Corporate Culture | Trends

Leading with empathy: How to achieve the value in understanding each other

While KPIs and metrics might indicate that teams have made the transition successfully, it is important to not lose sight of the unprecedented levels of stress among team members due to remote work, distributed teams, and elevated job expectations.

Picking up body language cues and stress signals in a virtual setting is difficult unless leaders are very intentional about it. A perceived lack of empathy from leaders can lead to morale issues and leave a lasting impact on the organization culture.

Empathy is not just a ‘HR initiative’

Middle managers have become the only touchpoint for most team members in the virtual work environment. The days of hallway conversations, drop-in discussions and casual check-ins are behind us. During times like this, it is important that every manager in the company is trained on how to listen effectively and how to coach team members, especially when they are also under immense pressure to deliver.

Managers are pressed for time and their interactions with team members are often limited to a series of questions:

“Why are you lagging behind on your metrics this month?”

“Why are you unable to work with your peers to remove bottlenecks?”

“Why are you not closing more deals?”

“Why do you need so much time off from work?”


This innocuous three letter word could be one of the biggest contributors to creating a perception of a lack of empathy. Managers who believe they are driving a culture of accountability by using such ‘why’ questions to keep people ‘on their toes’ fail to realize that this strategy might not work very well with high performing employees.

Questions starting with ‘Why are you?’ lead to defensiveness

Lead with empathy

The ‘Why?’ question (used in an ineffective way) makes people adopt a defensive posture right away. Some employees look for excuses and try to shift the blame. High performing employees might see this as a lack of trust and their engagement and performance levels could start dropping. Over a period, this could lead to demotivation and your best people might leave the organization while others might stay and continue to drive mediocrity.

Questions starting with ‘How can I?’ demonstrate empathy

Instead of asking a series of ‘Why” questions, managers might want to try asking the question “How can I help?“. This could lead to a productive discussion instead of eliciting a defensive response. This question also helps slow down the conversation and allow the manager to understand the root cause of issues.

The question “How can I help?” demonstrates empathy and a willingness from the leader to be a player-coach. It also sets an example for team members to do the same for one another.

Tactics for meaningful leadership requires training

The ‘How can I?’ question instead of the ‘Why are you?’ is just one tactic but it demonstrates the need for management training that is focused on how to manage high performers in the virtual workspace.

Empathy is not just a feel-good factor

The difference in the world record time for a 100m dash and a 110m hurdle race is ~25%. A 10% increase in distance takes ~25% more time to cover due to the hurdles along the way.

One of the priorities of managers should be to identify and remove hurdles of team members to enable them to operate at peak efficiency. Team members encounter all kinds of new and unforeseen difficulties as they adapt to the virtual workspace. They are spending more time to generate the same results and are facing unique hurdles in the process. Being unaware of these change in dynamics could lead to sub-optimal results in the long run.

A focus on identifying and removing hurdles from the path of team members can make them more productive, motivated, and engaged. Coaching people on how to identify and remove their own hurdles makes them grow as leaders. This leads to tangible results for the organization and is much more than just a ‘feel-good factor’.

Empathy builds trust and improves teamwork

We started the first leadership team meeting (Metrics Monday) and the last leadership team meeting (Retrospective Friday) with the question “what two words describe how you are feeling right now?”. Folks were tentative for the first few times since they did not know why this was relevant. We would hear answers like “good”, “fine”, “doing ok” etc. As we got to know each other better, the quality of the responses started getting better.

We would hear words like “excited”, “optimistic”, “having fun”, “relieved”, “encouraged”. The anecdotes that followed usually put a smile on our faces. We would also hear words like “overloaded”, “exhausted”, “frustrated”, “tired” and “sad”. This opens the floodgates for meaningful discussion on why someone feels frustrated or unsupported. If someone is overloaded, other team members would jump in and ask how they can be supportive and how they can shift priorities around to help take things off someone else’s plate for the week. If someone was sad, they would usually share the reason and we know that they have lost a loved one or they are facing unusual headwinds and need to be given some space during the upcoming week.

This dialog builds trust and provides a safe environment for everyone to drop their masks (figuratively) and be themselves. This also helps us value each other for who we are and be supportive during tough times.

Take the time to build it right

Like most leadership skills, empathy does not happen overnight. It takes time and effort to build a culture where team members feel valued.

As organizations continue to adapt towards the ‘new-normal’, leaders are encouraged to consider the ‘human factor’ very seriously and invest time and resources to create a work culture that promotes empathy. Clients will also benefit from such a work culture, and this could prove to be a competitive advantage for organizations.

About ISOutsource

ISOutsource is a modern technology consulting company and was recognized as a ‘Top 10 Security Solutions Provider’ by a leading magazine among many other accolades during the year 2021. We are well-positioned to serve and grow our client base in Washington, Oregon and Arizona helping them move from reactive to transformational in their use of technology.



Naveen Rajkumar is the CEO and President at ISOutsource.

He has over 20 years of digital transformation experience and is passionate about creating thriving communities or happy, productive, and supported businesses.