Ahead of the forthcoming CTO Craft Con 2021: The Delivery One, we picked the brains of Bryan Helmkamp to understand why OKRs are the key to alignment and get our hands on his tips for effective planning.

Hi Bryan, thanks for joining me today! Let’s dive right in, what’s keeping you busy at the moment?

We’re very busy at Code Climate at the moment! A big initiative we’re working on right now is a major release for our Velocity product, which we’re doing this summer. So it’s a lot of planning around that: talking to customers, hiring and onboarding new team members and engineers. 

Great to hear! And how will that focus shift towards the end of 2021?

Following the release, I expect the second half of the year will primarily be focused on getting it into the hands of our existing customers, as well as new ones. Our customer base has been expanding rapidly which has driven a significant expansion in our efforts in terms of customer onboarding and rollouts within a number of large organisations and enterprises that are looking to take on the product or use data in engineering. We work closely with them on deploying it at a large scale and helping transform their enterprises, which may have thousands of engineers in them. 

As Code Climate is currently scaling, how do you optimise alignment between teams, especially now that they’re entirely distributed?

While we’re totally remote right now, for me personally, I’m looking forward to being able to have some level of in-person collaboration again. We made the leap from being a primarily co-located team in New York City to being an entirely remote team, about a year ago. And it’s gone quite smoothly, I think. 

We use a lot of Slack, but have also leaned into some of the collaboration processes that we established prior to going remote. We’ve also stuck to our guns in terms of having clear objectives and we use an OKR system to communicate what we’re trying to achieve across the company. 

A big initiative for me at the end of 2020 was reworking some of our internal communication cadences around how we’re sharing information i.e. what we shared synchronously over Zoom, and what was shared asynchronously over written updates in Basecamp etc. It’s been going quite well.

One of the most challenging parts however, is onboarding new employees in a remote environment. It’s been a solid project, because our headcount has more than doubled since we became fully remote. At this point, more than half of the company has never been to the office and in many cases, never met any of their colleagues in-person. So we’ve been trying to bridge that gap with a focused onboarding process.

How has your leadership output had to change over the last year?

The last year has coincided with a significant push for us to expand our leadership ranks. So in my role as CEO, that’s been one of my top focus areas over the past six months, working on recruiting, hiring, and onboarding, new leadership roles. Much of the leadership team we have today consists of people who joined us as we became fully remote. 

What are your secrets for effective planning?

Not sure I have secrets! I like to think about what the appropriate amount of process is, relative to the problem that needs to be solved, or the size and scale of an organisation. And that’s a rapidly changing context. As such, we’ve added a bit more process in the past year than we had before, because we’ve grown and more departments and teams means more meetings. 

So I would say my ‘secret’ is to approach planning and operational processes from a zero basis. That is to say, if you imagine clearing your calendar entirely, what would you add to it? As opposed to thinking about it from the standpoint of: what would you remove from a process to make it more streamlined? Often the latter does not lead to proactive thinking about how something can be completely rethought. And that’s what I try to do regularly when it comes to planning projects.

As a result of the pandemic, people’s engagement has shifted and some of their motivations have changed – have you noticed that? And how have you changed your approach in terms of motivating engineers and developers?

The pandemic has affected everybody differently, and in multiple ways. I also think the impact has evolved because we’ve now been in it for a while. So for us, we’ve tried to take a very personalised approach in terms of the way that we’re managing and leading the team. 

Code Climate managers have done a great job of getting a good understanding of how the individual team members that they’re responsible for, are doing in terms of what’s on their mind and what is keeping them up at night. Sometimes, those will be things that are work-related and other times, not. Then they will try to find avenues to give people the space to focus on what is most exciting to them. In some cases, that might mean taking on a new initiative and learning a new skill. In others, it might be improving at something they had been working on in the past. 

I’m not sure there’s a one-size-fits-all answer for that one; I think it’s something we’re still learning as well.

Have you noticed an impact on delivery as a result of people’s changing circumstances?

On the whole, I think we have continued to be able to deliver our software initiatives at a strong pace with good, consistent efficiency and quality. 

At the beginning of the pandemic when we first became fully remote, some people started working longer hours because there wasn’t that much else to do. While that was fine for a bit – they seemed to need something to focus and make progress on – it isn’t sustainable. One of the things we monitor for now is burnout risk; we try to be very proactive about making sure that people are taking time off so that they’re not burning out. People are naturally reluctant and unsure about taking a vacation if they’re not necessarily going anywhere. But it’s necessary to still take breaks.

Finally, what books would you recommend to delivery managers?

Accelerate:The Science of Lean Software and DevOps: Building and Scaling High Performing Technology Organizations by Nicole Forsgren PhD et al, is fantastic. 

I also published a book last year on software delivery called The Engineering Leader’s Guide to Cycle Time.and free digital copies are available online here

Also, James Shore’s book The Art of Agile Development (he is currently writing the second edition) is highly recommended. 

Thank you, Bryan!


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