It is a certainty that at some point in your leadership career, you have had to deliver a difficult message, navigate issues that will adversely impact people, and/or you have had to find ways to talk with someone who feels harder to communicate with than others. Likely, you’ve come across all three scenarios (and more).
The reality is that as leaders (and as managers), you will regularly have to communicate information related to a hard decision you have made or you will be the conduit for sharing a decision made elsewhere, but in both cases, that information has an impact on people that needs communicating. There will also be times when your conversations aren’t necessarily related to tough decisions, but perhaps there are people in your team or in the audience you serve, who have a different style, approach or demeanour to your own and therefore discussions need to be more carefully considered and thought through in advance. The common thread here is that as leaders of people, we want our communication to land in the best way possible and in a way that feels clear, kind and respectful to both (or all) people involved. Easier said than done I know.
When working with organisations in the way that I do, one of the top issues that comes up time and again, is communication – particularly in relation to delivering hard messages and in navigating discussions where the other person (or people) seem distant, uncommunicative, disinterested or upset. Leaders tell me this can be one of the most challenging aspects to the role and when it doesn’t feel like it has gone well, it can weigh on minds and divert attention for days (even weeks or months in some cases). Leaders also tell me that they want their managers to feel confident and capable in this respect too, so that a culture of good communication can be built throughout the organisation and across all layers of leadership and management.
As with most things in leadership (and life more broadly), there will be aspects you can do something about (and are within your direct line of influence) and aspects that are not within your gift to control. Having difficult conversations is one of these. Unfortunately, there may be times when no matter what you do or say, the conversation won’t go well. In other instances, with a careful, caring approach, you can help a hard conversation to feel more palatable. The key here is to be confident that you have done everything possible to reach an acceptable outcome (within your control), not necessarily to have an acceptable outcome every single time (outside of your control).
So, what are some of the ways (within our influence as leaders) in which difficult conversations can be handled well? Below, I am going to explore two scenarios – communicating difficult messages and communicating with people who have a style that differs to yours – as each differs slightly in focus. This is based on my own experiences over a 20+ year career, drawing on my experience as a leader and as someone on the receiving end of a wide range of leadership styles. One common piece of advice I would give across all scenarios, is to draw on the expertise of your HR or People Lead. Particularly if you need to ensure that whatever you are communicating is legally correct and aligns with organisational policy – it never hurts to sense check with someone who specialises in this area.
Delivering difficult and/or sensitive messages
Leading conversations where you must deliver hard messages is never easy and anyone with an ounce of emotional intelligence will worry about delivering the messages in a way that will cause least upset, worry or unease. We know we have to communicate, but it can be difficult when we don’t know how the other person (or people) will respond. Here are some things (in no particular order) that have stood me in good stead over the years when delivering difficult messages, as well as things I have observed in other leaders when being on the receiving end.
- Prepare and structure what it is you need to say – being kind is being clear. Giving some time and thought to what you need to say (and in what order) will help you to feel more confident and will help recipients to feel clearer on what is being said to them. The order that works well for me has been: to briefly refer to the purpose of the conversation (so the person knows from the outset what they are there to discuss), to give background information as to what has led here, to outline the decision process (if there has been one), to clearly outline what decision has been made and why, then to finish with what this likely means for them – moving after this into questions/thoughts from them.
- Offer kindness, empathy and understanding – whilst clarity is important, so too is tone and authenticity. Finding ways to show authentic care for people makes a big difference to the way that difficult messages are received. Some people say ‘I shouldn’t show emotion as it’s not about me!’ and whilst they are correct that they are not the focus, not showing emotion with people can make them feel more vulnerable, misunderstood or that the interaction is too clinical. Balance is key.
- Actively listen – there’s a difference between listening to hear vs listening to speak, and people tend to pick up on which mode you are in. Giving people our full, undistracted attention when they’ve received information that might be difficult, sensitive or upsetting is really important. We can demonstrate active listening through body language and responding to specific points they have made after they’ve received information.
- Avoid being defensive – when we go into defence mode, our focus shifts to explaining ourselves or seeming ‘right’ rather than appreciating the other person (or people’s) perspective. This is a hard thing to avoid, particularly if people are responding to us in a very upset, agitated or even aggressive manner. Sometimes, stepping out of the room to give people space to digest and collect their thoughts can be a good way to avoid defending – usually by saying something like ‘I think it might be helpful for me to give you some space for a moment as I know that I’ve given you quite a lot of information to digest. I will be back in a few minutes so we can continue the conversation’.
- Ask them what you could provide to help – sometimes asking people directly, will avoid second guessing what ‘good support’ looks like, and allows you to be clear on their individual needs. Sometimes they can’t tell you straight away so you could also suggest they can follow up with you at a later time, after some thought. Sometimes they might ask for things that are impossible for you to provide. In which case, explaining why you can’t provide these things but offering something that you can do instead might help.
- Keep your commitments and follow up afterwards – it’s important that we see things through even after the difficult information has been delivered, for a number of reasons. Firstly, it can take people time to really digest the information, and it can hit them harder later on and/or raise questions further down the line. Secondly, authentic caring isn’t just ‘in the moment’, it has longevity and people need to feel that. And thirdly, keeping our word as leaders is how people know you can be trusted, even when they are not happy with the information you’ve delivered. Checking in on people through phone calls, emails, text messages or follow-up meetings is a good way to show that you appreciate that difficult information can take time to land and that you truly care how they feel.
Navigating conversations with people who are disinterested, distracted, distant or upset
Sometimes, we need to have conversations with people (who we manage, are in a team with, or we work to serve) who we either know going into it or we pick up quickly within minutes, it will be harder to converse with. This can be for any number of reasons ranging from differing communication styles to mood on the day, through to differing levels of interest in the topic(s) to be discussed.
Keeping in mind that we cannot control how other people think, feel and behave, my advice with this is to do what you can from your side to be inclusive, encouraging and mindful, but accept that in some cases you might not feel the conversation has gone exactly how you would hope – and sometimes that’s okay. Here are some approaches I’ve tried that have often been helpful:
- Begin conversations with some ‘informal’ talk to relax you both (or all) into it – but keep in mind that some people don’t like informal (or ‘small’) talk. Asking a couple of informal questions (such as ‘how is your day going?’ or ‘how was your weekend?’) before beginning the full conversation often helps people to ease in and to feel more comfortable. However, for some, it may feel the exact opposite. Test the water with one or two questions and if it feels as though someone doesn’t want to engage at that level, accept it and move on into the main conversation. Not dwelling on or pushing the informal talk when the indications are that someone doesn’t want to engage is important as it respects their boundaries.
- Setting psychological safety – this is important with everyone as it underlines that they are in a safe space where they can be assured of confidentiality, respect and that honesty is welcomed. Even just a few minutes spent at the beginning of a conversation can reassure people that you want them to feel safe. I am not implying here that this alone is how psychological safety is built (it’s a much larger piece of work relating to culture, behaviours, language and more), but it can be a small way to remind people that their safety is important to you.
- Be informed by them – you will undoubtedly pick up from their words, body language and other cues whether a shorter, more direct conversation might be welcome or something more detailed and prolonged might be better. What I would say with this though, is don’t assume a preference on one day is the same every time you meet them. Part of building emotional intelligence as a leader, is the ability to adapt style and approach to those we work with, alongside and serve. Having an eye to social indicators can enable us to communicate more effectively with different types of people.
- Gently address the ‘elephant in the room’ – sometimes in conversations with people, it might feel as though they are distracted, disinterested or not fully present. Again, this can be for all sorts of reasons. If it begins to feel as though the conversation is becoming unproductive for both sides, it can be worth gently (and I use this word purposefully!) surfacing what you have noticed but with the caveat that they can correct you if they think you have it wrong. For example, using a phrase such as ‘Alice, I could be wrong (and please do let me know if I am), but if feels as though your attention might be elsewhere. Is there something on your mind it would be helpful to talk about?’. The other person can then open up a little so you understand why they are not fully invested or, they can tell you that you have it wrong but will often then show a bit more investment. In the latter case, I usually round it off with ‘Okay, sorry if I have that wrong, lets continue on then but do let me know if you want a break or to raise anything that might come up for you’. This leaves the door open if they want to share later, why they’re not fully present or engaged.
- Sense check their understanding of the conversation at the end – sometimes if we have quite different communication styles, we think we’ve communicated really well but it’s actually not been received in the way we’d intended. Playing the conversation back, or better still, asking them what their key takeaways have been, helps to make sure things have been understood and/or gives a chance to clarify where there’s ambiguity or misunderstanding.
Ultimately, in both scenarios (and the whole spectrum of wider people related scenarios) the key is focusing on aspects that are within your influence as a leader (i.e. your communication, your body language, your clarity) and knowing, with confidence, at the end of a difficult discussion that you have done everything possible to help it land well. It won’t always land well or feel comfortable, but you can at least know you did all that you could. In my experience, treating people with kindness, humanity, dignity and understanding goes a long way – so when we lead with this, we can know we did right by people to the best of our ability.
If you are looking for a specialist with in-depth experience and insights to work alongside you as you develop your people strategy, organisational strategy and/or your approach to culture, please visit my website at: www.elevatingleadership.co.uk or get in touch at alice@elevatingleadership.co.uk







