Today's article is the third in a 5-part series in which I share the ten most common mistakes I see first-time CTOs make and ways to avoid them.

If you found this article and would like to read the series in order of publication, jump to the bottom of the page, where you'll find a link to the previous articles.

Today's mistakes relate to the area of planning, both at the personal level and at the organizational level.

I hope you'll find this helpful and actionable.

Let's get started!

#5 Being 100% in reactive mode.

Now that you're responsible for the team, everybody seems to request your help. Your calendar is quickly filled with invitations from different directions: the executive team, peers who want to sell you on their ideas, team members who wish to share their concerns and frustrations with you, and so on.

In addition, you have all the usual recurring meetings for one-on-ones, team rituals, goal setting and follow-up, etc.

Every day, a new fire requires your attention: one day, it's a significant production incident; the next, it’s an HR-related emergency or an important client who is unhappy with the quality of the service your team is offering.

In such a scenario, it's easy to lose control of your calendar and let what comes your way rule your day.

You'll always be trapped in a pure reactive mode until you carve out the required time to step back and figure out how to address the systemic issues causing all the fires. Nobody will do it for you; everybody is hungry for your time and attention.

You need to build a solid discipline of planning and dedicate a nontrivial amount of time and attention to proactive work while ensuring the most pressing issues are being handled. This exercise might feel impossible initially, and you might be afraid of letting people down.

The sooner you build a healthy planning discipline, the sooner you'll see reduced chaos, urgencies, and fires.

I wrote an article a few weeks back examining an unusual source of productivity inspiration: Richard Feynman. Though his approach is too radical for today's workplace, I distilled some key lessons that can be applied in the context of engineering leadership.

A lesson from Richard Feynman for Engineering Leaders Sergio Visinoni · Feb 7 Read full story

#6 Having a Tech Roadmap separate from the Product Roadmap.

As you start defining your company's technology strategy, you might feel the temptation to start building your roadmap separately from the product roadmap.

You tell yourself it's easier to take this approach than to negotiate a unified product and tech roadmap with your product counterpart.

Easy is rarely a synonym for effective.

When building a tech roadmap in isolation, you're essentially pushing down all the unsolved prioritization issues to the team. Your team will be torn between executing on the product roadmap and finding time to execute on your engineering roadmap.

This will promote tribalism, frustration, and lost opportunities for your business.

Remember, you are a business leader. This means you need to formulate all technological investments in business terms. A tech roadmap could be a tempting backdoor to avoid that.

Instead, take the time to have those difficult conversations up front with your product counterpart, the CEO, or whoever is responsible for validating the overall set of priorities. Once those critical investments have landed in the overall roadmap, there will be more substantial buy-in around them, and your teams will have a more explicit set of priorities to work with.

I wrote an entire article on this topic and why I think a split roadmap is an anti-pattern. You will find here:

Split Product and Engineering Roadmaps, an anti-pattern Sergio Visinoni · Apr 10 Read full story

Today, I described two more of the ten most common mistakes I've seen first-time CTOs make.

Your situation might resonate with some of them, and you might struggle with other aspects I didn't cover here.

Each case is different, and generalization can help us start thinking about our case from an outside perspective.

I hope you enjoyed today's article.

See you next week!

Q3 Free Mentorship Promo!

Since starting my solopreneurship journey, I committed to regularly paying forward to the community.

In Q1, I offered free sessions to people affected by layoffs, and they all found new jobs.

In Q2, I've been working with 4 members of the WIT community. I’m still wrapping this one up, but the feedback has been very positive so far. Here is a piece of feedback that really made my day:

Your guidance has led me to make significant changes in my objectives, priorities, and the way I organize myself, both at work and at home with my husband. I am deeply grateful for all I have learned and for the positive impact you have had on my life in these three months. Then I think, what must your life be like? If mine shifted so much with just four sessions, you, who have yourself at every moment =). Thank you.

Positively impacting people's lives drives me to continue offering these free sessions. Something is important only if you're willing to sacrifice a non-trivial amount of time and attention for it.

I want to continue this tradition of paying forward to the community. In Q3, I need to consider a reduced availability due to the holiday season. This is why I'm offering a single slot for a first-time CTO, with FREE monthly sessions between July and September 2024.

This offer is open to anyone who has been promoted to a CTO role within the last 12 months. If that's you, you don't want to miss out on this opportunity.

Submit your application via this form. The deadline for submission is Sunday, July 7th, 18.00 CEST. Feel free to share this offer with people in your network who might be interested.

Previous Articles in the Series

If you want to read the previous article in this series, you'll find them here.

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