Why ‘winging it’ doesn’t work. Negotiating difficult conversations

What is a high-stake conversation?

In business terms, this is a conversation that has the potential for significant gains or losses.

Some common high-stake conversations in the workplace are: recruiting a senior manager, going for a job interview, performance discussions, giving negative feedback or negotiating a sale, changing the price or terms of a deal.

My own business has been built around helping organisations and individuals to navigate and master these situations, which I have ‘coined’ Bold Conversations™.

If I had a dollar for every time I’ve heard…

I’ve done this before, I’ll just wing it.

Preparing for a high-stake conversation is one of the most beneficial time investments you can make.

Even with prior experience with the same high-stake conversation, it’s likely the stakeholders were different or something about this current situation is not the same.

You will have a far greater chance of a better outcome if you invest in the strategy of the conversation.

Do you think a marathon runner’s plan is to simply sprint an entire race from the starting gun?

Unlikely. They will have numerous considerations along the way. They will consider, who and where are my opponents at each stage? Where will I pick up my pace and when can I afford to taper it? How will I know when my energy is dropping? When will I hydrate and how much?

Many people enter a high-stake conversation like a sprint. They aim to get all their best material or selling points ‘vomited’ all over the audience the first chance they have. This approach never wins.

Here are 4 questions to consider when strategising your Bold Conversation.

1. What is the outcome you’re seeking?

In the shortest word-count possible, what exactly is your objective?

If you find you can’t keep it short, it’s likely that there is more than one objective to be achieved, which will then require its’ own separate strategy.


“What’s In It For Me?” By nature, we’re all self-centred, so expect that your audience will be asking themselves why they should care about your objective and that they will be looking for what’s in it for them.

The WIIFM should always be taken into consideration as this is what allows you to tailor your pitch to your audience. After all, this is how we base our decisions – “how will this affect me personally?”

So ensure you can articulate how they will be impacted (negatively or positively) by your outcome.

3. What are all the possible reasons you’ll be rejected?

Yes, all of them. Brainstorm your list as long as it may be, no matter how small the reason may be. The longer the list, the better prepared you’ll be.

4. What is your solution to each of those reasons?

Do you remember those childhood books “Choose your own adventure?” where you were able to participate in the story by making choices, such as “turn left to go through the forest or turn right to go through the wetlands”? You then had to alter your course, depending on how your choice panned out.

Approach each objection the same way – if they object to X, we can overcome it with Y. If they don’t like the cost required, we can reduce some costs from XZY project.

Keeping in mind that you ensure every solution addresses the answers to point 2 above.

Being unprepared for a high-stake conversation is never ideal. If you want to ensure the best possible chance of achieving your objective, then strategising your high-stake matter is essential.