I’ve always had a hard time writing while working full-time. I put (nearly) all of my waking energy into the business I’m working for, with the remaining energy going to family. Additionally, sharing the internal details of what I’m working on feels like “trade secrets,” “insider information,” or other content that would be owned (or at least reviewed) by my employer. On top of that, let’s be honest: working in public is scary.

One of the best things about writing a weekly newsletter was how it forced me to slow down and think. Of course, I was busy filling out applications, interviewing, networking, and more, but I still made the time to think holistically about where I was and where I was going. The contracting life from October to May was a unique blend of full-time work with a lot of autonomy, making it a bit harder to find the time to write, but ultimately, I (mostly) kept up the pattern.

Joining Thurgood full-time in June, I put writing externally aside as I felt I no longer had a good perspective to help those laid off and needed to focus inward on building a new business. I recently reconnected with former coworkers and realized I hadn’t publicly announced my move from fractional CTO to cofounder & CTO. Much of my writing has turned inward as I’ve worked to help crystalize and document our strategy and experiments. Now that I’m a few months in, I have some time and am ready to surface some of the work I’ve been doing. I doubt this will return to a weekly newsletter, but it should be more regular again. 

Thinking through writing

I’ve read many times that “leaders are readers.” While I agree you need diverse opinions and thoughts to shape your leadership and direction, reading is also helpful as it shapes your writing. Writing is key in capturing, crystalizing, and synthesizing your thoughts. Writing slows you down to evaluate and test what you’re saying. Let’s break this down:

• Capturing
  • Thoughts can be so fleeting that pausing to write slows you down, and if you give yourself the liberty not to edit as you write, you’ll find several ideas floating around in your brain. Putting them down somewhere frees you to let them go and see if they resurface, refine, or die on the vine.
• Crystalizing
  • Because writing is slower, you can tighten your thinking, test your opinions, and see the holes in your thought processes. First-draft ideas are still just first drafts but replayed in a second draft, email, or speak to others, are much more refined and ready for debate and consumption.
• Synthesizing
  • Putting down your ideas allows you to see the patterns between them or to combine two ideas into something that’s even more powerful than the original parts.

Mistake #61 – Thinking inside the box

For years now, I’ve been part of a much larger organization, and I could (generally) trust others to run the finances, sales, and other key parts of the organization. As a founder, those are (partly) my responsibility, too. Once we secured an initial pre-seed round of funding for Thurgood, it was easy for me to go completely heads down on getting the technology in place to support the rest of the company and neglect the broader details.

As an engineering team, we did a good job keeping things lean and shipping early. Unfortunately, I failed to create a concrete enough picture of the engineering budget to forecast our spending through contingency plans. As we launched to public users in June, we quickly began to encounter a variety of significant headwinds. Our user base did not organically grow, our application was not sticky, and our user acquisition channel was slow. Of course, additional experiments would be needed to get these rolling, but the timeline for securing additional funding was slipping beyond our runway. 

While running the Incubator at Indeed, we had a rule of thumb for engineering teams not to build anything that wouldn’t move the needle on their current runway or one runway beyond. That’s a luxury only afforded to corporate startups. As a venture-backed startup, our vision is even more narrowly focused, and unfortunately, the length of the runway is the biggest variable we have control over. We had to lengthen the runway as much as possible to buy time for our experiments on growth to be run and had to close out our contracts and lay off two very qualified full-time engineers. 

So we’re back to a group of founders, each pulling as hard as we can on this rock to get it rolling.

For over a year, I’ve been writing (mostly) weekly updates from the post-layoff seat to contracting and soon to a new full-time role. I’ve seen my writing go from optimistic, to broken, and back again. It’s been a wild year, and unfortunately, 2024 is shaping up to be challenging too.

Photo by Clay Banks on Unsplash

This week another 1,000 Indeedian’s joined a club they didn’t choose to be a part of, ex-Indeedians. Like many of my former coworkers (Indeedians and ex-Indeedians alike) I’m putting my time, my network, and my camaraderie out there for you all. If there’s anything I can do to help, please reach out: on OnlyNewMistakes, via Substack, LinkedIn, email, SMS, or whatever works best for you. 

Rather than telling more of my story, I’m going to grab a few of the better bits of support from previous posts and re-share them for those who’ve been laid off recently. Rather than make this just a straight link dump from previous posts, I’ll provide a few updates/insights that have come with hindsight since those posts.

1. Immediate reactions & next steps – week #1 
   1. The first thing I see is the optimism in this post. I still thought we were in the same old tech market. We are not. It has changed. Be prepared to search for a while and to have fewer options than you would have previously.
   2. Networking is crucial. You have the time. Reach out to the unemployed and connect. Reach out to people who are working too. Get recommendations, referrals, tips, resume reviews, and anything else they offer.
2. The funnel of despair – week #5
   1. Lots of folks (including me) shared their stats along the way, but the ratios of jobs applied, interviews, and offers are VERY real right now. Creating a system to track your applications, and following up is important.
   2. That mountaintop-to-valley-to-mountaintop ride of the “Morale over time” chart is very accurate. Be prepared for the rough days and have a plan. Get out, get some sun, and see friends.
3. Using the tools well – week #13 & week 32
   1. From making sure you have an active role in your LinkedIn to trying other tools (Otta, BuiltIn, etc.) make sure you use your tools well.
   2. AI tools for resume review and cover letter writing are quite good and can save a lot of time when you are firing off a lot of applications.
4. Focusing on what you do well – week #22
   1. Writing down things you do (and did) well and reading those frequently was a lift when my spirits got low. I emailed my list to myself and snoozed it each morning to the next day or two so that it was a regular message reminding me to focus on my strengths.
5. LinkedIn supertips – week #21
   1. Using the Social Selling Index to understand your LinkedIn profile’s strengths and weaknesses and how to improve your profile’s ranking.

There are weeks of other content here or on any of the other platforms I share this content on: OnlyNewMistakes, via Substack, LinkedIn. I hope it helps. 

I’m several weeks behind in writing and wanted to jump back into it, so today’s newsletter is a collection of four short notes rather than the previous format (not that I was ever super strict about the structure of this newsletter.) I hope you enjoy it.

Week 52 was an emotional one for me. Seeing the calendar roll past March 22nd (the one-year anniversary of Indeed’s layoff) meant recognizing that it’s been a year since I felt stable in my income, work, and career. There were a lot of emotions wrapped up in that week, and I wasn’t ready to write about them. 

Now that I have the distance of a few more weeks, it’s easier to see that I had put a lot of my self-worth into what role I was playing and the company I was working for. Much like COVID taught me about the value of connection and networking (a story I can share or re-share in the future,) the layoff gave me more clarity about what matters in my work. Ultimately, it’s about working with people I like, on a mission I value, and making tangible progress. Those things were less and less the case for the last year or more of my time at Indeed.

While I’m not 100% back to where I was at Indeed, my new roles have given me a chance to work with some great leaders on missions I am excited about and to see businesses formed from nothing. I’m learning (a lot). I’m enjoying the work (a lot). And I love the teams I’m working with. There is not much more I could ask for.

Living Life at 100 MPH

The last two to three months have been extra chaotic. With the fractional CTO work kicking into the highest gear in February and our kids’ Spring sports kicking off (often before Winter sports had fully wrapped up), we went from standard four-kid-family busy to ultra-busy. But this isn’t me #hustle bragging. This is me being honest.

I’m exhausted and behind. I wanted to launch HeatCheck and acquire users. I wanted a second startup to move away from Excel sheets and to a custom product to run its business. I expected to be running a cohort of executive coaching sessions. And I wanted Thurgood ready to launch by this month. None of those things have happened on my schedule. They’re all significantly moving along and approaching our goals, but each still has its hurdles.

On top of that, one of the first engineers I hired at Indeed passed away suddenly at the beginning of March. It was a real shock and a reminder that it was time for simplification. While the contracting life has paid the bills, and I’ve learned a lot about it, I don’t think it’s my long-term play. I’m starting to trim back the contracts and not actively seek others. I want to see each of these things across their respective finish lines. I want to reconnect with friends. I need to get back to working out regularly. I have to have some margin in my life. So that’s my next challenge, trimming and replacing with life-giving activities (friends and exercise in particular.)

Launching Early

Two startups I’m working with will launch very soon but look different. The bootstrapped HeatCheck is approaching a marketing launch that will hopefully begin to bring in users and revenue. Thurgood is about to kick off its pilot and see the first users on the platform as well (although revenue will likely lag a bit behind that pilot).

Reid Hoffman is often quoted as saying, “If you’re not embarrassed by your MVP, you’ve launched too late.” In the case of HeatCheck, I’ve been partnered with that team for over a year now, but the nature of a bootstrapped product is that every penny spent comes from someone’s pocket, so you’re constantly wondering when the right time to get real users into the product would be. Thurgood is VC-backed, which has allowed the team to run faster (hiring a few contractors to start and soon a founding engineer) and the marketing budget to do a pilot kickoff next month.

Both will still have a handful of rough edges and feature “cul-de-sacs” at launch. We’ll keep working those out based on user data and feedback. That will be a fun and exciting new phase for both projects. I can’t wait to get there!

Recovery Weekend

No baseball last weekend meant a recovery weekend. Usually, it’s two baseball games on Saturday and one or more on Sunday (play until you lose). We still had a handful of activities in the week leading up to the weekend off, and of course, there were still a few things to do on the weekend. Still, on the whole, it was things we wanted to do that allowed us to catch up on housework, see Dune Part Two in the theater, and plan a few upcoming family activities. Now that the weekend is nearly done, I’m looking to the next few weeks and realizing that it will be a full schedule between now and the end of June. 

We’re somewhat at the mercy of the kids’ schedules, but I think I need to schedule a “do-nothing” weekend every three months or so. Maybe the kids are still coming and going, but we arrange for carpools or plan for them to miss their activities that weekend as well so that, as a family, we can collectively catch our breath. I know Summer will naturally give us a few of these as there are fewer outdoor sports thanks to the Texas heat, and in fact, after some of the kids are dropped off for their various camps, we’ll get some quality 1:1 time with the remaining kids. So, even as busy as the summer looks, I’m looking forward to the recharge that comes with it as well.

This post is being drafted from beautiful Glenwood Springs, Colorado. Since we’re on vacation it’s much shorter than usual, but I was going to post this to LinkedIn last night and I realized that it was more or less a micro-update. I hope everyone has a great Spring Break! 

Today I did a hard (for me) thing. I don’t have great balance on the whole. I have wide feet with high arches. 

This makes skiiing a tough choice for me. Rental gear rarely fits well, and by well I mean it rarely produces anything less than excruciating pain. I’m clumsy on ice and fall a lot. It just doesn’t come naturally to me (and snowboarding isn’t much better.) 

But as the bruises and aches can attest I did ski today. I learned, I improved, and I survived. I even had fun. Sure, I’d love to keep up with my family but that’s a lot more lessons and practice away. For now, I’m happy to have taken the challenge and learned to (somewhat) enjoy something my family enjoys very much. 

So let me encourage you with two things today: 

1. Take the challenge! Try something new and push yourself. Let me know what you do! 

2. For those with a family or a partner, find something they enjoy and make it something you can enjoy (even just a little) too.

​​

Fun

With two startups trying to launch and one trying to raise a round of funding, things are hectic right now for a team of one. In a typical year, I’d be volunteering as an election clerk, happy to take calls with new startups that are looking for a user experience interview, and volunteering with my kids’ various activities. When I was a Senior Director running an 80-person engineering organization, my calendar was often booked completely solid from the start of business to the end of the workday, and at least one day a week booked again from the kids’ bedtime to my bedtime with Tokyo meetings. It was standing room only in my calendar.

One of the biggest realizations I had over the last few years is that managers and executives need maker time, too. Scheduling my time to work on proposals, budgets, performance reviews, and more was a requirement. I had to actively manage my calendar, not allow it to manage me. I’d take a stab at how long a particular task would take, block out time on my calendar to accomplish it, and invariably move that around as meetings came onto my calendar. The great thing about seeing it visibly on the calendar as I rearranged things to accommodate people was that I could visually (and viscerally) know I was delaying my deliverables and work. 

Now that I’m solo and working with several startups, having ChatGPT and CoPilot has made me much more productive, but I still have to pay attention to my daily, weekly, monthly, and quarterly goals. I’d be lost entirely without those goal trackers and a to-do list. Occasionally, I’ll get away from tracking and prioritizing things and find myself just flailing from one urgent item to the next with loads of anxiety. Sitting down, writing everything down, prioritizing, delegating, dropping, and executing on items always gives me more peace, and things get back on track quickly.

Slipping Into a Traumaversary

As we approach the one-year mark since the Indeed layoff, I want to warn about the concept of the “traumaversary.” It’s a well-documented (even if not wholly provable) phenomenon in raising adopted children and others who experience significant traumas. Many situations can trigger feelings of loss, anger, sadness, and more throughout the year. I’ve seen birthdays, anniversaries, vacations, and so much more trigger those feelings. So, as the first anniversary approaches, plan to do something for yourself. 

Slip or Slide?

One of the startups I’m working with has offered me the full-time CTO role starting at the end of my current contract. Having contracted for almost six months, I’m debating whether to remain a fractional CTO or dive head-first into a dedicated role. I love the team. I’m enjoying the product. We have funding and will be on track to secure more this summer. All signs point to joining. I could just slide right into that team quite easily.

But being a fractional CTO has a few perks. The cash compensation is better (if I can continue to secure enough contracts). I have more control over when and how much I work. I also get to work with several teams at the same time. 

I’m torn between the two opportunities. So, it’s time to consult my “personal board of directors.” I have a few close friends I regularly meet with when I have big decisions. We catch up other times to hang out and chat about other stuff, too, but occasionally, I will ask them for lunch, beer, or coffee with a clear agenda. My board of directors comprises several people from different perspectives, and each plays a slightly different mix of roles in my decision-making process.

A few are close friends with a similar spiritual background, and they help me consider how my relationship with Christ may guide my decision. A few others know the business and technology scene inside and out and can help me guess the challenges I’m likely to face and my chances of success. Last, but certainly not least, a few others give me guidance on choosing well with regard to my family and obligations to my children. 

I’ve had this kitchen cabinet for years now, and they’ve helped me through a lot of hard decisions. I highly recommend the process, and if I can be this sort of mirror for any of you please reach out.

Fun

Indeed grew their headcount by 750% over my seven years there. We interviewed tens of thousands of people across hundreds of roles. Hiring was vital to the engineering leadership role when we were in hypergrowth from 2016 to 2020. I interviewed hundreds, maybe even a thousand people, but ultimately, hiring wasn’t personal. It was a part of building teams, finding the talent we needed, and unlocking new possibilities for the company. It’s just business.

Now that I’m working with early-stage startups, hiring is incredibly personal. These teams are going from founders to hiring their first employees. One of the startups I’m partnering with has hired a Lead UX Designer and a Head of Product and is actively recruiting a Founding Engineer and a few engineering contractors. We’re building the minimal product at the same time that we create the minimal team. 

Joining an early-stage startup is an entirely different proposition from joining a multi-billion dollar, profitable, established company. Convincing engineers and others to jump ship from the (relative) safety of a prominent organization in this climate has been challenging (to say the least.) The good news is that there continue to be people who want to test their mettle by jumping into the startup world. 

Get in the arena

“It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.” ~ Theodore Roosevelt

This quote was something we used as a badge of honor for leaders of projects in the Indeed Incubator. It’s a good reminder, no matter what challenge you are facing, to face it head-on. I know startups are not for everyone, and that’s fine. But everyone has a challenge in front of them: personal, professional, or something else entirely. Challenging yourself and overcoming or learning from that challenge is what matters. 

Each one mentors one

Interviewing is time-consuming. A friend just mentioned getting 700 applicants for an unposted software opening. There’s a lot of work to go through 700 applicants, even if you don’t personally interview each one. One of the best techniques for scaling your recruiting efforts (in addition to many other areas of your business) is to have “each one teach one.” 

Implementing a mentorship program (apprenticeship, shadows, succession planning, all just different flavors of the same ice cream) is an incredible tool for providing growth, resiliency, and continued alignment within your organization. Hiring is a beneficial area for mentorship because it will give you two sets of eyes on key interviews and candidates. Often a second person in the room comes away with very different perception on the strengths, weaknesses, or biases of the candidate.

The key to any good mentorship program is to have clear goals and measures so that you know when the mentorship is complete (and to move in that direction with clarity and purpose.) For example, getting interviewers to a place where they can confidently lead interviews and evaluate talent is an excellent unlock to doubling your interview capacity. 

Fun

I never wanted to be fully remote. As an engineer, I recognized that the ability to work from home was there once the high-speed internet became ubiquitous and most company services were accessible via VPN. Going heads down for most of the day on challenging code was incredible. However, I needed the in-person interaction to get code reviews, feedback on designs, and to stay connected to my team. “Maker time” (dedicated time to focus and stay in a flow state) was key.

After I moved into management, I had less interest in being remote. My ability to quickly connect with my team members and peers, get everyone in a room and discuss issues, and connect easily trumped my desire to avoid the commute. Plus, I didn’t need “maker time” nearly as much anymore; “manager time” (collaboration and discussion primarily) worked great at the office. 

I interviewed for a fully remote role in 2015 but didn’t want to be a manager and only see my team face-to-face a handful of times each year. And then 2020 came around. By then, I had been managing teams in Tokyo and Seattle and only seeing them a few times per year (although I had leaders in each location who saw them much more often, of course.) Like everyone else, I was thrown into fully remote management. I still think it’s less ideal for managers and a boon for engineers, which is why I particularly like a version of hybrid that allows everyone flexibility to come in when it’s convenient for them. However, we’re all still figuring this out and probably will be for another decade.

In-person collaboration

As we get closer to launching the stealth startup, the team has been increasing the face-to-face time. Even working side by side for half the day the other day, I realized several topics I hadn’t discussed with the team. A few minutes later, those were put to bed. It was a good reminder that the speed & seriousness of conversation should be directly proportional to the fidelity of the conversation. 

• If you want to go fast, get the smallest group of people necessary into a synchronous conversation on the topic.
• A face-to-face conversation is best if the material you’re discussing is sensitive (performance management, for example).
• Email can be an excellent medium if you can wait more than a day for the answer.
• If you are blocked by something and need a reply today but not immediately, instant messaging/Slack/SMS works well.

Work → Social

Concerning work-from-home, the cat is out of the bag in the long term. Aside from highly regulated industries (security, finance, etc.), for those of us in tech, we will have some work-from-home component to our jobs for the foreseeable future. And honestly, it’s good. The balance of picking up my kids from school, enjoying lunch with my wife, and (thinking about) working out has generally been a good addition. 

While I enjoyed the work relationships I built over the last 20 years, ultimately, we were never much more than “work friends” in most cases. I knew about their kids, birthdays (sometimes), and vacations, but for most of them, the main thing that brought us together was work. Occasionally, I’d make a longer-term friendship around another shared interest (Broadway, baseball, board games, our kids/spouses, etc.). But that was rare.

Since COVID sent us all to work from home in 2020, I’ve leaned more toward my “non-work friends.” We already had friends in our neighborhood, through our church, and through shared activities (primarily kids’ sports). It’s been challenging to make this transition, but the reward of having friends who supported me in the layoff and transition to a fractional CTO has been incredible.

Fun

Last week, I explained my role as a CTO/lead developer on HeatCheck and as a Tech Executive Coach. In addition, I’ve also been working with a startup still in stealth mode, and a property tech company that had almost no technology team before I joined. Each of these companies needs something slightly different from me. For HeatCheck, I’m setting technical direction and implementing solutions in green field space. For the Tech Exec Accelerator, I’m writing training and coaching leaders. For the stealth-mode startup, I’ve been their product lead, and now I’m recruiting (more on that in a moment.) For the property tech company, I’m providing technical direction across an existing (albeit fledgling) business.

It struck me tonight that the sum of these parts was the best part of my last job. Setting product and technical direction, recruiting teams, and coaching individuals. I get to do that with a lot less email, meetings, and commute these days. Of course, none of these projects stays the same very long. They start with product leadership, merge into recruiting, and very soon if all goes well, I’ll be leading a team of engineers and designers to build and launch a new application. Let’s talk about recruiting for a minute.

Stealthy Recruiting

Stealth-mode startups are a funny thing. You’re constantly in this limbo between sharing too little to garner interest and divulging too much that scares people off. This is a startup, after all, and by definition, “startups are bad businesses.” They aren’t suitable for everyone. Even if you are right for a startup, sometimes the timing is off. I had a two-month-old when I joined Bazaarvoice nearly 17 years ago. My wife did not understand. Thankfully, I had good counsel, and that turned out for the better.

Now, I’m the engineering leader, pulling in the initial critical roles to “prime the pump” on this team. We’re trying to fill the key roles of a contract product UX designer and a founding engineer. I’ve had to break my days/work up into smaller compartments to keep track of all of the candidates, interviews, and emails necessary to do this. (I had gotten very spoiled by the support of great Talent Acquisition partners over the last few decades.)

Wall Time vs Company Time

One of the most unexpected observations came when I started working with the property tech startup at a quarter-time rate. They needed technical guidance, but due to budgets (both theirs and also in my capacity), we could only align on a quarter-time contract. That means, each week, I get approximately 8-10 hours of work on their project. So, over the last two months, I’ve logged approximately 8-10 days’ worth of work for them. Meanwhile, they’ve moved the entire company forward by two months. The impedance mismatch between those has led me to do things differently:

1. I didn’t go through as much rigor in the product definition and feature set analysis as I usually would have to validate the needs and designs.
2. I am ruthlessly prioritizing work and using automated tools like ChatGPT liberally to speed up my development, writing, and more.
3. I’m careful to remind myself that I’m quarter-time, and I’m still finishing “week two” on this project, not week nine like my mind wants to believe.

Trying to keep up with the rest of the team and company is a fun challenge. To keep pushing to do the engineering work faster, more efficiently, cheaper, etc., is a skill not practiced in a long time in software engineering (for the most part), but that’s a topic for another day.

Fun

I had a hard time processing the video shared by Brittany Pietsch this week, and it pushed me to think more about my layoff. I had generally reached the “acceptance stage” (Kubler-Ross stages of grief model: Denial, Anger, Bargaining, Depression, Acceptance) for the layoff, but that video pulled me back into the anger range again briefly. Thankfully, I’m now 9+ months removed from the layoff, and those feelings didn’t last too long. Afterward, I had a (somewhat) new revelation: Indeed’s layoff pushed me to do something I would probably have never done on my own, even though I had considered it for a long time. Starting my own company and contracting with several different companies (simultaneously, no less) has been one of the most growth-inducing moves in my career. 

This week and next, I wanted to share about the projects I’ve been working on the last few months. I’ve alluded to them previously, and at least one is still in stealth mode, but the fractional CTO/consulting world is a new one for me so hopefully sharing learnings from this will help others decide when/if to make the jump that I should have more seriously considered years ago. 

The truth is that this work is not that different than my last role at Indeed. There I was leading between seven and 15 teams working on early stage new product innovation. I helped coordinate staffing, budgets, roadmaps, architecture, alignment, and much more. The biggest difference now is that I don’t have a support staff to help me do all of this. I always ran a lean organization, but I also preached as often as I could that “a team of one was no team at all.” But that’s where I am right now. Let’s start back in April of 2023 with the first post-Indeed project I took up.

Commiseration & Encouragement

The day I was laid off, I reached out to two good friends. One invited me out for a beer that afternoon/evening, and the other said “let’s grab coffee in the morning.” Both were exactly what I needed. A chance to vent, commiserate, and complain in a safe space, and then quickly a place to move into brainstorming what’s next and action. In fact, over coffee the friend explained that he had started HeatCheck just a few months before and had been building the MVP with WordPress and ChatGPT. I took a few weeks to think things over and since I had no serious job prospects, figured that sharpening my development skills by rebuilding his application on a more scalable, flexible platform would be a good challenge. Over the course of about a month of work I was able to build the application (including all of the Stripe integration and Progressive Web App hooks.) Not too bad for a rusty old programmer with a fair amount of support from Github’s Copilot. 

I took a break from building this to take the family on vacation, and when I came back finished off the mobile applications (iOS & Android) and started preparing for a more public launch. As we speak we’re preparing the last bits of data for several more sports (Baseball, Softball and more), and working on a Gmail integration for emails & notifications. This project has been a great push to get my hands on code, deployments, monitoring, and all of the nuts and bolts of shipping software that I had gotten so far removed from.

I <3 Coaching

I started my career teaching due to the Dot-Com Crash in the early 2000’s right as I was graduating with a Computer Science degree, specializing in web development. That meant there were little to no web development jobs, and post 9/11 most of the software jobs I was seeing were in Defense related companies that I had no interest in joining. I got the chance to teach Visual Basic and Java over the next year and a half while working on my Masters degree in Information Science & Technology (effectively Applied Computer Science & Management combined). I really enjoyed teaching and always thought that it might be interesting to go back to that space again another time. 

In August I was approached by Emergent Execs (an executive coaching firm here in Austin I had used previously to help train new managers) to help develop a Technical Executive Accellerator curriculum. Over the next few months I wrote a synopsis of the course, dug through existing executive coaching materials, and consulted friends to see what topics I had to include in this training. We’re now thick into the sales and marketing phase of the program launch. Meeting with prospective attendees to see if they are a good fit, would be interested, and have budget for such a program.

I’m excited to share my experiences and materials with managers, directors, VPs, and CTOs in product, engineering, and UX over the next six months. I really want the course to be an accellerant for people’s careers and a meaningful improvement to the teams’ they lead. More than anything, I’m excited to be coaching individuals one-on-one again, as that’s one of the things I miss most post-Indeed.

Fun

Happy New Year! Welcome to 2024. It’s time to start a new journal. I’ve kept journals for over 10 years and have notes from my time at Bazaarvoice in 2010, maybe even earlier if I look hard enough. They’re helpful for reflection, and occasionally, there’s something I did previously that I cannot find in my brain but still exists on paper in a journal somewhere. Thanks to Bullet journaling, I have an index and page numbers, and the whole journal is more or less chronological, so finding something I’m interested in is generally possible.

However, in the last few years, I have moved away from pen and paper for my daily journals. I still love the tactile feel of a good journal and a great pen, but the simplicity of the Remarkable for me to be able to have all of my journals (personal, work, 1:1s, church, and more) at my fingertips at any time is too much to ignore. I switched to the Remarkable when I got mine back in late 2021 and never looked back (except for travel journaling, but that’s different.) 

Anyway, I digress. I wanted to tell the story of how vital writing has been to processing all of the changes that 2023 brought. This weekly journal has been an outlet for how things are going, a way to keep up with those going through it alongside me, and simultaneously a way to connect with others beyond my immediate network. Journaling has been incredibly important as 2024 came around, and every contact I have went into hyperdrive (recharged after the holidays, or ambitious to get stuff done early in 2024…who can say.) So, today’s focus is handling the full steam ahead of the New Year charge.

Acknowledgment

Like clockwork, every year in January, the gyms are packed. Recruiting (usually) kicks into high gear as new annual budgets open up and everyone returns from the holiday break. And those returning to the office have a renewed vigor to dive back into work. It all culminates in a lot of action, but what progress? 

Some people set annual goals before the New Year celebration, while others wait until after, but no matter when you set the goal, the question is how you will track and obtain those goals. Many frameworks exist – OKRs, KPIs, MBOs, BHAGs, etc. Ultimately, they are all just tools. The question is how to communicate those goals so that they’re understood clearly and how will you track the progress to know if things are working.

I know this will ruffle some feathers, but I believe OKRs are the worst form of goal tracking – except for all the others I’ve tried. I appreciate OKRs for their inclusiveness when you take the time to communicate high-level objectives and listen as the objectives and key results (the O & KRs) trickle back up. It takes time to get them right, which takes planning and preparation. But, if you 1) avoid setting overly aggressive Key Results (realistic goals work fine, and you can even recognize overachieving), 2) allow your team to adjust OKRs (within reason) when appropriate, and 3) don’t abuse OKRs by driving them to the individual level or use them for individual performance management, I believe you’ll get a lot of mileage out of OKRs. Here’s a good tip (5m read) for teams trying to improve their OKR game.

Mistakes were made

Mistake #41 is missing week 41. Due to the aforementioned busyness of the New Year, the week just flew by, and I didn’t get a newsletter published. 

More mistakes were made

For week #42, I wanted to discuss something personal. My wife and I have been married for over 20 years, but only in the last year (since the layoff, really), have we taken the time to collaborate deliberately. In the hecticness of raising four kids (yes, really) between the ages of 8 and 16, we had gotten into a routine of drive-by co-parenting. What I mean by that is that we were just rapidly throwing out items for discussion/planning/execution as we thought of them, rather than being intentional about how we planned our lives. Starting last year we moved to a model where we have a weekly meeting to discuss how things are going, and I borrowed heavily from a structure we refined for team meetings. It looks a bit like this:

Agenda

Agenda items that we have not yet scheduled, discussed or returned to. Copied to the Notes section each meeting as the start of the agenda for that meeting. This can be sorted, or sorted at the start of each meeting.

• Item A
• Item B
• Etc.

Action Items

Updated each week with the set of action items that are still remaining, due dates, assignees, etc.

Mine

• Item 1 (Jan 15)
• Item 2 (Jan 31)

Hers

• Item 3 (Jan 16)
• Item 4 (Feb 1)

Notes

Running history of meeting notes. Dated. Completed action items since last meeting are copied here.

Jan 10, 2024

• Item A
  • Notes from our discussion of Item A
• Item B
  • Notes from our discussion of Item B
  • Decisions are noted. Action items are too, and then put in the lists above.
• Completed action items (items completed since the last meeting, or in this meeting.)
  • Item 5 (Jan 1)

This structure was excellent for team leadership meetings, 1:1s, and other meetings. The only thing not covered here is “quick discussions” and “longer topics.” Pulling quick discussion to the top, and more extended topics get a scheduled date for discussion (along with assigning pre-work if needed to attendees,) makes sure that there is dedicated time for discussions that might otherwise always get pushed out.

Fun