Dennis and Jonathan had scheduled a two-hour conversation together about three weeks out after they’d gotten back from the conference. Dennis had felt that two hours was an insane amount of time to devote to a single conversation, and tended to prefer stand-up meetings and maximizing his efficiency.

He’d felt a pull to push back on Jonathan’s suggestion of two hours, but, again, he felt a unique level of trust with Jonathan, and so he went along with it.

Dennis noticed a few things happening since returning from the conference.

First, he wasn’t sure if it was the conversation with Jonathan, or simply attending the conference, or something else, but he was feeling much more open with his colleagues. Things at work hadn’t felt so bad, and he hadn’t felt quite as much frustration with their process. Dennis felt like there was some hope for ReggieCorp’s future.

Second, Dennis felt himself doubting the value of the two hours he’d set aside for a conversation with Jonathan. It was a huge chunk of time, and even though Dennis was feeling more open, his schedule was still slammed with things to do. As time pressed on, the combination of things not feeling quite as bad anymore, along with Dennis’s tendency to feel overwhelmed by his schedule both created pressing reasons to cancel the call.

By the time three weeks had passed, Dennis had made up his mind. He liked Jonathan — he really did — but he had clearly just met Jonathan at a really low point. Things were on their way up — slowly, but on their way up nevertheless — and consequently, Dennis didn’t want to waste Jonathan’s time. If Dennis was really honest with himself, he would also acknowledge that he didn’t want to waste his own time. He simply didn’t have the resources for that.

Dennis concluded he wasn’t willing to cancel over e-mail; Jonathan just seemed too nice for that. So he’d get on the call, make it clear early on that he really appreciated Jonathan’s time, and that things were generally doing much better, and then aim to end the call an hour earlier than they had planned.

Looking at his desk, he saw piles of unfinished work, and the thought of being able to clear that off before he called it a day felt gave Dennis an exceeding amount of relief.

It was five minutes past the hour when Dennis looked up from the work he was doing and realized he was already late for his call. Embarrassed, he picked up the receiver, found Jonathan’s number, and gave him a call.

Jonathan’s voice came through on the other end, “Hey Dennis!”

Dennis responded, quickly apologizing for his tardiness, and explaining that he just got himself lost in some work.

Jonathan acknowledged him gracefully. “I was beginning to wonder if everything was okay. I’m glad to hear it’s just work. How’s everything been going since we last connected?”

Dennis had prepared well for this part of the conversation, and shared strategically, explaining how things felt a lot better, how he had started to partner with the rest of his executive team better, and how, even though they weren’t out of the tunnel yet, he had a lot more hope and was pretty sure they were on the right track.

Jonathan acknowledged Dennis and celebrated that fact, then asked him simply, “Cool! What else?”

Dennis was slightly caught off-guard by the question. He’d planned to use this next part of the conversation to explain how he wouldn’t be able to make the full amount of time set aside for the call. He thought for a moment and then asked, “What do you mean?”

“Well, all of that stuff is awesome, and usually I find that people have a few things happen after they set up a conversation with me. First, saying YES to a coaching conversation is a vulnerable thing. I wanted to acknowledge that before we go further, and, along those lines, usually saying yes to something vulnerable means our fear immediately starts to work its way into the process. Consequently, people tend to come up with good reasons for not having this conversation.”

Dennis fidgeted a little uncomfortably while Jonathan spoke. That sounded familiar.

“And, usually we end up agreeing to a conversation when things are pretty dire, and there are a couple of consequences to that. First, things will naturally get better for a while, the same way that your knee pain starts getting better after you see a doctor, just because you tend to seek out a doctor when the pain is at its worst — it regresses towards the mean. And second, the simple act of saying YES to something like this will usually have you show up differently, at least for a while. Kind of like how making a new year’s resolution actually does have you show up differently, for a while. So I’m imagining the simple fact that we scheduled something might have lit a bit of a fire under you, at least temporarily.”

Dennis was willing to acknowledge that there was some truth to what Jonathan was saying.

Jonathan finished up, “So, anyhow, some of that may be true, or all of it, or none of it. That’s why I’m asking you what else. Did any of that happen? If not, what did show up for you since we scheduled this call?”

Dennis felt a natural desire to be cagey with Jonathan and keep his cards close to his chest, but he was again present to the experience he had had in the past: he genuinely felt that Jonathan didn’t have an agenda.

“Well, if I’m honest, all of that is true. I’ve been worrying about the two hours we’ve set aside for this call. And actually, even now I’m worried that we’re wasting time and should get started so we don’t waste any more time,” Dennis heard Jonathan laugh on the other side of the call, “My intention coming on to this call was to reduce it to one hour, give you time to do your thing, and then thank you and get back to the mountain of work that’s on my desk.”

“Got it!” Jonathan exclaimed, “That makes total sense to me. Things are busy, they don’t feel that bad anymore, you’ve got mountains of work to catch up on, probably even more since you were away at a conference, and two hours is an insane amount of time to set aside to simply have a conversation. Let’s get this shit DONE! Something like that?”

Dennis felt relief. It was nice to have his cards out on the table. “Yes, exactly like that.”

“Great, thanks for sharing that — really, it’s so much easier for us to just have this stuff on the table.” Jonathan paused before continuing, letting the gratitude land, “So over here, I’m not attached to how this goes, including the amount of time we spend. We can even end this call right now, if that’s what you think would serve you. I’ve set aside two hours to spend with you, but I’ve got plenty of other stuff I can take on, and I don’t mind if you’d like to cancel, reschedule, or shorten the amount of time we have together.”

Dennis interrupted, “Well, I don’t want to cancel altogether…”

Jonathan continued, “Okay. Well, how about this: let’s start with the coaching conversation, and maybe we get everything resolved for you in the next forty-five minutes. And either way, we’ll check in with you just before the top of the hour and we can see what you’d like to do. Does that sound good?”

Dennis was grateful that Jonathan left him with his out. He looked over to the pile of papers on his desk. They could wait for another forty-five minutes.

“Yeah, that sounds perfect. Thank you.”

Dennis was surprised to notice some emotion well up inside of him as he expressed his gratitude. He wasn’t used to someone honouring what was real for him and simply allowing space for it. Rather than spend any time with it, he quickly pushed the emotion back down so he could get focused on the conversation they were here to have.

Jonathan began by creating some agreements with Dennis, speaking briefly to confidentiality, and then asking that he and Dennis both be willing to lean in, take risks, and come from the space that anything is possible. Setting agreements up front like this felt a bit odd to Dennis, but he was game to play. He only needed to make it through forty more minutes, so he wasn’t too concerned.

“So, what are we going to take a look at?” Jonathan asked.

Dennis paused, realizing that in all of his strategizing, he had forgotten to take a look at this conversation and really get clear on what he wanted to get from it.

“Geez, I’m not sure. I mean, I’ve been thinking a lot about this conversation, but I just realized I’d been thinking more about how to manage the time it took up in my schedule, rather than what I actually wanted to leave the conversation with.”

Jonathan laughed, “Ha, that makes sense. And now here we are having the stupid conversation.”

Dennis laughed back. “Yes. Stupid conversation. Thanks for nothing!”

Jonathan sat quietly without saying anything, so Dennis sat for a while and thought about what might be worth taking a look at.

“Okay, well, how about this: even though I think things are improving, my time is still in high demand and feeling incredibly scarce. I mean, I was already shaving time off of this meeting — and thank you for letting me do that, by the way — and it just feels like there’s never enough. So, if you could create an extra four hours for me every day, that would be pretty awesome.”

Jonathan spoke, “Yes, that would be nice, and it sounds like a great place for us to start. So tell me about time. How does it go for you, what tends to show up, what is your experience of yourself with time, etc.”

Dennis paused to reflect before speaking.

“Well, generally speaking it goes kind of like it has today. There’s always more things I need to do than I have time. I’ve tried all kinds of tools and time management systems. I’m really good at the Getting Things Done system, and I like it a lot, but even though I’m able to sort, process and manage all kinds of things, I notice that it never seems to be enough. I feel like I’m chasing my own tail — I just can’t seem to get out in front of this once and for all.”

Dennis continued, “So it’s like, even if I got everything done today,” Dennis paused and looked disdainfully at the pile of papers on his desk, “I mean, like there’s this stupid pile of papers on my desk, and I want to clear it off, but even if I do, I know it’s not going to be the end of things. There’ll still be more for me to do.”

Jonathan spoke, “Yes, okay… that makes sense to me — I can relate to that experience. So let me make sure I have this straight. There’s never enough time, basically. You’ve gotten better and better at managing your time, you’ve mastered any number of systems,” Jonathan paused, “In fact, I’d be willing to bet you’re probably more organized and efficient with your time than the vast majority of people…”

Dennis interrupted, “Yes! That’s just it! It’s like, no matter how good and fast and better than everyone else I get, I just never seem to be on top. And then I start hating on people that seem to have a simpler job or less responsibility. Dude! I have fantasies at times about just working as an employee at a bowling alley.”

Jonathan laughed, “I’m so glad we’ve broken through the dude-barrier in our conversation. Shit’s getting real now!” Dennis and Jonathan both laughed, before Jonathan continued. “But that also makes sense to me. I remember it used to be Starbucks that I fantasized about working at. Just smiling at customers, no responsibility, just being friendly and connecting with people.”

Jonathan continued, “And hey, I’m guessing you may have even created situations in your life where you get to be the equivalent of an employee somewhere. Like, places where you don’t have much responsibility, and where there’s not a lot riding on your shoulders, and I’d be willing to bet that you have a different experience of time in those places. Is that at all accurate?”

Dennis stopped and thought.

“Yeah actually. Like, my friends and I go away on vacation once a year, and in those situations I just sit back and refuse to lead anything. I just let everything else happen, and it’s so much easier.”

“Anywhere else you show up that way, Dennis?”

Dennis thought some more.

“Well, I’m a member of a few boards, because people have asked me to join them, but I haven’t taken on any leadership role — mostly because I don’t want to get swamped with even more responsibility and work — and so in those places I tend to just show up the same way we’re talking about.”

“Okay perfect, so we’ve got some places where you’re responsible, there’s some stuff on the line, and there you just never have any time. And then there are these other places where you aren’t responsible — not necessarily irresponsible, but just not owning anything, per se — and in these situations, your experience of time is different.”

Dennis picked up the thread they were laying out, “Yeah. Except, I also notice that it’s fucking boring in those situations too. Sorry for swearing, but I really need to emphasize that. Like, yeah, there’s no urgency of time, but it feels like the entire universe is dying and being reborn during the duration of those board meetings. I’m climbing the wall, and part of me just wants to grab the reins and take over.”

Jonathan responded, “No need to apologize for swearing, we’re making good progress on this call: we’ve broken through both the dude- and the fuck-barrier so far.” Jonathan joked but continued on with his point, “Joking aside, this also makes sense. It sounds like we’ve kind of got this pendulum. You can either be up to something big, owning a lot as a leader, lots of responsibility, and have time feel scarcer than ever, or you can be sitting in the backseat, feeling like there’s an abundance of time but climbing out of your skin with boredom. Do I have that right?”

Dennis exclaimed with a mixture of relief and exasperation, “YES. That’s exactly it. So maybe I just need to find the right combination of responsibility, but not too much. That’s kind of what I’ve been doing with the board meetings and our executive team lately. I’ve been stepping back from some responsibilities, and trying to say NO more.”