Three tips for tough conversations

12 April 2021

Money & Life team

Money & Life contributors draw on their diverse range of experience to present you with insights and guidance that will help you manage your financial wellbeing, achieve your lifestyle goals and plan for your financial future.

Alison Hill provides three tips that will provide financial planners with results when having tough conversations.

Financial planning is a human business, which means tough conversations are an inevitable part of your role. While meaningful conversations are key for business success, it’s our ability to have a meaningful conversation with clients and staff during tough times that defines us.

Part of your ability to do this well is knowing what are the tough conversations for you – because this is different for everyone. For some, the tough conversation is the discussion around raising client fees; for others, it is the conversation with a client who is upset or emotional. It could be any one of a thousand scenarios, but the common denominator is this: all of these conversations are not easy.

So, how do you achieve results from these tough conversations?

1. Get specific

When we have the tough conversations, we often fluff around the subject and avoid being clear. Other times, we believe that we have been explicit but the other person steps away from the conversation and does the complete opposite thing.

This miscommunication is often because we use trait-based language, rather than bringing the conversation back to specific behaviours. For example, we might use a trait and say, ‘Sally is so hard-working’, but what one person means by hard-working can be very different from what the next person means. Confusion is eliminated if we get specific about the behaviours that we need to see more of.

For example, if you need team members to be more ‘friendly’ in a client service setting, clarify the specific behaviours you want them to do, such as ‘smile at the client’ or ‘ask clients if you can help them with anything’. Behaviour-based language makes what you want the other person to do explicit. Behaviour-based language also removes judgement from a situation; the conversation is about it – the behaviour – not about them as a person.

2. Make your point

Where you direct the conversation has a significant impact on the success of a tough conversation. Look someone in the eye when you’re providing them with feedback and it’s highly likely they will get defensive and the conversation will quickly become emotional.

Instead, direct the conversation to a third point, using the medium that is relevant for the situation. This third point might be a whiteboard, a report, a computer screen or a piece of paper where you map out the next steps.

Allow the issue to hold space in the third point medium. Throughout the conversation when you are talking about the issue, such as the rising cost of advice, direct the issue to the third point; whenever you are talking about solutions or strategies to move forward, bring the conversation back to the other person. The issue then lives outside of the person, helping to de-personalise the conversation.

3. Follow-up

The single greatest mistake individuals have around tough conversations is they believe that once they’ve had the conversation, it is finished. However, results come when we check back in with the person to clarify the next steps and if they have any other questions. You also need to follow up on any actions that have been agreed to.

The reality is that most people, given a choice between a positive outcome and a negative outcome, will steer their behaviour towards the positive outcome. So, have the tough conversation, get specific about the behaviours you want to see more of, use third point communication, and make sure you follow up with your clients or staff.


Alison Hill is a registered psychologist, co-author of Work From Anywhere, and CEO of Pragmatic Thinking. A culmination of her expertise across leadership, culture and psychology, Pragmatic Thinking works with organisations who drive change through building better leaders, growing better teams, and shifting cultures.