Why difficult conversations are part of SME leadership

“I can’t wait to have that awkward conversation today!” A sentence none of us have uttered!

But SME owners and managers need to have difficult conversations. Whether you need to address underperformance with a team member or deliver disappointing news to a client, difficult conversations are part and parcel of running a business. With the right approach, these conversations don’t have to be daunting and can end up being surprisingly productive. Here’s the Hour Hands guide to navigating difficult conversations.

Start with the right mindset: aim for progress, not “winning”

Before you dive in, check how you’re approaching the conversation. Remember that difficult conversations aren’t about “winning” or proving a point. They’re about solving problems, maintaining relationships, and moving forward. Before you even start a conversation, take a moment to clarify to yourself what you want to achieve. Then, when you’re clear on your goal, you can reframe the conversation in your head away from a confrontation towards being a productive discussion.

Choose the right time for the conversation, and the right location

Our two pieces of advice are don’t ambush people and don’t tell them on a Friday that you need to talk.

If you need to discuss a sensitive issue with a team member, schedule a private meeting rather than catching them off guard in the corridor. For clients, suggest a call or meeting rather than firing off a tense email. Set the meeting as soon as possible – and definitely don’t leave a weekend between the notification and the actual meeting otherwise fear and resentment can build. Also, ensure that the meeting is long enough so all parties have enough time to have a proper discussion without rushing.

Be direct but kind: how to say the hard thing clearly

Due to nerves or not wanting to upset the other party, it’s so easy to beat around the bush so much that the message gets lost, or to be so blunt that the relationship is damaged. The trick is to be clear and compassionate at the same time.

Our advice is to plan your opening sentence in advance. Instead of saying, “You’ve been making loads of mistakes lately,” try “I’ve noticed a few errors in the recent reports, and I’d like to understand what’s happening.” This addresses the issue directly whilst showing you care about finding a solution.

Apply the same principle to client talks. If their project will be delayed, don’t hide behind jargon or excuses. Consider saying “I need to be upfront with you about a delay. Here’s what’s happened, here’s our new timeline.” Clients like clarity and ownership.

Listen more than you talk

This is difficult but these are conversations not monologues. Once you’ve stated your concern, pause and actually listen to the response. You might discover there are circumstances you weren’t aware of. Perhaps your team member is dealing with a family crisis, or your client has additional information that can help you.

When someone’s explaining their perspective, resist the urge to interrupt or mentally rehearse your response instead, give them your full attention. Sometimes people just need to feel heard.

Focus on solutions

After sharing your individual perspectives, shift the conversation towards solutions. Ask questions that encourage conversation. We like phrases such as “How can we prevent this in future?” or “What support do you need from me to make this work better?”

For example, if a team member has been consistently late to meetings, a lecture about punctuality is likely to antagonise rather than solve the problem. Instead, explore whether there’s a personal issue such as childcare, whether transport is the problem or whether there’s a deeper issue that needs resolving. Where you can, you should work together to find a solution. This is the first step – we appreciate that further discussions may be needed.

Agree next steps: actions, deadlines, and accountability

Once you’ve agreed on a plan, ensure that you clarify specific, timebound next steps and state these in writing. If you’ve personally got actions, make sure you do them and put this in writing too. If you’ve agreed to check in again in two weeks time, put the meeting in your diary straightaway. Following up shows you take both the issue and the person seriously.

Be a successful leader

Tim Ferriss, an American entrepreneur, podcaster, and best known for his self-help books says that success is often measured by how many uncomfortable conversations we’re willing to have. It’s a powerful reminder that facing difficult conversations is more important than avoiding them – in life and in business!

Backing this up is the fact that the most successful business owners we’ve known aren’t the ones who avoid difficult conversations. They’re the ones who’ve learned to handle them well. Each conversation is a chance to strengthen relationships, clarify expectations, and demonstrate leadership.

Remember, being kind doesn’t mean being soft and being direct doesn’t mean being harsh. With practice, you’ll find difficult conversations become less stressful and more productive and your team and clients will respect you more for addressing issues head-on rather than letting them fester.

So take a deep breath and prepare what you need to say. Feeling confident enough to hold a difficult conversation is a great start and you’ll soon have another leadership skill in your business toolkit. And we promise, it gets easier with practice.