coaching prompts

I want to feel some semblance of order

Coaching prompts: Real accounts from coaching sessions

Illustration by Kiry Luc

Coachee: I’m exhausted. I have more work than I can possibly do in a day because we’re supposed to be doing more with less at work. I have 2 kids I’m trying to keep entertained in confinement. I’m worried about my 70+ year-old parents who enjoy sheltering in place less than my kids. Days are blurring together. And my work-life balance or integration or whatever you call it is a distant dream. I’m spent. [Seven-year-old sticks his head into the camera frame and stares blankly.]

Coach: What do you really want?

Coachee: I want to feel some semblance of order.

Additional Questions:

  • Apart from exhausted and spent, how else are you feeling? Which “emotion” words would you use? Which sensations do you feel in your body?
  • What would that “semblance of order” look like for you?
  • What are you learning about yourself during this time?

David’s Final Thought: I am reminded of the Serenity prayer which tells us to accept the things you cannot change and to have courage to change the things you can. For those who might think this is easier said than done, take a moment to consider a list of 5 things that you can change, no matter how small. And from that list, choose at least 1 thing that you will change.

I want my team members to be productive

Coaching prompts: Real accounts from coaching sessions

Illustration by Kiry Luc

Coachee: We were recently told that it’s mandatory for everyone to work from home for the foreseeable future. I just became the manager of a team of people who usually come into the office. There are a few remote employees, but most are on the ground with me. I have no idea how to make sure that everyone is doing their job. What do I do?

Coach: What do you really want?

Coachee: I want to be sure that the team members are as productive and effective as possible.

Additional Questions:

  • How have you ensured that remote team members remain productive and effective in the past?
  • What techniques have you used to stay productive while working from home?
  • What concerns you most about your team working remotely? What are some ways to mitigate those concerns?

David’s Final Thought: Trust your team to deliver. If an employee doesn’t seem to be as productive or effective, be curious and ask honest, open questions to determine the underlying reasons.

I want to ruminate less

Coaching prompts: Real accounts from coaching sessions

Illustration by Kiry Luc

Coachee: I’ve recently had a health problem recur that I thought was cured. The issue is keeping me from working out. When I don’t stay active, I get in my head. I’m realizing that when things take a turn that I don’t expect, I try to wait until they go back to normal. When they don’t immediately go back to normal, I get frustrated and impatient. Then I start to ruminate, which makes me feel worse. I don’t know what to do.

Coach: What do you really want?

Coachee: I want to ruminate less.

Additional Questions:

  • What are your expectations for going back to normal?
  • What would you prefer to do rather than ruminate?
  • What do you lose when things aren’t normal? What do you gain?

David’s Final Thought: Change is often disruptive and uncomfortable. That said, try to pause and consider what you have to learn from the change. Logistically, I recommend writing it down or talking to someone about it so you don’t keep those thoughts solely in your head.

I want to help my team be successful

Coaching prompts: Real accounts from coaching sessions

Illustration by Kiry Luc

Coachee: I’ve just become a manager of managers after hiring a manager to work for me. I feel like I’m winging it. I’m just managing the same way I did when I was a frontline manager, i.e. with openness and transparency, but I don’t know if that’s right or wrong. I could use some advice.

Coach: What do you really want?

Coachee: To help the team, and the new manager specifically, be successful.

Additional Questions:

  • What did you most appreciate about your boss’ approach when you first became a frontline manager? What did you not appreciate about your boss’ approach?
  • How do you want your team to behave?
  • Imagine that it is 1 year from now and the team has self-destructed (however you wish to define that). What are some reasons it has? Where do you want to focus your attention based on those reasons?

David’s Final Thought: As a team grows, be deliberate about who communicates what and when to whom.

I want to feel good physically

Coaching prompts: Real accounts from coaching sessions

Illustration by Kiry Luc

Coachee: Everything is going great. I’m spending time with my family. I see a light at the end of the tunnel with my projects at home. On the work side, all the travel I’ve been doing seems to be paying off as the customers seem to be happy. The only thing I’m struggling with is food and exercise. I’m eating way too much bad food, and I’m not doing enough exercise. So, I’m putting on weight, which doesn’t feel good. But I don’t have the time to plan my meals or go to the gym. I just need to be more disciplined.

Coach: What do you really want?

Coachee: I want to feel good about what I’m eating and how I’m staying active.

Additional Questions:

  • How would you characterize your relationship with food? With exercise?
  • How does eating bad food and not doing enough exercise serve you?
  • What would it look like for you to be more disciplined?

David’s Final Thought: The relationship we have with food is as old as we are. And it is often as complex as any other relationship we have. Before taking action to address the symptoms, pay attention to the relationship.

I want to be a good manager

Coaching prompts: Real accounts from coaching sessions

Illustration by Kiry Luc

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.

I want my team to be able to take vacation

Coaching prompts: Real accounts from coaching sessions

Illustration by Kiry Luc

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.

I want to feel calm when I receive critical feedback

Coaching prompts: Real accounts from coaching sessions

Illustration by Kiry Luc

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.