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Running a business: how to handle difficult conversations

4-minute read

Business owner and employee having difficult work conversation
Conor Shilling

Conor Shilling

17 April 2023

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Conflict and difficult conversations – it can be easy to put them off or avoid them completely. However, there are conversations you’ll need to have if you want your business to grow and run smoothly.

Read more for our top tips on having difficult conversations with employees, customers, and suppliers.

What are difficult conversations?

A difficult conversation is often ambiguous and could have an uncertain outcome. This may make one or both parties feel nervous or anxious about it.

For example, you may need to share some bad news, poor results, or a challenging truth.

Navigating these conversations may be complex and they could lead to conflict. As a result, they’re the sort of interactions many people naturally want to avoid, and spend a lot of time worrying about beforehand.

These types of conversations will rarely seem easy. But if you take the right approach and are well-prepared, you can give yourself the best opportunity to manage them smoothly and hopefully fear them less in the future.

Examples of difficult conversations in business

Most of the difficult conversations small business owners need to have will fall into one of three categories:

  • employee conversations
  • customer conversations
  • supplier conversations

Below are some examples of the challenges you might come up against on a regular basis.

Examples of difficult conversations with employees

  • discussing poor performance or missed targets with an employee
  • telling an employee that their role or hours are changing
  • communicating a complaint or grievance made against another employee
  • telling an employee that they’re being made redundant
  • rejecting a request for a higher salary or more holiday

Examples of difficult conversations with customers

  • dealing with a complaint related to poor performance or products
  • telling a customer that their prices are increasing
  • explaining to a client that a project is behind schedule or over budget
  • dealing with a customer who is consistently late in paying their invoices
  • a long-term customer telling you that they won’t be working with you anymore

Read more: 5 ways to tell your customers about a price increase

Examples of difficult conversations with suppliers

  • ending a relationship with a long-term supplier
  • explaining to a supplier that you’re having financial problems
  • telling a supplier that their service or product isn’t up to scratch
  • asking suppliers to reduce their prices or match a deal you’ve found elsewhere
  • explaining that you need products delivered more quickly

Read more: Negotiation skills – a guide for businesses

How to have difficult conversations when running a business

From being flexible to changing your mindset, here are five top tips on how to manage difficult conversations at work.

1. Be honest, clear, and concise

When you’re going into a conversation that has the potential for conflict or the outcome is unclear, it can be easy to lose focus.

By being clear and concise, you can make sure that the other party has all the information they need to respond.

Meanwhile, being honest and upfront can help you to stick to the point and not go off on different tangents.

If the subject you’re talking about is uncomfortable, it’s highly likely the other party will appreciate your honesty rather than being unclear and sugarcoating bad news.

That being said, although it’s important not to be emotional, you’ll need to think about how you can deliver unexpected or bad news in a sensitive way.

2. Be flexible and open-minded

When approaching difficult work conversations, you may have a desired outcome in mind.

By putting pressure on yourself you achieve this outcome, you could feel more stressed and anxious in the lead up to the meeting.

If you’re flexible and open-minded with your expectations, it’s a lot easier to view the outcome of the conversation as a success. What’s more, taking this approach could lead you to a better outcome than the one you’d planned for.

3. Think about the other perspective

Although your own viewpoint and desired outcome of the conversation will be front of mind, considering the other person’s perspective can help to make these conversations more productive.

Being empathetic and understanding how the other person views the problem can help you to choose what you say carefully and decide on your tone.

If you’re not sure how the other person views the situation, don’t hesitate to ask them during the conversation. Not only will this improve your understanding, but it will also show that you care about how it makes them feel. This can improve the chances of reaching a positive outcome that works for both parties.

4. Be prepared and ready to take action

Ahead of a difficult conversation, it can be easy to spend a lot of time worrying about how it might go. Instead, this time would be better spent preparing for the meeting.

By preparing thoroughly, you can reduce your stress levels and put your worries to productive use. As well as thinking about the other person’s perspective, you can prepare by listing desired outcomes and actions, plus noting down all the key information you need to share.

Although it can be tempting to write a script, this isn’t always a good idea as if the conversation goes in another direction you could be left feeling unprepared. As an alternative, bullet points can act as useful prompts without making things too rigid.

At the end of the conversation, make sure you’re clear on any outcomes and actions and be ready to take the next steps.

5. Change the way you frame difficult conversations

By framing a conversation on one of the above issues as a ‘difficult conversation’, you increase the chances of it causing stress or anxiety.

If you consider these challenging conversations as opportunities to make progress, help someone develop, or come up with alternative solutions, then you can approach them more positively.

Of course there will be some conversations - such as letting an employee go - that will be very difficult to frame positively. In this instance, you can frame the conversation as news that needs to be shared so that both sides can move on to more positive outcomes in the future.

Read more: Tips for creating the right environment for supportive conversations

What are your tips for managing difficult work conversations? Let us know in the comments below.

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Conor Shilling

Written by

Conor Shilling

Conor Shilling is a professional writer with over 10 years’ experience across the property, small business, and insurance sectors. A trained journalist, Conor’s previous experience includes writing for several leading online property trade publications. Conor has worked at Simply Business as a Copywriter for three years, specialising in the buy-to-let market, landlords, and small business finance.

We create this content for general information purposes and it should not be taken as advice. Always take professional advice. Read our full disclaimer

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