while building new teams, I have also gotten opportunities to inherit teams. While inheriting teams and working with them can be great fun for those leaders who love to lead teams, I must confess that it can also be a bumpy ride in the beginning.

Inheriting a team becomes more challenging, especially when you are joining a new company. Since you are a newbie, you don't really understand the culture of the company. While you may understand your functional area very well, you rarely know the accepted norms for cultural items like goal setting and performance expectations or historical context, which are critical for helping a team to be set up for success. 

It requires patience and persistence to inherit a team and come to a place where you believe that you can truly lead it well. Frankly, sometimes the journey might seem like fixing an airplane in mid-flight—you can’t switch it off, but you can’t also fly it effectively!

Here are seven practices that have helped me when I was given the opportunity to inherit and lead teams.

1. Listen, Listen, and Listen

Listen to your team. From your direct reports to skip levels to whoever else wants to chat with you. And then listen to your peers, leaders and everyone else around! Essentially listen to the organization before you start acting. Active listening will not only help you to know more about your team’s culture, but also help you gauge priorities, challenges and sometimes even possible solutions.

2. Be Thoughtful While Asking Questions

Of course, you will have a lot of questions but being thoughtful while questioning is important. The intent of your questions should be to advance a dialog and not shut it down. Focus on the why’s vs the what’s and how’s. 

3. Suspend Any Judgements

Recently, I read a quote somewhere “Don't Judge One's Story by the Chapter You Walked In On”. This resonates a lot with me, in context of inheriting a team. I always start from a place of trusting the team and make it a point to not judge the team’s capabilities without truly understanding their challenges. In fact, it is important to find ways to set up the team for success, before you go about evaluating them.

4. Build Credibility

During your initial days as a leader, it is also important to build your credibility with your newly inherited team. Remember to draw a line between supporting your team and promising something you can’t deliver. I have always tried to have the back of my team leaders while trying to ensure that I am not over committing in any areas. 

5. Set Your Goals, Early On

Goal setting is an important part of leading any team. It becomes even more critical when you are inheriting a team because you need to decide whether you want to align to the team’s goals or make them align to yours. Alignment is pivotal and it comes from goal setting. 

6. Help Improve Existing Processes

Many times, we focus a lot of our energies on changing things around. I would suggest not to get overwhelmed by this urge to change things. Rather, wait and make the existing processes better. That doesn’t mean you shouldn’t change anything. Just don’t try to fix what isn’t broken!

7. Finally. Assess, Reshape, Scale Up

Once you get a better grip on the functioning of your team and understand the company culture better, you should start to assess their capabilities, reshape if required and scale up with some quick short-term wins, while planning for the long-term vision and goals. 

These practices have helped me to manage the teams that I have inherited over the last few years. I would love to know what has worked (and not worked) for you!

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Talent is your biggest asset and managing employee turnover is one of the biggest challenges that we face as leaders. 

In one of my previous articles, I wrote about what happens when a top performer resigns. As leaders, we tend to concentrate more on the opportunities that our employees have outside and try to match those for our top performers to stay back. But do we look inward and evaluate if we are doing enough for our top performers to stay on a continual basis? 

In a survey of 2,000 employees, almost half (43%) said they are looking for a new job. Another report suggests that only 2 out of 10 people are engaged in their jobs. It is imperative for leaders to identify the reasons for which your top talent decides to leave or look for opportunities outside. 

Here are some of the most common reasons that I have come across for high performers to leave. These reasons may sound obvious to you, but think how often are you able to manage these for your top performers.

• Lack of Growth Opportunities, Internally

I have had the good fortune of working with many high performers. A lack of clear growth path could be a deal breaker for many high performing employees. 

At my last company, one of my top performers would never be satisfied to work on just one or two key initiatives. She would keep me on my toes to find challenging opportunities for her inside the company. Thankfully, I was able to learn how to be proactive at creating opportunities for her and was able to retain her successfully for more than four years, in a highly competitive environment.

• Lack of Empowerment to Create Outsized Impact

I believe in the Netflix philosophy of “lead by context, not control”. Context allows you to empower your teams to create a larger impact, an opportunity that every high performer appreciates. 

Your high performers’ relationship with you plays a pivotal role in their relationship with the company. It’s no secret that a large population of people leave and stay because of their managers. So, have your team’s back and communicate it to them. Give them the opportunity to take on audacious initiatives and make them feel comfortable to fall and fail. 

• Lack of Opportunities to be Heard

Top performers come with opinions and expect to be heard. They might not expect the feedback to be actioned upon all the time, but not getting a chance to share their thoughts can be disappointing and frustrating. 

• Lack of Alignment in the Company

Sometimes top performers feel that everyone is not focused on the key priorities of the company as much as they are. They start feeling that they are carrying more weight than others, which leads to them feeling burnt out. 

As leaders we need to ensure that, while different people will have different levels of outcomes at work, the effort is aligned in the same direction. 

These are some reasons why I feel top performers want to leave. What do you think are the top reasons for high performers to look for opportunities outside their organization?

Yesterday, one of my meetings ended 10 minutes early. While the meeting was scheduled for 30 min, we were done with the agenda and next steps in 20 minutes.  I chose to gave “Let me give 10 minutes back to everyone” a pass because as a group we were efficient and collaborative and finished the discussion before time.

The Covid-19 pandemic has changed a lot for us including the way we speak and our vocabulary. Apart from words like ‘herd-immunity’, ‘quarantine’, ‘social distancing’, ‘self-isolation’ becoming part of the common language, some words and phrases have caught hold of the corporate world as well. 

While I am a big fan of the trends that have emerged for different ways of working, be it remote or hybrid, I do feel that some of the new phrases that have emerged could be avoided! 

Here are some of the ones that I think we could stop using during meetings:

• Let’s wait for sometime for everyone to join

I learnt my lesson of punctuality the hard way. When I first came to the US for MBA at Stanford, some of us friends decided to meet for dinner at a particular time in the lobby of our residential complex. The first day I reached 15 minutes late, only to find that all of my classmates had already left for the restaurant. The next day, I reached ‘only 5 minutes late’ only to find a few people there but giving me cold looks. I soon understood that I needed to change myself and thankfully I did. 

I am one of those who like to appreciate people for their punctuality, rather than wait for the ones who aren’t on time. We are all managing life and work together, and it's totally fine if people are late to meetings due to unavoidable circumstances. In that case, I try to use the time to set the tone for the meeting rather than just wait for the people to join. 

Alternative: Thank you everyone for joining the meeting. While we are waiting for some of our colleagues to join, let’s start by writing down what we all expect to achieve from this meeting. 

• Let’s take this offline

To be honest, I am always confused about this one. Whenever somebody uses this sentence, I am always wondering if the intent is really to follow up on the topic, or is it a way to dismiss someone’s ideas, as the timeline here is indefinite. So, I would rather hear a definitive response which states how and when the topic should be taken up “offline”.

Alternative: This is a great point of discussion, but beyond the scope of this meeting. Let’s connect over e-mail/slack right after this meeting

OR Great point. Since this may take more time and probably needs just the two of us, why don’t I send you an invite today to discuss it in detail?

• I am going to give 5 minutes back to you all

Many of us have used this popular phrase. In fact, I have myself used this many a times but I recently realized how by ‘giving people a few minutes back’ we actually undermine the efforts of the group. 

I love it when a meeting ends early as it highlights that the meeting was efficient. But all of that accomplishment goes in vain when we end up celebrating the 5 minutes everyone got back. Rather, we should be celebrate the efficient discussion and the accomplishments of the meeting.

Alternative: This was a well organized discussion- thanks everyone for such an engaged participation

OR What an efficient meeting. Can’t wait to talk again!

Make Your Meetings Better

If you are looking for ways to make the most of your time during online and even in-person meetings then here are some tips that I follow:

• Create an Inclusive Meeting Environment

Whether you are managing a global team or a local one, today’s workplaces are diverse and it's our responsibility as leaders to make them inclusive.

For example, some people might not be outspoken inherently. This might be because of their culture, language, gender or hierarchy among other reasons. As a leader, I would urge you to be sensitive to these issues and encourage people to speak. This might sometimes even mean to politely ask people to add to the conversation.

As a leader, you should watch out for negative behaviors like people cutting each other or not respecting someone’s viewpoints. Create a platform to speak as well as to actively listen during the meetings.

• Time your Meetings

It is very important to maintain the schedule of your meetings- ending them on time is as important as starting them on time! Have an agenda before the meeting and try to stick to it. Many times, your colleagues may have other commitments, but if you are the leader they may hesitate to voice that out. Therefore, try not to extend a meeting unless really required and everyone’s available. 

These are just some ways that I try to make the most of my time with the team. Tell me what are your meeting dos and don’ts.

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“I have decided to move on and join another organization,” said one of my team’s highest performers. It wasn’t a conversation I was expecting. My colleague was a high performer, passionate about the company, promoted recently, paid as per competitive salary benchmarks and everyone in the company loved him. I could not think of one solid reason for him to move on. 

A McKinsey Study states that high performers are approximately 400 percent more productive than average performers. The gap rises to an astounding 800 percent or more in highly complex occupations. In such a scenario, how do you even let your top employees leave? 

So when this 24 year old top performer told me that he had decided to move on, my immediate instinct was that I had to do something to stop him.

I got to know that he was leaving for a similar role, but in his dream organization where the impact on his contribution would play out on a global level versus where he was at this point. I realized that while he may be a better fit in our team, the new role at the larger company was something he really wanted to do and he would feel unfulfilled if he did decide to forego it. So I decided to let him go.

As leaders, it is important to build muscle for dealing with the loss of top talent and moving on from there. 

Realize It’s Not Personal!

The first step is to realize that it’s not personal. The most dedicated and talented team members will leave for different reasons. Talented people are ambitious and as leaders the best we can do is to help them achieve their goals—within the organization or outside in many cases. This means that if you can’t offer them what they are getting externally, then it’s time to wish them luck and really mean it.  

People Leave for Different Reasons and Stay for Different Reasons

People leave for various reasons. Some of the most common ones are money, job title, company culture, team culture, growth prospects, work life balance, or a combination of these factors. Always try to know what is making them leave and explore if you can resolve it. 

Pro tip: If the reason for leaving is money, then tread very carefully.  The salary increase that you offer to your employees should still be within your organization’s salary range. If you go beyond it, remember that such information leaks more often than not.

Know That Talented People Outgrow Themselves Constantly

You hired talented employees because they outgrew themselves in their previous roles. Talented people outgrow themselves all the time and if you can’t pave the way for their future growth, then it’s time to bid them a farewell. 

When is it worth trying to retain your top performer?

The first intuition is to always try retaining your top performers. However, over a period of time, I have learnt to step back and evaluate when it’s time to let people go versus when I should go the extra-mile to stop them. 

• Decide if you really want to retain the employee. If yes, make sure you have a strong 'Why'. If the answer is no, don't try too hard!

• See if this top performer is also your lifeboat (lifeboat = some part of the business is at risk without the employee)

• Evaluate if the person is leaving for the right reasons and opportunities

A question that I always ask, when one of the top performers is wanting to leave, is “Would you like to stay if your problems here were solved?”. If the answer is yes, then you know that it will be worth trying to make the employee stay. However, if the answer is no, then more often than not, it's time to let the employee go. 

Praveen had been reporting to me for almost three years. However, suddenly one day he told me that he had decided to accept a new role somewhere else and would like to figure out a transition plan. Now, Praveen and I worked very closely for over five years across two companies and built immense trust with each other. I thought he was happy with his current role since he had previously never discussed the idea of leaving the company with me. Imagine what a shock this was for me! 

Without diving into what was bothering him or how to retain him, I asked him if he would like to stay back, if we solved whatever problems he was facing in his current role. When he showed interest in staying back, I started digging deeper into the situation. The problem was that his was not having the work-life balance he wanted as he was managing teams across different time zones. He believed that his next role would help him restore this balance. I then tried to understand more about the opportunity he had. I soon realized that it wasn’t a very exciting one and therefore I felt more confident that his decision to leave was mostly driven to manage his life outside work.  So over the next 72 hours, we chatted almost every 12 hours to work on the issues he was facing, made a corrective plan and mutually committed to monthly check-ins on the plan. He ultimately decided to stay back. And I am glad he did, because he had a stellar innings in the company post that! 

As a leader, it is important to realize that retaining top talent is one of the core responsibilities of the job. But it is even more important to be a leader, who is willing to step in the shoes of his or her team member and evaluate whether it makes sense to try retaining the team member or not. 

How do you feel when your top performers resign? What are the tactics you have used to retain them? I would love to hear from you on this!

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In my previous newsletter, I had shared some of my learnings from creating and working in high performing teams. While building a high-performing team is not easy, retaining and scaling it up is even more difficult!

During my entrepreneur days at EduKart, there was a time when the team grew 2x over a very short period of time. That meant that everything we were doing—supplier side acquisition, customer acquisition, product development, growth marketing—started to really speed up. While it was a thrilling phase, it was also extremely overwhelming for me, as a leader.

Suddenly, I was responsible for the growth path of 50+ talented and high-performing team members, who had shown trust in me as an entrepreneur and the vision of EduKart. While that began my journey of scaling up a team, when I look back I realize that I wasn’t really prepared. There were many important elements needed for scaling up teams that were missing. For example,  HR processes, opportunities for growth, and experienced leadership to manage the team.  

Once you have started building a high-performing team, scaling it up is one of those long-term plans, which needs to be executed from day one. Here are some learnings from my experience of going through this journey multiple times:

Create Coaching Moments

For scaling up a high-performing team, you need to create effective coaching moments. Such moments help not only to skill your team to perform their jobs, but also to empower them to constantly be a better version of themselves.

The coaching moments can be crafted by creating a coaching habit for yourself. Try to ask questions such as “What’s on your mind”, “What do you really want?” & “How can I help?” to your team members. By creating this habit of asking questions, you can help guide your team towards higher productivity by making them self sufficient. While formal and scheduled mentorship sessions are important, I have always found informal and spontaneous coaching moments to be of higher impact. 

Eliminate Politics by Staying Transparent

According to a recent survey by Robert Half, 65% of the employees surveyed said that it was important for them to engage in some kind of workplace politics to move ahead. In such a scenario, it becomes critical to minimize politics in an organization. Imagine if your high performers are worried about politics rather than the goals at hand!

The process to minimize politics begins with you, the leader! It begins with building transparency in your company. It happens many times that  as companies grow and more structures and policies come into place, employees start feeling disconnected from the decision making process and the power dynamics set in. One of the most important ways to avoid workplace politics is by reducing the distance between employees and company decisions. 

By promoting collaboration and transparency in the form of team meetings, town halls, team outings, you help bridge the gap and reduce the chances of workplace politics. This ensures that high performing teams continue to stay focussed on the things that really matter. 

Measure Progress Often

Goal setting plays a big role in ensuring that a high performing team delivers as a collective unit. However, setting the goal is not enough. It is critical to create avenues to continue measuring progress. 

For example, if you are using the OKR method for planning on a quarterly basis, it would be critical that as a leader you are reviewing progress periodically. This review cycle could look weekly or bi-weekly. Such quick reviews help the teams not only to stay focussed on the tasks at hand, but also force continuous collaboration within the team to solve challenges in a timely manner. 

Create Depth in Your Team

As your teams grow, strong managerial talent is very critical to keep and retain your high performing team. By creating depth in your team, through an additional line of managers, you not only build a deep bench at all levels of the organization, but also set yourself up for more important tasks.

Investing in your team will give out a strong signal that the company cares for the talent within and gives you the option to choose between up and coming internal candidates and experienced external candidates, as the company grows. 

Make Fun a Part of Work

I believe that enjoying what you do is as important as doing what you enjoy. Fun at work doesn't only mean participating in fun activities on a Friday, occasional office parties or games; but it means making your workplace more enjoyable for positive outcomes.

When your team has fun at work it encourages not only positive vibes, collaboration and communication but also promotes trust and creativity. Remember, the definition of fun at work can mean different things to different people. For example, Southwest Airlines is popular for its fun and witty in-flight announcements which also means they hire witty flight attendants.

If you're a leader working towards scaling a high performance team, then ask yourself:

• Do you have a solid leadership team to add depth to your organization?

• Is your team learning enough? 

• Are you investing in your team's career growth?

• Are you measuring progress regularly?

• Is your workplace environment positive or toxic?

• And most importantly, is your team really having fun?

The answers to these questions will help you create the processes for scaling a high-performing team.

What are your thoughts on this? Share with me.

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"Talent wins games, but teamwork and intelligence win championships”

- Michael Jordan. 

I keep on reminding this to myself, so that I never loose focus from building high performing teams!

The reality is that one doesn’t just hire a high-performing team. Hiring high quality individuals is just the first step in making a  high-performing team. This practice will, to some extent, ensure excellence and quality from individuals, but over the years, I have experienced that a leader owns the performance of the team and has to build the culture of performance, constantly.  You have to bring the individuals together and then create an environment to nurture their relationships, that can in turn foster their individual and collective performance at work. 

So if you are just starting this ever-evolving process of building a high-performing team, remember that it really depends on company to company, culture to culture and leader to leader. 

Here are some learnings that can help you to build a rock-solid foundation for your team:

Create Solid Norms for Your Team

The first step for building a high performing team is to set the norms early on. Essentially, a team should know what it stands for. 

For example, a team might disagree and debate internally but it should agree externally 

and stand for each other.

This is one of the most critical norms for me. I really believe in the power of internal disagreements and debates. But I also believe that it is equally important for a team to agree and commit (or even disagree and commit) before communicating with external stakeholders. 

Having shared values for a team that determines how the team should behave, especially in times of challenges and disagreements, helps to build a working relationship from the very beginning, when a team is coming together. 

Align Your Team to a Common Goal

In one of my earlier posts, I had stressed on the importance of aligning your team to a north star. This becomes even more important when you want to build a high performing team. 

Aligning your team to a common goal not only gives clarity about where the team wants to go, but also helps minimize personal conflicts. It clarifies what short-term and long-term success for the team could look like. 

Collaborate and Communicate

It is important to set up a culture of collaboration to boost a team’s performance. When different team members collaborate, they start to build trust in each other and communicate more freely. When team members begin to believe in each other’s power, they can win championships together, not just games. 

Constant collaboration and communication also helps to reinforce the norms of the group and the common goal of the team. High-performing teams use these opportunities to  keep each other focussed on the message. 

Set-up Trustworthy Feedback Loops

Leaders can not eliminate conflict totally. In fact, some of it is healthy and warranted. However, it is important to  create channels to manage it so that its impact stays positive. Strive to create open platforms where team members can share their feedback or any point of conflict without hesitation or any fear of repercussion. 

The foundation of these platforms is trust which means that team members trust their leader to act with fairness, genuinely help to find resolutions and pull in the needed experts as and when needed. On the leader’s part, they have to ensure that the behavior is consistent and in-line with the norms set for the group. 

Having set-up high-performing teams, I know it’s not an easy task. But when you have worked in one, you know the difference it makes. 

I would love to know how you have built high performing teams. 

In part 2, I talk about how to scale up high-performing teams. Read on!

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First thing first, entry level and middle management employees are super critical for your business. Yes, senior management is important (very important), but strong execution from the team at large is important for any business to succeed, especially for an early-stage company. This is the reason why I believe in the power of building entry-level and middle-level management for scaling up a business. 

As a business leader and an occasional investor, I have spoken to many entrepreneurs and business leaders, who are focussed on hiring a stellar senior management team but do not realize the benefits of investing their resources on hiring the right people across their business hierarchy. 

In fact, I have seen more mistakes happening in hiring at the middle level than at the senior level.  One must take conscious calls on whether the teams need more generalists or specialists, passion or experience, execution or industry knowledge.

Here are some of my learnings from my experience on hiring:

Most Entry-Levels Should Be Generalists, Open to Become Specialists

In an era of specializations, I always prefer hiring generalists for my entry-level positions. Why? Because I think generalists have better opportunities to identify their field of expertise based on their own real-life experience. 

This becomes more important in a startup because let’s face it, you might have a million dollars in your bank account but you will always be short of resources. A generalist who is ready to learn and take up new projects, will always be a better hire than an entry-level specialist whose expertise isn’t based on experience, but solely on the University degree. Ex. a fresh graduate in history may do very well as a marketing associate if he or she has made efforts in the past to take up marketing projects

Look for Passion Vs. Expertise for Entry- to Mid-Level Hires

Many entry- to mid-level hires bring in fresh ideas and energy in the organization. But this is only possible when there is passion. I put more emphasis on passion for entry level positions and on strong expertise and rock-solid experience for senior hiring. 

You can see some additional thoughts on early hiring in the newsletter “Early Hires = Important hires” that I posted sometime back. 

Identify When It’s Time to Change

Remember that your employees will evolve over time. As a leader you must keep a track of their evolution. Know when it’s time to move them to the next level. Generalists will become specialists eventually, passionate employees will gain experience and expertise overtime. 

As business leaders it is important to identify this change because the cycle of evolution is different for every employee. Moreover, as your company scales up, you will have to decide if you need more execution or experience. Easier said than done, this is a very important part of the hiring cycle and requires a leader to be stay observant always! 

Here is a story from my own professional journey- back in 2012 I hired Ritika, a content writer, fresh out of college for EduKart, my EdTech startup. She was open to learning new skills and taking up new projects. During her stint, that lasted just over an year, she started to manage our Social Media and eventually our Public Relations as well. She later moved put to pursue her Masters. I happened to rehire her after she graduated for a slightly senior role in 2014. The expectation was somewhere between a generalist and specialist profile. 

Few years later in 2019, when I hired her again, this time at Udacity, the expectations were completely different. She had become much more specialized now and I hired her for her industry experience and not so much for her passion.

I was recently chatting with Ritika and asked her how she felt each of the times she came into the interview process. She remarked “I always knew that it is not going to be easy to be hired by the same person for the third time. And I wasn’t wrong. The first and the second time at EduKart, the interviews were  mostly around what I wanted to do and what I wanted to learn. However, the third time, at Udacity, the interviewing was all focussed on what skills and experiences I brought to table. When I look back, the interview itself set the expectations for me!”

It’s Time to Invest in your Entry- to Mid-level Hiring!

So if you are looking for levers to scale up your business, pay attention to your entry-to mid-level hiring process. Look at your current team and ask these questions- 

• Are they the right people in the role?

• Are they the right culture fit?

• Can you empower them to go to the next level?

Do you personally look at the entry-to mid-level hiring process? Do you feel it is important to invest in these roles? I would love to hear your thoughts on this!

Michael Jordan said, "Earn your leadership every day." So, if you have a leader in your life who has the power and will to empower you, then call yourself fortunate. I have been lucky to have worked with such incredible leaders—many of whom were also my managers—during my stints at Udacity and Paytm.

I truly believe that managers can make or break your relationship with your workplace. Moreover, your manager holds the key to your advancement within the company, and many times, outside of it as well. Managers can really help scale you up! It is essentially a lifelong relationship, if executed well!

As I said I am grateful that I was able to build strong connections with many of my past managers.  So much so that Vijay Shekhar Sharma, the founder of Paytm and my manager during my first stint at the company, was also my first investor for EduKart, my edtech startup. Later, he proposed the acqui-hiring EduKart and I had the fortune of working with him again.

In fact, when I met Vijay for a candid conversation during my hiring process, I had expressed my keen interest towards starting something of my own. To my pleasant surprise, he still hired me at Paytm because he thought I would bring in fresh ideas and energy.

Many years later, when I got the opportunity to hire someone at Udacity who wanted to be an entrepreneur, I realised how open I was to bring him onboard the team. That’s the kind of impact a good manager can have on you. They can essentially make you better managers!

But how can you develop such a relationship with your managers which goes beyond your job? I believe that just like every other relationship, this relationship is also entirely based on trust. 

Here are five learnings I have had while building strong relationships with my managers.

1. Take Initiatives to Set Up Your Regular Check-ins

Managers stay busy managing multiple competing priorities. As a reportee, I have always recognized that it is my responsibility to set up the meeting cadence with my manager and ensure that we end up following the schedule on that together. 

Do not let the manager cancel if they are busy, instead ask for a reschedule. Remember, to make the  meetings worth their time by simplifying the conversation. Send out a pre-read or agenda if you can. Maintain an ongoing meeting journal and note the to-dos for both parties in it. Keep yourself and your manager accountable on the next steps, as they arise out of a meeting. 

2. Structure Your Conversations With Your Manager

It’s important to talk about the most important stuff first. When managers are busy, figure out what is top of your mind and most important for your manager to hear. 

You could use this simple framework to structure your conversation-  

5Ws (What, When, Where, Why, Who) and 1H (How)

• What do you want to talk about

• When do you want to say it

• Where do you want to say it

• Why do you want to say it

• Who is it about

• And finally, How does it impact the business

Have these answers before stepping in a meeting with your manager. 

You also want to make sure that your manager hears about the problems in your work or team through you first before anyone else. Therefore, do not shy away from starting the meeting with the bad news. A seasoned manager knows that all news can not be good or bad news!

3. Demonstrate Innovation and Initiative

I can’t stress enough on how important this is for your relationship. Every manager wants their team members to be a motivated lot! Showing that you're excited to take on new projects beyond your current KRAs can go a long way.

While every good manager tries to empower you, try to think how you can help and empower your manager. Think of the ways in which you can take some work from your manager’s plate. This will not only make them trust you more but also help you grow in your role.

4. Talk Long-term, Beyond the Daily Work 

Good meetings are just never about status updates. Yes, one may need to give updates on the most important topics. But at the same time, think about what long term value your work brings to the company and how you can do more of it. 

Drive alignment in meetings on what is most important for you to focus on and what it means for you, your manager and the company. You want to ensure that you are focussed on doing things that actually matter and that your manager is aligned to your agenda! 

5. A Good Relationship With Your Manager ≠ Best Friends With Your Manager

I have seen many people confusing a good relationship with their manager with personal relationships outside of work, which is not true at all. Your managers don’t need to know everything about your personal life. You do not need to be (you can be..) Facebook friends with your manager or intrude on your personal life to become a good employee.

A healthy relationship with your manager can be purely professional and still as strong as you want it to be. Just remember that you don't need to be a 2am buddy with your manager!

I have always focused on building trust through reliable execution and sharing of information in a timely manner. Make it an equal relationship. Talk about your aspirations, challenges and goals, and listen to theirs. Meanwhile, don’t forget to appreciate them for all the effort they put in behind closed doors for you to succeed.

Tell me about your relationships with your manager. If you’re a manager, I would love to know what works for you to strengthen the bond with your team members.

Hiring the first few employees is a big deal for any startup. The stakes are high. Your first hires can make or break your company in its early days. 

At Edukart, my education startup, I did not have anything much to offer in comparison to big companies, when making our initial few job offers. No lucrative salary packages, fancy office, benefits, or plan for growth, etc. However, I was still able to build a strong early team. 

Here are some of the tactics that worked in my favor:

Did not rush into hiring:  Hiring great employees takes time. Your first few employees need to set strong examples for others. Hence, I took time to ensure I found people who were really the right fit. 

Hiring the first few mid level hires was an extremely time-consuming process, but totally worth it. It helped me understand what sort of talent I was  looking for.

Made good use of my network: Recruiting agencies and consultants can be expensive in the beginning. So, I relied on personal networks and advisors for referrals. In fact, the first hire for EduKart was a recent graduate of a business school that was run by one of our angel investors. 

Paid a lot of attention to mission alignment: The first ten employees were going to be like co-founders. They were the ones setting up the company’s culture.  

So, I wanted people who cared about the company and  its mission as much as I did. People who brought the ownership mindset and were mission-driven, entrepreneurial, problem-solvers, and proactive in their work.

Gave assignments to test skills and aptitude: Many people are good at interviews. They know exactly how to sway the hiring managers. But, what has always helped me is testing their skills with an assignment. The assignment can be small, but it really helps to test the thought process of the potential hire. 

Also, for super young startups, it can act as a great filter — someone who is not interested to spend 2 hours on an assignment, may just not be a great fit

When I look back at the EduKart journey, the biggest mistake I made in early hiring was that I did not focus on a healthy mix of employees from an experience point of view. 

 Over the last decade, as I have gotten a chance to lead large teams and work with a diverse set of the employee base, I feel the word ‘passion’—when it comes to startup hiring— is  ‘overrated’, while experience and skills are ‘underrated’. 

Passion is very important but I don’t think we should compromise on the importance of experience  for it. Experienced employees are a huge investment, but can be extremely valuable in setting up processes and driving speed.

On the other hand, when it comes to judging for passion, I would suggest looking out for signs. It is very easy for people to say ‘I am passionate about your cause’ but are they up-to-date with what is happening in the industry or have they worked on projects in similar areas before? People who were genuinely interested in my ed-tech startup kept me informed of what they were upto and sync up often. 

Looking back at EduKart, I feel that I should have invested in hiring experienced leaders across critical domains early on.  I went all out on passion and built a solid team, but of less experienced generalists. As a result, we lacked the experience that could have helped us to prevent a lot of mistakes early on in the startup. However, I learnt from this mistake when I joined as the Managing Director of Udacity in India- my first three hires were all director level in Operations, Product, and Sales. They subsequently built solid teams around them and  we moved on all fronts faster. 

Your first hires are a big leap for you. Breathe in and take all the time you need to do it right! All the best and let me know if you have questions in the comment section below.