Senthil Rajagopalan of “Ask employees to conduct self-evaluations”

Ask employees to conduct self-evaluations: Self-evaluations are a great way to get employees thinking about what they’re doing well, and what they’re not doing well. Sometimes, the concern you wanted to bring up is something the employee is aware of. If they offer this on their self-evaluation, discuss action plans to help solve the problem. […]

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Ask employees to conduct self-evaluations: Self-evaluations are a great way to get employees thinking about what they’re doing well, and what they’re not doing well. Sometimes, the concern you wanted to bring up is something the employee is aware of. If they offer this on their self-evaluation, discuss action plans to help solve the problem. If they don’t address what you have in mind, discuss the issue with them in a call and collaborate on an action plan.

As a part of our series about the five things you need to successfully manage a remote team, I had the pleasure of interviewing Senthil Rajagopalan.

Senthil Rajagopalan is the president & COO at, a San Francisco Bay Area-based SaaS startup that helps companies improve their goal management and execution through their industry leading offering software. Senthil is responsible for marketing, sales & customer success at He has nearly 25 years of experience in technology and consulting, including 12 years working with enterprise customers in North America. He has been in B2B SaaS for the past 10 years, co-founding a startup in Bangalore, India. He is an OKR lead coach and a certified agile coach and spends 50 percent of his time with customers helping them with their goal management (OKRs) and performance management initiatives.

Thank you so much for doing this with us! Before we dig in, our readers would love to get to know you a bit better. What is your “backstory”?

I started my career as a business process consultant. This was before the days of enterprise resource planning (ERP). I used to be part of teams that analyzed business processes in enterprises and redesigned them to achieve dramatic improvements in performance using IT as an enabler. After executing several such projects, I moved to the U.S. as the dotcom boom was in full swing and had the amazing opportunity to work for a business-to-business startup in Austin, Tex. My colleagues include ex consultants with Stanford MBAs and a professor from MIT. Those were days of high-energy and a lot of optimism.

As the dotcom boom unraveled in 2001, I moved to New Jersey and started working in enterprise technology sales. After spending nearly 12 years selling technology to some of the leading enterprises on both coasts, I moved back to India in 2012 and co-founded a startup that aimed to digitize the pharmaceutical supply chain. After flying 100,000 miles per year in the previous 10 years, back and forth to the U.S., my life had taken an interesting turn. I was driving over 1,200 miles a month across various cities and villages in South India selling our technology to pharma retailers. During this time, I also had the opportunity to work through the Microsoft Accelerator Program and learned a lot from the very experienced mentors and my highly talented peers. I joined in May 2021. To a large extent this has been a return to my roots — using technology and consulting to help businesses achieve their goals.

Can you share the most interesting story that happened to you since you started your career?

The most interesting story in every job for me is when a customer that I sold realizes the full value of our products and offerings, and thanks us for helping them address a critical problem. It is always gratifying to see customers who placed their faith in us being “proud” of their decision, especially when they refer us to their close friends.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

In 2000 I moved to Austin, Tex. from India for an assignment. My manager had sent an invite for a meeting the next day at 9:30 a.m. The meeting was a teleconference with a high-profile customer on the East Coast. I strode into the office around 9 a.m. quite satisfied with myself about being “early for the meeting.” I went to my manager and asked if we could chat for a few minutes in advance of the meeting. He smiled and told me that the meeting had just ended. I was shocked, looked at my watch and said, “We still have 30 minutes till 9:30 a.m.” He smiled and said, “Yes, but it was at 9:30 a.m. ET, not PT.” Having just arrived from a country that did not understand the concept of different time zones, I was caught off guard and missed a meeting. I profusely apologized to the manager who was quite gracious about the entire episode. Becoming “culture smart” and learning the nuances of any new environment ahead of time was a valuable lesson for me from that day and on.

What advice would you give to other business leaders to help their employees to thrive and avoid burnout?

Burnout is unfortunately a relatively common problem and has a lot to do with a lack of engagement and recognition. This combination, especially under circumstances such as remote work or work during a pandemic, can create burnout that is hard to master. If your employees are showing signs of burnout, or you’re looking to prevent employee burnout, pay closer attention to employee wellbeing. Some strategies to help you do this could be to introduce an employee assistance program to help with work-related issues. This system doesn’t need to be elaborate — simply telling employees who they reach out to if they need assistance and giving them multiple ways to contact that person is sufficient.

Additionally, keep a finger on the pulse of your employees’ physical and emotional wellbeing. Pulse surveys, or even quick 1-on-1 check-ins to see how people are doing, is enough to make employees feel seen, heard and cared about. Moreover, you can promote health and wellness whenever it is possible. If employees seem overwhelmed, suggest a de-stressing activity, or encourage them to take some time for themselves or to log off right at 5 p.m.

You should also examine your organization’s work culture. If it’s common for employees to work late into the night or log in even if they are sick, adjust so that work is completed during working hours. Try to give as much time back to employees as possible — so if a meeting that usually takes two hours to complete can be cut in half with some extra preparation like sending out a detailed agenda or a prep email, do that so employees have more time to complete their work during work hours.

Actively listen to how employees are doing, the issues they are facing and what’s working well for them. Ask for feedback about how they feel work is going through pulse surveys or even in meetings. Support employees where you can and encourage them to reach out if they are facing an issue. If an employee feels seen and heard, their engagement will be higher, and they will feel more recognized in their role, preventing burnout and helping employees put their best foot forward.

Ok, let’s jump to the core of our interview. Some companies have many years of experience with managing a remote team. Others have just started this, due to the COVID-19 pandemic. Can you tell us how many years of experience you have managing remote teams?

I have managed remote teams for over two decades.

Managing a team remotely can be very different from managing a team that is in front of you. Can you articulate for our readers what the five main challenges are regarding managing a remote team? Can you give a story or example for each?

Managing a remote team presents its own unique challenges. Whether your company is adapting to a hybrid work model or is still remote full-time, you’re still faced with the question: What is the best way to manage your team?

The five main challenges of this would probably be the following:

Keeping productivity high

Adjusting communication

Keeping teams aligned

Minimizing employee stress

Defining priorities

In terms of keeping productivity high, I think that many organizations have successfully maintained an excellent work ethic. However, you need to ensure that productivity isn’t hindered by poor transparency or communication. If an employee is spending an hour or two out of their day sorting through emails, that is time they are not dedicating to their important work. It’s important to find where time is being spent, and if it’s not in the right place, put together an action plan to fix it.

This connects to the challenge of adjusting communication. Before, communication could be casual and quick. Now, it’s a lot more effort to set up a meeting, type out an email or call one another on the phone. Making sure you have software that allows you to quickly communicate with your team is vital with the current work from home model.

Without proper communication, it is easy for teams to fall out of alignment. If team members don’t know what others are working on, then collaborating is nearly impossible. To keep our team aligned, practices the principles of OKRs (objectives and key results). Everyone is aware of the corporate goals and how their team’s goals contribute to the same. As weekly reviews are made across the organization, people check-in with their progress and the results are transparent and available for everyone to see.

Employees can face a lot of stress in both work and their homes. Now that the workplace and the home are one, it’s easy for employees to not find a work-life balance and feel stressed. Checking in with employees and ensuring that they are asking for assistance when they run into roadblocks can help mitigate this. OKRs focus on outcomes (i.e. growth, customer satisfaction, etc.) rather than output (i.e. lines of code, number of sales calls made, etc.). OKRs also mandate weekly reviews of goals. This ensures that people are able to get early, regular feedback on their work and also get help from peers and managers to solve persistent problems.

Finally, remote teams could have difficulty defining their priorities. However, with OKRs, it’s possible for employees to see their priorities outlined from the very first day of the quarter, so if they are getting caught up working on something that doesn’t contribute to their OKRs, they can recalibrate and focus on what matters.

Based on your experience, what can one do to address or redress each of those challenges?

The best advice to give here would be to use a strategy and goal execution framework like OKRs to keep your team aligned. OKRs, specifically OKRs managed on an agile software like, can solve many of the problems that we see cropping up when it comes to managing remote teams and keeping employees engaged.

In my experience, one of the trickiest parts of managing a remote team is giving honest feedback, in a way that doesn’t come across as too harsh. If someone is in front of you much of the nuance can be picked up in facial expressions and body language. But not when someone is remote. Can you give a few suggestions about how to best give constructive criticism to a remote employee?

Even on any normal day, reviews and receiving feedback can be taxing for the managers and can give employees anxiety, as they bring in an element of scrutiny and can make or break an employee’s career. With COVID still a major issue in many parts of the world, and work-from-home becoming the new normal even post-COVID, there is no precedent for conducting performance reviews remotely. Managers should still give constructive criticism, but it’s best to follow a few key tips to accommodate for working from home:

Always show solidarity with employees: Make sure you have a strong culture of teamwork and collaboration so that when you do have to give criticism, it comes from a clearly constructive and objective place.

Recognize positive behaviors: Employees will be more willing to hear and implement constructive criticism if they are recognized and appreciated for the things they do well. If you continually recognize employees, constructive criticism will not sting as much.

Ask qualitative questions and listen: When giving feedback, it’s important to hear an employee’s perspective. If you’re noticing a recurring problem, give the employee the opportunity to explain what’s going wrong or how they plan to improve.

Ask employees to conduct self-evaluations: Self-evaluations are a great way to get employees thinking about what they’re doing well, and what they’re not doing well. Sometimes, the concern you wanted to bring up is something the employee is aware of. If they offer this on their self-evaluation, discuss action plans to help solve the problem. If they don’t address what you have in mind, discuss the issue with them in a call and collaborate on an action plan.

Can you specifically address how to give constructive feedback over email? How do you prevent the email from sounding too critical or harsh?

As a manager, it’s important never to be lost for words when it comes to giving constructive criticism. While employees might feel like their behavior and personality are being put on trial, criticism should come from a place of wanting the employee and team to improve as a whole. When giving feedback, make sure you emphasize why a certain action or behavior needs to improve. It also helps to include positive feedback as well, as long as it is genuine. If an employee isn’t providing useful check-ins on their key results on a weekly basis, your feedback could say that you appreciate their timely check-ins, but need to see more insight on how they are making progress so that other employees and teams can learn from one another.

Can you share any suggestions for teams who are used to working together on location but are forced to work remotely due to the pandemic. Are there potential obstacles one should avoid with a team that is just getting used to working remotely?

With the onset of COVID-19, a near-collective shift took place, uprooting offices and transplanting employees to their homes. Remote work is no longer a perk that companies offer their teams, but rather a necessity. This created and still creates a unique challenge for many companies. Offices were considered vital to the basic operations of a company. With this necessity wiped away, companies needed to adjust, and fast.

With the “new normal,” many teams can face issues with communication, alignment, and keeping a pulse on productivity. If a team is just getting used to remote work, it’s possible that they can fall out of alignment. The consequences of that are that less gets done, and employees can begin to feel frustrated and out of touch.

To avoid these obstacles, I recommend implementing a strategy execution framework like OKRs, and manage them on a transparent software such as OKRs are comprised of objectives– meaning qualitative, inspirational, time-bound goals that direct a team, and key results– or quantitative deliverables that are used to measure the success of the objective.

Companies that choose to utilize the OKR methodology see a myriad of benefits. These benefits include focus, alignment, commitment, tracking and stretching. In the context of the COVID-19 world and the new normal, these benefits become even more apparent. The OKR methodology doesn’t just organize companies, it forces them to adopt a pattern of goal prioritization and evaluation that becomes ingrained in company culture, turning abstract aspirations into concrete results.

What do you suggest can be done to create a healthy and empowering work culture with a team that is remote and not physically together?

Employee engagement and communication is key to keeping up a healthy and empowering work culture — no matter where your employees are working from. Employee engagement can mean multiple things, but when employees feel the work they do on a daily basis matters and is impactful, and when they are being recognized for their contributions to the team, they are more engaged.

The remote working model has changed the nature of communication. Instead of casually asking a question to a coworker a desk away from you or popping into your boss’s office to confirm your priorities for the day are in line, communication is more deliberate and purposeful. Leaders especially need to institute continuous feedback and provide many opportunities for team communication throughout the entire week.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

I would love to promote the importance of mental wellbeing and remove the stigma associated with addressing psychological issues. In several countries, including India, many people are hesitant to accept and address psychological issues with the help of professionals. A campaign that raises the importance of these issues and resulting in people becoming more open about their mental wellbeing would be awesome.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“Do not pray for an easy life; pray for the strength to endure a difficult one.” — Bruce Lee

I sincerely believe that life in the twenty-first century, with all the advances in science and technology, is truly a blessing for most of us. Still, whenever I face challenges thrown by life, this quote always inspires me to grind harder and make it happen.

Thank you for these great insights!

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