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Managing Difficult Conversations at Work

Last updated on: 
September 6, 2023
Utkarsh Sahu
The fast well prepared banner
About The Author!
Utkarsh Sahu
Utkarsh Sahu
Director Category Management at Interview Kickstart. With a toolbox of P&L expertise, inventive innovations, marketing magic, and strategic relationships, he is an ambitious management consultant having a passion for promoting business growth.

Difficult conversations are an inevitable part of working at any organisation. Most people try to avoid difficult conversations out of fear of being caught on the back foot, adverse outcomes, an inability to communicate, or simply because they’re too busy to deal with tough situations. 

Difficult or tough conversations can crop up at any time and for a number of reasons, based on different situations. 

They could be related to feedback, promotions, OKRs, interactions with colleagues (superiors, subordinates, peers), coaching or mentoring, interactions with clients, customer service, etc. 

Conversations can’t always be controlled but they can always be managed.

To help software engineers deal with this issue, we got industry experts to participate in a panel discussion on Clubhouse, hosted by Ryan Valles and Soham Mehta, the co-founders of Interview Kickstart. 

The session panelists comprised Interview Kickstart alumni and instructors working at FAANG, Tier 1 companies, and startups. 

The panel exchanged thoughts, opinions and views on how to deal with difficult conversations. They also fielded questions from the audience, made up of engineers from various companies and aspiring FAANG engineers. 

This article, based on the panel discussion, will cover

Conveying information and making requests

Soham Mehta, co-founder of Interview Kickstart and session host, kicked off the discussion by recounting a particularly difficult interaction he had at a former workplace. Panelists then weighed in with their opinions on how the situation was handled. They also highlighted and discussed other aspects related to the situation from their personal experiences.

“As a new manager, I was informed by management that a member on my team was not performing as required. I had to either get him to turn things around or let him go. 

Given the task at hand, I decided to approach the said team member and explain the situation to him. I also laid the cards on the table and told him if he didn’t improve his performance he would be let go. 

He acknowledged his failings. However, he then stated that he would require me to coach him to improve his performance.

At this point, I explained to him that as his manager, I could not be his coach. I believed every individual member of the team was responsible for their own performance and for fulfilling their role within the organisation. 

Having left him to his own devices, he promptly shut down all interaction on the subject.”

Given the above situation, the discussion panelists felt that, as a manager, refusing to help a team member was not a recommended course of action. 

Conveying information in a timely manner facilitates smooth and easy communication.

All managers face such situations at some point in their career. Managers expect engineers on their team to be responsible and accountable for their actions and perform as expected. 

While they should be, managers are ultimately responsible for the people of their team. This includes their performance and career growth as well. 

They should be fair in assessing a subordinate’s work. They should identify performance gaps and inform the team members of the same immediately. They should also try to alleviate the situation by offering solutions or guidance.

Having to devote their time to multiple tasks, managers are not necessarily required to coach team members themselves. 

However, as in the above case, in lieu of coaching, advice could have been offered on how to improve performance. Alternatively, a senior member could have been assigned the task of providing the help needed. 

Engagement levels act as cues to manage conversations

Being abrupt and authoritative with the subordinate did not yield a positive outcome. By asking for help, the subordinate indicated an interest in furthering the conversation. This was a sign of engagement. Positive responses indicate that the conversation can be steered in the right direction.

Discussions do not have to be concluded immediately

Pacing a discussion, especially complicated and challenging discussions, can facilitate clarity of thought and communication. 

A good way to handle counter arguments or requests is to hold off responding right away. 

Convey the need for time to think about the issue at hand. After having assessed the situation, continue the conversation with a clear response in an appropriate manner for the desired outcome.

Well-established processes create proper understanding and better communication between parties

Ideally, a subordinate’s performance should be tracked using key indicators to reveal performance gaps before the situation gets out of hand. Poorly defined relationships and processes give rise to frictious interactions.

In the above case, since the manager was new to the team, early intervention was not a possibility. The manager should have learned more about the subordinate’s past performance. This could have been done either by involving the subordinate’s previous manager or looking through communication on past performance, if possible. 

This way the conversation could have been approached with proper context for a mutually beneficial outcome. 

If information is not conveyed at the right time and in the right way, managers run the risk of alienating their teams. It may also cause team members to consider moving to another team or company. 

While the above mentioned case is recounted from a managerial perspective, the discussion panelists also examined the interaction from the subordinate’s perspective. 

They noted that the subordinate was also caught in a hard conversation. 

Reacting impulsively is a common mistake, especially when  interactions are unexpected or when discussing sensitive subjects 

Receiving performance feedback and discussing ways to act on the same is not easy, especially if one’s job is on the line. In this case, the subordinate receiving feedback should have asked for more data or specific examples regarding his performance. 

Understanding the exact areas that he was underperforming in could have helped him better assess corrective action needed. It could have also helped him ascertain if he could have resolved the issue himself or sought help from another member of the team.

By asking his manager to coach him without duly processing feedback received, the subordinate effectively shifted the responsibility for improvement in his performance to his manager. This put the manager on the back foot and elicited a negative response. 

Never assume authority in communicating with superiors or peers

Before requesting action or input, especially without the right authority to do so, it is advisable to first analyse the issue. Define the request or inputs needed and ascertain the right person to whom to address the request. Convey the same in a courteous manner with a clear purpose and outcome. 

Performance reviews are just one of the many subjects that make for difficult conversations. 

As part of the session, the hosts and panelists shared and delved into various personal experiences that involved difficult conversations in different situations, including their learnings from these instances. 

Outlined below are two such cases as recounted by Ryan Valles and Soham Mehta, founders of Interview Kickstart and hosts of the session. 

Confrontation and emotions

"At a former workplace, early in my career, I was placed on a project headed by an infamously tough manager. 

I believed I was performing well in my role, especially since our customer was happy with my performance. However, during a performance review, my manager rated me poorly, indicating I was not performing as well as I thought. 

I immediately confronted him on the issue, informing him that a low rating on my performance was not warranted. He obviously disagreed and my low rating stuck.

Years later, I faced a similar situation. Once again, I was rated lower than I should have been, on a project I was certain I was doing well at. This time, though, I did not confront my manager right away. 

Drawing on experience, I decided to go into this discussion well-prepared and with sufficient data to support my stance. I defined a clear desired outcome for the meeting. I even prepared written notes, planned, and rehearsed my conversation. 

I acknowledged the fact that I was not solely in control of the conversation because of which the discussion could yield a range of outcomes. I was prepared emotionally and mentally for this.

This incident made me realise that confrontation was not necessarily a negative construct. I could make confrontation less daunting simply by using the right approach. 

I could agree to disagree with my manager in a respectful, rather than emotional, manner and resolve the issue, more effectively than the last time, to my benefit.”

In response to this case, the panelists observed that confrontation was indeed a major challenge for most engineers. 

Avoiding confrontation only serves to hinder communication and exacerbate problems

Contentious situations are difficult to manage when emotions run high. However, effective communication can serve to resolve conflict. 

When challenging situations arise, it is natural to respond defensively and impulsively. The key is to tackle the issue as soon as possible and in as controlled a manner as possible. 

One way to approach confrontation is to plan and prepare for it. 

Schedule when and where the discussion should take place. Next, analyse the situation and gather all possible data pertaining to the situation.

Approaching a difficult conversation with data helps keep emotions in check 

Most discussions are entered into with feelings, not facts. 

Feelings can easily overpower rational thought and it isn’t uncommon to then react in regrettable ways. Managing emotions is very important in any conversation, more so in sensitive ones.

An intelligent way to manage emotions is to separate the message from the speaker and their behaviour. Focusing on what is being communicated, instead of who is communicating it, will help maintain objectivity. 

Another useful tool to managing emotions is controlled breathing. There are a number of breathing techniques that can be used to keep emotions in check, allowing for rational and clear thinking.

The following are recommended resources that  outline tools and techniques to manage difficult conversations

  • “Crucial Conversations: Tools for Talking When Stakes are High” by Kerry Patterson, Joseph Grenny, Ron McMillan, and Al Switzler
  • “Non-Violent Communication, A Language of Life” by Marshall B. Rosenberg

Data provides objectivity and direction to a conversation. It also helps establish a goal or purpose for a conversation as well as gauge possible reactions and outcomes. 

Trying to win an argument, as opposed to finding a resolution, can damage relationships between parties. Data should only be used to support a stance, not force a point. 

Data is especially important for performance reviews. It is hard to keep track of work and accomplishments between review periods, especially if reviews are not regular or frequent. 

Many engineers maintain work logs to document various aspects of tasks executed as well as achievements, appreciation and positive feedback received. This data can be used during performance reviews as an objective basis of discussion.

Performance data can also include managers’ expectations and how they define success. Performance measured against these expectations can help prevent difficult conversations from arising during reviews. 

Often managers fail to convey issues about a subordinate’s performance in time. When the issue arises, it catches the subordinate off guard. Performance data can also help subordinates initiate progress reviews, especially if managers avoid it or forget to do so.

When planning a conversation, it’s advisable to not focus only on delivering messages but also the repercussions of what is being conveyed. This will help structure a conversation, keep it objective, and help manage it for a desirable outcome.

Listening and empathy

“At a former company, I worked on a project in which the team decided to increase the pace of the release cycle. This appeared to go smoothly until the customer, a very important one at that, raised serious issues with the changes we made. 

My manager asked me to lead the conversation with this customer. Since I was brought in without any context about the situation, I asked my manager for details about the issue. Unfortunately, my manager, too, did not know much about the situation. On further investigation, I realised that the customer had not been adequately attended to and the problem had been escalating through the system for a while.

My first course of action to resolve the issue was to connect with the customer to gain a solid understanding of the client’s grievances. As it turned out, changes we had implemented to the project had major repercussions to their business. What we perceived as minor alterations, actually gave rise to major unforeseen complications that could only have been gleaned from our clients themselves.

After giving them the opportunity to air their grievances, I then proceeded to resolve the issue by offering a solution to their problem. I explained the reasons for increasing the pace of the release cycle and how they stood to benefit from it. 

Eventually, I managed to guide them through the discussion to a mutually desired resolution.”

All the discussion panelists agreed that listening was the key to resolving this issue, as it is in most cases of conflict. Their collective experience in dealing with unhappy customers revealed that in most discussions, listening played an important role.

Effective listening is a key factor to successful communication 

Listening to get the right context about problems can lead to quick and effective resolutions, as evinced in the case above. 

Instead of reacting and jumping right in with a possible solution, a more ideal approach to a complicated problem is to listen, take notes (collect data), understand (analyse) the problem in the right context, and respond after taking all factors into consideration. If a different viewpoint has to be expressed, explain rather than tell.

Empathy is an important tool to manage emotional responses

Sometimes, diffusing a tense conversation comes down to listening without responding. More often than not, people only listen to react as opposed to listening to understand the problem. 

An agitated party is likely to be more pliable once they have had the opportunity to air their grievances and have them acknowledged. 

Managing different types of difficult conversations

The session concluded with a section on audience participation. The hosts and panelists fielded questions from audience members on different types of situations that required hard conversations. Outlined below are a few of the questions and the panelists responses.

The COVID pandemic has disrupted work environments. With a lot of people working from home, personal and professional schedules aren’t always harmonized. Work can’t always be carried out as efficiently at home as at the workplace. How does one push back when they cannot take on new assignments or work within assigned timelines without upsetting their team or managers?

Saying no is always a hard conversation to have, especially when having to deny a request or instruction from a supervisor. One way to do this is to convey a ‘soft no’ instead of a ‘hard no’.

In the above case, an unsubstantiated refusal to take on work or work within assigned deadlines would not be appreciated either by a manager or the rest of the team. 

A more tactful approach would be to express a desire to take on the work assigned and follow it up with a reason why it can’t be done. For example, instead of saying “It isn’t possible to do that right now”, try saying, “I would love to take on the task assigned to me, however, owing to the current situation, I would be unable to execute the task to the desired standards at present. I would like to extend the timeline for the same or reorder my current tasks based on priority to accommodate the new assignment.” 

Given that the current COVID situation is new and challenging to most employees, it is advisable to remain as honest, transparent and communicative about personal challenges. 

Offer solutions or suggestions that would ensure smooth execution of tasks where tough situations arise to prevent frictious interactions.

Creating trust is imperative to effective communication 

Trust makes difficult conversations easier as all parties see each other in a positive light. Given that difficult conversations are bound to arise, one should always work at establishing trust through constant communication. This is especially true in new environments or when establishing new relationships, either with colleagues or customers. 

How should one approach conversations with a customer who has already decided on their course of action and appears closed to further communication? For example, how does one negotiate with a client who has decided to terminate dealings with the company?

Such situations pivot largely on the level of trust between the parties involved in the negotiations. When a customer has decided on a course of action, they tend to be closed to discussions and negotiations. 

If the client is worth retaining, it’s advisable to find out details about the customer’s situation and isolate the reason for their decision. There are many factors that affect a client’s interest in dealing with a certain company but dissatisfaction usually breeds over a period of time before it results in a customer parting ways. 

Customers often part ways as a result of a misunderstanding or an error that could have been resolved but was left unaddressed for too long. 

Actively listening to clients while allowing them to air their grievances is a good starting point to negotiate a solution. It is important during such negotiations to not get too wrapped up in convincing the employee or customer to remain with the organisation. 

Instead of taking micro steps debating circumstances, one should take leaps to shift the employee’s / customer’s mindset to a point where they are ready to reconsider their decision. This outcome is easier to achieve than getting them to go back on their decision.

How can a critical employee be retained if they have decided to leave the organisation for better monetary prospects?

When an employee decides to exit a company, managers are often informed after the employee has accepted an offer elsewhere. As with a customer who has decided to part ways, the best way to approach the situation is to initiate discussions to discover the employee’s reason to exit the company. 

Employees do not usually decide to switch companies solely for monetary reasons. Centre the discussion around the employee’s experience with the organisation and reasons that prompted the decision to leave. 

If the company cannot match the employee’s external offer monetarily, negotiate based on other areas of interest to the employee e.g. more challenging work, a change in teams, a higher title etc. 

Approach the discussion with prepared solutions or offers. This will substantiate the company’s willingness to retain the employee and provide the employee motivation to reconsider their decision.

However, in such cases, conversations should not focus merely on the short-term aspect of retaining the employee but should delve deeper into the employee’s long-term goals as well. If they appear to not be aligned with company interests, negotiating a short-term solution may only be the start of a recurring issue. 

It is not often that employees respond positively to counter offers. Managers should prepare for a negative outcome.

How does one deal with a manager whose conversations are ego-driven and who is closed off to others’ suggestions and perspectives?

Managers who are egoistic leave little scope for other participants of a discussion to be heard or acknowledged. They also tend to be very defensive, leading emotionally-charged conversations. One has to be tactical and wise in their approach to such conversations so as not to appear accusatory or argumentative. 

A group interaction is more advisable than a two-way conversation in such cases since ego-driven personalities tend to act less authoritative when dealing with more people.  Conducting  meetings with the participation of a higher authority can help soften an egoistic manager’s approach.

In a lot of cases, though, when managers appear ego-driven, it is, in fact, the subordinate who refuses to negotiate or reconsider their stance. 

Projecting feelings is commonplace and creates incorrect perceptions that lead to misunderstandings. 

This happens especially when one of the participants of a discussion fails to listen and focuses only on making a point with the intention to convince the other participant about their point of view.

Trying to convince an ego-driven manager will only make them more closed off. Instead, prepare for the possibility of a negative reaction. Pace the discussion to first focus on influencing the manager’s mindset instead of changing it. Communication will be more effective when one is ready to consider a different point of view.

As mentioned in an aforementioned case, the best way to maintain objectivity in an emotionally-driven interaction is to temper it with data. 

Document the said manager’s behavior with other team members. If patterns of consistently questionable communication can be established, the issue can be escalated to the next reporting authority or to Human Resources for appropriate intervention or action. 

However, if interactions with the manager are sometimes successful, draw on these outcomes. Understand why certain interactions elicited favourable responses and use this to develop a tactical approach to dealing with the same manager at all meetings. 

How can one resolve the issue of a manager constantly downplaying one’s contributions and achievements? What is the most effective way to change managers opinions or views if they are reading a team member wrong or get them to acknowledge team members’ efforts?

In such cases, it is up to the employee to initiate discussions. In doing so, don't catch the manager off guard by venting feelings about the situation. Instead, schedule a meeting and outline a specific purpose. Provide an objective agenda to form a basis of discussion. Plan and prepare for the discussion. 

The employee should collect data to substantiate his stance i.e. document tasks worked on, recognition received, achievements, and performance vis-a-vis team or individual goals. Getting informal 360 degree feedback is another key way to ascertain if the manager is assessing the employee’s performance fairly.

Collecting data may also help reveal certain gaps that could be addressed during the discussion e.g. if goals are not adequately established, it could lead to different interpretations of progress or success.

The employee should also be open to listening to the manager’s point of view. An employee may be biased in organising data for a self-review. Discussions should be based on data from both the employee and the manager. 

If there indeed is a performance issue that needs to be addressed, the employee should own up to it and set out a roadmap with the manager to rectify the same. 

Quick tips on handling difficult conversations

Tough conversations are a part of every work environment. Avoiding them is not only impossible but only makes having the conversation tougher. 

Difficult conversations don’t have to be daunting. Utilising the right approach, tools, and techniques for a given situation can make any difficult conversation at work easy to handle.

  • Address problems as soon as possibly, don’t avoid confrontation 
  • Build trust with colleagues
  • Establish a goal, purpose, or outcome for the conversation
  • Schedule the conversation, let all participants prepare
  • Choose a conducive environment
  • Be prepared, practice communication
  • Keep it objective, get context, collect data
  • Don’t get emotional, stay calm and collected
  • Be confident and tactful
  • Be respectful, and courteous
  • Separate the message from the speaker
  • Don’t get defensive or aggressive
  • Don’t assume authority
  • Listen to understand, not react 
  • Be empathetic
  • Reflect and review before responding
  • Be open to ideas, suggestions, and different points of view
  • Propose solutions, suggestions, or alternatives
  • Conclude the conversation with a clear course of action or buy-in from all parties
  • Document formal conversations for future reference
Posted on 
March 18, 2021

Utkarsh Sahu

Director, Category Management @ Interview Kickstart || IIM Bangalore || NITW.

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