How To Tell Someone What They Do Not Want To Hear

Disappointment hurts. Studies show the same part of our brain that is responsible for rendering the affective (meaning emotional, not sensory) reaction to physical pain also underlies our reaction to social rejection. Harsh critiques, an idea rebuffed, or being cut loose from a project — it all quite literally hurts. And though the studies may not have captured it yet, being on the other side of those experiences can hurt too.

It is only natural that we hesitate when we need to tell someone what they do not want to hear — it would be easier to avoid the unpleasantness for both of us.

I was thinking about this recently related to a conversation I had with an exceptional Aha! team lead. They were particularly excited about a person who had applied for an open role — after an introductory call during which the candidate was engaging and enthusiastic.

However after I had a conversation with the candidate, it was clear that they did not have the necessary skills for the job. Nor had they shared any interest in gaining those skills when I asked about their motivation to develop their career in those areas.

I could relate to why the team lead was initially excited. It is easy to quickly become connected to someone and to be hopeful about the practicalities needed to succeed. But it does not matter how much you like someone or how happy it would make them to hear you say yes. A leader’s responsibility is to determine if someone will be able to be their best and contribute to the team's success.

Exceptional performance can only be realized through thoughtful reflection and sharing your truth — as it relates to seeing yourself and as it relates to working with others.

Speaking that truth requires trust. And trust takes time to build, even though often that time has not yet passed. Recently I wrote about the idea that it is not possible to treat everyone on the team the same. In that blog, I noted that you need a steady pattern of rational decision-making from leaders that is in line with company objectives. This gives you and the organization more latitude for honest conversations.

A sturdy foundation is necessary — otherwise difficult conversations can unmoor people. Now, a caveat. There is nothing more demotivating than working in a company where you feel your ideas and input are not chosen or celebrated. So when you do need to tell a teammate something that you know they will not want to hear, it is important to be considerate in your approach. Here is how I try to do it:

Acknowledge what is good

Do not immediately go negative. There is a reason that the person has suggested a path forward — even if it is not the one that you want to take. Whether it is the time they have spent working on it or simply the desire to do their best work, take a moment to honor their effort and intention. And consider how what they have done is beneficial. Remember that people almost always want to do a great job and create value.

Ask to encourage investigation

“That will not work because…” Not so fast. You will gain more if you are able to get the other person to question their own assumptions. Try asking something like, “What would need to be true for that to work?” Or, "What do you see as the advantages and disadvantages of that approach?" The process of evaluating together without judgement can lead to teammates making better decisions in the future. And it will create a sense of a problem shared — rather than a problem assigned.

Address how you see it

Now you can give your point of view. Let the person know that you are telling them what you think because you want to help. You care and that is why you are discussing it. Demonstrate your kindness by paying attention to their listening style and adapting your delivery. For example, someone who is action-oriented will want to get to the point quickly, whereas someone who prioritizes relationships may interrupt to ask questions as a way to maintain connection. No matter what — use clear language so that there is no ambiguity.

Align around the reason

End with a specific reason. Everything you do comes at the cost of something you will not do. Maybe it does not support company values, business goals, or is simply not a priority right now. Maybe it was just a bad assumption that led to the wrong answer. When you can center together around the rationale behind your direction, people will feel less personally affected and view what you say more fairly. They will be able to accept it even if they do not fully agree.

Speaking from a place of truth does not mean you are unkind — as long as you do so with attention to respect and principles.

Of course, it might be a bad time for you to be heard. Personal circumstances or other factors you might not be aware of can derail the conversation. If things become emotional or even hostile, you can pause to let the tension diffuse. And it is always okay to suggest continuing the discussion later.

I believe that a leader’s job is to love the team enough to tell them the truth — even if it is not something they want to hear. It is also your job to create a considerate and stable environment that allows others to hear that truth for what it is.

And let's never forget: If we have the privilege to be responsible for speaking the truth, then we must also be open to hearing it from others.

Read more of The Founder’s Paradox.