Coaching Conversations in 2025

Enhancing Workplace Interactions and Preparing for AI Changes

Tim Hagen

Send us a text

Get ready to revolutionize your workplace interactions with our enlightening discussion on conversation readiness, situational readiness, and creating engaging follow-up dialogues. This episode is brimming with practical examples and valuable insights, including an unexpected common ground found between a boss and subordinate, proving that work is not the only topic to bond over. Prepare to transform your relationships into less of a work task and more of a pleasant engagement.

In the latter half of our discussion, we dive headfirst into the potentially unchartered waters of AI and its implications on the workplace. Clear the path of communication barriers as we unfold the vital role of emotional intelligence and conversation skills. We promise you, this episode is more than just a casual listen. It is a treasure trove for anyone looking to boost their communication prowess, build healthier relationships in the workplace, and equip themselves to ride the wave of changes AI is set to bring about. Buckle up to enhance your conversation readiness, situational readiness, and the art of meaningful follow-ups. Let's get started!

Welcome to Coaching Conversations

We have created a NEW and Innovative line of books called Workplace Coaching Books. These books use QR codes with embedded audio and video lessons speaking directly to the reader. Each book comes with assessments and journal based coaching pages where they document what they've learned and what they've applied. In addition each book comes with the self analysis link that prompts them to share what they've learned and what they've put into action leading to greater learner application a

Progress Coaching 360 is a dynamic leadership development system that equips managers and teams with powerful coaching skills through a blend of training, real-time practice, peer learning, and feedback. It combines expert-led instruction, a train-the-trainer model, group coaching certification, and monthly coaching pods where leaders practice, share wins, and tackle challenges. With built-in accountability and hands-on application using Coaching Cards and best practice sessions, Progress Coaching 360 turns coaching from theory into action—building a sustainable culture of growth, feedback, and performance.

Progress Coaching 360 teaches leaders how to coach and employees how to develop coachability skills. This unique combination helps build great workplace cultures.


Get More Info Here: https://form.jotform.com/251187914739165


Speaker 1:

Recently, I was on a live audio broadcast with my friend, julie Winkle Julie Owning, who wrote a great book Promotions Are so Yesterday and we were talking about technology and we were talking about some of the things that were going on in terms of will AI replace human touch-based coaching, and it was a spirited conversation and I can't let go of the conversation because I think it brings up so many things. We have to really deal for lack of better description with reality insider companies. So think about this For 31 years, I've owned this company called Progress Coaching. For 31 years, my number one objection was if I had time, tim, I would coach, and it's just bogus. Here's why Time is a mask for the real reasons. They don't know what to do and they don't know what to say. So in the pandemic hit guess what happened? Three things I've got to talk to my people about the new ways of doing business. I've got to talk to my people about what's coming new policies, new procedures, how are we going to work from home and those conversations had an impact. Now we all thought can you really work from home? Can you really engage virtually?

Speaker 1:

Let me tell you the story of two people Two people, one subordinate that did not like her boss. The boss did not like her. They worked at one of our client sites and they did not care for each other. They were very open about it, which was, quite frankly borderline unprofessional. And what happened was on one of their Zoom calls they use Zoom they both found out they had golden retrievers and they said I didn't know, you had a golden retriever. And the subordinate. The employee said, well, yeah, I breed them. She goes, you breed them. No, I'll stop there. They didn't become best friends Yet. They have greater context to each other. See, when we only have conversations about work, our relationships feel like work.

Speaker 1:

Then, when the pandemic started to subside, what happened? People went from ah, this is interrupted, at home, I don't have an office, do we have enough bandwidth to? I kind of like not driving into work? And some companies said, no, got to come back to work. Some companies said, well, we'll go hybrid. What do you want? All of those required conversations? Let me give you a context. They had one client who went from a very high 90% rate in the start of the pandemic, saying they could not stand the pandemic. They hated working from home. They wanted to get back in the office. Three years later, the same percentage. Yet now they want this hybrid work environment.

Speaker 1:

The company literally stopped building one of their additions, meaning they saved millions of dollars Tremendous benefit. They found out you know what. We can be pretty productive and the company's trying to find that balance, that policy that everybody can be happy with. We know the answer. Not everyone's going to be happy. Those require conversations.

Speaker 1:

Now one of the leaders that I saw present to her team said wow, this is what management wanted. I'm just delivering the message. You guys think I'm unfamiliar. She was selling out upper level management. I'm just here to deliver this terribly written idea of a procedure. It's not what a leader does. A leader has to be in alignment. It brings us to three strategies that make the workplace better. Now that we have AI coming, people are going to start freaking out. They're going to start wondering how is this going to affect me? How are we going to use this at work? Is my job going to be replaced? Those conversations are happening right now, exponentially.

Speaker 1:

I want you to write down three things Conversation readiness, situational readiness and conversation follow-up. First of all, a conversation is not an event. A good conversation is a series of conversations and interactions woven together. Number two conversation readiness. Let's start with number one. Conversation readiness is when you prepare. You don't just show up.

Speaker 1:

There's a debate in the coaching world of scheduled coaching versus in-person coaching, on the spot coaching. Now, I'm very much for scheduled coaching because on the spot we tend to gravitate to what is wrong or what I want to correct. How do I know that? Every time I ask employees, your boss calls into the office what's your first response? It's usually uh-oh, what do I do wrong? Do you know? I've never heard a positive response to that question in 31 years. Conversation readiness is I'm going to prepare, I'm going to give myself a few minutes. I'm coaching Joanne on conflict. I'm coaching Tom at 2.30 on his relationship with Bob. I'm coaching at 4 o'clock Bob to become a more influential leader. Those are great gravitations from conversation to conversation. Oh, in between we have people knock on our door and say do you have a second? And it's really going to be 19 to 22 minutes and you've got three reports due by tomorrow morning. We tend to be scattered throughout the day, in-person or virtually. Conversation readiness is critical. Situation readiness is that when you are ready with skill sets to coach.

Speaker 1:

So let me give you an example. Last week I gave them the rule and I said well, what happens when somebody comes to you and they're really upset? And I said, well, I used to go through it with parents of my coach Volleyball. They would come to me and they would say I just wanted to talk to your coach, you know why is my son not playing? And you could hear it in their tone and their energy. Now, if I had answered in that moment, what would happen? Would they hug and kiss me and say, oh, my gosh, you're right. My kid's terrible. No, what would they do? They would get more angry.

Speaker 1:

You always ask one of our general rules to start with two or three what questions? So what's your understanding of why your kid's not playing? Well, I don't know. That's why I wanted to talk to you. Well, what has he told you? And before you answer, are you aware that he knows the answer? All of a sudden, the anger starts to dissipate. Oh, he knows.

Speaker 1:

I said yeah, and I said I've got kind of a tough question. I hope I don't cross the line here. Are you OK with that? Well, sure, what Is this about you or your son? And before you say anything, take a deep breath and cancer. Honestly, yeah, it's just hard sitting there watching them sit there. I don't think you know what it's like.

Speaker 1:

I said what do you mean? I don't know what it's like. What's your understanding of my son in baseball? Well, what do you mean? I said my son got cut from the baseball team. I still go to baseball games with the coach who cut him. We've never talked about it. It's horrible to watch your kids sit or get cut. It's horrible. And I had that mom literally say wow, coach, I shouldn't have come here. I said of course you should have come here. It's about your kid. Your kid loves being on the team. I have one more question for you. She said what I go? What do you see when you watch our team and you see him on the bench? She goes. He's jumping around, he's laughing, he's high fiving. She goes. Oh my gosh, I get it. I never responded yet I responded through questions.

Speaker 1:

So situational readiness is having skill sets, knowledge, basis of how to handle something. The other day I was talking to someone who said I'm struggling with emotional intelligence. I get angry at my subordinates. I get really angry. As he's talking to me, I said take a deep breath and do me a favor. I'm gonna ask you to do something. Weird Guy said yeah, okay, what I said. Take a huge deep breath. I said this is my time. I'm not charging you. This is my time. Take a deep breath. Takes a deep breath. I said now calm me through what's going on. And as you're thinking of that answer right now, then I want you to answer what's the benefit of your people if you were to make an effort to inspire and motivate them? All of a sudden he comes back, takes a deep breath, said yeah, and he completely calms down. His emotions are down 40%. What was my situational readiness? I knew he was emotional, so I inserted using something called an opposite insertion question Walk me through calmly. Then I use voice fluctuation to my benefit. Now I'm a hyper guy, so that's not easy for me. Now, if I was just in the hallway scattered and he's telling me, I might run the risk of saying well, look you, dude, you gotta calm down. Probably wouldn't have been effective, right? Emotion breeds emotion. So I was ready, because I'm skilled at this and sometimes I don't practice what I preach.

Speaker 1:

Third conversation follow up when you have a conversation, like I did with that parent and, like I did with that gentleman, I followed up with both and I sent an email video email, mind you to the mom saying I wanna thank you so much for coming. She became our most supportive mom for four years. Kid just reached out to me for a baseball game at the Milwaukee Brewers because I could keep in touch with a lot of my players. I said how are you feeling? What can I do to make this transition easy for you? She said nope, I get it. She's completely reframed her mind why her kid was on the team. Had I told her he's not very good and he wasn't, I would say it in front of the kid and the kid would agree with me.

Speaker 1:

It's the same thing with the gentleman who was struggling with emotional intelligence. I actually have that conversation a lot and I said what are you gonna do to calmly inspire and motivate your people? Walk me through a diplomatic series of steps you're gonna do to praise your people at your next staff meeting. I get a call from his boss. He said I don't know what you're teaching or coaching to. It's like day and night differences. He said no, he's fighting it. It's not day and night difference, he's fighting it. It's about getting them in the place of experiencing something. So when we have the three conversational skills that we need conversation readiness, situational readiness and follow up conversations get better. The more we converse, the greater communication. The more we converse, the greater collaboration. The more we converse a coupled with better act of listening Truly listening not listening to think about what we wanna say while someone's talking, but really being in the moment and listening. Bosses who do that just became very tough to leave.