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Hiring in tech for leadership roles: our advice to hiring managers

May 2, 2022

Hiring is never easy, but finding critical hires - like leadership positions - can be even more challenging. If you’re hiring for leadership roles (especially for technical roles in engineering, software development, or product management), there are several things we recommend doing as you meet prospective candidates. 

1. Take some time to understand the position you’re hiring for.

Once you understand the goals of this new hire and what they’ll be responsible for, you’ll have a better sense of what level of experience you need to recruit at. 

For example - if you’re hiring an engineer who will be responsible for 1-2 direct reports in addition to working on their own projects, it may make sense to hire an Engineering Manager. Or perhaps you’re interested in hiring a highly skilled, highly experienced engineer who will be responsible for leading cross-functional teams. In that scenario, it may make sense to hire a Principal Engineer. 

2. If a candidate is an individual contributor, ask if they’ve led any projects or bigger initiatives.

As you meet with a candidate, it may become clear during your discussion that they haven’t led a team or had direct reports before. In those situations, it’s important to ask about projects or initiatives they’ve had a large impact on. 

For example, has your candidate led a group of vendors or contractors to complete a project? Or, have they been the main point of contact in implementing a new process that was cross-functional, and involved communicating across several different teams? Asking questions about how your candidates make up for a lack of direct people management (as well as noting their enthusiasm for taking on these projects and increasing their responsibilities) can help in making hiring decisions. 

3. Ask questions to determine how a candidate deals with ambiguity or lack of direction.

Many hires may be used to identifying a problem and solving it. For example, in some work environments - someone may be assigned a technical task and they are measured on their efficiency, speed, accuracy (or any number of metrics) in accomplishing that task.

But when moving into leadership roles, these lines can become a little more blurred. As a leader, you may not have all the necessary information you need to make a decision. Perhaps your data science team needs three weeks to help you find a solution to a problem (but your new product feature ships out next week), or you’re not sure if you should build a personalized dashboard for every client based on their specific wants, or have them all use the same dashboard (there are pros and cons to each option). 

To understand how candidates deal with scenarios like these, a great question to ask a senior engineering candidate could be: “Tell me about a time when you had to make a decision without all the relevant information.” A candidate’s thought process as they walk through that decision may matter more than if the decision was “right or wrong.” 

4. Take some time to understand how a candidate deals with different opinions and views.

Asking your candidate how they would handle different opinions (or resolve conflicts), can help you understand how they’ll deal with managing a team. As someone moves into leadership roles, they’ll likely be tasked with managing a diverse team at some point - made up of different ethnicities, ages, backgrounds, or even across different time zones. 

Similar to #3, there may not be a “right” or “wrong” answer to the different issues that will present themselves to your team - there may just be different viewpoints, influenced by those different backgrounds. Asking a candidate a question like “How do you resolve differences on a team?” or “Tell me about a time when you had to challenge a decision made by someone else” can give you insight into how they’ll respond to these differences in the future. Hint: It’s important they do so with integrity, and respect! 

Interested in working with Recruiting from Scratch on finding your next great employee? Send us a note, and we'll let you know how we can help! 

Want to see more posts on startup hiring? Check out this post on when to hire a Head of Product for your startup and this post on developing a hiring plan.

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