How to spot a toxic boss – before you work for them

Get the jump on two-faced toxic nightmares and avoid potentially getting miserably stuck – by using these tested tips

God, I really wish I could turn back time and write this article for my younger, more naive self – look how happy he looks! I could have saved myself a lot of pain, a lot of frustration, and a lot of grey hairs.

At least I’ve still got my hairs…

We’ve all heard of them, and if you’ve had the unfortunate pleasure of working with them, you know just how terrible it can get.

Toxic bosses.

Male or female (or other) – they come in all shapes and sizes: with a smile on their face, offering intoxicating career opportunities in one hand, and an emotional and physical beatdown in the other.

I’ve had the unique pleasure of working with some terrible people in my lifetime, in one of the worst breeding grounds for this type of personality: investment banking.

I will disclaim now, that for the most part, the large majority of people in this field are just pleasant, normal people (no Napoleonic complex, superiority complex, daddy issues, and so on).

Whatever the reason, whether it be the so-called complexity of the day-to-day, the promises of high pay, or the competitive field to get through to get in the door, this career seems to attract these emotionally stunted moths like wildfire.

And the worst part about these unheld-as-children hellspawn is that they can be so deceitful about their own personalities. I 100% know that these managers are not acting unknowingly – I’ve even remember hearing one particular specimen, in a moment of supposed personal reflection, say “I know I’m not easy to work with…” … you know?? And yet, to suit their own purposes, if they want to hire you, they will present themselves as the best, most sincere and emotive people on the planet.

All to be reversed on day one.

Trust me, you’ll need a thick skin to work with one – and dealing with one on the job employs an entire toolkit that we’ll deal with in a separate post –

but why even put yourself in this situation in the first place, if you can avoid it?

If you can avoid it in the first place – do so at all costs. You can potentially risk years of your own emotional health, and even career prospects, because of a toxic boss. You’re better off elsewhere.

Unless you’re the type who can easily quit a job – and this is after you’ve narrowed down your field of prospects, maybe even declined a few offers whilst picking one, and having jumped the hurdles of a usually very lengthy hiring process that can take months, multiple interviews, and tests (hmm… another topic again! for another post – how to improve the hiring process) – AVOID like the plague.

So how can you spot a toxic boss, before you join a firm? Easy! Right?

Through my 10 years of experience dealing with more than a fair share of toxic personalities, I’ve outlined the 3 must-ask questions you must ask before you join any firm that will potentially reveal a toxic boss – that I share with you now.

If you’re even hesitating for one second about someone you may be working with soon, please do read this – it’s for you.

The tactics you must employ

First – before we go over the 3 questions you must ask that will potentially reveal a toxic boss:

First and foremost – you MUST treat interviewing as your screening tool from your side

It sounds obvious but you must go above and beyond here. The hiring process as it usually is today is mostly flawed and you need to use what you can to not make a potentially terrible mistake of working for the wrong people.

Treat the interview process as a two way street, and the best opportunity you have to find out about someone. And this is flawed, because you’ll need to work past the facades that people put up. In fact, you should be asking for more interviews from your side, and meet with the same person as many times as possible, where possible, because the more time you talk with someone, and ask directed, purposeful questions, the more you can get a sense of who they are.

Too often I see interviews being conducted (or taken by interviewees) as a one directional exam. It should not be this way (another point for my hiring process post). No, an interview is a process of give and take – you need to be able to receive as much or more information from the hiring firm as they receive from you.

This separates the good candidates from the best – those who are confident enough in their own worth to ask probing fit-for-purpose questions, knowing that they are a great candidate and should only work at the best places.

Yes, you must answer the questions, and do well – but the most successful juniors I’ve interviewed, and the most successful seniors I’ve interviewed (on the other side of the table… see what I’m doing here?) are ones that understand this right to equally negotiate learning about each other.

Even in this process itself you can learn invaluable amounts of information in how the firm and its employees will treat you, or each other, in the way this quid-pro-quo is either honoured, or denied.

I’ve actually stopped interviews where I was applying for a role, and have walked out because I saw that the person interviewing me was, well, for lack of a better word, a dick.

She conducted the interview like it was a grilling exam, and spent the better part of an hour trying to “catch me out” on any detail that I may not know on a technical basis. I knew this might be the case from the start when she introduced herself proudly as the self-proclaimed “technical expert” of the team (watch out for these…)

I knew after about 45 minutes that this was not going to be a fit, so I calmly shut my notebook, told her this wasn’t going to work out, expressed my regret for not having the chance to learn more about her and the firm, and walked out.

By all means, definitely answer the questions. That is why you are there – so they can vet your level of understanding and skill. But I’m talking about the way this is done, when you can tell they are more interested in finding out what you don’t know, than what you do, with an air of condescension should you not understand the query or even – god forbid, not know.

Second – talk to as many non-offered employees or related connections as you can

Do not skimp on this step!

Expand beyond the interview scope. Ask to speak to juniors, of if offered a junior, then other juniors; other seniors, laterals, as many as you can make seem relevant. Try even reaching out to former teams, if you have cause to.

Your main concern here should be to get a background corroboration on your main manager – your direct manager – but also, by asking a couple of quick informal questions (outlined below, I promise) to those related to your team, you can suss out potential team member issues.

Third – remember, “they” will sugar coat it

Conflict of interests here – another reason why the hiring process is so flawed. The people you interview at the firm will likely want to paint a good picture of the firm or any hellspawn managers because it does not serve them to speak negatively about it.

Think about it – say you’re speaking to a junior about potentially working in the firm and you ask what she thinks about x manager – of course she won’t, without being guided, be forthcoming with the truth about any potential toxicity.

So it’s important to point out to whomever your speaking to that

  • you would like to speak candidly, and off the record;
  • that you are only trying to get as much information as possible up front, rather than walk into a situation that is turns out to be not what you expected

Beware tactful phrases here, in her response or in your questioning. Be polite, respectful, but by all means direct and clear.

Ask them about any difficult personalities in the work place, and ask the three questions (in the next section) regarding any identified problems.

If you are speaking to the manager in question, or other “tactful” managers – ever notice when someone just isn’t answering your questions, despite A LOT of words coming out of their mouth? Try to redirect after they try and confuse you – be gentle but firm and ask if they wouldn’t mind providing more details around [x]…

Often times, a toxic manager will “white lie” it here. You won’t get the honest truth (if you did, amazing!) so be prepared to read in between the lines. You are building a case, based off of empirical evidence, witness accounts, and personal interpretation. Use these tools provided to probe, but also, do not underestimate your gut when you don’t trust the answers.

The 3 questions you must ask that will give you a great indication of how toxic a person is

Ok – the questions you must ask.

These are only scripts – you can obviously tailor them in various other ways to meet your style. I’ve provided a few alternatives in italics below – but the point is the same.

Question 1: deadlines

  • Can you describe how you go about handling deadlines over projects that you’ve had advance notice? So, outside of surprise requests… I’m talking BAU (Business As Usual) here.
  • Tell me about last minute deadlines. Are these common, and how did you handle it? Why was it last minute?
  • How flexible do you consider a deadline you establish, provided feedback from your team?

You want to understand how much advance time they give ahead of any projects that they have clear sight over – not counting sudden ad hoc or surprise requests. You want to know how the person in question handles a project they have advance sight over. You also want to establish whether they can be flexible with deadlines – often a good manager understands that a deadline needs to move because maybe they overestimated, and it’s their job to manage the expectations around that deadline. Holding firm to a deadline simply because they promised it is a sign of a bad manager – he will burn you at both ends simply to provide it.

Question 2: micromanagement

  • Are you an iterative drafter, and like to work through versions, or do you generally visualise well what you want beforehand? How hands-on / involved are you, before you consider the task complete?
  • Do you value delegation of tasks?
  • Are you able to set a task, establish a deadline with your team, and then await the update, or do you feel it necessary to chase? How often do you chase?

The worst bosses through and through will micromanage you to death. Something about their personality won’t allow them to let go of a piece of work, or they will continuously ask for updates and versions, versions, versions. You are not a robot, or a monkey (my apologies to monkeys, actually) designated to crank out drafts for a person so that they can figure out what they want. You should be allowed space and thought to address the task given, thereby contributing your value-add.

I’m not saying that drafting, or iterative processes, aren’t allowed – I’m saying that your value is completely diminished when you’re treated like a automaton word processor or whatever function you’re doing.

In my experience, I remember to this day one of the first days working for one of these two-faced characters – mind you, it was all smiles and pleasantries up until this point in the various meetings and interviews – and being asked to deliver a piece of work that would likely take a few hours to do well.

Keen and eager, I set to the task, and imagine my surprise when this toxic boss came by my desk not even 10 minutes later to ask when he could have the work. Over the course of the next hour, he would chase me another several times – in the end I delivered something that in my opinion was rushed, and I knew I had a major problem on my hands.

By the way, if you’re thinking, well why don’t you just tell him to back off and communicate a reasonable timeframe? Of course, I did this – but the effects of this proactivity will wear off in less than a week, if not days.

Once a micromanager, always a micromanager.

Question 3: emotional at work

  • To the best of your knowledge, are you aware of anyone you’ve worked with describing you as being ‘difficult to work with”?
  • Have you ever been angry at work?
  • [if yes to either, describe the reasons why they said this]

This is the big one. I’ve asked this question, and usually the response is a surprising yes. Why?

Perhaps their answering no would be too far from the truth, and they know you can easily verify this, so in their mind, coming truthfully is the best tact.

The yes is usually followed by a detailed story of some incident – and this is important for you to know, sure, but more importantly for you is to note that they will paint this story as a testament to their drive, ambition, or ability to “bring home the deal”.

It’s also important to note – very importantly – that answering yes here does not in isolation signify a toxic boss. Some managers genuinely have a world view of being driven, and “tough” to get results – but also being fair. The “tough but fair” attitude in my book is actually commendable, because sometimes, some employees to get by delivering lackluster work. If a piece of work is rife with errors, then yes, it’s fair to be tough here.

It’s important to try and suss out the element of fairness here when asking this question.


Ok, so the three questions were more like topics but the scripts there are meant to inspire you to ask about these three areas. Deadlines, micromanagement, and emotional behaviours in the office are definite consistent threads I’ve seen in the worst of toxic managers.

Yes, toxicity exists beyond this scope for sure – I’m sure it can be based on the petty, and the personal – and I’d love to hear more about this kind of behaviour (comment!) – but in the case of spotting a toxic manager before you work for them, these tools will definitely give you some good insight.

I want to hear your toxic boss stories! All genuine contributions are welcome. Also, stay tuned here and on our YT page – I’ll be releasing a video on this topic as well.


  1. Honestly, i do not think there is such a thing as toxic bosses, as you step into their world, focus on organisational objectives, once you deliver, you will not have issues with your boss.

    Many times we find ourselves in conflict with other people like in the case with your blog, is because we do not understand each other very well, especially if we do not understand why we are in the same room together.

    Each one plays a role in every toxic relationship, boss or subordinate.


    1. For the most part I think you’re absolutely right.

      But I’m talking about some people that really are jerks or have a personality complex. I know, I’ve worked with them. I’ve seen people in tears, have gotten drunken work calls in the middle of the night, and more. Come back on Sunday – I’m posting a vlog with details on the bad examples I’ve seen! – cheers for your comment – Elliot

      Liked by 1 person

      1. You are right, it is sad that there people out there who take advantage of people because of the positions they hold or because of their privileges in society.
        i have also encountered such people, but i resolved to focusing on the work objectives and ignore their attitudes.


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