How to go on holiday as a CTO
- Sergio Visinoni from Sudo Make Me a CTO <makemeacto@substack.com>
- Hidden Recipient <hidden@emailshot.io>
Hi, 👋 Sergio here! Welcome to another free post from the Sudo Make Me a CTO newsletter. If you prefer to read this post online, just click the article title. As this is a free newsletter, I do immensely appreciate likes, shares and comments. That's what helps other readers discover it! How to go on holiday as a CTOTaking time off responsibly in a way that allows you to disconnect without causing anxiety, guilt or a gridlock.
Summer is in full swing in the Northern Hemisphere, which means holiday time for many of us. I'm writing this article during my last working week before taking a four weeks break. Being able to take such a long break in the summer is one reason I moved to solopreneurship at the beginning of 2024¹. I don't expect everyone to be in the same situation, but ideally, you should take at least a few weeks off during the summer. Taking such a relatively long break can be either a source of stress or an excellent opportunity for disconnecting, enjoying time with family and friends, cultivating interests, and traveling around. Whether it's going to be smooth sailing or anxiety-provoking depends mainly on how you're going to prepare for the break. In today's article, I'm sharing the strategies and tactics I consistently use to ensure I can enjoy my time off with minimal disruption caused by work-related interruptions.
How to prepare your holidaysHere are my seven recommendations to experience a great vacation where you can be fully present with whatever you decide to do without feeling guilty or anxious about what you might be missing out at work. Many of these recommendations apply to your regular professional life beyond vacation planning, and this is as good a moment to start introducing some discipline in your approach to work. The first one is a clear example of something you will want to practice regularly. Capture all your obligationsMany people in the tech sector, especially in leadership positions, have a habit of keeping track of their obligations, tasks, and duties in their minds. This could be due to different reasons, from a fundamental lack of discipline and habit for tracking things in a written form to the need to look impressive in other people's eyes by showing off their ability to memorize information.
Plenty of literature and research have proven the nefarious effects of trying to keep track of our obligations and duties in our minds. David Allen's Getting Things Done² is all about the concept that our brains are great at generating ideas, not storing them. Hence, you need a system you can trust to keep track of all your obligations and open loops outside of your brain. The Zeigarnik effect³ is a psychological phenomenon that causes our brains to keep memories of unfinished work or tasks. This drains our mental energy, making us less effective in dealing with all those pending tasks. One practice that has been found time and time again to appease the Zeigarnik effect is a very simple one: writing things down⁴. If you're about to go on a vacation, this is an excellent time to level up your practice of capturing everything. I recommend tracking every task and obligation in your system of choice. I don't care which system you use, as long as you have one and use it consistently. For ongoing work, make sure you add a summary of where you are, what your thoughts are on the next steps and why, and all the potential open questions you still have not answered. The more comprehensive you are in your notes, the more you'll allow your brain to trust your ability to pick this work up when you're back without trying to keep its cache warm. Use delegation as an opportunity to test the team's readinessThe worst thing you can do is to assume that no significant decision will be required while you are out. Things move quickly in our industry, and believing that your organization can wait for you to return can be either naïve or irresponsible. As you generally want to plan for the worst while hoping for the best, you must delegate responsibilities to your team during your absence.
Start from the principle that people are not there to sabotage your work. If they do, that's a symptom you have a massive trust problem. Work on that first. If you've been doing a good job at building trust and alignment within your team, more likely than not, things will work out just fine, and you'll discover that people can make a lot of good decisions when given the right combination of context and autonomy. Once you return from your break, you will have plenty of time to make adjustments to whatever decision will have been taken during your absence and provide constructive feedback where needed. This approach is a subset of what we discussed in last week's article about succession planning. If you missed it, you can find it here. Over-communicate well in advanceDon't assume people know and will easily remember you will be off. That's especially true for your peers and other C-level leaders in the organization. Make it a habit to remind people of your upcoming break early and often, and set clear expectations. Some tactics I've seen working well are the following:
In all these situations, make it clear that you are not planning to check in on work-related messages or emails during your absence. Set clear expectations and avoid ambiguous terminology that we sometimes use to make ourselves look better. Don't forget you're a role model; people will tend to do what you do regardless of what you tell them. If you want your team members to enjoy their time off, you should start by doing it yourself. Leave an emergency contact, and stick to itYou can never plan for when things will go really bad; therefore, you want to give people a way to reach out to you when needed. You're still the CTO, and specific decisions will require you to chime in, no matter how much you've been able to delegate proactively during your absence. I like to instruct people to call or text me on my phone if something important requires attention.
Even if nothing major happens, providing people with a way to reach out has a positive effect on two levels:
In recent years, I have had a couple of situations where someone on my team needed to text or call me while I was out. I was glad they did it in both cases, as we faced severe security-related issues on the platform. Being pulled in allowed me to help the team by taking some critical decisions that required the person ultimately accountable for them — myself — to be directly involved. Plan your first day backOn your first day after the break, you don't want to jump straight into action for two reasons: your mind will need time to transition out from the slower and more natural pace of your holidays, and you'll miss a lot of context and information to be up-to-date with the situation. After a break of two weeks or more, I recommend you block out the entire first day to get yourself up to speed again. I recommend you use that time for two types of activities:
Here, I want to take an opportunity to give you a pro tip.
Thirty minutes to one hour of such a debrief could save countless hours catching up with many messages. While you can achieve part of this through the one-to-one conversations I mentioned above, one thing entirely in your control is doing the same for your manager. This is something I practice and find very effective. On the day when your direct manager is back from a break — be it the CEO or someone else — you should leave them a structured and easy-to-digest message with a summary of what happened during their absence, what you think they should focus on or ignore, and an invitation to have a quick call with you if they need any further details. After all, making your manager's life easier is part of your responsibilities. Try this out next time, and let me know how it goes. Plan activities for your off periodBeing off doesn't mean being inactive and doing nothing. It means disconnecting from your profession's daily duties and shifting your focus and attention elsewhere. As you should know by now, one of my favorite activities is reading good books; there is nothing better than a long vacation to enjoy it even further. If you are short on recommendations, you can check out some previous articles where I shared reviews of books I read. Reading is just an example of an activity you can perform during your break that can impact or be related to your professional activity while allowing you to be disconnected. Another example of what I plan to do in the upcoming weeks is the following. I will work about 1,5 hours first thing in the morning daily on the content for an upcoming online course. I will use this more as a heuristic than a hard rule. It's OK if I miss a morning slot occasionally due to family plans or other reasons, but I'll try to stick with it most days. By taking this approach, I can make significant progress on something important while avoiding the typical overhead of scheduling, back-and-forth communication, and reactive work. Take stock of where you are, decide where to go nextLastly, vacations are a great time to reflect on your situation. From a distance, you can gain clarity on where you are and see the proverbial forest instead of just the trees. I recommend you take some time to think about where you are in your personal and professional life and where you want to be and figure out if you need to make any significant changes in the upcoming months. This thinking benefits from long moments of solitude. I recommend taking long walks, alternating between listening to inspiring podcasts such as Deep Questions⁵, and being alone with yourself and your thoughts. In my case, these walks are a great source of insights, ideas, and decisions. Enjoy your time off!I'll keep posting weekly articles even while I'm off, as I find this activity energizing. I have my morning blocks to progress on these articles without feeling pressured. I hope some of these posts will help you with your summer break thinking and reflections. If not, you will have quite some material to read after your break! If you're going on holiday soon, I hope you'll have an excellent time, and I will be happy to welcome you back with more articles after your break. For those of you who are still around, see you next week! If you found this valuableIf you found this valuable, here are other ways I can help you and your company:
1 If you're interested in this journey, check out an article I wrote after the first 90 days. A follow-up will come out soon. 2 This is a classic in productivity that everyone should have read at least once in their life. You can find it here. 5 One of my favorite podcasts, you can find it here: https://www.thedeeplife.com/listen/ Sudo Make Me a CTO is a free newsletter edited by Sergio Visinoni. If you found this post insightful, please share it with your network using the link below. If you or your company need help with one of the topics I talk about in my newsletter, feel free to visit my website where you can schedule a free 30 minutes discovery call. I'd be delighted to investigate opportunities for collaboration! |