Questions for Prospective Managers

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“Here’s something they’ll probably never teach you in business school:

The single biggest decision you make in your job—bigger than all the  rest—is who you name manager. When you name the wrong person manager, nothing fixes that bad decision. Not compensation, not benefits—nothing.”

Not my words. These are the words of Gallup CEO Jim Gallup on the first page of State of the American Workplace.

How do tech companies name managers?

Usually the powers-that-be choose from the ranks of individual technical contributors.

But managing entails entirely different skills than individual contribution, so an employee’s individual contributions cannot predict how they’ll perform as a manager.


It’s a high stakes decision, and you have worryingly little information from your prior experiences with candidates about how they’ll handle the role.

So how do you evaluate these candidates?

I don’t have all the answers, but I do have some questions. These questions can help you gain some more insight into how someone might perform as a manager. I’ll go over what I hope to get out of each question and share some examples of poor, fair, and excellent answers.

1. How did you decide that you would like to be a manager?

This question gives me a chance to understand why this person is making themselves a manager candidate.

What has their experience been with managing, or getting managed? How do they hope to contribute as manager, and what do they want to get out of it?

This is a good opportunity to listen for expectations your candidate might have about the job.

Are they excited about advocating for their reports, helping them grow, and collating their feedback to inform leadership decisions? Are they thrilled to strategize with other managers on building teams to follow through on your company’s most ambitious projects? Do they look forward to fortifying the company culture by building strong relationships with and among the teams they manage?

Are they prepared to put in extra time in the off hours, attend tedious meetings, chase people for time sheets, participate in disciplinary action, catch shit from both ends of the org chart, and balance what they can and cannot say to whom? Can they, and will they, advocate tirelessly for the report that they don’t personally like?

Because all of this—the shiny and the shitty—are part of the management job.

You’re looking for folks who are into the shiny and aware of the shitty. It means they’re more likely to lean into the choice parts of management and more tractable when it comes to the rough parts.

2. What do you think makes a good manager?

Presumably, this is how this person will try to manage.

It gives you a change to determine: is this person going to trend toward managing down, or do they trend toward managing up?

I shared my views here on why managing up is far preferable, but it does often require more professional development on the part of managers and their bosses (presumably in this case that’s you).

3. What’s your take on the diversity gap in tech? How can we fix it?

Terrible answer: “Biological differences.”

Still bad answer: “Pipeline problem.”

Better answer: “We need to figure out how to retain people and treat them fairly.”

Excellent answer: “These are the specific ways I’d like to bake inclusiveness into my management style.”

It’s preferable for everyone in your company to answer this question capably. But at an absolute bare minimum, your managers need to understand it.

4. One of your reports goes from being brand new to being the office expert on the tech stack…in 6 months. How do you respond?

This question is designed specifically to test your potential manager’s willingness to advocate for an employee. Here we have a clear case of high achievement: someone who possesses both the technical savvy to ramp quickly and the people savvy to be approachable so people see her as the ‘office expert.’

How is your potential manager working on behalf of this employee?

Are they making sure this person gets additional opportunities to grow and lead? What are they doing to make sure this person gets a raise? How are they checking in to make sure this person is happy?

5. You take on a report who has been programming for 6 months. How do you guide his career?

In my experience, managerial candidates tend to say something that starts out right-ish here. The sticking point is the time commitment.

A brand new developer needs support. They need hours of pairing time every week beside skilled programmers who have experience with collaborative teaching. They need book recommendations and tips about where in the codebase to find good examples of various techniques. And they need their manager to shield them from boss people wondering why that developer is reading a book at work or asking questions informed by zero tech background about how ‘well’ (the boss usually means ‘fast’) the junior programmer is progressing. The report also needs their manager to support them emotionally through imposter syndrome and, possibly, the explicit suggestion from cantankerous teammates that the junior programmer is a burden on the team.

This ain’t Karate Kid. It’s not ‘wax on wax off,’ then assign the programmer some menial labor, and ta-daaaaa! state champion programmer on your hands. Managing a beginning programmer is rewarding, but it is work. A manager needs to be prepared for that.

6. You take on a report who has been programming for 24 years. How do you guide her career?

What does management look like for someone senior?

This is the one I see more issues with, as some individual contributor with 5 years experience will launch into “Well, here’s how I could still mentor them…” No. No one has any business fancying themselves mentor to someone with five times as much experience as they do. Can they still potentially teach or show the more experienced report a thing or two? Sure. That’s how the relationship works between two practitioners of something. It in no way qualifies the far less experienced one to call themselves ‘mentor’ to the more experienced one.

Managing a more technically senior person isn’t about mentorship. It’s about advocacy and helping them be effective to leadership. If someone is 24 years in and some 5 year person is managing them, the veteran either chose to stay in individual contribution—often out of not wanting to get into the shitty parts of management—or they never got out of individual contribution because they’re prodigies on the tech part and couldn’t be spared by the business to do the managing part (or they’re flat horrible with people, but this is pretty rare).

In this situation, I want that manager thinking like a talent agent. I want them on the ball to get this employee what she needs. I want them helping this employee frame suggestions to leadership in ways that leadership is most likely to listen. I want them brainstorming with this employee to buttress those suggestions with specific examples from the employee’s vast experience. I want them backing up these collaboratively crafted suggestions in the leadership meetings.

7. Your direct report has received a Letter of Concern. The letter cites some past incidents and says that if he doesn’t show improvement, more severe measures will be taken. The letter does not say what the measures would be. Your report is upset and anxious about this. How do you respond?

First of all, with this question, I want to know that my potential manager either a) knows about the disciplinary pipeline of a company with HR or b) is prepared to ask above them about things they don’t know.

I choose Letter of Concern (LoC) because it’s a specific thing with a specific purpose: you can tell very fast if your manager is pretending to know what this is. You don’t want your managers out here pretending to their reports that they know things they don’t know. That’s a great way for you to get grossly misrepresented to your reports by your managers, and it’s going to cost you mad money when something doesn’t get handled and some employee leaves.

Second of all, what is your potential manager’s first order of business with the employee? Is it to help this employee come up with a plan to improve their performance, or is it to start by managing the upset and anxiety?

Upset, anxious people have a very hard time improving at things, so if improvement is what the company wants, something has to be done about the upset and anxiety first. Sounds like, in this case, the employee is nervous about a vague threat clause that customarily appears at the end of LoCs. Does your potential manager know what that clause means, so they can allay the report’s fears? If they don’t know what that clause means, are they asking you what it means?

Full disclosure: I got this example from a real scenario. An employee left a company because they got a Letter of Concern, asked their manager the purpose of the document, and the manager failed to obtain or provide a specific answer. So the employee thought the LoC was a Performance Improvement Plan (PIP), which is a different thing than an LoC.

A PIP is more well-known among tech employees, and it’s more serious job-wise than an LoC. A PIP means you’re running out of chances before you get fired. Sometimes, a PIP exists purely to create a paper trail to cover the company’s ass legally when you get fired.

So, the employee thought they had been served a PIP and went looking for a new job. They ended up with an offer somewhere else, and they left. The director eventually found out what had happened here and saw red.

The transparency rule of management applies here: in the absence of complete information, your employees will use the incomplete information to reach the most unfavorable possible conclusion for you. 

I want to see the transparency instinct in a managerial candidate.

8. You realize you’re attracted to a direct report. What do you do?

This is one of those questions no one likes to ask because it’s awkward, so instead we pretend it will never happen and are caught totally unprepared when it does.

Look. Institutional capital gradient in one direction + sexual capital gradient in the other direction = huge problems. We’ve seen it over and over, not just in tech.

The answer is that the report needs to get transferred to another manager immediately. No repercussions for the original manager because a) they haven’t done anything wrong and b) if there were, no one would report this. Original manager no longer takes part in discussions of the report’s performance or promotion, but maybe they get a little prize for being mature enough to remove an institutional capital gradient when it could harm a report.

9. You have two reports, one of whom is gay and one of whom is a practicing Muslim. One weekend in Orlando, a man who identifies as Muslim opens fire in a gay nightclub. What do you do on Monday morning?

This is another super uncomfortable question that we’re always unprepared for because it sucks to have to consider it. The result is, when it does happen, managers have no protocol, so they do nothing, and employees feel left out in the cold.

I’ve already talked about this exact situation here and then offered more general tools for dealing with ‘negative’ emotions in the workplace here, so I won’t rehash what I said. But the answer is that, when terrible things happen that are upsetting reports, it makes sense to check in with the reports and make sure they’re okay. A nice coffee and some time to chat can really mean a lot to someone when they feel like their pain is being ignored and their commercial productivity expected to remain constant (see: “I just witnessed the lynching of a black man, but don’t worry Ted, I’ll have those deliverables to you end of day.“).


My questions have an order. I start light: do they know what this job is, what are their strengths as a manager, their thoughts on inclusion, on high-achieving reports, on beginner reports, on veteran reports.

The late questions cover tougher stuff: a disciplinary scenario, romantic attraction, and very upset reports. It’s worth noting that I rarely get to these questions. If a candidate gives unsatisfactory responses on early questions, I don’t move on. I have what I need to make a decision. No need to make them squirm.

But if a candidate gets that far, I want to know how they handle the uncomfortable topics.

Do the late questions seem too hard or unfair? Am I giving inexperienced individual contributors insufficient opportunity to succeed in their manager interview? Maybe the problem is that you don’t think you would have answered these questions successfully when you got promoted to manager. That’s not on me.

Because here’s the thing: these candidates are interviewing for the most important job at the company, which is direct control over the people. I’m about to hand over those people’s experience to one of these interview candidates. I have a duty of care to these people. If I don’t dig in with a managerial candidate before I hand them direct reports, that’s dereliction of duty on my part.

What I’m looking for here is instincts: for advocacy, for fairness, and above all, for above-average empathy. Someone with these instincts has an excellent shot at becoming an excellent manager. When they first start, I still expect them to screw up all over the place. I expect that of someone starting anything new. But over the long term, those instincts line up with the instincts of the most successful managers in my experience (and notably do not line up with the instincts of the least successful managers in my experience).

Hiring managers is hard. But finding the right questions can make it a little easier.

If you took something away from this post, you might also like:

Disrupting Management: A Fix for Tech Culture?

Anger and Sadness in the Workplace

Advance your Tech Career: Why Make Yourself Replaceable, and How?

One comment

  1. Brilliant post. I just hired some managers and now wish I’d had these questions in my hip pocket. Moreover, I will be sure to think through my own answers to these questions, because I’m sure to interview for a management role at some other company one day. And maybe they’ll be readers of your blog.

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