Updated: Dec 3, 2020

When you start a new job, there are two information asymmetries that have a very strong impact on the end result of the process.

One is in the candidate's favour - He knows better than the hiring firm how good he is, how suitable, how much of a team player, his real motivations, etc. In other words, he knows if the hiring firm is hiring a dud or a star much better than they do (there are of course some exceptions).

The other is in the firm's favour - they know how good their platform is, what the culture is like, why the last guy quit, what will shock the new hire in week one and what he'll only discover in year two.

From a candidate's perspective, this latter one is devilish. By and large, for a firm the chioce is "is the candidate a star or a dufus". We're simplifying of course; but, if you get that right - and many firms have processes that do this very well - more or less the hire will be a success most of the time. For the candidate, it is much more complicated, because the choices aren't so binary. It isn't simply a matter of good or bad. it is nuanced. How much responsibility will I really have? How open is the culture? How supportive are they really of this line of business. Most of the time, the candidate won't even know what to probe into. He'll do a general probe, asking general questions to the best of his ability - but, without knowing where the bodies are buried, how do you know where to look for skeletons?

Below is a list of questions I have devised over a career of nasty surprises to try and ferret some of these things out. This is not exhaustive or bulletproof by any measure at all - but, just maybe, some of these questions will help open your eyes to some things you might have otherwise missed. At a minimum, they'll reduce the number of things you might get wrong by a little bit.

Some of these are generic; some more forensic, as you head down the list. To me, they're all quite important.

  1. Does this job play to your strengths - If you take on a senior, attractive role at a good firm where you have to spend 7 months a year travelling, and you have young kids; or have to be excellent at poring through legal contracts and agreements, but you're more big picture vision; or writing complex spreadsheets, where you're more a dynamic salesperson; you are structurally setting yourself up for failure. YOU NEED TO DO WHAT YOU LIKE DOING AND ARE GOOD AT DOING.

  2. Do you believe in the underlying model - Imagine that a firm hires you on big money to lead the in house legal team. Imagine their business model is clubbing baby seals and selling the skins. Ok for you? not ok for you? Do you think that is sustainable from a business model perspective? A bad model could be the 8th Gym brand in the city. Or office delivery dry cleaning. The answer to this question determines if you have a job in 24 months' time.

  3. Is the macro good - This could be an entire blog post on its own. In fact it will be. Basically, MACRO TRUMPS MICRO. Ie, if the industry/segment overall is growing, that's very good - because even a mediocre guy then grows with it. If it is contracting, then you need to be a superstar just to stand still. Run downhill, not uphill. Go somewhere with a good macro backdrop.

  4. Is there sufficient upside - If things go well, how much better off are you (in money, growth, prestige, name your metric)? If the answer is 1.25x, then that's a lateral move and why are you bothering? Go for places where you can become meaningfully better off in some way if things go to plan. Don't go somewhere you KNOW that won't happen regardless!

  5. Self actualisation/personal growth - I've taken moves that I knew were personal limbo, basically for the money. It is a steep price to pay, and it stunts you later on. Remember, no growth = negative growth, because you atrophy very very very quickly. Two years like that are enough to degrade you substantially and leave you materially less valuable in the job market. THIS IS NOT TO BE UNDERESTIMATED. The opposite is also true - strong personal growth can compensate for many ills (I've done that trade too). So ask yourself - where I'm going, will I be fulfilled by doing that job day to day; and will I be growing? If not, there better be something HUGE to compensate. or don't do it.

  6. Values/cultural fit - Again, this is really its own post. In a nutshell - your basic values need to be aligned with the organisation and its senior people (your peers/bosses). If, for example, you are an honest person, with a strong vision and the ability to withstand short term pain for long term gain; and they are liars which just care about next quarter's headline revenue number; trust me that is unsustainable, and you will find unhappiness and leave very soon, with another blot on your CV. If they like things old school, and you are all about tech enablement, ditto. Etc. BEWARE THE CULTURAL MISFIT.

  7. Understand the senior setup - Ask who the senior people are, how they relate to each other, how decisions are made, etc. Literally, a detailed org chart with connecting lines and dotted lines for who is what to do with whom. DON'T SHY AWAY FROM DOING THIS. This will tell you two things. First, which you REALLY want to know, is the nuances of the setup. Is there someone you'll end up having a dotted line into? Is there someone with an overlapping mandate, who will end up an internal conflict? Do your co-head bosses hate each other and you'll be forced to choose? Is the guy sponsoring you about to get pushed out? You don't want to land and then realise you've missed something hugely important, and it's too late; and you could have just asked. YOU NEED TO KNOW THE SETUP. The second thing is that this will tell you what environment you are stepping into. Is it collegiate and successful; or toxic, political and unproductive? Nobody will tell you this going in, but you need to ferret this out before you jump. It's a bit like joining a ship crew going on a five-year voyage. It would have helped Ishmael to know Ahab was mad.

  8. Decision culture - Again, this is quite nebulous and high level. Basically, find out how the decision making process works. The first answer will always be "all relevant people are consulted and feed back. Of course there is a boss, that ultimately decides; but overall it is very organic". This is the party line. What you're really asking is this - is there a healthy culture where senior people's views and mandates are respected and are impactful; or is it a dictatorship where one guy runs the show at his whim, boundaries (like don't call me at midnight Saturday) aren't respected, and when Napoleon decides to go to Waterloo you're all dead, period. Much of the time it is the latter, so delve into this.

All of these may or may not make you or stop you making a move; but are guaranteed to leave you much better informed, and with a much better feel for an organisation, then just "how is the culture here?". EACH MOVE YOU MAKE IS REALLY IMPORTANT - take the trouble to do your due diligence.