Over the past month or so, I’ve consulted several CEOs who have had trouble with their tech executives. Some are now with or searching for their third or fourth CTO/VP of Engineering. More often than not, these mismatches are not the fault of just one of the parties: both sides need to be better vetting and expectation setting as part of the hiring process. Some also need more coaching or mentoring after the tech executive has joined (for the CEO, for the tech exec, or both). If you’re a CEO hiring a tech executive or struggling with your current one, or an aspiring tech executive, here are some tips to reduce your risks of ending up in the wrong position.
The Job-To-Be-Done of a Job
Jobs-to-be-done (JTBD) is a framework pioneered by Clayton Christensen. If you’ve been involved in tech at all, you likely have already heard of it by now from your Product peers. In JTBD, you consider what job a product is hired to provide, be that product an app, SaaS service, a mattress, or a milkshake. Many CEOs grasp this concept when it comes to their product, but fail to do so when defining a job.
No matter if you are interviewing or being interviewed, you should clarify what job the tech executive position is intended to achieve. Failing to do so before accepting the job or making an offer will make things blow up at a later stage, which is a lot riskier and grossly more expensive to remedy.
Define Success: What would be considered a success for the tech executive within the next 6, 12, and 24 months? It is near-impossible to hit a target if you don’t know how it looks like or where it is.
Define Responsibilities: Tech executives are often in charge of People, Architecture, or Evangelism. People management is usually under a VP of Engineering, who is in charge of the delivery of software in the company, and the entire engineering team. Architecture has many forms, but most frequently means leading the tech capabilities of the organization or introducing technological innovation. Think Chief Architect roles, and sometimes a CTO. Lastly, Evangelism is used for companies that have a significant part of their product facing other technologists external to the company—platforms, SDKs, and APIs most often. A tech executive responsible for evangelism is likely to be speaking at conferences, creating partnerships, and so on. Knowing which of these responsibilities the CEO has in mind will help find the right person to fill the position.
Define Values: It is vital for executives of the company to share its values and mission. However, this is not often given enough attention during interviews. Both parties should discuss their ideology, beliefs, and motivation. I’ve seen mismatches between executives and CEOs stemming from not agreeing on basic culture. Some people want to keep the scrappy, garage-like behavior for years and others prefer a more relaxed and “grown-up” way of doing things. Some people might want to work at a company that takes a political stand in areas not directly related to it, and others prefer to remain focused on what the company is working to solve. Ensure that you have an accord here.
Discuss the Path: Every executive, being truly an executive and not a glorified manager, should have an idea about achieving and accomplishing the goals discussed. While not everything will be known beforehand, and some things are bound to change, candidates should have a sense of how to get these objectives done. Talking about the path forward provides both sides with more confidence: the CEO can see that there’s a plan that she can get behind, and the tech executive gains general agreement for her ideas.
Sometimes It Takes Three to Tango
When the tech executive is finally there and starts working, new issues will arise. It is just the way things are. However, there are situations where merely doing their best is not going to cut it. Sometimes, one of the sides needs to be coached (e.g., teaching the CEO to provide autonomy, or helping the tech executive speak business so the rest of the executive team can understand her). Other times, the relationship itself between them needs to be worked on.
I may be biased, as I do this for a living, but have another person involved in the first few months as a coach and advisor gets things up and running significantly faster. A typical example: CEOs often feel relieved when they hear it is perfectly natural, even for an experienced executive, to require a few months to grok the team’s situation and start showing improvement. This removes a lot of tension (the constant “did I make the right hire” question looping in their mind) and allows trust to be built.
If you find that you are struggling in the first few months, I highly recommend seeking support (even internally, e.g., another co-founder who’s not the CEO).
And, lastly, always remember that things always turn out to be different than how you first imagined them. It doesn’t necessarily mean that you made the wrong choice.
Get a sample chapter
Get the best newsletter for tech executives online, along with a free sample chapter of The Tech Executive Operating System 📖. Tailored for your daily work. Weekly, short, and packed with exclusive insights.