The incredible potential of difficult conversations

You messed up big time and you need to give your boss the bad news. Perhaps, a persistent request from your biggest supporter at work is difficult for you to accommodate. Also, someone is consistently undermining your role and you’ve simply had enough!

Sounds familiar?

1. Take a cue when faced with these tradeoffs

These situations are awkward, uncomfortable and they often smell of conflict. They almost always involve challenging tradeoffs. Would you make an excuse with your boss and risk breaking trust or come clean whatever the consequences? Will you resentfully accept the request by your biggest supporter or reject it with honesty and endure discomfort? Would you write a passive aggressive email to a colleague that undermines your role or would you be open to understand what is driving their behaviour?

Whenever you are faced with such tradeoffs you should know that you have a difficult conversation on your hands.

2. There is power in committing to have a difficult conversation

Avoidance is tempting. At great cost, I have learnt that difficult conversations are an instrument of redemption. If you avoid conflict, mistrust grows and relationships deteriorate. Moreover, you need to manage consequences of these strained relationships at the cost of growth. On the other hand, if you did come clean with your boss, you might get reprimanded, but your boss will always remember that you took responsibility for a mistake. If you honestly declined the request from your biggest supporter at work, they might actually appreciate it more. Also, it may turn out that the colleague who has been undermining your role, did it because of something you said at the team meeting. You are able to patch things up, and you don’t have to deal with the thorny issue anymore.

There is power in taking full responsibility for your difficult conversations.

The more positive outcomes you achieve, the less your aversion to difficult conversations.

3. How to prepare for a difficult conversation?


There is a lot of advise out there that says don’t frame it as a difficult conversation. However I have observed that it helps to acknowledge it. Self-affirmation that I have turned many such conversations around with a positive outcome is a great way to muster courage.

You could choose to frame it differently. Some choose to frame it as “getting closure”. That’s fine as long as you are not being vengeful about it.

Understanding Emotions

It’s helpful to understand what are the emotions involved between you and the other person. For instance, a colleague who is undermining your role may be insecure about theirs. If you even acknowledge their insecurity, you have a better chance of dealing with the situation. Others may perceive you as eccentric, overly nosey, perhaps there is fear.

I take cues from facial expressions, keen observation of body language when you are together, public comments in meetings, or simply how responsive someone is can tell a lot about emotional equation between you two.

Considering power differential

The person whom you are going have a difficult conversation with may be equal, less, or more powerful than you. This has implications on how you prepare for the conversation.

When I am dealing with senior executives, I want to be absolutely sure that I am not out of line. Senior executives, no matter how strict also appreciate honesty. Deceptive, sugar coated, and convoluted feedback serves to frustrate anyone, let alone senior executives who have to deal with difficult situations at scale.

While dealing with subordinates or peers I want to ensure I don’t come across as too sure of myself. Showing genuine appreciation for a different point of view is helpful. You cannot fake it.

Avoid gossip like the plague

You don’t like someone at work, it might be tempting to confide with your close colleagues. You might say, Lynsey is always trying to undermine me in every situation. She is so arrogant. You may feel like you have just released some burden, but you have just committed a big disservice to the potential success of your conversation with Lynsey. You have now framed and confirmed a biased perception of Lynsey. This will make it very hard for you to have a genuinely engaged, difficult conversation with her.

It’s harder to fill a cup that is already filled.

Manage the narrative in public very carefully otherwise the narrative will manage the situation.

E-mail, text, and the snowball effect

It’s tempting to respond with a very satisfying “ReplyToAll” and show that you are no less. The thing though, is that e-mail is free for all. The more people on the chain, the more free fall opinions, the more polarisation and the more agony. I call this the “e-mail snowball effect”. This is a sure way to ruin your chances to a productive conversation, and it’s certainly going to be more difficult now than it was before the drama that unfolded via e-mail. Please don’t take the bait. Even if someone else starts it be the first to end it.

Texting is worse. You think you are doing it 1-1, you feel powerful with a fire and forget mechanism. Please do remember that it’s two-way. There is no guarantee that it’s private and often it becomes a venting ground. Face to face or video, or at least a phone call is must.

Time it well

You shouldn’t have a difficult conversation when either of you are emotional, tired, anticipating a critical deadline.

4. Practice the following conversation principles

These work particularly well for difficult conversations but are equally applicable to any conversation.

Invert the pattern of interaction

Notice the pattern. You and the other person typically have patterns of verbal exchange. For instance an aggressive boss might react to a mistake by yelling or making a terrible remark. You might shrug off, back off into a corner or you might react verbally as well.

If you know that there is a pattern then try to invert it. If the boss yells, and you have a tendancy to react try a minutes’ silence. This will throw the other person off balance, and also most likely make them think their reactions as well. This technique is very effective!

Don’t get distracted

When you are discussing the other person might make personal comments. They might say but you never listen or say you always are late to respond to my work requests.

Acknowledge the first part of their personal remark and bring the conversation back to the topic. For instance you might say, “I appreciate that I may come across tardy or impatient, but today I’d like to understand if you are willing to change your publicly made comments as they undermine my role. This has an effect on my productivity and therefore affects everyone including the company”.

Deliberately slow judgment.

Be curious, this will avoid confirmation bias. This will allow right questions, entertain other point of view, and engage in a dialogue. Be eager to “understand” than score +1 points by proving that you are right and the other person is wrong.

Deliberately slowing judgment is a superpower

Articulate what needs to change without complaining. For instance, don’t say, “I find your publicly made comments humiliating and therefore stop making them”. Say, “I’d like you to be sensitive towards how your publicly made comments might affect my ability to perform my role”. That is a lot better, as it steers clear of personal blame and focuses on what can be improved without judgment.


When you are having a challenging conversation, it is natural to expect emotions such as anger, resentment, fear and contempt towards someone. However if you humanize those emotions you would find it a lot easier to control your emotions. For instance, you are extremely angry with someone for sending a publicly humiliating email to you. You can certainly prepare and have “the conversation” with them however it is helpful to think why they may have done such a thing? For instance you can say to yourself, “Martin has gone through a lot. This quarter has been incredibly difficult” or, “Martin has 4 young kids, and the pandemic hasn’t been easy on anyone. Everyone is not themselves sometimes”. This will put you in the right frame of mind instantly. It will avoid reactions and set stage for a good conversation, or make the one you are having already a lot better.

Don’t try to control the outcome

During a conversation focus on the relationship between you and the other person. Be genuinely okay with a negative outcome. This is not a negotiation, first you need to iron out an interpersonal issue. Even if you try to negotiate it’s not going to go down well.

5. If nothing works?

This is a completely plausible scenario. Even after sincere efforts and genuine conversation, if the other person remains in their square, and you have a dysfunctional relationship, then you have 3 choices.

Accept it, set a boundary or make a change. Which choice depends on all of the things we have already touched upon.

May the force of difficult conversations be with you!