Masterclass: How to deal with a difficult CEO

24 Jan 2019 By Katherine Graham

Having tricky conversations with senior managers should be in the context of the business's performance, not their personal behaviour

Working with a problematic CEO can be tricky – particularly if you’re the only HR professional in an organisation. Smaller businesses are usually more owner-led, and this can sometimes be even more challenging. When having a hard conversation or raising something you know isn’t going to be well received, use the mnemonic ‘SOS’ to ensure you are prepared.

The first ‘S’ stands for ‘self’. You need to think about yourself first and be honest about what you need – and want – to say, because sometimes there’s a difference between the two. Identifying what you need to say is sometimes the first challenge, and you should do this before starting the conversation.

Be honest about any baggage you might bring to the conversation. Should you have raised this earlier? Have you let it go on too long? You need to have your feet firmly on the ground in these conversations because many senior leaders are incredibly self-confident and articulate. When you start a difficult conversation, you’ve got to have all your bases covered in advance.

The ‘O’ stands for ‘other’ – so think about who you’re speaking to. The key is helping them hear your message and understanding their motivation. What matters to them may not be the same thing that matters to you. 

A key motivator for leaders is often their effectiveness. Rather than debating with them, explain it in terms of efficiency and effectiveness. You’re not blaming the behaviour or the person – you’re positioning it as ineffective work. In my experience, their ears really prick up if they think they will learn something that will make them more effective, but they will shut down if they think they’re being told off. Your aim in these conversations is to help them be better leaders, and you’re putting the emphasis on the fact their behaviour might not be best for business, not on the behaviour itself.

The second ‘S’ is the solution. You should enter these conversations with a clear outcome in mind. You want a mutual aim – something the senior person will buy into. One thing I found difficult with senior leaders is they’re not used to being challenged. They are very savvy and fast-paced, so you need to get straight to the point. At this level, it’s perfectly OK to be straightforward about the conversation you’re having. After all, you want a joint problem-solving approach that is based on honesty, courage and benevolence.

Katherine Graham is founder and chair of workplace relationship specialists CMP Employment

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