# 51 - Reflection **Kevin:** [00:00:00] Hello and welcome once again to the, it Depends Lessons in Technology Leadership, podcast. I, as always, am your host, Kevin Goldsmith and Happy New Year. Welcome to 2026. I hope you've had some good holidays. I hope that you've had an opportunity to take maybe a bit of a break and kind of break up your time. I thought about doing this Episode as the last one of 2025, but I think it's early enough in the year that this will still work, because what I want to talk about today is reflection. If you've been listening to the podcast. For a while, or if you've read my book or if you've read some of my newsletters or my blog posts, one of the things I've talked multiple times about is my self-reflection process and this being the top of the year, this is a time where you often get advice about [00:01:00] looking back and looking forward. It's something that I do every year. There's some prior episodes that you might wanna look at. One is called the personal strategy offsite, and that talks a bit about the process that I do. By the time you have heard this, I will have done that exercise. I wanna talk a little bit more about self-reflection as a leader or taking the time to, to think about how things are going, because it's not something I've always done. It's something I learned to do and it's something that's been obviously very valuable for me and coming up on this year, I will have now been a CTO for 10 years and, and thinking about this process and then thinking back to when I first took my first CTO job. I realized how easy it is once you've been doing a job for a while to just get used to it and you [00:02:00] know the job and you know how to do it, and it's very easy to just relax and things come up, but you've seen these kinds of things before so you feel very comfortable with it. And it's only through that process of looking back and examining how you do things and how you approach things and how you might do them better, that you improve not only as a leader, but as a person. I think, and I've talked about this in conference talks, I've talked about this I think on the podcast as well, another challenge, especially once you move into very senior levels in a company is that you don't really have much of a peer group anymore. I'm the only CTO in my company. I'm not the only executive, but my peers do different jobs. They have different specialties, they manage different kinds of teams. As a C level person, you don't get a lot of. Feedback. At my level, you're just expected to be [00:03:00] able to do the job without a lot of development. And it's not that I haven't had great bosses. I absolutely have, but at the C level, they're not spending a lot of time developing you. You are expected to develop yourself or to be fully developed. So that means that process of reflection becomes even more important. And that's why it gets very dangerous when you've been doing it for a little while, where it starts to become comfortable. It starts to feel a little bit easier, and that's a dangerous time because if you go with that and you relax into it, you are gonna start making mistakes. You're not gonna do the job well, and you're not gonna improve, and you owe it to the people that work for you to be improving and to be doing a better job for them every day. So it's January, when's the last time you stepped back and asked, am I so growing, or am I just executing the same playbook I've been running for years? Reflection isn't a [00:04:00] luxury. It's the thing that keeps you effective as a leader. You're helping your team plan their year. When's the last time you planned yours? What I've heard from others who are interested, they'll say, "I'm really interested in doing this. But I'm really busy." Like I take a whole day and I do that twice a year. that seems like a lot of time when you have six meetings every day, but reflection is what makes you less busy. I've recommended the book, the Seven habits of Highly Effective People by Steven Covey. One of the things in that book is the concept of taking time to sharpen the saw, which means spending time on personal development and how that actually makes you a more effective leader. It gives you time to improve at your job, which means you can take less time to do things . That reflection is what makes you less busy. And I talked about getting [00:05:00] comfortable. Success breeds habits. Habits become. Autopilot and autopilot means you stop asking why. Even if it is still working for you, why does this work? One of the reasons I do this podcast is it makes me explain why I do something or how I think about something that. Otherwise is just ingrained in my head. I don't really think about it. I just do it. It's habit. Talking about it helps me understand my own self and why I do things the way I do them because I'm explaining it to someone else. You can't lead your team's growth if you've stopped growing yourself. They need to see you learning, adapting, questioning your own assumptions. But senior leaders often convince themselves that they don't need this. I've figured it out, or I know it works, or I can go with my gut or the way it's been working , is fine. The reality is. The more senior you are, the [00:06:00] more your blind spots matter, and without structured reflection, you don't even know what those blind spots are. When I was starting out, I was just working. I was moving fast, I was growing quickly. I wasn't really reflecting on it. I, I was just doing it. It seemed like I was doing well, so I didn't question it. I didn't challenge it. I was figuring things out as I went. I just kept going. Once I started to have challenges, things didn't work exactly the way they used to. The things that had gotten me there were not the things that were getting me past there. I was leveling out. I was topping out and had to figure my way past it. I had no tools to figure out how to get past where I was. So I started spending more time reading and reflecting. I got a coach and he helped me just [00:07:00] by forcing me to question myself and challenge myself. And I was lucky enough at that time where I was working with a lot of peers for whom this was already a practice and who were very thoughtful about how they did their jobs. And so I learned from them as well. That taught me some lessons that I've kept with me since and has helped me as I've continued to grow. I haven't had that problem of topping out since, because I'm always questioning why I do things. I'm always looking and examining, is there a better way to do this? Which means that as new challenges come, I approach them with curiosity. I approach them with interest as a learning opportunity. And doesn't mean I'm always successful, but it means when I'm not successful, I'm learning as opposed to [00:08:00] moving on without having learned a lesson. But as I said, I'm 10 years in now, which means that some of the things that I used to have to really think about now I can shortcut. If I'm not careful or I can shortcut and then not examine was the shortcut correct? It gets easier. You do a job for a while, the job gets easier and that's great. That's the benefit of experience, but it can also be a trap if you get too comfortable. Before when everything was new and where I was constantly learning and I was getting things wrong, and then learning from those experiences. And really focusing on getting better. Now I have to be careful and not to become overconfident. And not to become complacent because I can shortcut things and generally it's gonna work out pretty well. And so now I have to force myself a little bit more to [00:09:00] reflect because I am. More confident in the role, but when I do, I still learn a lot about how I am doing the job, how I could be doing the job better. I talked about some of the process I do in prior episodes, the personal strategy offsite, that's one and then the other one is Own your calendar. Go back and listen to those if you want to get more details about how that specific part of this reflection process works. When I was younger, I would journal my way through problems. It's a really effective tool if you're good at it. It was a challenge for me. It wasn't always a natural thing to do, and so what I found was if I wanted to do it regularly, it was easier for me to create more of a structured process. So that personal offsite is part of that practice. That's a twice yearly practice. I step back, I assess the last six months set priorities for the next six months. It takes about a [00:10:00] day. Sometimes it actually takes longer, but I block out about a day for it. At the end of that process is a look back on the process itself and then before the next time. I'll update the pieces. I remove the things that aren't working for me anymore if I think I could use. Some new things, I'll add them in and because of that, it's not always the same amount of time or I find myself getting really into part of it and I take longer than I planned. But it's about a day. As part of that, I'm gonna set quarterly goals for myself for that quarter. 'cause I do this middle of the year and end of the year, so I'll set my Q1 goals for myself are things I wanna work on in the first quarter, and then I revisit that at the end of that quarter before that second half yearly. That's not a long process. That's mostly just to give myself little interim things and make sure that the things I'm working on are small enough that I [00:11:00] can focus on them. Then within that I set monthly look backs as well. That one I actually mostly use , if you're familiar with bullet journaling, that's a technique I've adopted and used over the last few years, and that has a monthly look back process. So I do that, that's where I also revisit the quarterly goals. I revisit the half yearly. At that time as well. So it's a good chance to kind of re make sure I've got all that in my head, make sure I'm tracking to the things I wanted to work on. And then every week, every Sunday night, I look ahead to the week and I look back at the prior week and I spend a little bit of time just thinking about. What I wanna change from the last week, what I want to do differently the next week, making sure I've got the bigger things I want to think about in my head. And also just kind of doing that prep for the week so that I feel like I'm ready to go. So , that's [00:12:00] basically it. There's the macro, the half yearly, then it gets down into progressively smaller pieces, the quarterly, the monthly, and then the weekly. If you buy planners and I've recommended in the past, and I will say, I'm not sponsored. There's no advertising in this podcast. I just like it. I used to use, and one of the things that actually helped me develop this practice, I will, I'll give a shout out to the Ink and Volt planners. That company is a great resource for folks who are trying to develop this kind of reflection habit. It's run by a tech executive. She founded it and I really appreciate it. It really helped me start using their process. Since then I've developed my own, that works for me. If you know anything from this podcast or from my book, I always will tell you it's better to develop something that makes sense for you once you have some grounding, [00:13:00] once you understand what works for you instead of just taking somebody else's off the shelf. I also recommend Pat Kua has a newsletter, and Pat's newsletter at the end of the year, he has his own self-reflection exercise, worksheets that he gives out. If you're looking for a way to kickstart this process, that's another great resource. if you want to try this stuff, but you don't know where to start. Those two are great, but there's lots of others, and you can just try one of those. The thing I would say is if you're going through it and it's not exciting you. It's not interesting you. You're not finding value. Don't feel like you have to do exactly those things. You can skip over pieces. Don't feel like you're obligated to do the whole process. I might try it. And see if it's working for you, but if it's not working for you, don't waste time on it. But instead, think about, [00:14:00] okay if these aren't the questions I should be asking myself, what are the questions I should ask myself? But it's good to start with something that is structured that you don't have to invent. You need to learn for yourself, what works for you and what doesn't. But it's a good place to start. So all this process I talked about might seem pretty rigid, but it's what works for me. And really it's not rigid, it's structured flexibility. I have a plan, I have the things I wanna work on for myself. I have the things I wanna work on for my company. I generally focus more on work. But there's things in there personally as well. I have the plan, but I'm constantly just testing it against reality. It's like building software. If you've heard me talk about Waterfall and then Agile. My plan isn't a waterfall plan. I'm not building Gant charts out for myself for the year. My plan is [00:15:00] a set of goals. And then week by week, I am reorienting based on what's happening to me, based on how things are going, and I'm adjusting. I've learned over time. To not set goals that are very specific, let's say to company deliverables. 'cause company deliverables change. Life intrudes and your best laid plans don't work out the way you want. And that's what that weekly thing is. It helps me adjust. So you don't need to do half yearly, quarterly, monthly, weekly. You can do just weekly or you and a very lightweight process. You could do monthly. You could do whatever works for you. This is what works for me. The reflection process again is really just what's working well, what's not working so well? What should I be doing differently or what should I try to do differently? But if you've never done it, start [00:16:00] with one thing. You don't have to do what I do. I didn't start with what I do. I built up to that. Over time. Block a half day, do some exercises. Do an ink and volt exercise, do the Pat Kua exercise. Invent your own. Find something else on the internet that works for you. Ask chat GBT to make you one. Do an exercise, just ask yourself some questions, and that's it. You've started down this road. If you're already doing this kind of yearly planning or half yearly planning, okay, add the next level. Every Friday, look at your week. Did you spend time on what you thought mattered? If not, why? What prevented that from happening? What might you do differently next week to move you towards the goals that you've set for yourself for the year? And if you're ready doing this, either 'cause you're using one of these planners or because you have your own [00:17:00] process, you can still improve. Reflect on your process. I think this has been one of the things that's really helped me and helped me do this consistently is that I am not locked into somebody else's process. I'm not locked into a process I set for myself 10 years ago when I started doing this. I look every time and go, is this process working for me? And if the process isn't working, I change the process. I introduce new things, I remove things. Every time I do this half yearly process, it's slightly different than the one I did last time because I've changed it and that also keeps it fresh for me so it doesn't feel rote. The goal isn't perfection, it's deliberateness. That is what I strive for. I strive to be deliberate in the choices that I make, and as I said, it gets harder as you get more comfortable in your role. If you've been in a company a long time, if you've been in a [00:18:00] job a long time, or if even you've been in multiple companies, but you've been doing the same job, it gets comfortable. You want to be deliberate. You wanna move from, "I'm busy" to "I'm busy on purpose." If you're hearing this and you think, I don't have time for this, this sounds like a massive waste of time. You probably haven't made it to this point in the episode, but if you feel like you don't have time, but you want to do it . Part of this process for me is making sure I have time for this in my calendar. When I found myself too busy to do that, sharpening the saw that Stephen Covey talks about, I find that I do worse at my job and my team suffers, and my company suffers. So if I give myself the time to reflect and look at how I'm doing my job, I do my job better, which is better for the people that work for me, and it's better for the people that employ me. [00:19:00] So if you're not making time for this stuff, your time is getting controlled by everyone else's priorities. You have to prioritize this for yourself. If you're leading other people, you owe it to them to be intentional about your own growth. Again, I'm doing this to be a better leader, but by being a better leader, I'm better for my team, I help my team and I help my employer. Another thing I've learned, having done this for over a decade now. Is that the practice matters more than the plan. Having that structure is infinitely better than having none. And am I perfect? No. I miss my weekly reflection sometimes 'cause I'm tired or 'cause I'm busy or 'cause I'm traveling or 'cause I whatever. It's like any habit you just get right back to it. But what I've found is that when I am doing it and I'm doing it regularly, I really appreciate it. [00:20:00] And if I keep at it, it gets easier and easier to do. If I get outta practice, it gets harder, but once I get back into it, it's really easy. And that practice, even if I'm not necessarily getting big insights, I'm still finding value from just taking the time to go and look back and think about things just for a few minutes. Absolutely helpful. And then sometimes I do get those big insights and that makes it worth it. And your team notices. When you're reflective, when you're adapting, when you admit this isn't working, let's change it. You're modeling the behavior you want from the people that work for you. You don't want them drones following a plan. You want them thinking and you want them to be thoughtful and you want them making good choices, and you want them to be deliberate about the choices and how are they gonna do that if you're not modeling it for them [00:21:00] so they can tell. People on my team can tell when I am doing this and when I'm not. If you're gonna take away one thing from this episode. You can't lead others to grow if you've stopped growing. Reflection isn't optional. It's not a nice to have. It's the thing that keeps you sharp, adaptive and intentional. Start small, block half a day, buck a quarter of a day. Just a few hours. Do a reflection exercise. Track your time maybe for a few weeks. See what you learn if you've done this before, using somebody else's planner or somebody else's process, or even your own. Revisit your process. See if it's helping you the way it used to. If it isn't, change it. Evolve it. The new year is a liminal space. We just had this nice break. Most of us. Maybe you traveled, maybe you spent time with family. You weren't working as [00:22:00] hard. We're into the new year, things are gonna start ramping up. You got a time here where you can take some time, be reflective and start the new year. Looking forward and starting with a new process, give yourself the gift of focused strategic thinking time. the best leaders aren't the ones who have it all figured out. They're the ones who keep asking better questions. Once again, I hope you had a great New Year's. I'm also gonna remind you once again, speaking at ConFoo next month in Montreal. If you're around I hope to see you there. If you're coming, let me know and we can meet up. I will see you next week in the newsletter. I will see you in two weeks back here in the podcast. Have a great week and have a great new year.