How to deal with difficult conversations when managing up
By Amy Jacobson | July 03, 2025|6 minute read
SHARE THIS ARTICLE
A difficult conversation is any conversation where the stakes feel high, emotions are involved and the outcome is uncertain. Most people avoid them for as long as possible, and then either explode or say nothing at all. Neither works. The good news is that difficult conversations are a skill, not a personality type. Anyone can get better at them.
Whether you are managing up, addressing underperformance, navigating a conflict with a colleague or telling a client something they do not want to hear, the same core principles apply. Here is how to approach it.
As leaders, we wear many hats in our different roles and environments. We wear one hat when we are leading our team and another hat as a team member working with managers, stakeholders, and peers. Each hat has a different role and requires a different set of skills if we are to be successful in it.
Mastering the competencies of managing up will decrease the number of difficult conversations we have to have and will help to provide solutions. The more we build these competencies, the fewer difficult conversations will be required, and our managing up relationships will grow, creating more balance and less misalignment.
Build relationships
Managing up our relationships with our manager, our manager’s manager, and the people above them is just as much our responsibility as the relationships we build when managing down.
Too often I hear leaders say that they never hear from their leader or from the CEO or anyone in the C-Suite. My first question back is, “When was the last time you made the effort to contact them?”
Relationships are a two-way street. Yes, everyone should be trying, but there is only one thing we can control in this world: ourselves.
Influence and add value
As a leader representing a team or department of the organisation, we have insights, information, and skills that can add value to conversations and influence decisions.
We should never be a seat warmer. We are there for a reason and that reason should be to add value as a team member and influence decisions.
People sitting in executive or senior leadership positions are pictured as having high intelligence and sometimes even as being the “high and mighty”. In truth, they are just human beings, the same as us. They don’t always have the answers, but they will make decisions based on the information they have. If we don’t provide input, or add value to the conversation, they don’t know what they don’t know.
Take ownership
Our mind is so quick to look for other people to blame or other people to take responsibility. Again, we reiterate ownership when managing up.
There is always some type of action we can take to improve a situation. It may not change the original decision, but it can make the decision a little easier to process or work with.
When we are in any form of middle management, the temptation is there to simply be a messenger between the front line and upper management. This shouldn’t be the case. As middle managers, we should be looking at all situations being fed up to us as a problem requiring ownership and a solution by us. It is our opportunity — and really our role — to stop the problem there at our level and manage back down the solution.
Communicate with solutions
Communication is an absolute given, but remember that communication is a two-way interaction.
It’s not just about being reactive to the requests for communication that come from above. It’s about being proactive with our communication and providing information through reports, updates, and any form of communication that provides insights into how our team/department is doing in line with our goals and the company strategy.
There should be some type of formal or informal agreement between leaders of what the expectation is when it comes to communication for both parties. This should include the frequency, the communication platform (for example, email, report, phone call, meeting), why it is important, the expectations of how it will look and what it will include.
Be highly independent
Team members who require constant assistance from their leader, either asking excessive questions, asking for opinions, or copying them into every email and communication, don’t project a lot of independence and confidence.
As we move into higher levels of leadership, being highly independent is not just an expectation; it’s a must-have. You need to be able to perform at a high standard independently as well as a team member.
Incorporate critical thinking
While there are many different definitions and steps to critical thinking, I like to reference Monash University’s definition: “Critical thinking is a kind of thinking in which you question, analyse, interpret, evaluate and make a judgement about what you read, hear, say or write.”
The Monash critical thinking model takes us through six core skills:
- Clarify your thinking purpose and context.
- Question your sources of information.
- Identify arguments.
- Analyse sources and arguments.
- Evaluate the arguments of others.
- Create or synthesise your own arguments.
Without critical thinking, we lose the substance to our decisions and communication. Building this skill makes managing up easier in every situation.
Adopt a united front
One of our biggest downfalls is to only see our “team” when managing down and think that this is the only team we should be focused on. We always have peers who are also middle managers. Yes, they might have completely different expertise or departments from us, but they will still be faced with similar people problems and management situations.
Too often when we are managing up, we don’t see the other people around the table as our team. Each of us goes in on behalf of our own team and becomes quite pushy or defensive to get the best possible outcome for the team that we manage down. It creates conflict and competition internally rather than a united team that is making decisions based on what is best for the organisation.
A united front is not just working together; it’s communicating together as well.
Frequently Asked Questions: Difficult Conversations at Work
How do you start a difficult conversation at work?
Start by getting clear on the outcome you want, not what you want to say, but what you want to achieve. Then lead with a question, not an accusation. Curiosity opens conversations; judgement closes them. Say what is happening from a factual perspective, acknowledge the other person’s position, and then move to: how do we fix this?
What makes a conversation difficult?
Any conversation where there is emotional risk, uncertainty about the outcome or a power dynamic involved. Performance conversations, giving feedback, saying no, addressing conflict, managing up: these all qualify. The difficulty usually comes from fear. Fear of the reaction, fear of damaging the relationship, or fear of not knowing what to say.
How do you manage a conversation with someone who gets defensive?
Defensiveness is a fear response. When someone gets defensive, they have heard your message as a threat. The fastest way to reduce it is to acknowledge their perspective before pushing your point. Listen fully, reflect back what you have heard, and then move to problem-solving together. Do not match defensiveness with more pressure.
What is managing up and how do emotional intelligence skills help?
Managing up means influencing your manager or senior stakeholders effectively, even when they hold the power. EI skills are critical here because managing up requires you to understand your manager’s emotional reality, communicate in a way they can receive, and have conversations that might feel uncomfortable without letting fear drive your behaviour.
Is there a framework for difficult conversations?
Amy Jacobson’s Ask It step from the 5-Step EI Framework is specifically built around this. The core principle: lead with questions, not conclusions. Listen to understand, not to respond. Acknowledge before you advise. And always end with a clear, agreed action, because a difficult conversation without a next step is just an argument.
