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Awkward conversations and how best to navigate them

September 23, 2019 5 min read

Awkward conversations and how best to navigate them

You know the conversations we’re talking about; those pit of the stomach interactions, often involving strongly held and opposing opinions, strong emotions or conversations otherwise classified as career-limiting, risky or controversial. 

Having recently read a brilliant article by Joel Garfinkle in the HBR,How to have difficult conversations when you don’t like conflict, I wanted to share this with you, along with a few insights that I’ve found helpful in this area.

While I am by no means an expert, I have gathered some helpful advice over the years which makes facing and embracing these types of, often important, conversations a lot more palatable. 

These are my top 6 examples to help you navigate awkward conversations:


1. Be clear on your overarching objective

Always be clear about your overarching objective before starting an awkward conversation. What is your ultimate goal? What is it that you really want to achieve? Having a clear objective upfront enables you to better navigate the inevitable reactionary motives that may otherwise cloud your judgment during the heat of the moment (ie, trying to save face, winning, getting even, or being right).

If you feel yourself (or the conversation) moving into reactionary mode, rebalance the conversation by focusing your mind on your overarching objective. Do this by checking-in and assessing:

  • would you be behaving in this way if you really wanted to achieve that bigger picture outcome?
  • imagine looking down on yourself and the other person having the conversation, and objectively assess a scene; have you allowed your emotions to take control and change the goal posts?

If yes, pause, and lift yourself back up into bigger picture solution mode.

An easy way to elevate your perspective back into this space – particularly if you find that both parties are falling into the “drama”, is to have pre-prepared publicly sharable “mutually beneficial purpose” statement about why you are having the conversation.

While your overarching objective is often personal - and the conversation is likely to form just a small piece of the puzzle required to take you closer to that bigger picture goal (which may, or may not, be of interest or benefit to your dialogue partner). A “mutually beneficial purpose” statement should be established and communicated whenever you feel the conversation going off track or where realignment is required so that both parties understand why it is worth you both navigating this uncomfortable terrain.

2. Articulate a mutual purpose upfront

The ability to articulate a mutual purpose upfront immediately establishes respect and lowers hostility.

It demonstrates that you have spent time considering both your own perspective and the other person’s position. And, while the conversation may be awkward to have, that you are approaching the issue on the basis that you wish to resolve the obstacle for the benefit both parties, not just your own benefit. 

To do this, take the other person out of “the issue” and think about what outcomes are likely to be shared by both parties. What is the common goal for the conversation?  It could be as simple as clarifying misinformation or providing further information to ensure that both parties have all of the details available to make better informed decisions.

A great way to ensure clarity in communicating your mutual purpose, and particularly for unwinding any knotted misunderstandings, is to provide contrasting examples of what you do and do not mean.

3. Contrast to clarify

Often during heated conversations we make sweeping statements or misinterpret information. Explaining what you intend (or are trying to achieve), as well as what you don’t intend / are not trying to achieve, makes it clearer to your conversation partner that “X = X” and does not “=Y”.

Use this technique in the following form: “By stating X, I mean X, I don’t mean Y. I am not trying to achieve Y. I am trying to achieve X”. Explicitly stating what you do not intend should deal with any misunderstanding or incorrectly interpreted information. Stating what you do intend should then encourage the other person to contribute to the dialogue and confirm or clarify their understanding of your messaging.

4. Foster safety by demonstrating inquisitiveness

If you feel the conversation heading into reactionary, defensive, or blame worthy territory, reset and check for safety. Much like Joel Garfinkle suggests, reframe your thinking and approach “hot” topics with curiosity and respect.

Question to learn more about the situation and gather further details, making sure that your questioning is not accusatory or blame-like in nature – as this will only inflame the situation.

5. Listen actively and paraphrase to confirm understanding 

While this may seem obvious, the best way to approach an awkward conversation is to be most concerned with listening to what the other person is saying.

All too often we fall victim to concentrating on what we should say next or trying to remember a pre-rehearsed response, when the critical piece to success is actually focusing on being present and paying attention to what the other person has said – which, in many cases, is different to what you expect. 

Instead, try focusing intently on listening to the other person and asking yourself:

  • What is the other person actually saying?
  • What is the other person’s body language telling me?
  • Do these messages align?
  • Do I need to re-establish safety by demonstrating curiosity and respect?
  • Do I need to re-establish safety by reiterating the “mutual purpose” of the conversation?
  • Have I let my emotions take over and alter my overarching objective?

Once the other person has finished speaking, paraphrase what they have said using different language to confirm your understanding of their perspective is correct.

Equally, if you feel the other person has not understood your position, ask them to relay what they have understood to confirm your messaging has landed accurately.

6. Lead with facts and then your story

Stories are subjective and are often emotive.

Placement is a wonderful tool to establish safety and then provide your version of events. To do this, first ask the other party if you may share your interpretation of the situation with them (placement).

The most persuasive and neutral way to convey your perspective is to begin with facts (information that can be, or has been, substantiated). You should then, unemotionally, share your interpretation of the facts (your story). Critically, when sharing your story with the other person, use tentative language; steering well clear of accusatory or conclusive statements. This will maintain safety and ensure that you don’t represent that you have drawn any conclusions about the situation before hearing their side of the story as well (which may shed light on your interpretation).

You should then actively encourage testing of your story and for the other party to share their interpretation of the facts (their story). Testing of any nature, particularly when you are directing flow, should be framed with a genuine desire to better understand the other person’s position and clarify anything that does not make sense.


If misunderstandings occur, revert back to contrasting examples and your mutual purpose statement to recalibrate the dialogue back on track.

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