The Art of Having Difficult Conversations at Work

This informal CPD article, ‘The Art of Having Difficult Conversations at Work’, was provided by Joe Husbands of Cornerstone Resources, who provide a bespoke HR service built for small businesses, charities and non-profits across the UK.

Research highlights that many managers find the hardest part of leadership is not the targets or the strategy, but the conversations they would rather avoid (1). Whether it is giving feedback on poor performance, addressing unhelpful behaviour, or tackling sensitive personal issues, these conversations can feel uncomfortable. As a result, they are often delayed, softened, or skipped altogether.

The problem is that avoidance rarely makes an issue disappear. In fact, it usually makes things worse. Minor concerns left unspoken can grow into bigger performance problems, strained relationships, or even formal HR processes. Learning how to approach these conversations with confidence is not just a leadership skill, it is a form of professional development that benefits both individuals and organisations.

Why We Avoid Difficult Conversations

There are many reasons managers hold back. Some worry about damaging relationships, others fear conflict, and many simply do not feel equipped with the right words or techniques. It is understandable because most of us are not formally taught how to navigate these situations.

But silence has consequences. A lack of honest dialogue can reduce trust within a team, create resentment among colleagues, and limit opportunities for growth. When employees do not receive constructive feedback, they cannot improve. When poor behaviours are ignored, they often spread. By contrast, timely and respectful conversations can strengthen relationships and support performance.

Shifting the Mindset

One of the most valuable changes managers can make is to reframe how they see difficult conversations. Rather than viewing them as confrontations, they can be seen as opportunities to support, clarify, and move forward.

For example, telling someone their performance is falling short is not about criticism. It is about giving them the chance to succeed. Addressing a behaviour that disrupts the team is not about blame, but about protecting the environment everyone works in. When managers shift their mindset in this way, the conversation feels less like a battle and more like an act of leadership.

Practical Steps to Make Conversations Easier

Preparation makes a big difference. Taking time to think about what needs to be said, why it matters, and the outcome you hope for can bring structure to the discussion. Being clear on the facts, and separating them from assumptions, also helps keep the focus on behaviour and impact rather than personal judgement.

During the conversation itself, listening is as important as speaking. Employees are far more likely to engage positively if they feel heard and respected. Asking open questions, checking understanding, and acknowledging the other person’s perspective creates the conditions for a constructive outcome.

It is also helpful to be specific. Vague statements such as “your attitude needs to improve” are confusing and unhelpful. Pointing to clear examples, for instance “when deadlines are missed it affects the rest of the team,” provides clarity and makes it easier to agree on what needs to change.

Linking to CPD and Professional Growth

Difficult conversations are not just a test of character. They are a capability that can be developed through Continuing Professional Development (CPD). Managers who actively seek out opportunities to practise, reflect, and improve in this area often notice benefits beyond a single conversation. They build stronger communication skills, greater self-awareness, and more confidence in their overall leadership style.

From an HR perspective, the ability to have these conversations early also prevents escalation. What might have become a grievance, a disciplinary process, or a team breakdown can often be resolved with a timely dialogue. In this sense, building confidence in handling difficult conversations is both a leadership strength and a safeguard for the organisation.

A Practical Tip

One way to accelerate development in this area is to learn alongside peers. Training that brings together managers facing similar challenges allows people to share experiences, explore different approaches, and practise techniques in a safe environment. This peer learning not only builds confidence but also provides practical ideas that can be applied immediately in the workplace.

Conclusion

Avoiding difficult conversations may feel easier in the short term, but it almost always creates bigger challenges in the long run. Managers who invest in developing this skill through CPD are better equipped to support their teams, strengthen trust, and prevent issues from escalating into formal HR matters.

With the right mindset, preparation, and practice, difficult conversations can become less daunting and more productive. They are not obstacles to leadership but opportunities to grow, both for the manager and for the people they lead.

We hope this article was helpful. For more information from Cornerstone Resources, please visit their CPD Member Directory page. Alternatively, you can go to the CPD Industry Hubs for more articles, courses and events relevant to your Continuing Professional Development requirements.

 

REFERENCES

  1. https://www.atana.com/blog/post/why-managers-avoid-difficult-conversations