“Tell Me About a Project You Led…”

Each day this week I’ll be sharing one of the questions I use when I interview for technical roles. I’ll unpack the question, when to ask it, and how to evaluate answers. You can see all articles in this series here.

Background

Who this is for: managers and leads, especially those at a Director level (manager-of-managers) and above.

What it measures: experience leading delivery teams, and the ability to manage effectively (read: enough management, but not to the point of micromanagement).

Managers are responsible for the output of their team, so when interviewing managers, it’s especially important to understand how they help their teams get work done. But, one of the most difficult parts of management is that the higher one is on the org chart, the less direct power they wield on delivery. As managers move up the org chart, they manage less by direct action and more through setting direction, clearing blockers, and delegation. If an engineering director with a team of 50 is writing code, something has gone terribly wrong.

So, this question, about a project they led specifically from a leadership role, can get you into that. It can give insight into a manager’s leadership skill and style, and show you how they affect delivery. This question is especially good to ask candidates for roles at the Director level (e.g. manager-of-managers) or above.

The Question

“Describe a project where you led a team responsible for delivery. Ideally, it should be shipping a digital product (e.g. app, website) that includes product, engineering, and design work.”

Follow-ups:

What was your role in getting work done?
What was your process for assigning work?
How did you interact with the team throughout the process, and at what points?
How did you spot problems, and how did you make corrections?
Was the project a success?
What kind of feedback did you give your team? At what points?
What went well?
What would you do differently next time?

What behaviors to look for

How do they describe the success/failure of the project? How did they measure it?
When and how did they check in with the team?
Do they help the team maintain focus?
What sort of leadership role do they play?
How do they describe delegation?
How do they explain when they get hands-on/“in the weeds” vs. staying high-level?

Positive Signs

👍 Has a method/playbook for managing projects (e.g. weekly planning, daily standups, or whatever), and can articulate why it was a good fit for this team
👍 Shows an understanding of the reasons why the project succeeded (or didn’t)
👍 Spotted and corrected problems before they become out of control
👍 Articulates early warning signs for problems
👍 “Delegates problems, not solutions” - e.g., helps subordinates understand the problem to be solved, and gives them the tools the solve it

Red Flags

🚩 Project management was ad hoc, not following any sort of structure or principles
🚩 Hands-on at a level that’s inappropriate for the team size or structure – can indicate micromanagement, see below
🚩 Corrected problems only after they become major, e.g. missed deadlines, budget overruns, etc.
🚩 Can’t explain what went well and/or what they’d do differently next time
🚩 Only gave negative feedback to the team/individuals

Discussion

Effective managers will set high-level goals, make sure the team is aligned, trust the team to do the work, verify that it’s getting done properly, and be willing to get into the weeds if required. By having a candidate walk you through an example project, you can get very clear information on how they lead.

The most important thing that I look for here is that a candidate has a system for leading projects. I’m less concerned about the details of that system, as long as they roughly align with the company values. But I want to know that they’ve practiced these skills enough to know what works for them.

I’m also looking for candor and introspection. Success is great, but if they can’t articulate the factors that led to the success, I worry that they can’t repeat that success. And, nothing ever goes perfectly; if a candidate can’t articulate a few things they’d do differently next time, I worry they won’t know how to learn from mistakes.

The critical part of asking this question lies in the follow-up questions. Expect to spend a good amount of time on this question – 10-15 minutes, at least, and perhaps more. You need to dig deep and get very specific to understand a candidate’s leadership/management skill.

For example, if they say “our team holds weekly planning meetings”, you might follow up with:

“What was the structure of those meetings?”
“What role did you take - did you run the meetings? Delegate that to someone else?”
“How frequently did you attend?”
“What did you do when there were disagreements at those meetings?”
… and so on.

If you don’t do this, you’ll just get a breezy high-level “everything was fine!” sort of summary. You have to be prepared to really dig in, and get the candidate talking very specifically about their behaviors leading this project.

Screening out micromanagers

This question also can help you find micromanagers, but be careful here; micromanagement doesn’t show up here in quite the way you expect. The opposite of micromanagement, assigning a huge project and walking away, is every bit as bad. You’re looking for managers who are involved “enough” – which can sometimes be quite a lot!

Effective management is pretty hands-on: a good manager is always up-to-date on the project, gives frequent feedback, and makes frequent small course corrections. These actions can trip up inexperienced interviewers. Especially the last point: if a manager explains that they’re nudging the team and making minor changes to the project plan every week, that can sound like micromanagement. And it might be – but often not. Think about driving a car: you don’t wait until all four wheels are off the highway to veer back into the lane. You make lots of very small nudges to stay heading in the right direction.

The key to looking for micromanagers is the second “red flag” above:

🚩 Hands-on at a level that’s inappropriate for the team size or structure

When someone gets involved at a level many rungs down the org chart, and does so when there are already competent people in the role they’re supplanting, that’s a warning sign. For example, if a Director of a large engineering organization writes critical-path code, or if a CEO attends individual grooming sessions and assigns story points for the team – this kind of behavior is a big warning sign for micromanagement.

Alternate versions

This question selects for the model of management articulated above. If your organization has different expectations of managers – perhaps you’re more of a “command and control” style, or you use a “player-coach” management style – the same question can work, but you’d need to adapt what you’re looking for accordingly.

This question is also relatively easy to adapt to other leadership roles, for example:

A version for very senior ICs (architect/principle-level) could ask a question about technical leadership. You’d be looking at how a senior IC sets direction and standards, how and when they coach more junior developers, when they choose to step in and code themselves, etc.
This question works almost as-is for product and project managers. These roles have some of the same project/product leadership responsibilities, but don’t typically have role power. So you’d be looking at how they use their relationships and communication skills to keep projects on track.

Questions?

Next week, I’ll publish a series wrap-up, summarizing the series as a whole and addressing a few big-picture topics. If you have questions, tweet at me (DM are fine too). I’ll address common questions in the wrap-up.

Jacob Kaplan-Moss