Management interview challenges

Two years ago I started on a management job-seeking journey. It was a weird time, height of COVID lockdowns and interviews in zoom were all the rage. Management interviews, fortunately, hadn't changed that much but I did - I had decided to take a step up. I decided to aim for Offers, methodically work full-time through my interviewing and honest-to-god prepare in advance to maximize my chances.

I applied for engineering manager roles, so I had technical interviews and many rejections. Some of the interview processes continued and I reached that point when I was finally asked about management. Here are some of the common questions and how I answered.

Management fit journey challenge

I usually had a "Tell me about a hard managerial or leadership challenge you resolved". I had one very good answer and an ok backup answer which I used depending on the situation. Both described the efforts I invested into the people I led and how through shared difficulties we found a great solution for the employee and the organization.

There are two things you want to hit correctly here:

Your answer requires context. You must practice telling as full a context as you can about the issue you faced, while maintaining privacy and an ethical amount of details. This is a careful balance. Too few details: you risk your choice sounding weak. Too many details: you risk breaching organizational ethical conduct (leveraging your employee's hardships for your benefit while throwing them under the bus is an ethical no-no).

You want an optimistic answer. Your story must be interesting with conflict and adversity. But, it must also be balanced and end with a powerful high note: we overcame the problem, we built something great together. You must show how through your leadership and involvement the problem was solved. Your story must address the employee's outcome, you and your team's results and the final organizational state.

My best answer was about an employee that I had coached in a junior developer position (you know who you are). We went from head-butting and arm-wrestling to me sponsoring this person to a leadership position.

The meat of the story was in the difficulties of handling a skilled, brilliant, but head-strong employee that resisted change and the process I was implementing with the team. Without diving into details, this was a process of trust building, coaching, and constant feedback. It was months of challenging work, but in the end this person became a pivotal part of the engineering department.

This success was everyone's success. The employee grew exponentially, the organization nurtured leadership and talent, the department was rewarded with good technological choices at the source-code level. I got the (incredible) adrenalin rush of witnessing my employee, now my friend, break ceiling after ceiling of achievement and soar off into their unlimited professional sky trailing smoke and sparks. This story has everything: adversity, difficulty, a twist and finally, catharsis and circle closing.

Yes, I wax poetic sometimes. I hope you, dear reader, get to experience something like this in your professional life. I expressed passion as I told it many times, I laughed and almost choked on every telling - it is that powerful an experience for me. I tapped into those feelings without shame or remorse with every telling, I happily relive the experience and shared it. I believe it was those things I delivered that made this answer so compelling to my audience.

Management fit termination challenge

The “Tell me about a time you terminated an employee” question is also a classic, but it requires some careful handling. Where the journey answer is boosted by passion and feelings, this one must be analytical, cool and even handed. Make sure you are yourself calm as you deliver it, it will be a difficult discussion about procedure, ethics and self reflection.

You must demonstrate:

• You understand the termination process
• Empathy for the other parties involved
• You acted in good faith and in an ethical manner
• Due cause by conduct or performance on part of the terminated employee
• Balanced the good of the employee with that of the organization
• Remembered your responsibilities as a manager at every stage of the process

Make sure you discuss what was done to avoid this end, what options were explored, and why, in the end this result was unavoidable.

Context and details are key here, again. Too many details may give the employee away and harm them. Too few details and you come off as callus and uncaring. Nuance is everything in this question and your answer must be very well planned and as adapted to your audience as you can make it.

For obvious reasons, I'll avoid an example for this one.

Management dilemma question

This used to be a common question: "Tell me about a difficult leadership choice you had to make", in my second round I heard it only once. Maybe because dilemmas are hard.

Dilemmas are tricky things. The problem with dilemmas is that the choice is usually between two bad options (otherwise, it's not a dilemma), so presentation here is key. You are tasked with explaining the context and the tradeoffs of the two options and why the choice is not obvious.

There are many ways to ruin a good dilemma:

1. The two choices are unrelated, or an apples-to-oranges comparison: should we draft a new SOW for our outsourced contractors, or should we order lunch for everyone in all the offices? These two could be related through costs... but one has to wonder what other costs out there should be compared instead.
2. The choice is obvious, or nearly obvious: even though both options are bad, they are in the same realm, which usually means one choice is a "little less bad". For example: we have to choose between two systems. One costs one-and-a-half million bajubies, the other cost one million bajubies, but required the team go through special training. This isn't really a dilemma because one can easily tally the costs of the special training (direct and indirect) and then compare apples to apples. Obviously the cheaper option wins (because no other parameters were considered)...
3. The choice is not between bad outcomes: I must choose between React and Angular. Both are excellent options, highly regarded and popular. Both options are fine, I just need to choose the better one. Lacking additional parameters for choice, I'll choose based on which flavor of syntax I like. Not exactly a Gordian Knot.
4. The dilemma is super-specific and requires a ton of context: The company must choose between two types of distribution curves. A logistic distribution or a normal distribution. The choice is critical of course - millions of dollars hinge on it, but explaining the differences and how they map to reality in layman terms is difficult. It will require explaining the math, the theory behind the business model and how the mapping is implemented. The chance for mistakes and misunderstanding is increased, and also one can easily downplay the decision.

So the dilemma you want should be critically important. You must be able to explain the necessary context and the parameters that were considered in a few minutes and then dive deep into just the one or two critical aspects. In the end, you want to reflect on the choice's results and what you learned from it, regardless of the outcome.

My story was about a common choice and easily relatable to any manager: my team had a few developers and one of them left (on good terms). I had a choice, begin recruiting a new team member, or stretch the team to keep our goals and capacity without a full contingent. I had a few parameters for this choice: cost (obviously), short term productivity (we were in the middle of a critical project), long term productivity, missing expertise for future goals and my own capacity to recruit and train.

Do I sacrifice short term productivity and some of my own tasks in an effort to fill the ranks but then gain an important boost to team expertise and have a strong team long-term? This process can easily take a few months. Do I forgo the opportunity to reduce costs (an important organizational achievement)?

Do I sacrifice long-term productivity, but then leverage this opportunity to grow the other team members into expertise and challenges they would not have encountered? This is risky but folds an important growth opportunity. Do I forgo the opportunity to bring in fresh blood (an important team building aspect of recruitment)?

I leave the conclusion to you, dear reader.

Extra points

You get extra points if your answers can all be tied together to the greater organizational context or personal achievements that you discussed. Kind of like "The Indian from the previous joke" sort of references. I planned my answers so I could tie all of them together. The choices made in my dilemma created the situation for my managerial journey to bloom. This sort of trick is constantly done in literature, cinema, and the bible. It's the best story telling.

I could show how my actions and choices impacted the organization on multiple levels, in different ways and at all stages of the interview. That's the best demonstration of capability I can think of.

In summary, management interviews are about people, choices (hard choices) and how we as leaders evolved and grew based on the challenges we encountered. Good managerial stories balance the organization with the individual, creativity with procedure and our personal ambition with that of everyone else.

Prepare, rehearse, adapt. Good luck.