Difficult Conversations at Work: How L&D Can Support New Managers
Managers guide, lead and motivate their teams. But despite the crucial nature of their roles, Personnel Today says that 77% of managers never received specialized training when they were hired or promoted. And a further 75% never – or rarely – were given additional training after their onboarding.
The outcome is a cohort of managers who feel unprepared for important responsibilities, like conducting difficult conversations. A normal and unavoidable part of work for most leaders, these interactions occur in every team and with nearly every customer. They also have many causes, ranging from personality conflicts to gaps in performance, motivation or skills. Though they can be intense, the right tools and approaches will help your managers adopt the mindset and behavior needed to reach a successful outcome. Here are 4 strategies L&D leaders can share:
1. Encourage your manager to talk to themselves
Having an internal discussion about a conversation before it takes place provides a chance for your manager to ask questions they might otherwise overlook. For example:
- Why is the idea of this conversation making me uncomfortable?
- What exactly is making me feel worried?
- Am I afraid of ruining a relationship that I’ve worked hard to build?
- Am I concerned about stirring up conflict instead of resolving it?
- Am I afraid that I lack the skills needed to communicate effectively?
When they’ve considered these questions, and developed strong answers, they’ll lessen their anxiety and the chance of feeling unprepared when the pressure is on.
2. Encourage your manager to talk to someone else
Remind your manager that a difficult conversation (which will take place with a certain person and focus on a specific situation) should resemble a conversation they’d have with someone else about that person and situation.
For example, have them imagine that they’re going to discuss things with your HR lead. They wouldn’t blame them for what happened. Instead, they’d likely outline the situation, stick to the facts and discuss possible solutions. This is exactly what a real-life difficult conversation should look like. Facts and logic need to take precedence over emotion and blame. Collaborating with HR can help your new manager separate the emotional side of a situation from the logical one, making these interactions incredibly valuable.
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3. Suggest a word association game
Encourage your manager to think about what they want to say during the conversation and write down words that come to mind. Once they’ve made a list, have them add associated words and phrases and then review them. How do these notes make them feel?
Maybe they planned to say that “Akeem feels isolated.” But the word “isolated” can have negative connotations and might lead to an unpleasant reaction. Instead, it could be better to say “Akeem feels like he’s unable to participate or contribute.” This gets the message across without assigning blame. Being particular about words might seem trivial, but it can make a big difference.
4. Engage in a roleplay session
The idea of roleplay can fill some people with dread. But there’s no need for your manager to act out an entire conversation. Instead, have them focus on working through various scenarios, anticipating what could happen and determining what questions the other person may ask.
This approach shares similarities with our 1st suggestion: Have your manager talk to themselves. Remind them that coming up with the questions they’re likely to face requires fully engaging with the situation. It’s not enough to simply try thinking about it from someone else’s perspective. They should take notes, work through several scenarios and think deeply.
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Helpful scenarios to get your manager started
Practice makes perfect, so encourage your manager to try out some of these roleplay scenarios to prepare them for real life conversations.
- Scenario #1: An employee is speaking to – and about – another employee in a disrespectful way.
What your manager might normally say: “I don’t appreciate your tone or the way you’re speaking to Ishani. Please stop. That’s not the way you talk to someone. I won’t allow it in the future. You should apologize to her.”
Their likely goal in this context is to realign their employee’s behavior. But this kind of interaction is likely to make the other person feel defensive, unappreciated and misunderstood. That’s why the most important question they can ask themselves before trying to change someone’s behavior is “What’s my mindset?”
The more aware we are of our own mindset (and how it makes us behave) the clearer our goals become. And the closer we’ll be to achieving them. Here’s a better response your manager could provide in this scenario:
“Do you have a moment to talk about what happened with Ishani? I appreciate how hard you’ve been working on meeting your sales quota this quarter. And I know you snapped at her because you want the rest of the team to reach their targets. In the future, maybe you can show her more empathy. She’s also under lots of pressure. How do you feel about apologizing?”
A statement like this will make the other employee feel more valued. By identifying with their situation, and showing them how to be softer with Ishani, your manager can hopefully avoid inflaming the situation. A culture built on empathy and understanding is always better than one based on harsh reprimands.
- Scenario #2: An employee is continuing to work fully remote from another country when company policy allows for only 50% remote work.
What your manager might normally say: “Our company policy says you can only work remotely 50% of the time. You’ve been in another country for weeks now, so please come back. And the next time you want to work from abroad, let your manager know.”
At first glance, this conversation seems like it would get results. The employee would probably feel like they don’t have a choice and stop working from abroad. But your manager will also create resentment and erode trust. The employee might ask why they can’t keep working in another country and feel like the manager doesn’t believe they’ll actually get things done. Your manager should try saying something like this instead:
“I know our remote work policy wasn’t clear in the past. But we’ve updated it and believe it’s important that we spend time together as a team. If you have any issues or concerns, please don’t hesitate to speak up. Otherwise, can you let us know what your plans for working remotely look like in advance? Hopefully, we can find a way to make things work for everyone.”
In this scenario, your manager makes it clear that their employee isn’t following company policy. In real life, they should ask why this is happening, as having a deeper understanding of the situation will allow them to better assist the other person.
How learning and development can help support new managers
Supporting new managers, and providing learning opportunities, is vital to their success. They need the right skills and knowledge to excel, and many begin their roles with more promise than expertise. But the right training can fill gaps in knowledge, help them develop new strengths, and make a difference for your organization.
Eager to learn more? Reach out to us and we’ll tell you about how we can help you support your people.
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Senior leadership and boardroom teams invest heavily in commercial strategies to win market shares. Yet the most important and honest information driving strategy circulates in teams underneath, never making it to the table where decisions are made.Jeroen Kraaijenbrink, Executive Coach and Strategy Consultant at Kraaijenbrink Advisory, has spent years working on what he calls the honesty gap. We sat down with him to understand what the honesty gap actually is, where it lives in organizations, and why fixing it requires a leadership shift.How do you define the honesty gap?There's a narrow definition and a broad one. The broad one is: we have created organizations and systems where it's barely possible to be honest to yourself, about yourself, and honest to other people.Honesty isn't just lying. It's integrity, being authentically connected to other people and being aware of your own emotions and your own biases.The honesty gap, in a narrow sense, is the fact that truth and information don’t travel vertically upwards in a company. It's often hard to speak openly to your manager because it’s become rational not to. Many people have the experience: 'I've tried it once but then I was punished for it, or was ignored, so let it be, never mind.' That's the fascinating part: it's not good for people, it's not good for organizations and yet we somehow keep this system intact.Is it less about individual dishonesty and more about a collective culture?A lot of the most important information going through your company is between people and in conversations. You need to find a way to have an honest conversation, where the things that matter get on the meeting table, not just in the informal circuit. And I think that's pretty rare.A more systematic definition is that we're not using the collective intelligence of a company enough. We can radically improve it because we’ve made it rational to hide the truth and to keep things to yourself. A lot of it may not be intentional, but the very fact that someone is in a position above you automatically creates this tension: 'What do I show? What don't I show? Because my next performance appraisal is coming up.'Where does the honesty gap typically show up first, and who owns the problem?It starts with leaders. Solving it needs one leader at the top, the CEO at least, being open and reflective enough to admit that there is an honesty gap and that they are part of it. That's the self-reflection you need for any improvement and any change. Like in coaching: you need to be aware that there is stuff to improve. You don't need to be a perfect leader, but you need to be open enough to admit that there is an issue.You talk about the 'persona trap', what is that?You're stuck in a persona where you perform in a certain way within your company. You have a role, a position, a reputation, and that locks you into specific behaviors. The worse the match between who you are as a person and how you need to show up in your organization, the more inner conflict that’s created. Especially at the top, it’s a problem for many executives. They're supposed to be the people who know it all and be decisive. While if you're honest, you don't necessarily know everything, you’re uncertain and have anxieties.The inner core of the honesty gap is breaking the performance, breaking the acting you feel you must do. If you've put yourself in a role of being the strong, decisive, number-oriented leader, that's how you have to behave. But most people don't feel very comfortable in that kind of role because it's not who they are.Can you fix the honesty gap through individual coaching alone or does the system have to change?Part of it is a personal change, part of it is a system change. You can be on your own and be very authentic, but if the system doesn't change at all, you’ll struggle to break the honesty gap.What you need to do is work on the people, the culture, and the system. Ideally that has to include the top, because otherwise it stays at the level of the person being coached. If it's a team lead or a mid-manager, that person can partly create an island in the organization, a safe space for their team and their department. But still, the appraisal systems, objectives, and culture are company-wide. Why is this so hard to shift, even when leaders recognize the problem?We have normalized this idea that you have to be strategic in what you tell and what you show. You have to show up in a certain role at work. It's also the result of how we have separated work from life, which is a very unnatural thing. It's from the industrial age, because for any other species, work is life. But now there’s a split between work, with all the routines in companies, and then your private life. There's just one you, you're the same person at home as you are at work. The good news is that the honesty gap can be closed. While many companies have unintentionally created environments where people hesitate to speak openly, organizations prioritizing trust, authenticity, and psychological safety can unlock a competitive advantage. When employees feel safe to share concerns, ideas, and perspectives, collective intelligence grows, decision-making improves, and stronger relationships emerge across every level of the business.
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