coaching prompts

Coaching prompts: Real accounts from coaching sessions

Coachee: I was just promoted to manager, which I’m really excited about. It feels great to help all of my directs with their problems. But I still have a lot of IC (individual contributor) work. I’ve been trying to do both, but I can’t keep up. The only other options are not to do the IC work, which I have to do, or to tell my directs I can’t help them, which means I’m not being a good manager. Ugh, I guess I’ll just have to suck it up and not sleep instead.

Coach: What do you really want?

Coachee: I want to get my work done and be a good manager.

Additional Questions:

• Who have been some of your best managers? What characteristics and behaviors made them the best?
• What do you ultimately want for your direct reports?
• How could your direct reports support you in this situation?

David’s Final Thought: If a direct report comes to you with a problem, ask them what they would recommend and why.

Coaching prompts: Real accounts from coaching sessions

Coachee: There are 7 people on my team. There’s one who is out a lot. But he has a doctor’s note right now so I can’t do anything. Another’s husband is sick. And two more are on vacation. At this point, there are 3 people to do the work; I’ve jumped in too. But we’re not keeping up. My team has commented that they can’t take vacations without hurting the team. It seems they’re right. Sigh.

Coach: What do you really want?

Coachee: I want to have enough people to get the work done and to create space so they can all take a vacation.

Additional Questions:

• How is it determined who can take vacation when?
• What happens if the work doesn’t get done?
• What are other potential options other than working longer hours?

David’s Final Thought: In the short term, prioritize the work relentlessly and ask for help from your boss and peers if you feel comfortable doing so. In the long term, work with your team to set boundaries around vacations and determine backup plans for similar situations.

Coaching prompts: Real accounts from coaching sessions

Coachee: Like any business owner, I want my customers to be happy. I also want my customers to give me feedback when they’re not happy, so I can address their concerns. But, every time one of my customers gives me critical feedback, I feel like I’m not doing enough and I get really anxious. It doesn’t make any sense. The feeling just takes over, and now it’s starting to impact my health. I don’t know what to do.

Coach: What do you really want?

Coachee: I want to feel calm when I receive critical feedback.

Additional Questions:

• What would it look like to do enough? To be enough?
• How does the anxiousness serve you?
• In which situations have you stayed calm after receiving critical feedback?

David’s Final Thought: Sure, critical feedback can be a gift. It can also hurt to hear it. If it hurts, pay attention to the feeling to understand where it comes from and what else is happening in the moment you feel it. 

Coaching prompts: Real accounts from coaching sessions

Coachee: I was in one industry and then made a move mid-career to another industry. I have been promoted to senior roles in both industries. I’m looking for a new senior role, but I don’t think they want someone with my limited and unique experience.

Coach: What do you really want? 

Coachee: I want to figure out how to tell my story.

Additional questions:

• What prompted you to choose the initial industry? What prompted you to make the mid-career move?
• How do you define “limited” and “unique”?
• What is the importance of being in a senior role for you?

David’s Final Thought: People will listen if you have a compelling and thoughtful story to which you and they connect.