Middle management lessons

Things I've learnt or unlearnt over the past 13 years

I’ve been working for 13 years; by tenure and actual position, I’m now in middle management. Over this time, I’ve learnt a few things - or, in some cases, had to unlearn things I thought I knew - and have decided to write them down. All these are cliches, but cliches that many people (including my past self) often reject:

• Sometimes you should rely on judgement and common sense more than on data and research

• You should learn to manage upwards

• It’s helpful to think about what you’re trying to achieve when you talk/write, and to consider how you come across

• Hard work probably matters more than talent

Judgement Vs Data

In an older blog, I had written a long diatribe on how much the phrase ‘gut instinct’ grated on me. I stand by this to an extent: ‘gut instinct’ is trite and overused and not particularly pleasing as a turn of phrase in the first place, and many people misuse it - they rely on instinct in situations where they just haven’t had enough experience to develop it.

However, I’ve since worked at companies that pride themselves on being ‘data-driven’, and I’ve learnt that there is such a thing as being overly reliant on data. One well-known issue is analysis paralysis: there are too many managers these days who are unable to make a decision without 90%+ confidence. Such a level of confidence is hard to attain in all but trivial situations - and so these kinds of managers end up endlessly debating and requiring more research without never making decisions. This is particularly jarring when people agonise over decisions where the choices really aren’t all that different:

A second concern is that often the common-sense and obvious answer really is the right answer, so going with it saves time. Over the past 20 years it came in vogue to question established truths, and to point to counter-intuitive findings to prove that human experience and judgement are fallible. Books like Thinking, Fast and Slow led many of us to believe humans are irrational, and that we should force ourselves to conduct sober analysis instead of relying on experience and knee-jerk reactions.

Many of the studies that discovered these findings have since been debunked; humans are not as easily confused / misled / nudged after all. Yet lots of people still have an allergic reaction to drawing on experience. This, together with the trend of ‘flat hierarchies’ where even senior leaders are reluctant to lead by fiat, preferring to build consensus, means that organisations move too slowly, gathering more and more data points to ‘drive alignment’ instead of moving fast using judgement.

(Incidentally, common sense would have served well both those psychology and behavioural econ enthusiasts who started believing almost magical effects, and those critics who seem to have overcorrected, and claim, for instance, that there are no such things as priming effects. Does priming work? Of course it does: fill the missing letters in the following list of words: CAT, D_G, R_T. You probably went for DOG and RAT, not DIG or ROT, right? Does this mean that you’ll walk measurably slower if I talk to you about Florida? No, probably not. You don’t have to run studies to guess the answer to these questions with a high degree of certainty!)

I’m not suggesting here that companies gut their data departments and go back to basing decisions on anecdotes (in fact, one of the most useful functions of data teams is to remind leadership that notable anecdotes are usually noise, not signal; more generally, data teams can do a lot to help identify issues and problems). But most organisations should learn to move quickly, and use data to evaluate their decisions and iterate - not demand absolute certainty in advance.

(A third issue with ‘data-driven’ companies is that they obsess over an endless number of experiments and micro-optimisations, all the while they neglect their higher-level strategy. I’m a huge fan of experiments - and of setting up an org in such a way that running experiments is straightforward, and can be done repeatedly / by default for any change; but I also think that worrying about things like button positioning and font size and colour scheme when you’re failing to address core customer needs is a little silly. So while a data-driven mindset ought to be cultivated, this must not be done in a way that causes people to obsess over details while neglecting the basics; in most cases, a thousand micro-optimisations are less effective than one macro-optimisation.)

Managing upwards

For most of my career, I’ve been terrible at managing upwards. I focused on doing my work, with very little communication to my managers - I felt that giving status updates without asks was unnecessary and pointless, that talking about successes was distasteful, and that bringing up problems showed lack of initiative and autonomy.

This started changing when I started managing people myself. One of the people I managed in particular was very diligent in preparing an agenda ahead of our weekly 1-1, covering everything they were working on that week; for most items on the list they’d just give me an update on what they’d done; for some, they’d ask for my help or advice. Far from finding it pointless, I found this practice extremely useful: it helped me understand what was taking up time and effort, what was working well across the organisation and what could be improved, what they were naturally good at and where I needed to invest time in coaching them, and what their achievements were - which made it much easier writing their annual review.

While I quickly realised that this kind of upwards management is not annoying but valuable to managers, I didn’t start doing it myself right away - it’s one of those things that just didn’t occur to me. (It’s strange that! It’s often the case that things that should be obvious simply do not occur to people - n.b. Madoff’s response to why he didn’t flee to a country that wouldn’t extradite him. See also the next section of this post :))

But eventually it did occur to me, and I have started being more diligent in keeping my managers informed on what I’m doing in more detail. And it works well!

Purposeful communication

Another thing that ought to be easy to do, but which many people seem not to do (I still rarely do!) is to try to see themselves from others’ perspective. Like, when you say something, can you try and imagine another person saying that same thing? How does it come across when you see/hear a third party saying it? Good? Cool? Lame? If the latter, why do you think it’d be cool if you say it?

(One thing that I think trips people up here is that when we imagine things, we do so in a cinematic setting. In cinema and TV people get away with saying things that would be incredibly obnoxious in real life. James Bond can order a martini - shaken, not stirred; if your mate does this at a bar, how will they come across? TV characters can have catch phrases - real-life people, not so much. So, when I say ‘imagine someone saying what you said’, try to imagine them in a real setting.)

More generally, many of us (certainly I) aren’t particularly conscious of our communication. I like to think aloud - talk and say things without clear purpose, just to voice my thoughts. There are times and settings when this is useful; but probably more often than not, it’s counter-productive. This is especially true with non-verbal communication, including email and instant messaging. A lot of people are not only bad at expressing their thoughts and objectives clearly, but seem unable to decide what form of communication to use.

The best practices I’ve observed are:

• Before you communicate, be clear in your own mind on the outcome you want your communication to drive: is it to solicit information? To secure agreement? To provide information (with no further action required from the recipient)?

• Plan your communication with that purpose in mind. Provide the relevant information.

• Then, put yourself in your recipient’s shoes and think how you’d respond to the communication you have planned - would you do so in the way you want the recipients to respond? Would you have all the information you require?

• Finally, think of the best medium through which to communicate:

  • If you need to provide extensive context, or require a paper trail/documentation, use email;

  • If you have a quick question, expect some back-and-forth, or need a quick response, use IM;

  • and if it’s a complex issue that requires a lot of detail and explanation (or several people to contribute), use a meeting or a workshop.

  Of course, there will be some grey areas, and you’ll have personal preferences and strengths (both yours and your recipients’) that you need to take into account (including, for instance, dyslexia; or, if you’re more analytical than charismatic, you may find that your writing is more persuasive than speaking). Still, I think these guidelines will help a lot.

Hard work Vs talent

School and university fail bright kids in two ways: first, they turn learning into a chore, and sadly, many pupils never rediscover its joy; and second, they fool students into thinking they can get by coasting. And it’s true that if you’re smart, you don’t need to work very hard - despite what one reads in the media about how selective schools are getting, it’s relatively easy to make it to top (or if not top, second-tier but still elite) unis.

(For instance, the acceptance rate at the UK’s top unis are:

• Cambridge: 19% (and 34% for post-graduate!)

• Oxford: 17.5%

• Imperial: 14%

• UCL: 63%

The Oxrbidge rates are inflated, because UK applicants can only apply to one of the two, not both. Still, over half of the people who apply to UCL - ranked 9th in the world - get accepted; over a third who apply for a masters at Cambridge get in (though of course there is some selection bias here). And once you’re in, it’s easy to do well - at UCL, almost a third of students graduate with a First.)

So there is a large number of young men and women who, up to age 21 or so, are rewarded simply for being born smart. They do not learn the habit of hard work; if anything, they learn to sneer at it: they see their peers studying longer hours to get to the same place they got without breaking a sweat, and they become arrogant.

And then they enter the workplace, and more often than not, they find that things don’t work quite the same way. There are a few reasons for this. One superficial reason is that at work, one’s output isn’t as visible or immediate as it is in school, and so people start observing the input - the hours put in, the number of analyses conducted, the quality of the decks produced, the meetings held. In school tests, questions have a right and wrong answer; bright students tend to intuit the right answer, scribble it down, and get full marks (even if they don’t show their working). Their harder-working, not-as-bright peers learn to be more methodical, show their steps, expound on their work. In the workplace, this serves them well: because it is harder to ‘prove’ that a particular approach is right, managers and executives want to see long, detailed documents justifying it. Bright coasters haven’t learnt to do this.

(These bright coasters (including my past self) are often annoyed by this state of affairs - they object to being judged on their input, or on trivial details such as formatting, or being told they need to write long documents / give presentations to justify their recommendations. But these requests are not needlessly bureaucratic; they make sense. Business decisions are taken in contexts with high ambiguity, and they’re hard to get right - as per my previous points, it’s fine to rely on judgement once you’ve developed it, but when you are early in your career, you do need to prove you have good judgement, to an extent at least.)

A second reason is that at work, there isn’t a finite number of questions one needs to answer. So, someone who works hard will answer more questions than someone who coasts (by which I mean, they will complete more projects).

Despite these two reasons, bright but lazy people can still do well in the workplace; but they will rarely be exceptional (unless they’re very lucky - that also happens!). Ultimately, doing exceptional work is really, really hard; harder than getting into Cambridge, harder than graduating suma cum laude. And so, if you’re used to doing well without trying, the first time you do something like work that does require effort, you’ll stumble.