Difficult conversations are difficult!

Over last several months, I had several conversations with the mentees assigned to me by LinkedIn mentor program, as well as with engineers in my company. Interestingly, in most of the cases, I had same recommendation for them – have that conversation that you feel is too tough to handle.

Now, it is possible that it is a case of ‘if I have a hammer, everything looks like a nail’. It is also possible that given this was perf review season, people had similar issues. Either way, here I am, talking about difficult conversations!

What is a difficult conversation? Any conversation that you think you need to have, but you feel it will be tough for you emotionally and you don’t know how to have this conversation. In most such cases, one or more of the following are true as well, and their presence makes it a difficult conversation:

  1. It involves one or more incidents which has affected you emotionally
  2. It requires you to be critical to the other person
  3. It is very important for you to address this issue, but keeping a good relationship with the person is equally important for you

As you can see, ‘difficult’ is written all over it!



Here are a few situations which create the need for having a ‘difficult’ conversation:

  1. You feel your manager is biased against you and you need to confront your manager
  2. One of your peers criticized you in public and you are super angry/embarrassed.
  3. You don’t agree at all with the feedback given to you during your performance review and want to rebut them by meeting your manager again.

It is important to understand why people find it difficult to have such conversations:

  1. They don’t know how to broach the topic.
  2. They don’t know how the other person will react
  3. They don’t know how they will deal with other person’s reactions
  4. They don’t know how to control their own emotions.

This problem also exists because most people don’t have the skill and experience to have such a conversation. So they avoid it. The result is they lose an opportunity to get such an experience and learn the skill. It becomes a vicious cycle that they find to get out of.

My advice in all such situations is simple: be courageous and set up the meeting to have that conversation. Then prepare for it hard. When the meeting starts, wade into the difficult topic honestly and demonstrate candor at all times. Learn from the experience and do better next time when another such situation comes up.

If the resolution of the issue is important to you, you will find courage to have that conversation. This is something no amount of advice can help you do, you have to do it yourself.

Once you have decided to have that difficult conversation, you should prepare well because it is an important conversation – irrespective of the outcome.

A pre-requisite to having such a conversation is to be able to give feedback effectively and to receive feedback effectively. Giving and receiving feedback are key skills to learn and they are eminently learnable and you improve as you practice it more.

To prepare for such a difficult conversation, you should focus on 3 aspects:

  1. Opening the conversation
  2. Handling the response
  3. Managing your emotions

Opening Statement

This is completely in your control, so write out your opening statements and pick right words and phrases to use, picking specific examples. Focus on phrasing your statements around your feeling, and avoid judging other person’s actions.

Consider these 2 statements for a situation like #2 above (your peer criticized you in public):

Statement 1 – “When you said in team meeting I don’t know anything about blockchain, I felt embarrassed. I felt belittled and small. I have been disturbed since and I can’t do my work well.”

Statement 2 – “You belittled me in front of everyone and embarrassed me. You have done it so many times, why would you do it?”

Statement 1 is all about you and your feeling, and it is hard for anyone to say you are wrong, because it is your feeling and no one else knows more about it than you. Statement 2 is all about the other person who can always jump in and try to justify and show that your judgement is wrong; you immediately start on a wrong footing. So try to craft your opening statement that resembles Statement 1 rather than Statement 2.

Handling the response

If you think about why you were afraid of having this conversation, you should be able to anticipate the response well! There could be different types of responses depending on your opening statement, but I will assume you will prepare your opening statement well and not create additional problems!

You should try and anticipate the emotion as well as content. For example, taking Statement 1 above as your opening statement, there are multiple responses possible (since you know this person, you will be able to figure out which subset applies to you):

  1. The person apologizes and tries to assure you that was not the intention.
  2. The person gets angry at you and accuses you of being too soft, not able to take feedback, etc.
  3. The person gets emotional
  4. The person is shocked
  5. The person tries to explain what actually happened in that situation

Of course, this is not exhaustive list of responses, but general idea is that there are 2 kinds of responses: either the person displays a positive emotion/intent (apology, emotional, shocked), or a negative emotion/intent (anger, rebuttal). If it is the latter, most likely you didn’t paint a sufficiently grim picture of your feeling, your emotional state. Do better next time, seriously!

If you feel you are unable to handle this negative response, be willing to stop the conversation and pick it up at a later time – there is no point in continuing and aggravating the situation if you can’t control it.

If you have a positive emotion/intent displayed, you have handled the conversation well. You now need to engage in a constructive conversation that will strengthen your relationship with the person and also resolve the issue. Remember that such issues are mostly solved at emotional and relationship level, very rarely at a logical/cognitive level.

Managing your emotions

If you are not careful, your emotions can distract you from your goal in this conversation. It is not a problem if you demonstrate emotion, it is a good thing in fact, because you do need to emphasize that the issue is caused at emotional level. The problem occurs when you are not in control of them. For example, let’s say the response from the person shows negative emotions. If you are not careful, you can reciprocate and the matter will get worsened. You need to be aware of your emotions and be willing to stop the conversation if you think you can’t control your own emotions.

It is hard to have a difficult conversation. However, good news is that whatever you learn when engaging in such a conversation is very transferable to another similar situation, so this is a lifelong learning that you engage in.

There are many good books that I have found useful in learning how to handle such conversations, the two I have found extremely useful are Crucial Conversations and Fierce Conversations.

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