Previously published on Forbes on June 17, 2019
The success of a venture-backed company usually depends on two main factors: its technical innovation and the velocity with which it introduces new products. In order to sustain these competitive advantages throughout their growth, companies must ensure that the delicate relationship between the CEO and the CTO is effective.
The CEO and CTO have a fluid relationship that changes over time. As the company grows, the relationship evolves because of the expansion of the executive team beyond the original founders. As the company grows, investors may also replace the CEO with “a real business person.” Sometimes, the CTO decides to leave the company and its politics to found yet another company.
I’ve experienced this rapidly shifting dynamic from both sides — as an outside CTO coming in to replace, or supplement, the founding CTO and welcoming a new CEO after the VCs replaced the founder CEO. In both scenarios, I have observed (and suffered from) misaligned expectations between the CTO/VP of engineering and CEO that lead to frustration and a lack of effectiveness on both sides.
With the benefit of hindsight, I have written two letters. The first, which I will present here, is one that I wish I would have written to my CEOs so they could have understood the nature of my job, my contribution and how to get the best out of me. The other, the letter that I wished I had received from my CEOs, is so they could have understood how to be most effective not only in leading the engineering team but also in understanding my role on the executive team.
Here’s the letter that I, as a CTO, wish I had written to my CEOs:
I want to thank you for placing your trust in me to be the new CTO of your incredible company. During the interview process, I thoroughly enjoyed our exchanges, and I was equally impressed by your past accomplishments, your business sense, your knowledge of the market and your drive.
Since you mentioned that you are “not technical,” yet you are responsible for leading a company whose success is highly dependent on the strength of its technology, I thought that I would take a running start in our relationship-building by sharing my thoughts on what will make our relationship effective.
My primary advice is that you allow me to do the things I am good at without second-guessing me. You hired me because I have proven more than once that I can build and lead a team of world-class engineers and launch world-class products into the market. While I expect to be challenged, like every member of the executive staff, when I say that developing a new feature will take three months, please don’t ask if it could be done in two weeks. I too want to win. The three-month figure will not come out of thin air, as my team and I will have spent time coming up with this number. If we ever need to build something with roughly the same features in two weeks, it will have to be an extremely watered-down version that we’ll call “demo-ware,” (which does have its place in certain circumstances), or we’ll need to pare the release down to one or two features.
For my team to succeed, I will also need you to work with the whole executive team to create an actionable product road map. By “actionable,” I mean that the priority of the features needs to be vetted by the business team and that the engineering team will need to be given the time to estimate the scope of major features so that the time frames published on the road map are realistic. If we follow this process, a sanitized version of the road map can be shared with the sales team and even customers.
The other major benefit of an actionable road map is that the engineering team can build a technology roadmap that will allow us to develop breakthrough features because we’ll have had time for research, experimentation and prototyping. Conversely, a road map that zigzags is not conducive to engineering efficiency because it wastes the time spent on design and planning work required for major features that are deprioritized. All of us in engineering understand that sometimes a major opportunity presents itself and that the whole company has to pivot to take advantage of it. We embrace those opportunities because we want to win just as strongly as you do. Yet the decision to pivot should consider the impact on engineering velocity as well as the new business potential.
Building a good product road map requires that we understand each other about schedule estimates: Loose requirements, changing priorities, a high velocity of development and accurate schedule estimates are not compatible. If you — and by extension, the business — require reliable schedule estimates, then engineering needs precise requirements that do not change, plus the time to work out a solid design from which a list of tasks and a schedule can be derived. If the nature of the business requires frequent changes of priorities, then let’s not bother with detailed estimates. Since it is a rare business that does not see priority changes, I strongly recommend that both the business and engineering teams embrace lean product and agile development methodologies.
Finally, at the risk of stating the obvious, engineers have different personalities than salespeople. When the engineering pen is quiet, it is not an indication of low morale. On the contrary, it shows that engineers are focused on writing code. I know that can be disconcerting to extroverts.
We’ll have to move fast in the journey we have undertaken together, and to do that, we need to communicate directly and trust each other. This letter is my attempt to do this, and if you’ve made it this far, there’s a good chance that we are at the start of a productive and fruitful partnership. I can’t wait.
The letter I wish I had received from my CEOs will be published in a subsequent article.