Category: work

A Record of Your Accomplishments

I opened it and my heart dropped.

A former report reached out asking for help revamping his resume.I had worked with this guy. He is hardworking, smart, and dependable. Yet nothing on his resume showed that. His resume introduced someone who had “participated” and “supported” instead of “led” and “managed.”

I did a revision that more closely resembled the good work I saw him do. He found a great new opportunity shortly after.

I thought it was a one-off when just a few weeks later I got another call. This time from a former colleague. Her company had been acquired, and she was going to be out of a job by the end of the year. She had been looking but had not landed a single interview in months. I told her to send me the resume.

Same story.

I called her back immediately. I had been part of the team that hired her almost a decade ago. I asked her: how is it possible that your resume was better then, than it is now?

The resume is a tough document. In a world where so much of our identity is tied to our work, the resume becomes the record of our accomplishments. People want it to be faithful to their job descriptions, but they end up with a document that undersells their actual impact.

I offered to rewrite my colleague’s resume. I started with one question: what is your value proposition? What is the one thing you can do better than anyone else?

She was surprised by the question. She had not thought about it.

If you don’t know what you’re bringing to the table, you end up with a list of tasks that go from one to the next with no cohesive thread. A resume without a value proposition is an inventory not a story.

The core premise was not forthcoming, so I asked more questions. What projects did you oversee, and how did you contribute to their success? What are you proudest of from this experience? Did you make any changes that improved the processes, the company, or the team?

This is value creation. Most people have it. You just need to uncover it.

As important as what to include is what to exclude. Faulkner called it killing your darlings: removing the parts of the story that you love but that don’t serve the narrative.

My colleague had repetitive bullet points describing junior tasks that didn’t feed the pictureof an accounting professional with the power to automate manual systems and improve processes. She had done that work. It was real. But it was pulling the story in the wrong direction.

As we continued working, my colleague raised a concern that a lot of accountants share: how do you include numbers on a resume?

Salespeople have performance dashboards. They can say things like: increased revenue by $10M in my first year. Cost centers, accountants and other support roles usually have a hard time pointing to initiatives that made the company money. Success means getting the job done on time and as expected. Nothing flashy.

But you can add numbers in other ways. I asked my colleague to think about the number of accounts, countries, vendors, invoices, and entities she managed. These provide a sense of scope. Hours or days saved each month through process improvements, increases in accuracy, reductions in errors. These tell a story of continuing improvement.

After working on her story, I rewrote my colleague’s resume. She used it to apply for a few roles and started getting calls back almost immediately.

We spend so much time optimizing our resumes for the ATS (Applicant Tracking System) that we forget a human will eventually read it. Your resume still needs to tell a story that is compelling, specific, and that truly represents what you bring. The algorithm gets you through the door. The story is what makes someone want to meet you.

I think that sometimes a poor resume is connected to a poor sense of self. So when writing that record of your professional accomplishments, be kind to yourself. You are more qualified than you think. Your work matters. Let’s tell the story of why.

On Budget, On Time, Almost Never

Most projects don’t fail at the end. They fail at the beginning. The people involved just don’t know it yet.

How bad is it? From a database of 16,000 projects, only 0.5% were completed on budget, on time, and on benefit.

These numbers come from a book called How Big Things Get Done by Bent Flyvbjerg and Dan Gardner. I just read it, and it should be required reading for anyone starting any project. The authors focus on big infrastructure projects, yet the lessons apply to projects of any size.

The book reminded me of all the failed projects I’ve witnessed in my career and how they were doomed from the beginning.

It starts with a question most teams never ask: why are we doing this project? Is it mission critical, or are we just following a trend? AI strategy projects come to mind. Everyone wants one. No one is asking the hard question of why.

Then comes planning. How much will the project cost and how long will it take? Usually the answer is a number pulled out of thin air without so much as a benchmark. People tend to assume that their project is unique, that it will somehow take less time, cost less money, and produce better results than similar projects undertaken in the past.

Who has not heard that story before?

And once the project starts moving, there is rarely a system in place to alert anyone that it’s running off course from the beginning.

I took a job with a company that was implementing a new ERP (Enterprise Resource Planning) system due to go live a few months after my first day. This project was one of the reasons I took the job. It pointed to a company that was serious about process improvement and growth.

Two months after I joined, the project was cancelled.

It was not a total surprise. After onboarding, I hit the ground running participating in the testing phase and quickly noticed that the project was not where it should be. I was not the only one with that thought, so leadership hired a consulting firm to audit the progress.

The project was already a year behind schedule and a million dollars over budget. The consulting firm confirmed that there was no way it could go live in a few months. Their estimate: one additional year and one more million to complete. That would have put the project at three years and three million dollars, as long as everything went right from that point on.

The project was dead.

I was full of questions, so I reached out to the most senior person in the department.

Question: Who from the accounting department was part of the implementation team?

Answer: Why would the accounting team be part of that?

The problems started to become clear. No one from the accounting team had participated in any aspect of the project. The very expensive consultants were supposed to deliver a turnkey solution.

Question: Was there anyone from the company who functioned as the bridge between the company and the consulting firm?

Answer: The IT Director.

Question: And was the IT Director removed from his day-to-day duties and allowed to focus on the project?

Answer: Of course not.

This project was never going to happen.

No one had asked whether the original budget and timeline were even realistic. In my experience, any transformation project that doesn’t plan for at least three years is setting itself up for failure. No internal team had been assigned to the project. The very expensive consultants were trusted to deliver a solution for a business they didn’t understand. And the one person designated as the bridge between the company and the consultants was doing it as a side project on top of their actual job.

The real cost wasn’t just the money or the time. For people like me, who took the job because the project signaled ambition and seriousness, the company went from forward-looking to stuck in the past overnight. The project didn’t just fail. It told everyone paying attention what kind of company this actually was.

A million things can go wrong during a project. But it is usually just a few things early on, the questions nobody ask, the resources nobody commits, the warnings nobody builds a system to catch, that decide whether it fails or succeeds.

DOE (Depends on Experience)

DOE. Depends on Experience.

They showed up on a recruiter’s LinkedIn post advertising opportunities at an “amazing” company. Senior Accountant or Manager, DOE. Senior Accounting Manager or Controller, DOE. Salary ranges also DOE.

Why?

Title and salary should not depend on the experience of the candidate. They should depend on the nature and requirements of the job. I have discussed title inflation before, so I will try not to repeat myself.

There is a moat the size of an ocean between a Senior Accounting Manager and a Controller. So which is it? Is the role a Senior Manager job or a Controller job?

If you need a Controller, hire a Controller, and pay for a Controller. Hiring a Senior Accounting Manager and expecting them to somehow do the job of a Controller is setting both the candidate and the company up for failure.

You’ll get Senior Accounting Manager output, and everything else will fall through the cracks.

But the candidate can grow into the role, right? Someone might argue.

How? I ask.

A company that can’t tell the difference between a Senior Accounting Manager and a Controller doesn’t have the accounting leadership to develop one into the other. So who exactly is going to grow this candidate into the role?

A recruiter reached out to me the other day for a “Controller track, Accounting Manager” role.

I laughed. Where is the track?

These imaginary tracks sound less like a well-defined road and more like a self-guided tour through a forest. No map, no compass. Good luck getting to the other side.

I used to work with a woman whose title was Senior Manager, Fixed Assets. Fixed assets, for the non-accountants, are the physical assets of a company. Think equipment, land, buildings, vehicles. Things the company uses to create value.

She was six years away from retirement and wanted to hire her replacement. The role she was really hiring for was Junior Accountant.

Her pitch to new hires: work hard and in six years you can sit in my chair and have my job. She hired two young people who quit in quick succession, unimpressed with what she had to offer.

She then hired an older, and as she put it, more “mature” candidate who would have the patience to wait his turn.

I pointed out that a forty-year-old with over a decade in accounting accepting a Junior Accountant position was possibly a red flag.

She had to terminate him after a week because after five days he still had not managed to learn how to turn on his computer.

She couldn’t understand why there were no qualified takers for this great opportunity. Why weren’t more people willing to take a junior role with low pay that would eventually transition into a middle manager role with possibly still low pay?

This sounds like a joke, but it gets worse. Even that laughable opportunity didn’t actually exist.

Six years is an eternity in corporate America. The company could have been bought and sold many times over. Her department could have been outsourced to a third-party firm, which I saw happen to other teams during my tenure. Or the company could have decided to move the whole function upstream to corporate.

This was not her company, soit was not her track to promise.

It’s time to stop. Stop advertising two roles as one. Stop posting senior roles at junior prices. Stop promising career paths that don’t exist and that aren’t yours to offer.

This is the role. This is the pay. We hope you grow with us, but right now we need this job filled and we need the right person to fill it.

That’s not cold. That’s honest. And honest is what candidates deserve.

Embrace the Chaos

“Embrace the chaos.”

This was the advice my friend didn’t expect to receive.

She called me asking for help updating her resume and preparing for interviews. She told the story of many toxic workplaces. Vague and ever-changing strategies. Lack of resources. Poor communication. High achievers leaving with their institutional knowledge, and managers whose only competency seemed to be delegating work.

She was done with her job.

To her surprise, my advice was to embrace the chaos instead.

I told her to prepare a vision for how things should be done, with her in charge, and present it to the CFO. After all, what’s the worst thing that could happen? The CFO could simply say no. And in that case, I would help her update her resume and look for another job as planned.

Here’s the thing about chaos: in a well-run organization, every problem already has an owner. There is no gap to fill. In a chaotic one, problems are orphaned. Nobody is in charge of fixing them because nobody has been asked to.

So my friend spent a few weeks documenting what was broken and wrote up a practical plan for how she would fix it. Nothing elaborate. Just a clear assessment and a path forward.

What people forget is that if you hate your job and feel like you are drowning, you are probably not alone. Your colleagues are feeling the same way. So is your boss. So is your boss’s boss. Everyone is waiting for someone to arrive with a plan to fix things.

If you are willing to be that person, to own the mess and bring the plan, you can turn a bad situation into the biggest career opportunity you’ve had.

My friend followed my advice. She got a promotion and a salary increase that would have taken a typical accountant many years to reach.

I would never suggest joining a toxic workplace on purpose. A toxic workplace can burn you out and make you question your own worth. I know from experience. But if you are already working in chaos and can’t leave for whatever reason, don’t just survive it.

Use it.

The Math is Not Mathing

Accounting Manager is the single worst job in accounting.

That was my comment on someone else’s LinkedIn post about what Accounting Managers do. It received thousands of impressions. Apparently, I’m not alone in my belief.

What I didn’t say in that comment is why. Not just why the job is bad, but why it matters. Because the damage isn’t limited to the people in the role. It reaches everyone around them.

There is a concept in organizational development called the Leadership Pipeline. The idea is simple: manager roles are linchpin positions. Without them, organizations can’t sustain themselves long-term.

The literature is clear that the most difficult career transition is the one from Managing the Self to Managing Others. The people who get promoted are the ones with the strongest technical skills. The ones with the interpersonal and relationship skills needed to succeed as a manager get left behind. What makes you good at the first job is not what makes you good at the next one.

Still, this is not an insurmountable obstacle. Training can go a long way.

But of course, that’s where the real failure happens.

I remember being a first-time manager and having my Director reprimand me for scheduling too many training sessions with my team. They should know, she would say. My response: how? Who taught them?

She didn’t have an answer because there wasn’t one. Nobody had taught them. Nobody had taught me either. The company expected people to become managers overnight and then blamed them when they struggled. The training budget was zero. The patience was less than that.

A less experienced person would have taken that feedback and stopped the sessions. I doubled down.

But most new managers don’t push back. They absorb the message: training is a waste of time, your team should already know, figure it out. And then they spend the next several years managing by instinct instead of by skill, burning out, and wondering why the job feels impossible.

Over the years, I’ve had friends take steps back in their careers because they didn’t want to ‘babysit’ a team. I’ve never liked that comparison, but I understand where it comes from. When you’re given a team with no training on how to lead them, managing starts to feel like supervising instead of leading.

But here’s what people miss: the team feels it too. Nobody wants to be managed by someone who is clearly overwhelmed, clearly untrained, and clearly just trying to survive until the next close. Reports can tell the difference between a leader who is developing them and a manager who is just keeping track of them. When both sides feel like the relationship is broken, it transforms from a people problem to a design problem.

And the math confirms it. The increase in pay from individual contributor to manager is rarely proportional to the increase in stress and responsibility. You take on twice the workload, lose your overtime eligibility, become accountable for other people’s output, and get a raise that barely covers the difference. The math is not mathing.

This is the first consequence that people feel in their careers, long before the pipeline runs dry. The job stops being worth it.

And young people have noticed.

A little more than a year ago, I was having lunch with a group of junior and staff accountants  from another team. The conversation turned to the career ladder, and every single young person at the table said they didn’t want to ever become managers.

They saw their own manager and thought: too much work for not enough money.

Gen Z is choosing to stay in individual contributor roles. The more entrepreneurial ones are pursuing side hustles and their own path. The famous 5-9 after their 9-5.

They are not wrong.

The real question is what happens 10 years from now when there isn’t a pipeline of experienced managers who know how to build and lead a team. What happens when we forget how to get things done through others? What awaits us when the institutional knowledge of how to develop people, run a close with a team of varying skill levels, and turn a group of individuals into a functioning unit has simply disappeared because nobody wanted the job?

The optimist in me thinks that when faced with that crisis, companies will finally invest in real managerial training and build compensation structures that make the role worth taking.

The pessimist in me looks at current leadership, at how they’re letting things deteriorate in real time, and thinks that by the time anyone notices the pipeline is empty, it will already be too late to fill it. And when that happens, we won’t just be missing managers. We’ll be missing the people who know how to fix the problem.

The Worst Job in Accounting

Believe it or not, becoming an accounting manager was aspirational when I started out.

Being a manager meant making more money, having more freedom and flexibility, and having real power and autonomy. There used to be a clear distinction between managers and working managers. Managers oversaw teams: onboarding, training, reviewing, and assigning work. Working managers did all of that plus carried a full load of their own deliverables.

That distinction no longer exists. Now all managers are working managers, juggling workloads sometimes heavier than their direct reports’ while also being expected to manage their teams in their downtime.

Devaluing the title destroyed what made the job aspirational.

The worst part is that we did it on purpose.

In a recent episode of the Optimist Economy podcast (recommended listen), titled “No Overtime for the Supervisor of Sandwiches,” economist Kathryn Anne Edwards discusses overtime. Midway through, my ears perked up. She puts words to something I’ve observed for years but couldn’t quite articulate.

Edwards discusses how in 2004 Congress raised the salary cap for overtime eligibility. In response, businesses did what she calls the “systematic managerial titling of workers.” To avoid paying overtime, companies took employees who had just become eligible and gave them managerial titles. Managers are exempt. Problem solved. One of the most outrageous examples: hostesses becoming Directors of First Impressions.

I am not an economist, but this clarifies so much of what I’ve seen in my career.

Early in my career, I reached a breaking point waiting for a promotion. I was ready to quit when the company’s CFO called me to his office. He argued that the problem was not the lack of a promotion, but my attachment to a title. His words: we all know what you do for this company and we value it, so what does it matter what your title is?

I looked at the nameplate on his desk. It read: Cofounder / Chief Financial Officer.

I said: so we can change that to Janitor, and you wouldn’t mind, right? I mean, we all know this company wouldn’t be what it is without you.

He paused. Then he smiled. You’re right, he said.

Titles matter. They matter to the people doing the work. They matter when you’re looking for your next opportunity. A title is one of the few data points a potential employer uses to understand the scope of what you did. And it matters on the other side too: when a candidate evaluates a role, the title is how they gauge what the job is and what fair compensation should look like.

By overusing and outright abusing managerial titles, companies broke the compass. Accounting Manager has become the single worst job in accounting.

And things are getting worse.

In recent months, recruiters keep reaching out to me about Accounting Manager and Senior Accounting Manager roles. Their opening line is always the same: this role is expected to run the entire accounting function.

They outline the responsibilities. I listen. Then I let them know that what they’re describing is a Controller, not a Manager, and I advise them to go back to their hiring team and rethink the title and the compensation package.

The title inflation that started as a way to avoid paying overtime has now become something else entirely. It’s a way to get senior-level work at mid-level prices. That’s not a broken system. That’s the system working exactly as designed.

When Everything is a Priority

In a sea of “tell me about yourself,” someone asked an interesting question at an interview the other day.

The hiring manager asked me how I prioritize when everything is a priority. In this era of doing more with less and fast-moving environments, it is a fair question, and it started a meaningful conversation about how we work. It’s a question most people answer with instinct. There’s a better way.

When prioritizing, I use three pillars: risk, visibility, and materiality.

Risk.

In accounting, there are areas of the financials that have a higher propensity to cause harm if things are missed or not kept under control. Revenue recognition and accruals at reporting period ends are common examples. These areas tend to be the focus of compliance efforts. A useful signal: if an area comes up time and time again during audits, it is probably high risk. The question to ask: what happens if I get this wrong? If the answer scares you, that’s where you start.

Visibility.

Leadership will always have one or two KPIs (Key Performance Indicators) that they track closely while monitoring growth or the lack of it. Maybe it is a metric that once caused a major issue in a senior leader’s career, and they’ve learned to watch it closely ever since. You’ll know what these are quickly. They will be the first or second thing asked about during review meetings. It keeps you from getting caught off guard. When leadership asks, and they will, you need to have the answer. The people who advance prioritize based on what leadership is actually measuring.

Materiality.

Materiality is the accounting concept that only information significant enough to influence stakeholder decisions needs to be highlighted in financial reports. Most companies set a quantitative materiality threshold, a minimum dollar amount that triggers further review or action. If an issue falls below that threshold, it won’t necessarily be ignored, but it won’t be prioritized either. In accounting terms, “it is not material.” This is the pillar that gives you permission to say: this can wait. Most people never give themselves that permission.

These three pillars often overlap. When something is risky, visible, and material, that is where you focus first. No debate needed.

But here is what I find interesting: these are accounting concepts, but the logic behind them applies far beyond accounting.

When choosing what to prioritize in any context, ask yourself: What is the risk of not doing this? Do the people who matter, your team, your boss, your family, consider this important? And will this decision meaningfully change the outcome, or is it noise?

Those three questions can cut through most of the paralysis that comes with competing priorities. Not everything that feels urgent is risky. Not everything that is visible is material. And not everything that is material is visible. Knowing the difference is where good prioritization starts. And in a sea where everything feels urgent, that might be the only thing that keeps you afloat.

Know Your Numbers

Graduation season. Commencement speakers across the country are talking about AI, and how it will change everything. Graduating classes are booing them. They just spent four years and a small fortune preparing for careers they’re now being told might not exist.

I won’t pretend to know what AI will or won’t do to the professional lives of new grads, but I do know what determines whether people make good career decisions or bad ones.

It is not just talent, or timing, or connections. It is whether they are acting from confidence or from fear. And that almost always comes down to money.

At some point, most people will be in a job they hate. And although you can always change jobs, the process can be lengthy and difficult. In the current environment, it might feel downright impossible.

You never want to stay at a job that is affecting your mental or physical health just because rent is due on the first. You don’t want to be pushed into actions that could hurt your professional reputation for years just because you don’t have a single month of savings.

When I talk about a safety net, I don’t mean millions or even hundreds of thousands of dollars. If you understand your numbers and know your burn rate, how much you absolutely need to survive for a period of time, you can act.

Early in my career, I found myself at a job that was toxic. I was not valued and had spent years waiting for a promotion that never came. Worse, the job had started making me question my own worth. A voice in my head started whispering that maybe I wasn’t good enough for that promotion.

I had to leave.

I started looking for another job, but I felt that the toxicity and the long hours were not letting me perform my best at interviews. I needed to leave and cleanse myself of that place. I would not advise this as a first choice, but it was how I felt at the time.

I looked at my numbers and decided that I needed $5,000. This was over 15 years ago. Things were cheaper, and I had a lot fewer bills to pay, but that and some part-time temp work should be enough to get me through six months.

From that point, my focus was on saving that $5,000. Once I had it in the bank, I quit. And things worked out. When I look back, I always see this as the real beginning of my accounting career. A small amount of money and confidence in my numbers made all the difference.

But it is not just about escaping from a bad situation.

A friend recently reached out to me, completely bummed out. A company had contacted him with his dream job. The job he wanted since he was a kid. He loved the company, the mission, the team. The role was a perfect next step and promised a lot of upside. But it came with a 30% pay cut. The company was a startup that couldn’t match his Fortune 10 salary. He was offered equity, but promises of future riches do not pay the bills today.

He looked at his budget and couldn’t figure out how to survive with 30% less. With a heavy heart, he turned it down.

I hope this experience makes my friend take a hard look at his numbers.

Most people don’t think about money as a career tool until the moment they need it to be one. A new job that requires a move. A new opportunity that requires a pay cut. The chance to pursue a dream. All of those require a reserve of money and the clarity to use it.

It all comes down to money. Having cash in the bank gives you freedom. And most importantly, it allows you to act from a place of confidence, not a place of fear.

Ironically, even if you decide to stay at your job, knowing that you could leave changes everything. You speak up more. You walk with more confidence. You hold your convictions more firmly. And that makes you a better leader and a better employee, the kind that good organizations notice and reward.

To new graduates, I still don’t know what AI will do to your careers. But I do know this: learn your numbers. Know what you need. Build a cushion. Everything else gets easier from there.

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.