Between a rock and a hard place: navigating strategy conversations with cynics and pessimists
All of us in innovation, transformation or digital jobs inside banks sit within strategic priority spaces. We are there because the executives and the board believe that what we represent is useful, vital or inevitable. The end result is we get hired.
The emotional context in which that happens varies wildly from effervescence, to resigned acceptance to abject fear, but that actually makes little difference. Because once in, what you do may be a strategic priority and you may be its poster child, but the what and the how is not left to you and neither is it debated with the senior sages that hired you.
Your strategy, your budget, your pilots and deployment schedules, your business plans and proposals don’t get seen by the top guys whose strategic priority you are, until you’ve gone three rounds with the custodians of BAU whose strategy is – quite rightly: make money, keep the ship upright and sailing and don’t break anything.
You can’t argue with any of that.
Both because none of it is wrong or unhelpful and also, literally, because you can’t argue with the premise of “if it’s not here already, I have no space for it”.
The high priests of “if it ain’t broke don’t fix it”
Realists are the friends of the innovation team. They instinctively get agile, they understand iteration, MVPs suit their mindset and they know that the future is coming fast. They are our most natural allies.
Among them, however, there is another species lurking chameleon-like, looking and sounding a lot like our realists but packing a potent venom peculiarly suited to killing aspiration. They are the cynics and you will know them because they will be scoffing at big ambitions in the name of realism, every chance they get.
They will be the ones who confuse the practical with the familiar, who will dismiss anything that is not yet complete as fanciful, and anything that is not yet proven as childish.
They will be the ones who erect boundaries.
They will be the ones who will drown a proof of tech in paper questionnaires. They are the ones who will debate governance for days, without pausing to discuss the actual project and who will demand a six-week risk assessment for a two-day trial.
They are the ones who will ask you for transparency, demanding a series of metrics irrelevant to your work and when you try to explain how you actually work and suggest meaningful metrics that actually demonstrate your progress and don’t require a full-time resource translating what you actually do into this irrelevant language, they will dismiss you as philosophising. They may even issue a covert challenge that only people who have something to hide refuse to report.
Bite your tongue, don’t say that only people who refuse to learn want the world chopped down to the shape they are familiar with, all else be damned.
Saying it won’t change a thing.
You have found the cynics and they outnumber you.
Cynics in their natural habitat
Good software and good business starts with purpose. Good meetings start with purpose. Good everything starts with purpose.
What is this for, who is it for, how useful/important is it and what would it take to do it? Equally, what would happen if we didn’t do it?
Only when you know the answers to all this do you move to the next set of questions. What else do you need to know? What would you need to test or ascertain. Where do you start.
The realists will follow you on this journey which is part thought, part design, part fieldwork, part prototype – paper, Keynote and buggy code.
The cynics will stop you on your tracks before you even get into your first discovery session. To them purpose is theoretical, what they what to hear about is feasibility.
And if you point out that you don’t know what you are building yet, you will be dismissed as unprepared so tread with caution.
To pit purpose against feasibility is lunacy.
Because feasibility matters, it’s just not the start.
Those who start with feasibility won’t fail. But they won’t go very far either. Those who start with purpose and balance desirability with feasibility and business value go anywhere they like, eventually. It’s a long and windy path and folks not travelling it don’t have visibility of every bend on the road. When you invite them in, is when they join in.
So, since you are the one who starts with purpose, eat your own dog food and invite the cynics in when there is purpose to their joining: when the feasibility piece is ready to be fleshed out, stress tested and signed off.
They will be right at home and you will find them much friendlier when faced with a task they understand.
Keeping the wolves at bay
It helps to think of the work place in terms of attitudes as well as aptitudes as the latter can be taught, the former not so much.
When you are looking to get things done, the cynics will forever be around. You need to work with them, you need to placate them, you often need to meet them more than halfway and if you are clear about what they do when they are not interacting with you, you will not find them hard to deal with. You will even appreciate what they bring to the party.
Just make sure you go to their party and they don’t come to yours.
Cynics abound but they make terrible UX designers and bad engineers – and before you say, no way have you met Steve the wiz kid in the algo team, I say don’t confuse grumpiness with cynicism. They are worlds apart.
Cynics still come into IT and they may get by as PMs, architects or InfoSec (sorry guys but it’s true, plus not all architects and Info Sec folks are cynics) but they can’t build things. If they can dream of something that doesn’t currently exist and commit their time, energy and intellect to working out why it doesn’t yet exist, what would it take to change that; if they commit time to actually building things, line by line and stroke by stroke they have you fooled. They may talk a good corporate cynic game, but no cynic can dream and then build to the dream and still deserve the cynic badge.
To build you start with purpose, you think about what good looks like, before you think about what may stop you or what may go wrong. You think about what may work first and test it rather than think it and then put pen to paper imagining disasters.
It helps to check in with yourself as you go along: not just “is this working?” But “is this the thing we want to build?”
If not, stop. You are going the wrong way, towards something feasible, but not useful.
Get personal
We lose our way many times a day. As humans and as professionals. We make one choice after another, we take one step after another. We get into conversations that go wrong, we are presented with false dichotomies and skewed choices and we don’t always find the language to re-set these conversations. We act in the moment, in the context, in the circumstances. What else is there to do?
Actually, a lot.
Start with purpose. Stay with your purpose.
We are not just protecting your employer’s time and resources, this is your life you are spending doing things that may be feasible, but are not useful. Is this how you want to live?
Is this feature you just spent three hours defending part of why you are building this solution? Is this stakeholder you spent 20 minutes on the phone to, getting yelled at, part of your purpose? Wasn’t their involvement just FYI?
Is the conversation you are being drawn into constructive? Is it trying to solve something? Is it informative? Is it at least amusing? Is it helping someone think or feel better?
If not you may want to consider getting yourself off the treadmill of venomous repetition.
As a person, as a developer, as a project manager and as a business.
Most of the noxious, miserable things you do that make you hate your job and your life are actually fundamentally misaligned to the purpose you are serving.
You can blame it on the cynics but that won’t help.
If you guard your purpose even the cynics will find theirs. You just need to remember to drive, the cynics come along for the ride but are not allowed at the wheel.
Speed bumps and pessimists
You have negotiated the cynics, you have worked out which stage of the journey to bring them in on, how much of your thinking needs to be complete in order for them to be able to engage without risk of hurt or injury to your relationships, the project or your team’s motivation. You have your feasibility study. You are good to go, foot itching on the gas pedal.
And your heart sinks when you realise that what you envisaged as an open road is actually a narrow lane festooned with traffic cameras and speed bumps, figuratively speaking. The road ahead is littered with signs of mistrust: constructs to prevent you from erring, in full expectation that you will try to.
I am of course referring to the layering of internal controls we impose on ourselves, not trusting that our employees have the knowledge, maturity or moral compass to make the right decisions unsupervised. Digest that for a moment.
The truth is that every banking organisation has institutionalised pessimism and you now have to contend with anything between three and seven risk departments (no the numbers are not made up, we can compare notes one of these days) who expect the worst. They have seen things go awry and expect them to do so again, they have seen markets wobble and expect them to do so again, they have seen regulatory fines and would like to never see those again.
They expect the worst from their suppliers, from their customers, from you.
They are the Eeyore of corporate life and much like the gloomy donkey, they can’t help it. You start from a dream and the art of the possible, they start from horror statistics confirming that everything that can go wrong, eventually will.
They are actually incredibly helpful people to speak to again and again when you are framing your work. They are constructive, if you ask them the right questions.
Your error – mine too, at first – was asking them to believe from the get go.
You are asking Eeyore to lead the dance.
What if you asked them where the dance may fail instead. You listen carefully and adjust. You bring them in when you need them – and you do need them. You ask them to do what they are meant to do and do well. You listen and adjust.
You adjust the music volume and pace, the instructions for the dancers, you check the fire escapes. You ask them again.
It takes time but you are the one with the vision and the purpose and you never expected the work to be fast. This is part of the work, as much as writing code is.
Spend the time. You will find them tapping their feet to the music before long.
Ask people the questions they are empowered, able and willing to answer.
Invite them to the dance but don’t force them onto the floor.
This will frustrate you both along the way. But in the end you need both the cynics and the pessimists, not just because they have the power to say no to your work (although that too) but because their viewpoint is useful. They will help you iterate and foresee and plan and test even more thoroughly as you are getting to your purpose.
They may not believe until a lot of the ground is covered, that’s also ok. That’s your job and it doesn’t happen overnight.
Ultimately the cynics and the pessimists are simply raising the same question that keeps you up at night: can we manage the risks, what will happen if this doesn’t work, is the downside worth it?
It’s unfair to ask them to answer for you.
Where you are heading to is the only benchmark for assessing if the risks, toils and efforts are worth it.
Start with purpose. That’s the only way to determine what the end game is worth.
Then spend time finding the right time to bring the cynics and the pessimists onto your journey. Stop trying to make them see what you see and find them a place that is both useful to you and allows them to feel useful. Let them find their own purpose that accelerates you along your way. It will take time and effort. But it is always worth it.
By Leda Glyptis
Leda Glyptis is FinTech Futures’ resident thought provocateur – she leads, writes on, lives and breathes transformation and digital disruption.
Leda is a lapsed academic and long-term resident of the banking ecosystem, inhabiting both start-ups and banks over the years. She is a roaming banker and all-weather geek.
All opinions are her own. You can’t have them – but you are welcome to debate and comment!
Follow Leda on Twitter @LedaGlyptis and LinkedIn.
