An executive coach’s step-by-step guide to having difficult conversations with the underperformers on your team.


No manager wants to have uncomfortable conversations with their team members, and few topics are harder to broach than that of underperformance. For new leaders, perhaps those who have just received significant investment and are facing new levels of potential growth, addressing issues of underperformance in a team member can seem as much a test for them as it can for the employee.

At the same time, it’s essential to handle such conversations sensitively and rationally. Currently, cross-sector layoffs, especially in the tech industry, have employees on edge and acting cautiously. This can make receiving constructive feedback surrounding performance that much more painful for some.

Balancing the demands of the business in terms of performance and behavior standards with responsibility and care toward employees can be a difficult line to tread, but it’s a duty leaders must step up to.


When faced with any problem, including these kind of “people problems,” you have three rational options:

Accept the problem fully, with a peaceful heart, knowing that you, and the business, can live with it.

Walk away from the problem. Let the employee or client go; buy out the partner or investor.

Do something to change the problem—and the only thing you can change is what you think, do, or say.

These are the rational options.

What most of us do, though, is pick an irrational and unhelpful option: Do nothing, complain to our friends, nurse our resentments, and wait for the other person to miraculously change. This option doesn’t do you or the business any good at all. It may soothe your ego, but it doesn’t solve the problems you face.

If you decide that you or the business can’t take the first option to accept the problem—because, for example, the underperformance is too great; nor are you ready to take the second and walk away—perhaps because the relationship is too important—you are left with the third option: Change what you think, do, or say.

Having tough conversations is one of the challenges that leaders often struggle with. Most of us avoid conversations we assume will be difficult because we don’t like conflict or upsetting people. In reality, more damage is caused by avoiding these discussions or by having them poorly. Once you know how to get yourself into the right mindset to have a tough conversation, and how to structure what you say, these conversations aren’t tough at all.



When you prepare for any management conversation that feels difficult, keep in mind what can be called the Manage Mindset Formula:

The Manage Mindset = Brave + Kind + Clean

Your team needs honest, constructive feedback from you about what they are doing well and what they could do better. You need to put their need for constructive feedback ahead of your own discomfort about having these conversations. Be brave.

If the only time you ever give feedback is when things are going wrong and you’re frustrated, you won’t help your direct reports improve. Genuine praise and signs of appreciation are as powerful in shaping behaviour as constructive criticism. Be kind.

Use “clean” rather than “charged” language when communicating to manage. Charged language is highly emotive and will likely trigger a defensive reaction. Clean language removes as much judgement, accusation and emotion from the conversation as possible and allows for open and constructive dialogue. Keep it clean.


The next time you notice unhelpful behavior from a team member and decide that you have to address it, try this three-step process:

Step 1: Prepare feedback.

Make sure you are in the right headspace, be calm, constructive, and future-focused. Coaching can sometimes help with this. Next, prepare your feedback, being specific and focus on actions, not personalities. Start by answering the following questions:

What did the individual do? Be specific—e.g., “They rolled their eyes in the meeting this morning,” not, “They are so disrespectful all the time.”

What was the impact of that behaviour or action—on you, the team, the meeting, the work?

What would you like the individual to do more or less of in the future?

Step 2: Signpost feedback.

It’s important not to spring feedback on an unsuspecting person. Signpost to the individual that you’d like a feedback conversation with them. For example, send an email saying, “Let’s schedule some time to talk about today’s meeting. I noticed a few things that concern me. I’d like to share some feedback and have a conversation about how we could improve things moving forward.”

Step 3: Deliver feedback.

When you sit down with the individual, set a constructive, solutions-focused tone. Do this by repeating what you said in the email, verbatim. Then, deliver your feedback using the following framework:

“When you . . . [their action], the impact was . . . [your experience], and my request moving forward is . . . [your desired solution].”

For example, “When you rolled your eyes, I felt uncomfortable and I noticed the team shifting uncomfortably in their seats. My request moving forward is that you remain aware of the impact of your behaviour, speak up if you disagree with what I’m saying, or speak to me privately if you are frustrated or angry.”

When speaking about the impact of the person’s behavior, only talk about what you felt or observed. You can’t speak to what other people experienced, and you don’t want to find yourself in a debate about what the team thought of the person’s behavior.

Use clean language. Avoid words like “should,” “always,” and “never,” and the accusatory “you.” Start sentences with “I” and keep your tone neutral and calm. The statement “I’m concerned about your attention in meetings and the impact that’s having on the team” will get you a lot further than a charged-up “You are always checking your phone and you never pay attention and it’s annoying everyone”—even if the latter is just what you want to say!

Aim to keep conversations calm, constructive, and solutions-focused. If the individual starts defending or debating, reflect that back to them and then re-deliver the three-step feedback above. “I notice this conversation is getting heated and I just want to bring us back to my first comment: ‘When you . . . the impact was . . . and my request is . . . .’” If the individual is too upset or defensive, suggest that you pause the conversation and reconnect when they feel calmer.

For new leaders, especially those of rapidly scaling businesses (who are learning their management and operational skills on the job as their company takes off), these difficult conversations are an initiation into true development as a leader. In uncertain times such as these, employees will be extra cautious and potentially sensitive. Recognizing this, but still stepping up to have uncomfortable discussions, is the sign of a true strong leader in the making.


Rachel Turner is cofounder of VC Talent Lab and author of The Founder’s Survival Guide. VC Talent Lab is a coaching partner to multiple global investment funds and works with founders from a wide range of sectors and at various stages of growth.