How do I have difficult conversations with my boss?

How do I have difficult conversations with my boss?

By Bryan Chuang

As an employee myself, I find it very challenging to hold difficult conversations with my boss. Given a choice, I’ll shun away from these conversations as I believe it’ll be emotionally taxing on both parties, and I don’t wish to sour the harmonious relationship that I have with my superior. However, over the years, I’ve come to realise that when faced with particular issues or situations, having difficult conversations is inevitable. In fact, I’m not alone in this. Peers around me also find it arduous to carry out difficult conversations with their bosses, and maybe you might feel the same way.

I’ve discovered a few practical handles, which I found useful for holding difficult conversations with my boss, and I would like to leverage on this opportunity to share them with you. 

Gain positivity

As we label the conversation as ‘difficult’, we’re more likely to experience negative emotions such as fear and nervousness. We’ll enter into the conversation with these emotions, which will definitely affect its quality. Hence, see the conversation as an opportunity to voice our concerns, explore next steps, and even develop ourselves personally and professionally.      

Get objectives straight

As we approach our boss for a difficult conversation, we need to establish clarity in terms of what we are looking to achieve out of that particular conversation. As Stephen Covey says, “Begin with the end in mind,” only when we have clear objectives, will we then be able to steer it towards the desired direction and outcome.  

Get real

The truth will set us free. Be 100% truthful and authentic in the course of the entire conversation. This may well be the most challenging handle. We may be afraid that by being authentic, it will backfire. Our boss might turn their back on us as we speak what is true. Yes, it does take us a lot of courage to be real and authentic. But this is what having difficult conversations is all about. We need to present the truthful side to our boss, so that it’ll be a productive conversation that truly addresses the issue that we’re raising. Please don’t get me wrong, I’m not suggesting that we let our tongue loose to everything that comes to our mind. We need to be truthful and tactful at the same time.        

Give respect

Respect begets respect. As we show respect towards our bosses throughout the entire conversation, it shows that we value them as individuals and we allow their voice and opinion to co-exist with ours. Actively listen to your boss and try to see from his or her perspective. This will definitely contribute to preserving your boss-employee relationship. 


I hope that the above handles would help you gain the competence, and in turn, the confidence and commitment to hold difficult conversations with your boss. Yes, having difficult conversations with our bosses is challenging. But if we’re able to handle and manage the entire conversation well, it’ll greatly benefit us, our boss and our work team - what matters most will be addressed, ways to advance will be identified, professional relationships will be deepened and breakthrough performance will be achieved.

Do you have other tips to share when it comes to having difficult conversations with your boss? Please comment or write in to me at