That’s Why You Hired Me

Another CEO declares middle management dead. Flat organizations are hailed as a corporate utopia full of efficiencies and cost savings.

I understand why this dream appeals to people who have survived bad middle managers. But as someone who has been a middle manager, I can confidently say that middle managers are the heart of most organizations.

They operationalize the vision of leadership.

VPs and other C-suite executives come up with dazzling ideas. It is up to the middle managers to make them a reality. No VP that I know will sit with a team to make the small go/no-go decisions. Whether a variance is worth flagging or just noise, how to code a transaction that spans two entities, which reconciling items to escalate and which to resolve on the spot. These might seem like small decisions, but they are the decisions that can paralyze a team and stop progress.

I remember one occasion when I received a request from corporate. They wanted my team to document some processes. I had a team of four, and each one had a task or two to document. I sent the team the request from corporate and asked them to start working on it as soon as close was over. I sent two separate reminders, yet I grew concerned when no one reached out with questions. In my book, no questions mean no work.

A few days before the deadline, I set up an in-office 20-minute meeting to go over the progress and answer any questions. My boss pushed back. He said: why do you need a meeting? You sent clear instructions. This is a no-brainer. I said: just trust me.

At the meeting we found out that no one had even started working on the project. I was proven right.

One person didn’t even know there was a project to work on. He asked if he was cc’d on the emails. He was. The second one received the emails but didn’t think they applied to him. His thought: if I had to do something, someone would tell me in person. The third one knew about the project but somehow confused the deadline date with the date he was supposed to start. The fourth one understood the assignment but had not done anything about it… yet.

After the meeting my boss asked me to stay behind. His exact words were: what the f* was that? He couldn’t understand how this group of people had not understood the assignment.

I responded: that’s why you hired me.

Someone might respond to this story with: you just had a bad team. Hire better people. To that I say: I hired the best team I could afford.

Good talent is expensive, and most companies are not willing to write a blank check. But even if your company is willing to pay top dollar to hire self-directed talent, where do you think that talent came from? The best professionals I know had great middle managers showing them the ropes for years. Giving them feedback and helping them along the way.

Leaders are built, not born.

A friend of mine started at the bottom and retired from the C-suite. At 65, she still credits her first two bosses for the trajectory.

So you’re a deep-pocketed company that decided to outsource the development of its people to other companies and only hire the best and brightest. I ask you: how long before the best and brightest get tired of self-directing and going above and beyond without any room to grow?

Imagine you have a team member who takes it upon themselves to onboard new hires and resolve ambiguity for the group. This person is already doing the work of a middle manager. They’re just not being paid for it, titled for it, or given anywhere to go because of it. How long before they figure that out? The distance between an individual contributor and the C-suite is too wide to cross without steps in between. Unless you have a top-notch internal leadership program that can bridge that gap, your best people will leave to get the growth they can’t get at your company.

I met someone recently whose company had removed all middle managers. He proudly said that it had been a year without any measurable loss of productivity. And I believe him.

But what will your productivity be in three to five years?

I do believe that if you have a strong team, probably built by a strong middle manager, where everyone knows what they do and there is cohesion, you can remove that middle manager without much change. At first.

Things start to shift once the team changes. People leave. People get hired. The strategy changes. But someone has to handle the next new executive ask.

That’s when the team starts to suffer. That’s when the bottom line suffers. That’s when you feel the absence of the middle manager. Another CEO can declare them dead. But they’re the ones keeping the company alive.

Impossible Questions

I knew better, but I did it anyway. I clicked on a clickbait article about hiring red flags.

Some of the advice was basic. Never hire someone who badmouths their former employer. Never hire someone who asks no questions. Never hire someone who doesn’t show curiosity about the company or the role. Fair enough.

But there was one that didn’t sit well with me. The author argued that you should never hire someone who can’t answer the question: “Tell me about your biggest failure.”

The argument was that someone who couldn’t answer this question didn’t have enough self-awareness to be a good performer.

I disagree.

Not because this is untrue, but because this is what I call an impossible question.

If you answer truthfully, you are highlighting your shortcomings to the hiring manager. And you don’t know what that manager considers a disqualifier. You try something relatively safe, only to find out you’re sitting across from someone who sees that particular issue as unforgivable.

If on the other hand you try to be strategic and answer with a non-answer, or a strength disguised as a weakness, you look disingenuous. Your application moves to the rejection pile.

Heads you lose, tails you also lose.

People know what their biggest failures are. They probably lie awake at night reliving every moment. They just won’t tell you. It’s not a lack of self-awareness. It’s self-preservation.

“What is your biggest weakness” is another question in this category. It gets asked less and less these days because people have realized it doesn’t tell you anything about a candidate’s ability; other than their storytelling and spin abilities.

By asking impossible questions, interviewers aren’t being clever or fishing for red flags. They are setting people up for failure.

And the interview process doesn’t need more help at being terrible. It’s already broken and getting worse by the minute, with algorithms removing qualified candidates automatically and recruiters who can’t be bothered to close the loop after taking up someone’s time for weeks.

As interviewers, we can do better. Ask what the candidate has built. Ask how they think through problems. Ask what they would do in the first 90 days. Those questions tell you something real.

Or better yet, ask them to ask you questions. See how they think and what they care about. That will tell you more in five minutes than any rehearsed failure story ever will.

The Questions That Were Never Asked

I could tell something was wrong the moment my friend picked up the phone. She had just spent a “ton of money” paying someone to rewrite her LinkedIn profile and they had done a terrible job. A bad, no good, horrible job whose only use would be as kindling for a fire (I’m paraphrasing here).

I was surprised since she had used a professional. Let me take a look, I said. Maybe I could help.

The package included a resume, executive bio, and a LinkedIn profile with instructions about how to populate the site. I read it all and thought… it was perfectly okay. It was professional and well written, easy to read, full of the buzzy keywords. I started to wonder what the real problem was.

I decided it was an issue of misaligned goals. I asked my friend some questions to find out.

Questions like: What is the main purpose of this profile? What do you want people to take away when looking at it? What kind of tone do you want to convey? Who is your main audience? Besides company names and titles, what do you want to communicate about your career?

She was surprised by the questions because her LinkedIn profile writer never asked them. But more importantly, she herself had not thought about them. She asked for a couple of days to sit with it.

Once she came back with answers, I had the clarity I needed to do a rewrite. I sent it to her a few days later, and she loved it. This was finally what she wanted. What she wanted all along.

She thanked me for all my hard work. What she didn’t know was how little work I had done. I pretty much changed the point of view and did some surgical rewrites, but overall, the foundation was the same package she had paid for.

This made me think about how many projects and pieces of work get tossed every day because we don’t ask simple questions about the end goal at the beginning. About how we discard good work just because it doesn’t match the fuzzy picture we have in our minds.

The professional who helped my friend never asked about the ultimate goal. She assumed it was the same as everyone’s: maximize recruiter engagement. And she delivered exactly that. A well-put-together yet generic result.

My friend failed to see the potential in what she already had. A few strategic questions and a few precise rewrites were all it took to get to the desired outcome.

Good work gets thrown away every day. Not because it’s wrong, but because nobody asks what “right” is supposed to look like.

Fire 30% and Call It Innovation

The interview was going well until it wasn’t.

I was sitting across from a VP who was clearly proud of the company’s multi-year financial transformation project. They were upgrading the ERP (Enterprise Resource Planning) system and adding new tools, including some with AI functionality. It all sounded exciting, and I told her so.

This is when the tone of the conversation changed.

She said that the downside of it all was that six months after go-live, whoever got this position (I was interviewing for a Controller position) was going to have to let go of 30% of the accounting department. I asked where these metrics came from.

A 30% layoff in six months seemed extreme to me.

From her response, it became clear that there was nothing behind the number, just the familiar logic that technology should always mean fewer people. She assumed six months was enough time to work out all the bugs after implementation, and that 30% seemed like a big, round number that would show a nice return on the project investment.

I pushed back. In my experience, automation implementations don’t lead to less work. Yes, the simple repetitive tasks go away, but they get replaced with review and control work. Plus, accounting always has a long list of “nice to haves” that can now be addressed.

The VP didn’t seem to like being challenged. She argued that even if the work didn’t go away, I would still have to fire people and replace them with others who had the “right skill sets.”

I challenged her again: “Why don’t we simply upskill the current staff?” It would be easier, and cheaper, since those people already understood the business and the workflows.

She didn’t have a response and quickly changed the subject. She got off the Zoom shortly after, and I knew I was not going to get this job.

And I was okay with it. This was clearly not a company run by executives who value their people.

To quote Ethan Mollick, almost no one is showing any ‘imagination’ when it comes to what AI could actually build.

Business leaders are almost exclusively focused on how AI can help them lower costs by replacing humans. Reducing headcount is the oldest and most basic way to make your numbers look better for a few quarters. But it doesn’t create a foundation for growth.

Why aren’t leaders focused on doing more? Going into new businesses. Creating entirely new categories. Helping their people become capable of work that didn’t exist two years ago. The VP I interviewed with had a chance to build something. She had a team that already knew the business. She could have invested in them. She chose to cut instead.

I’ve Seen Stuff

And just like that, we are in 2026.

After grad school I started this blog to organize my thoughts and share them with the world. I’ve always had so much in my head that it just made sense.

But then life got busy. I started my career, sometimes working two jobs. Suddenly, there were fewer and fewer hours in the day, so I decided to pause writing. The entire time, I was planning to come back once things calmed down. Well, it is now 2026, 14 years since my last post.

So what have I been doing for 14 years? I got my CPA and built a career in corporate accounting. I’ve worked inside companies whose names you’d recognize, alongside people whose personalities matched the size of the brands. I survived a global pandemic. And recently, I spent a year in a CFO Executive program at Columbia that changed my perspective on a lot of things.

As I told someone at a job interview the other day, “I’ve seen stuff.”

My new goal is to post consistently for the next year. Start with a goal, build a habit.

Still, as I revisit my old posts, I realize that my thoughts have not changed much. I have more nuanced opinions on a couple of things, but overall, I still stand by everything I wrote back in the day.

I don’t know if that is good or bad. On one side, it shows conviction and consistency. On the other, it might show inflexibility. After everything I’ve done, you would think my thinking would have evolved more. Adam Grant, author of Think Again and a big proponent of rethinking your assumptions, would probably disapprove. But I’d rather be honest about where I stand than pretend 14 years turned me into a different person.

Let’s restart this journey and see where it takes us.

Good Old Girls Club

Recently, I was having coffee with a good friend and past professor when our conversation turned to the subject of women in power, or more specifically, the lack of women in power. We were both puzzled by the fact that women who “make it” don’t help other women succeed, thus continuing the cycle. Where are the Good Old Girls networks?

This seems to be an even more compelling subject than I thought since the gentleman sitting next to us felt compelled to interrupt our conversation to share his opinion in the matter. Our coffee shop neighbor turned out to be a surgeon. He worked with several powerful women, and he believed that these women were simply smarter than men; their brain power was without equal. These women—he said—were also mean, “catty,” controlling and power-hungry. They were the complete opposite of the men who made it to the top, who were smart—although not as smart as women—but also “good guys.” In his experience, men were more balanced, working not only to be top performers, but also working well with others, helping their fellow-men move up the ladder.

This conversation was still in the back of my mind when a few weeks later I read an article in The Economist that talked about a study done at Washington University in St. Louis. The study had proven that women do indeed not help one another. Women in the study were afraid that if they helped another woman, and this woman underperformed, the underperformer’s failure would cast a shadow on the woman who recommended her. On the other hand, if the newcomer was a success, she then became competition for the few token female positions available. And finally, women did not help other women because of fear of it being considered gender favoritism. In essence, a lose-lose situation for all women.

There is clearly a problem here; the important question is how to solve it? I think radical action should be implemented in the way of quotas. Norway did it in 2007, and today at 40.1% Norway has the highest percentage of women board participation in the world. Some might argue that this is a form of affirmative action. Well it is, but that doesn’t mean it isn’t needed. Women aren’t only half of the world’s population, they’re also 60% of its college graduates, yet they represent only 3% of Fortune 500 CEOs and hold just 15.2% of board seats in these companies. This is an endemic problem that requires dramatic solutions.

And hopefully, by making it easier for women to reach the top, those who succeed will feel less like gladiators that had to claw and kick their way to the top, and more like team players, thankful for the opportunities given to them and thus more willing to help others around them; just like men.

Riding the Wrong List

In a NY Times article, Netflix’s Reed Hastings, was named among 2011’s worst CEO’s. Hastings was demonized for raising prices and trying to break his company into two separate entities, one that would focus on its existing mail delivery DVDs and a second that would focus on its streaming services. Personally, I don’t believe that Hastings deserves to be on such a list; quite the opposite.

Many protested Netflix’s price increase. I am a Netflix user and my rate went up by a whopping $4.00. Some might argue that it’s not the total dollar amount, but the idea of a 20% increase. I must admit 20% sounds high, but these extra costs came to reconcile for streaming services Netflix had been providing at no additional charge. Netflix streaming services were an instant hit in my house, so much so that my living room TV is now dubbed the Netflix TV. I even returned the cable box since it wasn’t being used any more. I saw the value of this service instantly and knew it was just a matter of time before Netflix raised its prices. It was too good to be true. After all, all that content is not free. Admittedly, raising the prices slowly would have allowed Netflix to benefit from creeping normalcy when actions inflicted in slow, small steps go on almost unnoticeably.  A strategic misstep on Reed Hastings’ part perhaps, yet not enough to be one of worst CEOs of the year.

The division of his company is another complaint.  Netflix success blossomed from the demise of the once mighty Blockbuster.  It figured out a way to eliminate late fees and still make a profit.  Netflix changed the way people got their movies, and influenced the way they were watched.  After years of growth it’s now an institution that just like Blockbuster before it runs the danger of eventually becoming irrelevant.  Reed Hastings is working hard to ensure that Netflix remains atop its perch.  His actions are straight out of The Innovator’s Dilemma (by Clayton M. Christensen) which states that well-managed companies can only survive in the long-term by developing disruptive technologies, technologies that might take them away from the practices that made them industry leaders in the first place.

Wizards and Statues

Earlier this week the Academy of Motion Picture Arts and Science released its list of Oscar nominees. And surprisingly, Harry Potter and the Deathly Hallows Part 2, the last installment of the iconic series was missing from the list of nine movies competing for this year’s Best Picture Award. In the interest of full disclosure, I’m a huge Harry Potter fan who owns every film and book in the saga.

But back to the point that I want to make — as we approach the February 26 awards ceremony, the conversation will change from who the nominees are and those who were unfairly ignored, to the ever shrinking audience for the televised event. We will also hear about the Academy’s next gimmick to become more popular. Like the disastrous 2011 attempt to become hipper by having James Franco and Anne Hathaway, two young stars host the show.

I have a question for the Academy: If you want to attract a larger audience, why don’t you nominate movies that people have actually watched? Just like in sports, most individuals don’t watch games simply to awe at the beauty of the athleticism; instead, as fans, they have a vested interest in one or both of the teams competing against each other. For the majority of Americans, or foreigners, as the Oscar is an international event, what is the drive to watch a movie they haven’t seen beat another 8 movies they haven’t seen? Pass me the remote.

You cannot be a popular brand if you do not offer a popular product. This is not to endorse the notion of only nominating commercially successful films, of course, but rather a request that a film’s earnings be not held against it. The Academy can’t ignore popular taste while expecting millions to tune in. Do popularity and high box office make a movie any less worthy of a Best Picture Award? Is art real art only when it is enjoyed exclusively by a select few? I think not. It’s time the Academy learns to give its audience what they want; before its audience decides that the Academy is no longer relevant.

What is the problem with training?

The other day I was talking with a friend who has a long and successful work history and is now trying to change fields. She was frustrated because the feedback she kept getting from recruiters was “stay with what you know. Right now employers are only looking for people who can hit the ground running.”

 This phrase-“hit the ground running”-stuck with me because, in my experience, that is very difficult to do. Even if you performed the same job within the same industry, a new position in a new company always comes with new challenges. After all, each company has its own culture, its own set of procedures, its own way to do things.

 I was once passed up for a job at a medical practice because I had no healthcare experience. The person who was hired (who had healthcare experience) lasted two weeks and shortly after I got a call asking if I was still interested in the position. I took it, and worked there for almost 3 years.

 I think that a better way to approach hiring is to focus on culture match, flexibility, and attitude. Skills can be taught, but you’ll never be able to change a personality.