Business Transformation

How to take the difficult out of difficult conversations

Rebecca Houghton

According to a 2019 study VitalSmarts, over 50% of employees are avoiding having difficult conversations with their boss, colleagues, or direct reports. What’s worse is that 11% have actually quit their job rather than tackle a tricky topic with a colleague.

Fast forward to 2021 as uncertainty, ambiguity and social distance all take their toll on our working relationships, and it’s evident that clear, concise and constructive conversations have never been more important.

The prospect of having a difficult conversation makes us feel anxious, guilty and worried.  Being on the receiving end of a difficult conversation makes us feel the same – with an additional shot of adrenaline that makes us defensive or even aggressive about receiving it.  Why? Because very few of us enjoy having a difficult conversation – so we put it off, or dance around it, or simply remove ourselves from the environment.

VitalSmarts research shows that 50% of us avoid the other person at all costs.  Social distancing and remote working might feel like a blessing in these situations, but you know you’ll have to face them – and the issue – at some point.  37% of us skirt the issue which means we are giving out confusing messages, are probably prone passive aggressive comments or classic sugar coating and a huge 37% of us consider quitting their job or moving internally to get away from the prospect of having a difficult conversation.

It’s exhausting even looking at these stats.  Who has the time and mental energy for actively avoiding a colleague, or for thinking up creative ways to not quite say what’s on your mind? But the ability to raise issues in a multi-dimensional way is crucial for collaboration and for managing up – and has been ever-more important in a remote environment.  So here are a few ideas to help you take the difficult out of difficult conversations:

Stop avoiding avoidance.

Our brains are wired to avoid anything that we perceive as a threat.  And a difficult conversation – whether we are originating it or receiving it – is threatening.  It wouldn’t feel difficult otherwise.

Most of us are passive about our avoidance – we simply ignore it and hope it will go away.  My advice is to be proactive in your desire to avoid a difficult conversation – get comfortable with nipping small issues in the bud so they don’t have a chance to become big ones.  You don’t have to be confrontational to do this – phrases like ‘for some reason I am feeling uncomfortable about that idea’ can create an open and constructive conversation without it getting personal or heated.

Recognise you are judgemental

Economist Dan Kahneman tells us our brains are ‘a machine for jumping to conclusions’: and the fact is that our brains make stuff up to fill in the gaps – we can’t help ourselves.  We are naturally judgemental.  So next time you decide that Bob is always late for meetings with you because he has no respect for you, stop and reframe.  Just ask Bob why he’s late so often.  Don’t assume you know why – that’s when you offend Bob and things get difficult.

Recognise tension-drivers to avoid it getting personal

We often target the individual’s behaviour or style, judge their intent and decide they are wrong.  All of this adds to up to one thing – they are being difficult, and their behaviour is to blame.

In fact, difficult conversations usually have their root cause elsewhere, and if you can take a moment to stand back and assess the tension-driver, you’ll find the conversation is far more objective and is far easier to approach.

  • Conflict of interest – your desired outcome simply conflicts with their desired outcome.  If this isn’t tabled throughout your relationship, then the chances are it will be end in a fight to the death – or at least, to the win/lose.  To avoid that, why not start a simple statement – “I want to find an outcome that works for us both.  This is what I want – what do you want”.  Then problem solve side by side rather than in opposition.
  • Lack of trust – did you jump into the work stuff before you took time to build some rapport?  Initial small talk leads to common interests and shows an interest in each other that indicates respect. Without that minor investment, you’ve already made the conversation far harder than it needed to be.
  • Different views of the facts – we humans love to be right, and this is a classic trigger of a difficult conversation.  Marriage counsellors often ask would you rather be right or happy.  Logically, we choose happy, right?  But relationships frequently fail because of our belief that we have to get our point across – we have to be right!
  • Different values – values-based conversations are always going to be difficult, and often can’t be resolved.  Whether gun or birth control, climate change or even return to the office, values-based arguments cannot be wrong, so you can never win them.  Teams or individuals that are locked in a values-based argument often exhibit a ‘them and us’ mentality.  Wars have been started for less!

To take the difficult out of difficult conversations try to have an internal conversation first: examine what baggage you bring to the table.  Have you contributed to this? Are you being judgemental?  Then review the environment: Is there a tension-driver at play?  How is that affecting you both? And final, turn your statements into questions: write down all your judgements, assumptions and friction points and turn them into open statements instead.


Written by Rebecca Houghton.

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Rebecca Houghton
Rebecca Houghton, author of ‘Impact: 10 Ways to Level up your Leadership’ ($29.95), is a Leadership and Talent Expert and founder of BoldHR. Rebecca builds B-Suite leaders with C-Suite impact by working at an organisational, team and individual level. Her passion is helping to evolve how leaders think, take action and relate to others, working with leaders and leadership teams to achieve greater impact.


Rebecca Houghton is an opinion columnist for the CEOWORLD magazine. You can follow her on LinkedIn.