Lockdown Lounge #8 – Challenging Conversations

Challenging Conversations: How to increase your chance of a positive result

Is there anyone who relishes a challenging conversation? Who wouldn’t like an opportunity to increase their chances of getting a positive result from one?

This was the theme on the Loungers’ minds as we approached the 8th get-together of this most convivial of convocations. Here conversations might get challenging, but always with positive intent and always with mutual respect.

However, another matter was weighing on the minds of the coaching baristas as they polished their glasses, cleaned the virtual tables and ensured that all conversational condiments were on hand to facilitate the Loungers’ experience.

This was to be the last ever Lockdown Lounge.

What’s in a name?

But when one door closes, another opens. Although this was the last Lockdown Lounge, a new virtual cocktail bar was already being furbished with all the attention to detail that the Guildhall Coaching and Mentoring Faculty could bring to bear – of which more later.

But for now, we were in the Lounge. Our host, Jane, welcomed visitors as they entered. Every fortnight the Lounge had been open, taking models from coaching and mentoring to draw critical and thought-provoking comments and to help make sense of our experiences in Lockdown.

Those coaching baristas, keeping a keen eye that all was in place, were JoPatCarlosTrevor, with Chris in charge of the menu on this occasion. The Loungers were ready, the lights dimmed and the atmosphere eager and expectant. Time for the aperitif.

Make a point, or make a change?

Very few people actually enjoy confrontation. But does confrontation really have to be part of a challenging conversation?

Chris revealed what was on the menu for today: ‘challenging conversation’ has two words, so let’s look at them separately.

Firstly, challenge. The plan is to minimise the confrontation in that challenge.

Secondly, conversation. Let’s make the exchange of views productive and useful.

The underlying question is this:

Do you want to make a change or do you want to make a point?

There’s nothing wrong in trying to make a point. Sometimes we need to get things off our chest, feel we’ve said what needs to be said, just – frankly – to be selfish and cathartic. These are genuine emotions.

But that doesn’t get things done.

Do you want to make a change or do you want to make a point?

Coulda, shoulda, oughta…

Discomfort comes from our own perceived shoulds and oughts and needs. These are our internal rules and when they’re breached, we feel challenged.


If there’s challenge in the conversation, it’s going to be with someone who has  done one of three things:

  1. They have transgressed against our internal rules, or…
  2. We perceive their behaviour or language to be a threat to our well-being, or…
  3. We perceive their language or behaviour to be a threat to someone or something that we care about.

If we can analyse what it is that’s under threat, or what ‘rule’ is being broken, we can bring ourselves into a more objective space. Jo took us through some of the processes to do that in Lockdown Lounge #7 on Perfectionism. Reframing our ‘rules’ to become ‘preferential states’ – from ‘this must be…’ to ‘I would prefer…’ – can take the sting out of the situation and help to lower the tension.

Reframing was discussed by Trevor in Lockdown Lounge #6.

What’s in your control?

When something impacts on us, it’s either something we can control, something that we can influence, or something in which we only have an interest.

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It’s important to uncover where the issue lies. If you have neither control nor influence, then possibly the answer is not to have that challenging conversation, but perhaps to reframe so that you can find acceptance – or even remove yourself from the situation entirely.

What’s at the root of the challenge? And that brings us to another important question.

What system are you on?

Why are you having this conversation? What’s the purpose? Is a conversation really the best way to get the outcome you want?

According to psychologist and economist Daniel Kahneman, we have two distinct systems for processing information. System 1 is fast, automatic and easily influenced by the immediate environment. It works on situations like this:

  • Check whether you’re in a large room or a small room.
  • Complete simple phrases like “fish and …”
  • Ducking when a ball is thrown at you.
  • Instinctively react to body language.
  • Answer simple puzzles like 2+2= …

System 2 processing is slower, reflective, and takes into account long term goals and intentions. For example:

  • Focus on a television screen in a crowded environment.
  • Read social signals and modify your behaviour.
  • Tell someone your address.
  • Complete a financial document.
  • Deciding which route to take.

When systems become complex, overwhelming or pressured, System 1 kicks in. It’s faster, plays the percentages, and it’s focussed on short term goals.

However, it neglects the bigger picture and underlying values.

The person you’re talking to may well feel challenged by this conversation, too, and there is every chance of triggering their defence mechanisms and their System 1 thinking.

Is a conversation really the best way to get the result you want?

Nudge, nudge

In terms of achieving your ideal outcome, it might be worth considering nudge theory.

In nudge theory, positive reinforcement and indirect suggestions influence the behaviour of others. A good nudge is one that alters behaviour without closing off any options or trying to bribe or force. As an example, if you’re trying to promote healthy eating, putting fruit at eye level in the shops is a nudge. Banning junk food is not.

Nudging techniques aim to alter the situation to your advantage so that when System 1 decision-making kicks in, it gives the most positive or desired outcome.

Can you change the environment to improve your chances of a positive outcome? Could you even just nudge them into doing what you want them to?

Now, that can feel a bit calculated and manipulative. But done well, you are simply clearing the confrontational brambles so that you’re both looking at the same landscape.

Another way of looking at it is this: is the situation best resolved by trying to hammer out a solution, or by a gentle drip of nudges. Both systems have their advantages.

So now you’ve decided that this situation is in your circle of control (or at least in your circle of influence), you’ve decided that a conversation is indeed the best way to deal with the issue…

There’s one more question to ask.

Should it be you?

Are you the right person to be having this conversation?

What are your motives? Be honest with yourself.

Is this an argument you have to win, or a problem to be solved?

If you really want to make a change, are you prepared to be flexible? Can you remain objective?

Do you want to make a change or do you want to make a point?


So you’ve decided that this situation is either in your control or in your influence.

You’ve decided that it’s better to challenge than to nudge.

You’ve decided that you’re the right person to be in the room (or maybe the only person willing to be in the room).

And you’ve decided that you want to make a change.

Zoom out

Time to get some perspective. Time to Zoom out.

(Probably not the best name for an exercise with all of us pretty much Zoomed out at the moment…)

This is a four part exercise to gain clarity and perspective.

The key to this exercise is to get things out of your head in whatever way works for you. Chris suggested writing things down, drawing a mind map, or talking to a friend.

Step 1

Write down the situation in as brief a manner as you can. One short sentence, preferably, maybe two.

Step 2

Imagine zooming out from this current situation. Take a helicopter view. Check in what you can now see in your peripheral vision.

How many people are impacted by this current situation? Remember the earlier Centre of Control.

  • Who has interest in the outcome?
  • Who has influence in this context?
  • Who has control here?

The point about writing it down – or drawing it, or saying out loud – is that it helps to filter out the noise in our heads. When we hear our own thoughts out loud, they tend to lose their power and they become much more manageable.

Step 3

Think of as many possible outcomes from the conversation. What’s the worst that could happen? What’s the ideal outcome? What would you be prepared to tolerate?

From these outcomes, draw out the consequences. How would you deal with those outcomes, or how would they impact on the ecology of this situation?

Write it down.

Step 4

When you’ve got it all laid out and you can see all the possible consequences, outcomes, participants in the situation, do one simple thing. But do it out loud.

Give yourself advice.

Imagine you are your own best friend. Write yourself a letter or an email. Put an arm round your own shoulder.

How does that feel?

Has zooming out given you a fresh perspective?

How do you feel?

The Loungers were getting thirsty. Time to sample the brew.

Chris invited us all to think of the last time that we had a challenging conversation, and to do a bit of visualisation.

When you picture yourself about to go into a potentially challenging environment, what animal are you?

Are you…

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Or what?

And with that, Chris served up the prompts for discussion.

Out in the breakout rooms, the conversations ebbed and flowed as they always did. Topics were picked up, dropped, varied and brought back again, all under the watchful eyes of the Guildhall Coaching Associate bartenders.

Challenging situations seemed to bring up very deep feelings. Those of us who thought of ourselves as people pleasers were particularly troubled, as were those who had been brought up in an home environment that was happy and lacking in conflict.

“Before a challenging conversation I talk to myself for days, imagining all the things that I could say”

“I can manage conflict on a professional level – but it’s much harder with close friends”

Other chats came back to the idea of the animals. Amongst other suggestions were mouse, rabbit or a lion, and one Lounger even turned the question back on its head.

“What animal would you like the other person to be? Does that change how you talk to them?”

And seeing it from the other person’s point of view could help.

“It’s worth trying to accept and empathise with the other person’s tendencies. Their reactions must just be because this really matters to them.”

Time for the next round. Chris was on hand with the conversational drinks trolley.

What do you want?

Chris moved on to discussing how we can best prepare ourselves so that we feel as confident and as resilient as possible, remembering that this isn’t an argument to be won, it’s a situation to be resolved. Do you want to make a change, or do you want to make a point?

He invited the Loungers to imagine two different scenarios:

Firstly, imagine that you get the perfect outcome – the miracle has occurred, the other person has agreed with everything you said and bowed to your superior wisdom.

What’s the most ludicrously positive outcome that you can think of?

Now take another moment to really focus on what the bare minimum is that you want from this conversation. The smallest possible step that will move the issue onwards.

What’s the minimum that you’re willing to tolerate?

Once you have these two scenarios in mind, you know that what you want lies somewhere between those two.

Rather than imagining a binary success/failure outcome, think of the spectrum of positive outcomes there are. There probably isn’t a single preferred outcome that if you don’t reach, the conversation will have been a failure.

It’s also worth a considerable amount of time to think what the other person wants out of the conversation. What’s their minimum effective step?

What can you do to make them feel that they haven’t ‘lost’, or been ‘defeated’ at the end of the conversation?

Preparing for the conversation

Let’s start at the very basics, just to check in with our feelings.

Remember that you’re talking to another human being. There are circumstances, values and past experiences that are influencing their thoughts. You may not be aware of the wider context that leads them to behave in the way that they do.

You don’t have to like or respect the other person, but ultimately, the problem is best solved by both of you. Then it has a better chance of long lasting change.

Remember also that the other person might not be prepared to change, and you cannot insist on it. You have to work with what you’ve got.

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Very often, quotes like these can come across as vapid clichés.

But Viktor Frankl is a remarkable psychiatrist who survived four separate concentration camps. His first wife died in Bergen Belsen, his father in Theresienstadt, his mother and brother in Auschwitz – so this quote is not a well-meaning platitude, it’s borne out of harsh experience.

So let’s look at what you can do to prepare.

Check your head

Get yourself mentally in the zone with this simple checklist. You might not be able to tick them all off, but the more flexible you can be, the better chance you have of not triggering the System 1 thinking where the other person feels the need to defend themselves.

How are you feeling?

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What are your intentions?

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Are you prepared to be flexible?

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And perhaps most importantly, remember that HOW you say things is just as important as WHAT you say. These can be the little nudges that keep System 1 responses at bay.

Conversational tips

It’s time to talk rapport. It’s one of the most important tools in your possession.

Chris was keen to stress that this doesn’t mean that you have to like or respect the other person, but building rapport in some way gives your arguments and statements extra weight.

  • Try to make the space you’re in as conducive to relaxation as possible.
  • Don’t sit facing them, sit at adjacent sides of a table if possible.
  • As early on in the conversation as you can, find something that you have in common.
  • Avoid interruptions as much as you can – if you’re going to get coffee, get it at the start.
  • Remember to look at them, nod when they make a point, smile if you get an appropriate chance.

Listen. Really, actively, listen.

Listen Up

There are effectively four levels of listening in normal life (six if you include ‘not actually listening’ and ‘listening to let the other person get something off their chest’).

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The enemy of good listening is interrupting.

Interrupting diverts the flow, gets people obsessed by detail rather than the big picture, and triggers System 1 responses.

In Nancy Kline’s book Time To Think she suggests a conflict-resolution exercise called ‘Timed Talks’.

  • Set a timer for 3 minutes. Taking it in turns, each person is allowed to talk – completely uninterrupted – for three minutes. When the timer goes off, no matter where they are in their sentence, they stop.
  • Repeat – even if one of you has run out of things to say – until both people feel that they’ve said all that they want to.

There’s more to the exercise than that, but the essence is the structured off-loading. We all want to feel that we’ve been listened to.

But three minutes is not long enough to get on a soapbox, it’s not so long that the person you’re talking to has forgotten the point they were going to respond to, but once you’ve got the initial rush of words out of the way, 3 minutes allows deeper thought and more honest responses.

This, if used with the methods to build rapport above, can make the person you’re talking to feel more open.

They can’t pretend they haven’t been listened to.

Stick to the point

It’s easy for conversations to drift or divert, particularly in a challenging conversation where System 1 thinking is always just around the corner.

Chris presented a method of structuring a challenging conversation that Trevor had shared with him. It’s a 5 part structure, with the lovely acronym of POINT.

Stick to the POINT and you’ll get better outcomes. This is the one opportunity where you can make a change AND you can make a point!

Of course, you might not be in charge of the structure of the conversation, but you can nudge it on its way.

You may not have control, but you do have influence.

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This was dealt with earlier. Just one thing to add – remember to collect as much relevant information as you can. Facts and figures can give your argument objectivity, which brings us on to…


Be objective. Begin by describing.

Describe the situation using facts and observations, not opinions. Describe the possible consequences. Describe your concerns, without getting personal.

Be clear about your intentions and share the goal that you have in mind.


Make sure the other person feels involved. Invite them to share their perspective and ideas and be prepared to do a lot of listening.

Look for connections between their concerns and your issue. Ask if they see a connection between your stated observations of their behaviour and the impact you’ve described.

A non-confrontational way to do this is by phrases like ‘I’m wondering…’ or ‘I’m sensing…’. For example, ‘I’m wondering if this is related to the issue we talked about last month’.

‘So that…’ is an incredibly powerful way to put things into perspective, as mentioned in past Lockdown Lounges. Try to find the ‘so that…’ that will increase the buy-in from the other person. ‘I’m hoping that we can change this behaviour so that…’. ‘I’m asking for this, so that…’

Ask the other person what they think the options are.


Next steps.

Agree what you’re each going to do, and by when. Find harmony in a way of measuring or recognising how things are getting better.

Schedule a follow-up conversation.


Thank the other person.

Thank them in a way that’s meaningful.

Thank them for their support, or for their listening, or for their time. Find a last way to connect and build that rapport.

Time to talk

Having got to the P.O.I.N.T., it was time to get to the point. The point of the Lounge.

The conversations. The chance to share. The opportunity to connect. The reaching out of Loungers who might have nothing else in common but the desire to relate.

Chris brought out the main course, presented as a set of amuse-bouches, a stimulating smörgåsbord, a platter of captivating canapés.

Strolling with these snacks to the breakout rooms, the Loungers prepared to digest the tasty offerings that had been tantalisingly dangled.

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Soft but prepared

One Lounger came out with this phrase that seemed to perfectly encapsulate the approach to challenging conversations…

“You want to go in soft but prepared…”

Although the conversation wandered as much as it ever did, once again, the same sort of themes resonated in all the break out rooms.

Running the conversations in our head isn’t always useful.

“I always predict what the other person will say and that gets in the way of my reaction to what they’ve actually said – I’ve already written the script.”

“Listening without planning my responses lets them know that I’ve heard what they have to say.”

“I try to protect the other person from what I think they’re feeling. Protecting their fragility robs them of the right to have a reaction.”

Reflect on the other person’s point of view.

“Be authentic that you’re dreading the conversation. Use ‘I’ to show how you’re feeling”

“Often both of us actually want the same thing – we both want a more positive outcome.”

“This person is not my enemy.”

And most tellingly,

“Build a bridge for them to come across.”

Parting thoughts

Chris had one final digestif, a little taster to take away.

But before that, he reminded the Loungers that these skills of being prepared, actively listening, zooming out and structuring a conversation are like muscles that can be developed by practice – and not just in challenging conversations.

So the challenge was to find a way to practise each of these models in some small way, in as many different conversations as possible.

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Final farewells

And with that, the Lockdown Lounge closed its doors for the final time. Fond farewells were said…

“Just a big thank you for the sharing in my group. I really appreciate the depth of reflection. Thank you.”

“I’m going to remember that it is viable to engender a conversation that is measured and constructive though it may be long overdue and full of strong emotions”

“Dealing with trigger, self-healing and soothing is an important step to explore. Thank you to everyone involved in these insightful sessions.”

“Today was really helpful, the focus and topic-based nature of the session gave me time to unpack something specific. Very well led”

“Thanks so much , it was really helpful – just wish it was longer!”

The Lounge might be closing but only for two weeks as the Guildhall Coaching Associates redecorated the pad, cleaned off the tables and redesigned the menus to become…

The Launch Pad!

More of which to come…

(and if you enjoy my writing, why not buy me a coffee at Ko-fi.com/chrisbrannick? It’s not expected or demanded, but I’d be really touched. I live on appreciation and coffee… in that order)

The Launch Pad is run fortnightly by the Guildhall Coaching Faculty. To book a place at The Launch Pad meet up on Zoom on either 9 September, 7 October, 4 November or 2 December 16:00 to 17:30 UK time, send an email to: coachingandmentoring@gsmd.ac.uk headed ‘The Launch Pad’.

Please note that numbers will be limited.

The exercises offered to our readers at home are sometimes slightly modified in the light of feedback from our Loungers.

Photo by Victoria Borodinova from Pexels

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