Do you wish to proceed? y/n

If you play video games, particularly adventures that take many hours to complete, you may be familiar with an experience you sometimes get just before the end. The list of sidequests is dwindling and you have run all the errands for your party members. You suspect that you are nearing the conclusion of the story, when an option pops up, something like this:

Do you want to proceed? (You will not be able to return past this point.)

If you’re anything like me, when you see this option for the first time, you say no, you save your game, you check your inventory, you upgrade everything that you can upgrade, and you save your game again for good measure. And then you say yes.

If you don’t play video games, you can get the same feeling by administering a computer, even if it’s just your own laptop. Sooner or later you will get prompted to apply an upgrade, accompanied by a message something like this:

Do you wish to proceed? y/n

If you’re anything like me, when you see this option for the first time, you hit n, you check that your backups are in order, you check that nothing important is running, and you take one more backup just for good measure. And then you hit y.

If you manage a software deployment pipeline or service management system, you probably build checks like this into your process. There are some changes that are fine to make automatically, and there are others where you want to give yourself time to think.

I sometimes think it would be good if we could build similar simple checks into other decisions that we take in enterprise computing. I’m not thinking of the governance and approval processes that most organisations already operate. Whether those are effective or not, they often deliver complex, nuanced and caveated decisions: subject to making these recommended changes, or recording the risks in the risk register, this design is approved by this committee to proceed to the next stage of the process.

I am thinking of a simple, binary choice: Do you wish to proceed? y/n

I can think of several situations where such a prompt would have been useful to me:

Launching a programme

You’ve spent months making the business case for this programme. You’ve aligned all the stakeholders. You have the backing of your sponsor. You have even received a project code from the portfolio management system. You’re ready to go!

Do you wish to proceed? y/n

Are you really ready to launch? Do you have your teams in place? Do they understand the mission? Do you still have sight of your objectives, or have you lost sight of them in the approvals process? Do you really wish to proceed?

Continuing a programme

The programme has been running for nearly six months now. You have made your first production releases. You have experienced many setbacks. The team has pushed from forming to storming: you’re hoping that they’re going to start norming soon. You’re about to embark on the next phase.

Do you wish to proceed? y/n

Is the programme still focused on the same goals? Or have you got distracted on the way? Is the team really starting to gel, or are they just getting too tired to argue any more? Are you motivated by the goal, or is it just momentum? Do you really wish to proceed?

Finishing a programme

You’re nearing the end! You’ve had to extend the time and the budget, but you eventually hit your milestones. You are getting respect and admiration from your sponsor: they know how hard it was to get here. You’re about to declare victory and call the whole thing done.

Do you wish to proceed? y/n

Are you really done, or have you just run out of money and energy? Did you really achieve your goals? What is going to happen to this thing when you walk away? Have you created a product or simply finished a project? Do you really wish to proceed?

And so on. We can apply this same mental check to many other decisions, such as deploying a new technology, or buying a new product.

Unfortunately, life does not usually give us these simple prompts. Perhaps that will be a feature of Augmented Reality in the future, but in the meantime we’ll have to create them for ourselves.

I am not suggesting that we become hesitant, or that we spend all of our time attempting to second guess our decisions. But I am suggesting that, unlike video games and systems upgrades, it is not always obvious when we have reached a point of no return. If we are leaders of change, we should look out for such points, and make sure that we are not carried across them by momentum or by process. We should make our choices explicit, and pop up that mental dialogue box in our heads.

And, when we are ready, when we give ourselves the answer y, we should commit and move ahead with confidence.

(Views in this article are my own.)