Hiring for a Director of Engineering

Ken Pickering

VP, Engineering at Starburst Data



For any tech leader, hiring for a Director of Engineering role is one of the most challenging tasks they will have to encounter in their career. They will be hiring a person with significant experience who will aspire for significant responsibility too. That should be someone who will profoundly impact the organization and alter how the organization will develop in the future.

Actions taken

Before delving into sourcing and conducting initial conversations with potential candidates, a VP of Engineering or CTO should have a thorough understanding of how this person would fit within a larger picture -- how they would complement the team, what they can bring to the organization, and what are their core competencies and values. There are two facets of the interview -- the one assessing technical skills and the other assessing soft skills.

Technical skills

A Director of Engineering has to be an expert on the development process and adept at working with product management, iterative management and design. They should be exceedingly technically competent and be able to conform to the best practices of the industry. I personally never hire non-technical managers for any role in the engineering organization. They don’t need to have a CS degree but they need to have experience working as engineers or in some similar technical capacity because technical credibility is a foundation to build trust and respect with your team.

I expect directors to be very technical and would have two architects or high-level principle engineers vet out their architecture and software design skills. While they are not expected to code daily, they are expected to read and interpret software and be able to understand what their teams are building. They will have to navigate different technical opinions, and their job would be to steer the team toward the best solution. Part of it refers to technical conversations with other people across the organization, and the other is about their engineering instinct and deciphering what it is telling them.

At the director level, breadth is more important than going deep into details and being able to marry higher-level business context with what the team is building. But when circumstances require, a director needs to dig deep into the specifics of the problem. During the interview, I typically present candidates with problems requiring that they rapidly understand the problem space and be able to dig further using their expertise or work with an architect navigating a complex series of tactical decisions.

Finally, it is important to understand what process a person practices and is fond of -- is it a Lean-Agile, Kanban, or some version of Scrum -- and how that fits the organization’s development process.

Soft skills

The primary skill I look for in a director is a bias for action. I am keen to hire people who are into delivering on things and are not afraid to make a decision, take a stand, and navigate whatever comes from that decision. Startups typically want to rapidly evolve their product(s) and are entirely focused on delivering, while larger companies may have different priorities.

The other thing I find essential is people’s drive and ambition to do what it takes to get the job done. For example, I expect a director to roll up their sleeves and do sourcing of candidates if there is not enough recruiting support. They should be making intro calls and doing phone screens, meeting people for coffee, and networking if needed. I look for people who will be responsible for the whole thing, from the beginning to the end. Directors should be people who will do things whether they want to do it or not, and who understand that something that is not their fault is their problem and needs to be fixed. Surprisingly, many people would rather seek excuses and avoid the discomfort of claiming ownership of problems than trying to find the solution.

Another tremendously important soft skill is collaboration, particularly being able to collaborate with product management. Directors should be able to walk through the roadmap with their product counterparts and get constructive feedback on the roadmap. It should include assessing how they perceive the problem space and how they would involve and invest themselves in the roadmap.

Soft skills are much harder to assess, and you have to do a lot of social screening. STAR behavioral questions could be quite handy; for example, how they handled their conflict with Product or what worked/didn’t work when building their last team.

Lessons learned

  • You will have to figure out within the first 90 days if a person would fit as a director or not. Because of the significance of the position, I would write a pretty intricate 90-day plan for every director I would hire. We would map out the goals and expectations, and they will be encouraged to share their inputs. It would constitute a roadmap for their onboarding and setting them up for success. Sometimes, perhaps a month later, you will have to have a difficult conversation about a mismatch in expectations and how you can help them course-correct.
  • The only worst thing about firing a leader after 90 days is keeping them. I’ve seen a detrimental impact a bad hire could have on the organization, and you have to make changes and course-correct as early as possible.
  • You need to be able to differentiate when you are hiring someone with the same skill subset as yours -- when that is good and when not. Sometimes you need people with entirely different skills set from yours to augment and complete your organization. There were times when I had to hire people who are much stronger than me in project management. Therefore, I am always asking myself if I need a person who should be more focused on software development and product initiatives or complex projects with intricate timelines and schedules.

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Ken Pickering

VP, Engineering at Starburst Data

Leadership DevelopmentOrganizational StrategyDecision MakingEngineering ManagementCareer GrowthSkill DevelopmentLeadership RolesEngineering ManagerDirector of Engineering

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