Ability to have difficult conversations is a key leadership differentiator

Vani Kola
5 min readOct 3, 2018


Source: CurvaBezier/Adobe Stock

Thanks to Google Maps we have a personal navigator with us at all times to guide us through sticky traffic situations. However, there is no app which can help you navigate your way through a difficult conversation. In the fast-paced and dynamic start-up environment, there are some situations where entrepreneurs often find themselves struggling to steer safely out of a conversational jam.

A research titled ‘The Difficult Conversations Survey’ of over 200 managers by Globis suggests that over half (53%) of respondents’ report avoiding difficult conversations because they lack the training and 56% avoid them because they lack experience in handling such situations.

Recently, I conducted a poll on this topic on Twitter. 36% of the respondents said their most difficult conversation is with their employees, 34% said that it is with their co-founders and 30% said it is with their Board of Directors.

Situations like changing the responsibilities of a co-founder when the organization scales, firing an employee who is consistently not performing, having a conversation with an investor who is placing unreasonable demands or a board meeting with no consensus, are quite common.

Given that the average age of technology entrepreneurs in India is 28 years, they may have limited experience in managing high-stress situations diplomatically. How these conversations are handled, can demonstrate maturity or the lack of it. For successful entrepreneurs to become successful leaders, learning the art of managing such a conversation is critical. Like any other soft skill, the ability to turn a difficult conversation into productive outcomes too can be inculcated with the right tools.

Communicate for collaboration

Let’s take a situation where an employee is not performing. You need to have a conversation but do not want to hurt the employee by saying the brutal truth. By communicating your point subtly and not giving a completely honest feedback, you might avoid having a difficult conversation. However, this would not serve a long-term purpose of employee’s performance improvement as the gravity of the situation might be misunderstood. Good coaches and mentors need to give honest feedback while being empathetic.

Having said that, there is little reason to begin a difficult conversation on a combative note or to treat it like a debate or a trial. When negotiating the relationship between countries, diplomats seek to understand the other person’s concerns and priorities’ in order to harmonize interests. They do so by adopting a collaborative mindset, assuming that their counterparts are coming in with the same mentality.

Communication for collaboration is the prequel to developing an ability to listen and staying clear of blaming the other side for the problem; conditions vital for successfully handling critical conversations.

Emotional intelligence is a key leadership differentiator

According to a research by Laura Wilcox, Director of management programs at Harvard Extension School, “90% of your career success, especially at the highest levels, comes from EQ when IQ is roughly equal.

The work environment is generally positioned as a place where logic and reasoning is given priority over emotions for problem-solving and productivity. However, the above research effectively negates this perception as a myth. Emotions are an element that must not be simply dismissed.

Let us take another example. When an organization scales, the early-stage organizational structure may not be relevant anymore. A co-founder, who was earlier responsible for a few departments, may not be the right person now, to own the same responsibilities. Communicating this requires a lot of emotional intelligence, as the co-founder who had put his heart and soul into building the company, might not take this well.

By working on their emotional intelligence, young entrepreneurs can successfully reflect upon common problems in their path of adept handling of tricky conversations. What is the root of their disproportionate reaction to a situation, what are the non-verbal cues they should pay attention to; how is their tone impacting the conversation; are some of the prime pain points which can be effectively addressed by harnessing self-awareness and self-regulation.

Timing and environment are important

Few of the many factors that can positively or negatively influence a conversation are the timing and the environment they are held in.

The timing is very significant; it is important to understand the concept of a ripe moment as a major element in the processes of starting a difficult conversation. Addressing a problem prematurely or leaving it till it’s too late can exacerbate the situation. For example, if the right feedback for performance improvement is not given at the right time, it may lead to a situation where you may want to let the employee go.

In a similar vein, for startups and its founders to grow into great organizations, it is imperative to create a psychologically safe environment for its leaders and co-workers to have open and honest communication. This implies cultivating an environment that encourages talking about uncomfortable issues without feeling the need to withhold or mask information.

Elimination of fear of being judged harshly, of eliciting resentment or facing alienation are key requirements for an organization to transition into places which encourage courageous and feedback conversations.

Address the next steps

Approaching a difficult conversation with a collaborative mindset and by applying self-awareness is only half the battle won. The ability to follow up and build a relationship after a hard conversation matters just as much as the skill of tackling that initial difficult conversation.

Suppose, at a board meeting, you need to have a conversation with your board of directors about pivoting the strategic direction of the company, and there is no consensus among the members. It imperative to make the decisions urgently and building consensus becomes crucial. However, this is a three-part process which requires firstly, clear communication around the need for pivoting, secondly, the appreciation of the fact that you were able to come together, identify and discuss a big issue and thirdly, proactive communication around the next steps which takes the conversation forward to its logical conclusion.

Focusing on what should be done after having a difficult conversation is just as important as having the conversation itself.

There is no rule book to follow while handling difficult conversations. They have been termed ‘difficult’ because of the fear of being perceived as mean or sometimes worse. But the willingness to have these conversations shows a keenness for rectifying the situation than concern about popular perception. What is needed is the emotional availability and agility to handle these conversations. Perhaps emotional agility can be a new leadership differentiator, certainly giving people with it an edge over people without it.

Disclaimer: The article is the independent opinion of the author and does not represent those of Kstart or Kalaari.



Vani Kola

VC @Kalaari. Committed to entrepreneurship in India. Yoga enthusiast, Daily Meditator, Occasional runner & mom of two girls.