CTOs Worry About: COVID-19

Welcome to What CTOs Worry About: a newsletter in which I revisit a decade of conversations with CTOs about their problems and the solutions they’ve tried. I’ll also incorporate my own experience as a CTO and entrepreneur, and from time to time I’ll interview my friends. Tweet your own tech leadership questions to @bkanber with #ctoworry, and I’ll try to include them in an upcoming newsletter. Subscribe now to join a weekly subscribers’-only discussion.


Most of the time, tech leaders face common and relatable problems. We face growing pains as companies and have to figure out how to balance our teams, provide career paths for employees, and so on.

Today though, in mid-July 2020, we’re facing some pretty uncommon problems. I’m hearing lots of new concerns from CTOs over the last four months: employee health and safety, economic collapse, shifting to work-from-home, figuring out how best to support Black Lives Matter, and whether (or how) to attempt a slow shift back to office work.

My plan for this newsletter was to go over old conversations, because over the years I’ve found that there are a finite number of core CTO concerns. But that type of advice isn’t as valuable today. The next few newsletters will therefore consist of more timely topics, and this week’s will be COVID-19.

Here’s what I’m hearing CTOs worry about most.


Are you keeping your offices?

What are your (company’s / team’s) overall plans regarding office vs work-from-home moving forward?

This question was more popular back in May and June, as many companies were adjusting to remote work and trying to figure out if it was viable long-term.

I’m seeing about 60% of companies and teams keeping their office situation “as-is for the foreseeable future”, meaning that they’re going to keep the office but continue to WFH until it is safe or until some other factor changes. In general, these respondents are larger companies with a lease on a single large office space.

I’m also seeing most companies with multiple offices trying to figure out how to combine/reduce/eliminate office space. Here I’m seeing all sorts of permutations; keep the NYC but close the midwest, keep the west coast but close NYC, eliminate the overseas office and have them be WFH, etc.

Of course, a number are going fully remote now. The companies that I see doing this already had a good remote culture in place while maintaining a colocated office. An interesting thing to look out for is how sales and marketing teams will adjust to remote work; the companies I see going full-remote already have a solid product/engineering remote culture, but colocated sales/marketing. This isn’t necessarily a “CTO worry”, but we will need to figure out how to keep extroverted members of the team (regardless of department) fulfilled through quarantine and remote work.

In short, everyone’s just doing what seems best for them. I do worry that some companies are underestimating the effort it takes to develop a strong remote culture. Everyone pulling together to tough-out a few months of WFH is different from shifting your organization to a permanently distributed one, so watch out for landmines here.

Leave a comment


We have people desperate to come back to the office.

Are there any policies that make sense?

This question circulated around in mid-June as NYC had flattened the curve and kept it flat for a bit. THE RESPONSES TO THIS QUESTION ARE THEREFORE OUTDATED.

I DO NOT RECOMMEND YOU ATTEMPT A TRANSITION BACK TO THE OFFICE. Cases in the USA are surging as of this writing and I strongly recommend everyone continue strict social distancing and work-from-home policies.

Now that the disclaimer’s over: last month, I discussed with several CTOs what a return back to office work might look like. Is it possible to do it responsibly? If so, how would it work?

There was unanimous agreement on the following points:

  • Return to office work would be opt-in, and ideally limited to the lowest-risk population (how a company could enforce this was beyond us)

  • Office occupancy would be kept very low, 25% or less

  • Good office ventilation (open windows) required

  • The company would need to provide PPE and at very least, cleaning equipment and training, or at best, daily professional cleaning

However, even then, we still couldn’t agree that it was a good idea or safe to return to the office. We brainstormed for a while and came up with some more bullet points to play with:

  • Only people who can walk to the office can use it (ie no commuting allowed)

  • Co-working in Central Park with PPE and social distancing

  • Only one person in the office per day

And even then, we still couldn’t agree that any of this would be a good idea for the company to officially support. So, even when the curve was pretty flat and we were feeling confident, we couldn’t come up with a great way to return to office work quite yet. At best, we were able to come up with a few safety precautions. Again, I do not advise anyone to attempt to return to the office unnecessarily. It is all of our responsibility to flatten the curve.

Leave a comment


We have a team member who’s always been a bit abrasive in written communication.

They’re good in-person but now that we’re remote, it’s becoming a problem. How can we address this?

There were a few variations of this question recently, but it boils down to the basic issue of an employee who was “marginally toxic” pre-COVID becoming more toxic now that communication is largely written and asynchronous.

The obvious reaction to this is “you should not retain a toxic employee”. Since this isn’t a 1-on-1 advice session, only you can know your circumstances. Perhaps it is not possible to let that employee go.

I find that whenever there’s a discussion of a toxic employee, the first question that must get resolved is one of self-awareness. How aware is the employee that their own behavior is seen as toxic? Have you (the manager) ever addressed it with them directly? (A surprising number of managers only dance around these issues, but it’s important to have the hard conversation.)

One idea that floated around this conversation was a code of conduct or a looser “styleguide” for Slack/GitHub/Jira tasks. I’ve not seen anyone implement this yet, so the jury’s out for now.

One of these conversations landed on a good point: if you decide to retain an employee that you know is toxic, it’s now entirely your responsibility to a) figure out why they’re toxic in the first place and fix it and b) protect the rest of your team from that toxicity at all costs.

This really only applies in cases where someone is just marginally toxic, and perhaps is just reacting to recent circumstances rather than displaying chronic behavior, and is also otherwise a very valuable team member.

In one case, the employee in question was one of the early team members, had always been pleasant to work with, and developed some of the core systems early on. However, this person had become more abrasive in written communication over the last year (still pleasant in-person), and it reached a breaking point during the early weeks of COVID lockdown (with no more redemptive in-person meetings).

We discovered that the employee had long shown signs of unhappiness in their work. After contributing and developing core systems, that person’s role shifted to maintenance and support, and had become increasingly frustrated with seeing his work be managed by sales managers and customer demands. Additionally, this person was now in the customer-support loop, and spent most of their time just adding reactive patches, doing maintenance, and fulfilling feature requests.

This is fortunately one of the cases of employee toxicity that may be resolvable. A recommended course of action was to immediately eliminate that employee’s customer support duties (as that seemed to be a large point-source of stress for the employee), and then to figure out if there are any greenfield projects they could take on in Q3.

The moral of this story: some employees are slowly and quietly driven to the brink by the circumstances around them. It’s easy for a manager to accidentally lead someone into a situation like this. If you see a typically-reliable employee start to become more difficult, you had better take a step back and try to figure out if there is a root cause nearby.

Leave a comment


How are you adjusting your roadmaps for Q3 and Q4?

Everyone’s Q1/Q2 roadmaps got messed up — and now CTOs are wondering how other companies are adjusting to this. They’re asking questions like: how far out are you roadmapping? How are you adjusting for remote/WFH? Are you incorporating plans for office reopening?

I’m hearing most CTOs assume that their teams (if not their companies) will be WFH through the rest of 2020 at least.

I’m also hearing some CTOs making downward adjustments to WFH productivity modeling. One CTO said “I’m assuming 4 productive hours per day per employee”. The general consensus is that productivity is a little lower at the moment, but we’re all hoping it’s a temporary condition caused by undue stress, fear, and unexpected life changes.

Overall, it seems like it’s not a bad idea to plan for a less productive Q3, and use the next quarter to focus on how we can support our employees through this transition so that they can approach normal productivity levels again in Q4.

Another general consensus seems to be that nobody is long-term roadmapping at the moment. Most are looking only a quarter ahead, and trying to bullet-point out two-quarters ahead, but all are braced for goalposts to move rapidly and unexpectedly.

Companies who typically do big, annual roadmapping exercises in Dec/Jan are still planning on attempting it. Perhaps we’ll stabilize enough in Q3/Q4 that a 2021 roadmap is possible to plan.

But for now, don’t sweat it. Do your best to plan Q3 around helping employees thrive remotely, and take it sprint by sprint for now.

Leave a comment


Thanks for reading this July 12th edition of What CTOs Worry About. Please subscribe and take part in this week’s subscribers’-only discussion.

Have your own CTO or tech leadership worry? Tweet @bkanber #ctoworry and I’ll try to fit you in to the next newsletter!

And don’t forget to tell your friends!

Share What CTOs Worry About