Who will ask you the tough questions?

How can one short conversation undo months of decision making and design? And how can that be a good thing?

If you have been a technology architect for a while, you probably spend time trying to make difficult decisions. You may be defining the architecture for a major programme, or an essential platform, or an important business initiative. You are in the cut and thrust of choices and arguments and opinions every day: it sometimes feels as if you will never get out. But finally, clarity begins to emerge: you find the answers to the most important questions, the ones that unlock the rest of the work. Are we going to pick this product or that product? Or this partner or that partner? Or this approach or that approach?

You know that there is lots more work to do, but now you feel that you can proceed with confidence. The most difficult decisions have been taken.

And then you encounter . . . that person.

This is the conversation you have been subconsciously dreading. Not because you don’t like the person: in fact, you have been working together for many years and get along really well. Not because you don’t trust the person: in fact, you know that they are mostly right most of the time.

It’s because you know that they are going to ask you the innocuous question, ‘How’s it going on <X>?’ And you’ll start explaining that <X> is now going much better, because you’ve made these big decisions, and now you can get on with the rest of the work . . . until you realise that they have that look.

‘Why did you decide to go that way?’ they ask. You try to explain, but you start to get a sinking feeling. All of the reasons that seemed like good reasons when you were in the middle of decision making, suddenly seem much weaker. Did you really choose the product on the basis of functional fit, or was it to keep the noisy stakeholder quiet? Did you really defer that tough choice because it’s best made later, or was it because the meeting had already gone on too long? Did you really think that was the right delivery structure, or were you just trying to give everyone enough responsibility to keep them happy?

You realise that you are not as confident in your big decision as you thought you were. Now that you have to explain it outside the bubble of the project team, to someone you respect, you can see all of the compromises and concessions that you really shouldn’t have made. And your sinking feeling is even stronger now: you realise that, not only do you have to re-do some of your work, you have to undo some of the consensus that has emerged in your team. And you’re going to have to be the killjoy that breaks the news.

Of course, you could ignore the implicit challenge from your colleague. You could defend your choices, even though you’re not confident in them any more. You could even use the difficulty of changing direction as a reason not to change course. <X> has momentum now! (Even though it might be momentum in the wrong direction.) But that would not be a position of architectural or personal integrity.

If you’ve been in this situation then, believe it or not, you are lucky. It means that you have someone in your life who will challenge you, who will pull you out of your bubble and make you re-examine your decisions. In a very good recent book, No Hard Feelings, people like this are described as part of your challenge network.

The book suggests that, just as everyone needs a support network to help them when things are tough (or just when they need a bit of encouragement), they also need a challenge network to make them stop and think. The people in your challenge network can be as important as the people in your support network. Indeed, it is usually a harder job being part of that network: it can be a lot harder to ask ‘Why?’ than to say ‘Well done!‘

If you don’t know your challenge network (and I didn’t know I had one until I learnt the term a week ago), then it’s worth figuring out who might already be in it. Who is that person you have been avoiding sharing that difficult choice with? Who is the person who tells you what you need to ask rather than what you want to hear?

And if you really don’t have anybody you can rely on to challenge you, you’d do well to think about finding somebody (and to ask yourself whether all those decisions you’ve made recently were as good as you thought they were). There are ways to build a panel of challengers. Peer review makes us better, whether it’s a formal part of your local methods or not: try inviting some peers to review your work, even (or especially) if you think it’s perfect. And make sure that you give them permission to give you difficult feedback: you’re not just looking for affirmation.

Challenge is good for everyone, but is particularly important for technology architects and technology leaders: we make decisions with long term consequences for our customers, our companies and the people who work for us. We know in our hearts that we often get it wrong, but we sometimes need to hear it from others before we believe it. In the HSBC Technology Architecture team we try to follow the principles of Zang Jing Ge: technical excellence, communication mastery and leadership power. But we also try to remember that technical excellence means learning from others, communication mastery means listening to others and leadership power means inviting challenge.