Magic mistakes and how to make them

Written by Leda Glyptis
13th August 2020

Do everything in your power to minimise the avoidable mistakes and the impact of the less exciting omissions

What is the biggest mistake of your career?

Do you know how many times I get asked that?

And for a long time I have struggled to make the truth sound… truthful.

Because the truth is I haven’t made big mistakes. Not in the way you are thinking.

Few survive big fails in our industry and live to tell the tale. I have made a lot of little errors though. And a handful of what my ex-colleague Tom Evans’ little girl calls “magic mistakes”, the kind that mean you end up miles from where you were going and exactly where you are meant to be. The process is messy. Scary. Often painful. But ultimately pure magic comes from it and that is all that matters. Or rather. That is what matters in the end.

Epic fails

Culturally, embracing failure is both new and alien to banking.

And with good cause.

Have you noticed how banking bods never talk about the big, monumental errors of judgment they made in the past and what they learned from them?

It’s not just because the myth of infallibility is strong with us all (although that too). It is because those who made big mistakes, especially if they were errors of judgment, don’t survive to tell the tale.

The people behind the libor scandal are doing time.

CTOs overseeing a failed murex implementation or a core banking swap-out that went on forever and cost the earth found themselves “open to new opportunities” very quickly.

Errors in judgment cause financial or reputational damage to banks. They cause fines, regulatory intervention and distressed customers. Such errors violate the institution’s and the person’s moral and fiduciary responsibilities to the community, the shareholders and the regulator.

This is not where you fail fast. This is not where you fail at all.

Not because you are infallible, invincible or oh-so-clever. But because you have the onus of responsibility on your shoulders. From your granny’s pension to the funding supporting global trade and infrastructure. You don’t play on the margins of that.

You manage risk. You second-guess and challenge your assumptions.

There is a reason why compliance and legal say no nine times out of ten, within financial institutions.

Mistakes will be made, often huge ones. But let it not be out of haste or carelessness.

Errors within financial institutions can be disastrous and hence all necessary precautions should be taken to ensure they are avoided.

Not for the sake of anyone’s career and reputation. But for the sake of others: their livelihoods and their future financial security.

Errors of omission and commission

Not making epic blunders doesn’t mean we don’t fail daily, though.

Me and everyone else around me.

We make mistakes.

Miscalculations, wrong associations, incorrect assumptions. Plenty of those happen daily in every office. But the reality is those are easy to manage. You have KPIs and leading/lagging indicators around them. You monitor. You report against them. So when they are not working, you are all over it. Whether you try to rewrite history, correct the course or pivot has more to do with you and the organisation you are part of than the errors of commission themselves. But the point is, you notice. You act.

It’s the blind spots that are a different story altogether and the errors I like to hear speak of. The things you didn’t do because it didn’t occur to you that they were needed, that they may be a problem, that that was even a thing.

It could be something huge and glaring (like the time we sent a fully-referreed academic journal to print with a double h in the word ‘ethnic’ on the cover page because, it turns out, our proof-reading process didn’t include the front page being checked as that didn’t change much issue to issue. So nobody looked at it. Someone fat fingered it. Nobody noticed. Long story short, we changed the proofing process as a result).

But it could also be something subtler.

Like the time we discovered some folks were relying on a system in a way that was unmapped and entirely unexpected. The system was not supporting their business and, when we grandfathered it, we discovered that a team in a different division was up in arms as they could not get the subscription details they needed for some new issues (share management services, party time).

At first we were like: who are you people and what are you smoking?

Then we slowly realised that this team had been using the newly decommissioned system as a reference library.

They were doing most of their work out of spreadsheets where securities were listed using just a CUSIP code knowing that all additional info could be pulled out of the system if needed.

They didn’t appear as users anywhere because they didn’t produce or consume data. They just looked at it.

Their needs were not mapped.

They had not even been informed that the system was reaching end of life because, frankly, we didn’t know they cared. And nor did their bosses.

But care they did.

Their spreadsheet was rendered useless overnight, they couldn’t do their job for a few days and, anyway, long story short, they didn’t like me very much after that.

I have a dozen of those stories for every project or programme I have ever worked on. For every piece of business I have ever concluded. The things that we couldn’t think of (robots need a gender in some countries because you can’t give them access credentials without humanising them. And if you have not spent a morning naming your RPA nodes while the world is on fire, you have not lived), the things we should have thought of (if you are trying to anonymise data that lives on a spreadsheet, you will have to do it manually; and it will take a while) and the things we know now (before re-engineering a process, do check that the regulatory requirement it serves is still a requirement; you can thank me later). Sometimes the omission is tiny. Sometimes it’s glaring. The point is, not thinking about something means that when it hits, you have no time, resource or headspace for it. It makes you scramble, it makes you panic. It may make you sloppy. It may make you antsy. It will hopefully make you creative and adaptable, as these things keep happening and you keep learning how to deal with the unexpected. How to ask weird questions and bake in contingency for the weird stuff that is bound to come your way.

These are the errors I want to hear about.

The things you didn’t think about that left you on the back foot.

What did you do?

What did you learn?

Did you fix them and move on? Did you work around them? Did you give up? Did you come back to look at the wider issue underlying them.

There is no wrong answer.

But I want to hear how people deal with the unexpected. And how it arms them for a volatile future.

Are the things you didn’t think of, actually, mistakes?

I would say so.

Not, perhaps, if you take the word to mean “the state or condition of being wrong in conduct or judgment”.

But if you work to a technical definition, things change: if an error is a measure of the estimated difference between the observed or calculated value of a quantity and its true value, then things look very different.

We are now talking about the distance between where you were going to and where you got to.

And I say, yes, the things you didn’t think of are very much mistakes. Often the best kind.

Magic mistakes

If a mistake measures the distance between what you expected and what you got, then its actual value is in the eye of the beholder. And for me, the whole idea of experimentation, failure, iteration, pivots and growth is not about some wise parable involving a burnt cake and a cold desert business starting in desperation. For me it is about doing things that are well thought through and measured but still don’t work out. And they leave you in a new place. With a lot of learnings. And the ability to do something next that would not have been possible had you not ended up in that place of suboptimal outcomes.

In my case, my entire career in finance started that way. A set of choices that didn’t work out as planned. A set of learnings and skills acquired along the way. A new set of options that I would not have considered at the start of the journey. Because I didn’t need to. Because I didn’t see them. Because I didn’t yet have the skills needed to crack that nut open. Because I was a different person then.

All of it.

None of it.

It doesn’t even matter.

That’s the story of my career.

That’s the story of Slack, emerging out of a failed gaming venture.

That’s the story of Listerine emerging out of a failed cleaning product.

Every time I take a sip of single malt I like to think of all the ways in which something went terribly wrong, some valuable resource seemingly wasted, before the thread that lead almost every civilisation under the sun to distilling spirits was fully unwound.

My point?

Don’t fail big. And don’t fail fast.

Try not to fail at all.

It hurts you. And it hurts others.

If you can think of a question, try to answer it. If you can see a fork in the road, account for it. If you know a storm is brewing, prepare for it.

There will be so many things you didn’t foresee. And so many things that don’t work out as planned, that you will need all your energy and ingenuity to deal with those, that it really does help to have done all the homework up front.

Because if you do all the homework. Plan. Second guess. Sanity check. If you do all the heavy lifting and testing and cautionary work up front, you achieve three wonderful things all at once.

First you prove your good intentions and sound judgment. To yourself. Colleagues and partners. And it matters.

Second, you control all known variables and build tool kits, disciplines and stores of experience for all the unknown variables coming your way. You become, by degrees, a little better at weathering storms. And it matters.

Third, you arrive at a new place – whether it is your intended destination or not – with a clear conscience, the trust of your fellow travellers, a good few learnings and a bit of earned wisdom. And it matters. Because this new place may not be where you were heading to but it is where you are so it becomes where you are starting the next chapter from. And if the starting point is new, then so are the new destinations opening up in front of you.

A mistake, perhaps.

But a magic one.

And if you can’t avoid making mistakes – and you can’t; and if you can’t avoid missing things – and you can’t; then do everything in your power to minimise the avoidable mistakes and the impact of the less exciting omissions. So you are ready, willing and able to catch whatever comes out of the next maelstrom and turn each upheaval into a mistake of the most magical kind. And that is what matters, in the end. Till the next magic mistake starts the process anew.

Leda Glpytis