Having hard conversations in business: How to evolve your business communication confidently

hard business conversations

Have you ever been faced with having a hard conversation in business, but floundered? Have you thought, I knew I should have said something, but didn’t?  I certainly have. And so have lots of the people I work with.

Struggling with a particular challenge in the professional arena, they’ve sought counsel from me about what to say and how to say it. This conundrum has made me realise that in business as in life, there are times when hard conversations are necessary, but most of us don’t know how to navigate through them. 

Hard conversations in business present in many forms. 

Dealing with a difficult client.

Negotiating a contract.

Chasing up overdue payments.

Bringing a project back on track.

Missing a deadline.

Addressing performance with an employee or boss.

None of these situations is easy. At best, we might fumble through. At worst, we may totally botch the conversation and find the situation worse than before we opened our mouths.

Why are hard conversations in business so….hard?

It is human nature to avoid the uncomfortable. Most of us simply don’t want to have a hard conversation, particularly if we can simply look away or avoid it. Humans will move away from pain rather than towards pleasure, and that’s exactly what happens with the kind of conversation I’m describing.

We think – and perhaps hope – the situation about which a hard conversation is required, will somehow – miraculously – disappear, absenting us of responsibility and a need to address the issue. We think and hope: If only it would just go away, everything will be fine

Although I have no scientific evidence to prove it, I think the reason most of us lack confidence about hard conversations in business is we simply have no idea about how to have them. We don’t know what to say or how to say it. We feel out of our depth. Sometimes we’re even paralysed into doing absolutely nothing. 

Let’s face it, few of us know how to have conversations like this in life, let alone in business. It’s any wonder we want to run and hide or just pretend there’s nothing happening here

But this approach will only take you so far. You may experience a temporary reprieve, and even a little relief, but unless the crux of the issue is addressed, don’t expect it to last long.

What happens when we can’t manage hard conversations in business?

The problem with not having a way (or several ways) for handling hard conversations in business is it can leave us feeling frustrated, angry, and resentful. We might feel disempowered, annoyed and distrustful too. 

It may cause us to over-react and make poor decisions.

We may say and do things we later regret.

Careers, projects, and businesses can be put at risk.

We may tolerate unacceptable behaviours in others and ourselves. 

There may be serious financial repercussions.

We might contribute to gossip and unpleasantness. 

Hardly the basis for any healthy relationship, this poisons communication in business as much as it does in any important relationship. Quite simply, an inability to have hard conversations is toxic and disempowering – both for business and for us personally. It’s also the complete opposite of conscious communication.

As I’ve sought to evolve my own awareness around skilling up and having hard conversations in business, I’ve been able to help others. Let me share what I’ve learned.

It takes courage to have hard conversations in business

Our desire to shy away from hard conversations is closely linked to fear. I can relate to this totally. 

What if that person doesn’t like you after you’ve shared your concerns? 

What if they no longer want to do business with you? 

What if your employee leaves or you get sacked?

All this could happen – and more. The truth is, there are many ‘what ifs’ that could stop us from having hard conversations, but few of them carry any real merit. 

There’s no doubt it takes courage to have hard conversations in business. This means we must draw from a deeper internal reservoir of strength if we’re to enjoy more conscious communication in business – and the enriching outcomes that arise from it. Where fear limits us, having the courage to ‘go there’ in a business conversation has the power to transform us and the outcome. We build our conscious communication muscle and outcomes we imagined impossible come to fruition. 

Hard conversations require honesty too

A coach in helping people achieve emotional sobriety in life, Roslyn Saunders advises that it takes honesty if we’re to enjoy healthier relationships. This applies to the business arena as much as it does to any other area of life. I’m not sure which comes first – honesty or courage – however, both are essential.

Honesty is illuminating. It shines a bright light of awareness on what’s really going on. Where we’ve previously overlooked behaviours or decisions that niggled at us, once we have view things with honesty and awareness, we’re challenged to speak up if that’s the best way to address it.

The relationship between courage and honesty is closely interwoven with how we value ourselves. When we’re no longer prepared to overlook inappropriate behaviour from a colleague, challenge a way of doing things that doesn’t serve us in business, or approach a client or employee who isn’t respecting us, it means we’ve started to place a meaningful value on ourselves. In fact, this appreciation of our own value provides the foundation on which we can manage hard conversations and evolve our communication to be more conscious.

When you can, prepare well

If there’s a hard conversation to be had, a little preparation goes a long way. Whether I’m doing it for myself, or supporting a client, taking the time to prepare what to say and how to say it, is a confidence booster. 

A go-to tactic I use is to write things down. Not just because I enjoy writing, but also because it means I can stick to the most important messages I want to communicate. There’s also less chance I’ll be derailed into territory that’s not relevant to the issue at hand.

While it may not completely alleviate the nerves, it’s comforting to know there’s a plan in place. And even if things don’t go exactly as you’d envisaged, just having thought through what you want to say – or not – is an empowering exercise. It’s also a pathway to more conscious communication.

The best person to do this kind of preparation with is someone you trust. They should also have a level of emotional intelligence that affords them insights you might overlook because of your proximity to the issue at hand. For conversations both big and small, I ‘workshop’ with a trusted advisor – someone who can remove the emotional overload, finesse the words, and even help me practise speaking them. 

Hard conversations in business will always come up so finding that person from whom you can seek wise counsel on communication is every bit as important as any other business advisor.

If you can’t prepare, say and do nothing (or very little) until you can

Most of us have been caught off guard or felt ambushed by a challenging situation in business or life. Maybe you’ve even faced a few of these situations. If drawn into a difficult conversations in business unexpectedly (that is, you’ve had no time to prepare), it’s easy to shut down or talk too much. Because we’re socialised to ‘do the right thing’, we might find ourselves drawn into reacting when a more considered response delivered at a later time would serve us better. 

In these situations, saying and doing nothing or very little might be the most ideal approach – at least until you have time to do your thinking. Cicero said Silence is one of the greatest arts of communication and he was right. If we can pause before speaking, allowing space (an essential element of conscious communication), we may very well find the right response arises in us with very little effort at all.

Establish clear boundaries for communication in business

Early on in my freelancing days, I found myself metaphorically bouncing back and forward between client demands and my own needs. With a lack of alignment evident between the two and unsustainable working relationships in place, I realised something needed to change.

With conscious thought, I developed guidelines for working together. Quite distinct to the terms and conditions of our transaction, these guidelines set clear parameters for how we would relate to – and communicate – with one another while working together. These guidelines don’t cover every possibility, but they do make it clear the success of our relationship, and therefore our communication in business, is based on some fundamental principles.

Among these are a directness and respect in communication. Roslyn, the emotional sobriety coach I mentioned earlier articulates it nicely: Mean what you say, say what you mean, but don’t be mean when you say it. What this means is that we can communicate in ways which are respectful to all parties, regardless of the circumstances. We can put forward our position without making the other party ‘wrong’ and while also holding our own posture.

Hard conversations are an opportunity to grow our communication quotient

As our communication evolves to become more conscious, I’d like to see us reframe what hard conversations in business mean to us. Although we might want to make the issue about the other person, a more conscious approach calls us to make it about our own evolution. Easier said than done, but entirely possible.

Really, hard conversations in business are an opportunity to grow our communication skills and ourselves. Let’s learn to embrace it and communicate consciously, even if our voice is shaking.

4 Comments
  • Great wisdom – thanks for the refreshing reminders. In particular , I appreciate once again the great advice of ‘being well prepared’ and even giving those hard conversations a test run with a trusted friend. Sure beats the monologues I have had in the past with myself as I say all of what I wished I had said if only I had the courage to say it!!! Thanks for encouragement to develop this skill further. And I really appreciate the words of Roslyn Saunders to ‘say what you mean and mean what you say but don’t be mean when you say it!’

  • Very worthy advice – so many skirt around issues and as a result resentment builds. As you say, and as you have worked out, it is best to set parameters in the beginning so everyone knows where they stand. Also once set, keep the parameters.

  • This article is so well written. I would like to be a person who can have hard conversations well, as I believe they can be a road to deeper satisfaction in business and personal relationships. Thank you.

    • Hi Karin – Thank you so much for your comments. I feel that being able to have hard conversations is a continuous work in progress. Just like going to the gym and maintaining our fitness, I find I need to keep building strength into my ‘hard conversation’ muscle.

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