Welcome to the Box of Conversations

There are three key one to one conversations that we should have with our team:

  1. The check in conversation
  2. The reward conversation
  3. The career conversation

And hopefully you don’t have to use this one very often, but if something is going wrong:

  1. The difficult conversation

So we have put together some cards to help these conversations flow a bit better. No complicated forms or training modules – just human conversation starters.


  1. Don’t think of the topics as separate meetings – use in the flow of your one to ones.
  2. Try not to read the cards like a script or it may seem disingenuous. Start with one or two you like and see where the conversation takes you.
  3. Don’t worry about having the perfect conversation – we are only human after all.

Suggested timing:

15-20 mins as often as they need

A check-in is an opportunity to catch up, show appreciation, agree or adjust priorities, discuss recent work and provide coaching. Tell your team when you’re available so they can book their own check-in.

Conversation Starters

Suggested timing:

30 mins as often as they need

Today’s flatter structures mean it’s not always possible to move up the career ladder. But that doesn’t mean everyone needs to stay in the same place. Career development today is about making the most of your team members’ strengths, giving them the chance to learn new skills and opening doors for them.

Conversation Starters

Suggested timing: Build into check-ins

Having a conversation about pay can be awkward, but it’s an important discussion to have – the more open and honest the better. If you are able take the issue of money off the table and pay well that is the ideal, but if you are restricted by budget or you already pay market rate you may need to explore other options to recognise. Why not surprise and delight great performance with spot rewards that are thoughtful e.g. time off, vouchers, development etc. and of course, let’s not forget the power of personal thanks and appreciation.

Prepare in advance by thinking through these questions:

Conversation starters

A difficult conversation could be one of the hardest parts of being a leader. It’s no fun for the person on the receiving end either. Be known as a leader that nips issues in the bud.

Conversation examples