Difficult Conversations

We try to take the same medicine we prescribe our companies.

For example, we try to proactively and healthily manage conflict as it is issue we bang on about a lot. We are also committed to transparency and well, we have had to have a few difficult conversations lately at Tribe, which has prompted me to write this.

I won’t go into details out of respect for the other parties, but they were mostly focussed on trying to diagnose whether all parties were aligned and on the same page, whether that required us to apologise, change behaviour manage expectations or ask others some difficult questions.

What we got right was these difficult conversations were initiated by us, and quickly, so that the misunderstanding could be rectified asap, before things got out of hand or escalated or false assumptions were made. It required us to have respect for the other party and the views of the other party — which manifested as trying (not always successfully) to take the emotional reactivity out of it and to resist going to a place that assumes the other party is trying to do the wrong thing, is in the wrong, or has the wrong view. Often when we get outraged by some conflict, it’s because we make assumption about the other persons motives, aren’t able to set that aside long enough to create curiosity around why they took a conflicting view or action.

What we got wrong was not taking emotion completely out of the conflict management (and we owned and apologised for it), and then ironically taking a too impersonal approach (pendulum swinging too far the other way), and making incorrect assumptions about expectations.

The result was our recent difficult conversations got everyone to a position of understanding, but not without a healthy dose of empathy, mental and emotional knocks, dents to the ego — and that was only on our side of the equation. I hope, ultimately it will forge a closer bond with all parties. Time will tell. The alternative though, is we don’t have those conversations and misunderstandings grow into resentment, and worst case assumptions become reality. But it forced us to meditate on some practical strategies that might help others who are going through something similar.

Climate change is one of these issues we do not seem to be able to have a difficult conversation about

Consequences of Avoiding Difficult Conversations 

I lament how the inability to have difficult conversations negatively impacts our political discourse, our economic discourse, our scientific discourse and how this impacts usually, the most vulnerable in our community. Politicians often avoid entering into difficult conversations about their policy and approach (and are even less enthusiastic when its being interrogated retrospectively), they duck and weave and do what their pundits have told them will be the least likely to cause public or adversarial criticism.

The economic discourse similarly is not willing to have difficult conversations about whether our neoclassical economic approach is still fit for purpose, and perhaps what might be a more appropriate framework for policy in this era where unlimited productivity is likely not compatible with our ecological constraints (for example, climate change).

Our scientific discourse, which has arguably been the most committed to remaining a contest of ideas, has lost credibility in the eyes of the public because our inability to have difficult conversations around issues we have now intertwined into identity politics– for example a difficult discussion about the truthful learnings about what we as a society got right and wrong in the pandemic approach.

Now to be sure, not all of this is because we struggle to have difficult conversations, some of this is because issues get hijacked by those seeking power, influence and attention and become weaponised and our media and the algorithms rails it runs on, are set to outrage.

But collectively we are genuinely no longer practiced at identifying and then deftly stepping over these speed bumps designed to prevent us from having a conversation of ideas and facts, and do so healthily even when it’s difficult. At this point you are probably saying “well, duh”. And of course this is obvious, but what is not obvious is how we remediate this because if we don’t, we will get the world we deserve.

Whilst the words may be slightly different, we find these 15 resonate with most directors who have sat on boards.
Was this a difficult conversation — you betcha bippy it was. Was it healthier approach than historic conflict resolution strategies, sure. Did it work long term? less clear….

The Power of Difficult Conversations 

My cofounder Don talks a lot in his work with our companies, about how conflict is a natural part of life, and by that statement, thus a natural part of our relationships and business. And we see this in companies we support, all the time. It’s not weird, its normal. Its only dysfunctional if people handle that conflict poorly. But the reality is for people in the collective to handle conflict well, it requires buy in to do so, from both parties. And that’s easier said than done. But for all the reasons above, we as a society are no longer practiced at healthy conflict which requires courage for difficult conversations. The courage to have difficult conversations is one of the things I’ve been trying to help my niblings get better at, because I think it’s one of those skills that will set them up for adulthood far better than me fast tracking them an internship at PWC 😊.

Difficult conversations can be powerful, whether it’s to put the past behind you, to apologise, to gain better understanding of the other party’s perspective and better navigate a mutually acceptable solution, or to work out where you may not, in fact, be correct and to learn things you may not have known before. Earlier this year my nephew had an extremely difficult conversation with his old boss about how he felt like he let his boss down, and the reasons why he thinks he did. Initially this was to be accountable for his actions that he wasn’t proud of, but that difficult conversation turned into a pivotal moment for him which has changed his career trajectory and his personal life. And he learned something about himself — the power of accountability, how to foment courage, and the positive things that can happen when you are courageous.

This sounds lovely doesn’t it, but also it wouldn’t be balanced without also pointing out how difficult conversations can also lead to pain and suffering — whether it causes hurt in someone else, or it results in the others party exploding into rage, violence or causing your professional, social or familial exclusion and isolation. These are all scenarios I have also experienced from having difficult conversations and why having difficult conversations are not without risk and require courage. And boringly, usually go better when you have a plan that helps all parties take the emotion out of it. Like all things, your ability to do this improves when you practice it more..

Breaking up with someone via a post-it note — the anti-difficult conversation strategy

Why we don’t have difficult conversations 

Personal relationships — we don’t want to disappoint or upset someone we value in our life. But the reality is, if you never confront genuine conflict within that relationship or dynamic, then you don’t truly have an equal relationship with that person. At best, you don’t actually have a relationship borne in trust and respect but merely the perception of one, and at worst it creates the environment for exploitation. And let’s be clear, eventually this dynamic will be exploited.

Personal identity — we want to look like the person who has their shit together who isn’t bothered by others, or we want acceptance by a group and don’t want to be the person who rocks the status quo (the difficult person). We are so committed to this personal brand, we won’t have difficult conversations for fear of being kicked out the cool kids group, seen as difficult or ‘emotional’. This lack of being able to have difficult conversations has led to some pretty screwed up shit in history, and you want to be on the right side when the autopsy is done.

We think we won’t have the answers in the moment — we worry about what will be said in response to our initiation of a difficult conversation, and our ability to think on the spot to answer. But this assumes emotional escalation, and the art to difficult conversations is to avoid or reduce emotional escalation. That buys time to respond and converse thoughtfully, and honestly.

We convince ourselves the status quo is actually fine — mostly we do this to avoid putting ourselves into a position of conflict and to maintain psychological safety. “I can deal with it (rather than have the conversation)”. But the reality is avoiding conflict is historically in every regard — psychologically, emotionally and professionally — a terrible strategy for managing conflict. Eventually it will come out and when it does, it will happen in ways that are unhealthy — like passive aggressiveness, undermining, sabotage and worse — and likely catastrophic. It’s better to rip the bandaid off and do it early, than pull it off slowly, ripping each painful hair by painful hair.

Financial and professional security — sometimes, having a difficult conversation can be the thing that could put your job and your livelihood at risk. And that adds a layer of risk management that certainly needs to be taken into account.

Dont make this face

Why we fail at difficult conversation

We have them while too emotionally charged — Emotion will undo the most stoic of people, it causes us to say and do things we never thought we would. It also triggers in others defense mechanisms which can be explosive, brutal and potentially terminal for the relationship. Now, unless indeed we are a simulation, we can’t turn off the emotion tap, but we can practice ways to tame it sufficiently to ensure we are applying a lens of objectivity.

We don’t think through an approach and how it might be received by the other party — The way I approach difficult conversations with someone who is incredibly emotionally reactive is very different to the way I do it with someone who is an internaliser, a thinker, and data driven. I also try to see how the issue that I’m having the difficult conversation about might be perceived by the other party — why might they have done or behaved in a certain way? I try to think through how I might respond in the event of different scenarios. For example, I assume a scenario where there is no malice behind it and an approach for resolution, I also assume scenarios where there is malice or poor behaviour behind it and an approach for that too. I arm myself with all of them (and how I might respond in each of those scenarios) before I attempt it.

We don’t communicate well enough –when there are information gaps which is what infrequent, inconsistent or poor communication creates — it is human nature to fill that gap with the worst possible option. In the background this causes people to make incorrect assumptions, gives time for emotions to escalate, creates distrust which makes having a difficult conversation impossible.

I try to weave the Princess Bride or Taylor Swift into all business related topics.

How to have the difficult conversation

– Talk to someone else who is not involved and thus more objective, and get their feedback about the situation and your intended response. It could save you looking like a goose, and help calibrate if the conversation is needed, and possibly how to approach it.

– Learn the difference between impulse and reaction. Impulse is the immediate way in which you would respond — the desire to ‘set someone straight’ ‘tell them how you really feel’. This is almost always driven by some inward focussed personal emotional insult — hurt, shame. Reaction is how you choose to respond — done well it is a carefully considered, multi dimensional response where you have thought through the intended and unintended consequences. When done well, this is almost always informed by outward focussed outcome — what do you want to achieve, how do you want to be perceived while achieving it, how can I make the other person feel part of the solution. Learning your impulses and how they can be difference to your actual reactions is an important skill.

– Be very clear about the facts — the best way to take emotion out of a difficult conversation is to clearly articulate the facts first to yourself, then to the other party. There is a reason litigation requires both sides to agree to a set of facts before a trial begins, its so it can operate functionally from the same playing field.

– Take a phased approach. Write down your response first — the time taken to write something can help cool emotions — even send it via an email first to initiate the difficult conversation, to ensure you have said what you need to say with your words chosen carefully. But back it up with a face to face conversation, otherwise its not a difficult conversation, it’s a difficult email. Conversations need to have both parties buy in, especially difficult ones or they don’t work.

– Think through all the scenarios first – both benign and malevolent motives, and all the ways the other party might respond. This is the best way to also think through the intended and unintended consequences — you may not be able to control those consequences, but being mentally prepared for them can help you accept them when or if they inevitably happen.

– Be prepared for and genuinely open to feedback. This really means difficult conversations are predicated on the art of listening. Really listening to the other party. You can’t achieve understanding if you don’t hear the others party’s perspective. You can’t solve the impost without understand their problem. You can’t improve your contribution to the problem when the important feedback is actually for you and your approach.

– Communicate, communicate, communicate. Over communicate. Mastering the art of difficult conversation is neither simple, nor is it easy. But it is a necessary leadership muscle to develop strength in if you want to be successful in the long term. As Brene Brown has eloquently summarised “He or she who is willing to be the most uncomfortable is not only the bravest but rises the fastest.”

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