How do you coach an employee through a difficult situation? Take the time to understand what’s going on for them before you try to fix anything. I always start with rapport, professional empathy and clear confidentiality. Then I pace the person, let them decide how much they want to share, and ask for their point of view instead of jumping in with advice. Stay with whatever they’re feeling without rushing to rescue them, help them separate what they can control from what they can’t, and hold what I call ruthless compassion: kind to the person, and honest about what needs to change.
Why managers find this so hard
When someone on your team is struggling, the instinct is to do something: give advice, offer a solution, or pass them on to HR. Each of those can feel helpful. But to the employee, a quick referral can sound like “I don’t want to deal with this,” and advice given too early can sound like you’ve already decided what the problem is.
Coaching asks something different of a manager. Slow down, understand first, and trust that the answers are more likely to hold if the person finds them for themselves.
Start with rapport, empathy and confidentiality
Nobody opens up to someone they don’t trust. Before anything else, the employee needs to know three things: that you are on their side, that you care about how they are, and that what they tell you stays in the room (within the limits of your role, which you should be honest about).
Professional empathy means you can understand how someone feels without taking it on yourself. You stay warm, and you stay steady.
Take the time and pace the person
The most important thing is to take the time. Pace the person: go at their speed, and let them decide how much they are willing to share. Open the door rather than pushing through it. A simple invitation does more than any clever question: “Tell me what’s going on.” Then ask for their take on the situation, so you understand it from where they stand.
This is paced coaching. You ask, you listen, you notice, and you ask again, following where the conversation needs to go.
Coach to understand, then coach to improve
I’m not a fan of directing in these conversations. The order matters: first coach to understand, then coach to perform and improve, and work out together what will work best for this person.
That means observing and noticing before you guide. When you do guide, you are gently helping them towards where they want to go, and where they need to go, not telling them what to do.
Follow the energy, and don’t rescue
People in difficult situations may be upset, annoyed or angry. A coaching manager can sit with that without needing to make it go away. Follow the energy of the conversation and be comfortable with silence and strong feelings.
This is not a rescue situation. Rescuing takes the problem away from the person and makes you responsible for it. Understanding keeps them in charge of their own way forward, with your support.
Listen for the meaning they give it
Two people can face the same situation and experience it completely differently. What matters is the meaning the employee is giving to what is going on: what they believe it says about them, their job or their future. Explore that gently. When you understand the meaning, you understand the impact, and you can see where coaching will help. More on this in my guide to emotional intelligence at work.
A common example: when someone is underperforming
Most of the time, someone who is underperforming already knows. Sometimes they don’t want to admit it, or face it. Confronting them head-on usually makes them defend themselves.
What works far better is giving them the chance to say it themselves, without accusing or shaming them. Ask how they think it’s going, what is working well, and where they could use a little more support. Be open and allowing. The message underneath is: I want to help you here, and if we understand it together, we’ll be able to solve it, or at least find some answers. From there you can explore together what input they need, where they need more help, and where you can help. See also how to manage an underperforming employee.
Know what you can and can’t change
Some parts of a difficult situation are uncontrollable: a family matter, a health issue, a change in the business. Others are controllable, and coachable. Help the person separate the two, then focus your coaching on what they can do.
For what lies beyond your role, be sensitive enough to ask whether they would like someone else to talk to, and who could help them. Offered this way, it becomes part of the support you’re giving.
Ruthless compassion
Even if you can see they could be doing better, or should be doing better, stand back and stay in a place of compassion. Ruthless compassion means being kind to the person and honest about the situation at the same time. You don’t lower the bar, and you don’t judge the person for struggling to reach it.
After the conversation
Agree a next step, however small, and a time to check in. Keep what was shared confidential. Then notice how they are doing over the following days. The follow-up often matters as much as the conversation itself. If the conversation was hard to start, my guides to avoiding difficult conversations and giving feedback at work can help, and so can building psychological safety across the team.
Coaching an employee through a difficult situation: FAQs
How do you coach an employee through a difficult time?
Take the time to understand first. Build rapport and confidentiality, pace the person, ask for their point of view instead of giving advice, and stay with how they feel without rescuing them. Then help them separate what they can and can’t control, and coach on what they can.
Should a manager give advice or direct the employee?
Not at first. Coach to understand, then coach to improve. Advice given too early tells the person you’ve already decided what the problem is. Gentle guidance works better once you understand what is really going on.
What is ruthless compassion?
Being kind to the person and honest about the situation at the same time. You stay compassionate about what they are going through without lowering the standard of what needs to change.
When should a manager suggest someone else to talk to?
When part of the situation is beyond your role, such as a health or personal matter. Ask sensitively whether they would like someone else to talk to, and who could help, so it feels like support rather than being passed on.
Can managers learn coaching skills?
Yes. Coaching is a skill that improves with practice. My coaching skills training for managers works on real situations your managers face, so the approach becomes part of how they lead.
Next step: Book a free 15-minute call to talk about your managers, or see our coaching skills training for managers.
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