Failure is an option as an IT leadership tool

The old saying that success has a thousand parents, but failure is an orphan, is especially true in IT. CIOs are skilled at demonstrating successes they have accomplished in their careers, but they rarely comment on their failures.

The problem is that failures are as much a part of any IT organization's history as successes. IT projects that fail to meet objectives are common, including expensive misfires such as ERP implementations or cloud migrations gone wrong. The AI era has introduced a new level of failure, as countless AI pilots have crashed and burned.

But embracing -- or at least recognizing -- failures can play a positive role in CIO leadership, according to Gartner analyst Rob O'Donohue. He encourages corporate leaders to build a "failure resume," which documents career hiccups in the same way a traditional resume highlights accomplishments.

In this Q&A, O'Donohue describes the meaning of the failure resume and why it can be a valuable IT leadership tool. Career failures may not be a badge of honor, but being forthright about them can provide important lessons, as the road to IT leadership is not strictly technical.

Rob O'Donohue

Why is it important that CIOs highlight their mistakes and failures, and what's behind the idea of the failure resume?

Rob O'Donohue: In most organizations -- and especially in IT -- I find that while they talk about leaning into mistakes, learning from them and creating a mindset of risk taking, very rarely do they actually follow through on it. [Gartner research showed that] most leaders -- nearly 50% -- have a fear of failure. They don't openly talk about failure. It's not seen as a badge of honor -- it's a negative.

My concept was to create your failure resume and with that, you're reflecting on the things that you've failed in over your career. Like with any resume there might be an academic angle, a professional angle, a personal angle -- what are the big failures that you've had? And thinking about if those were turning points in your career, was that an inflection point where things started to go well?

How is this a useful tool for leading an IT organization?

O'Donohue: With the failure resume, there's another tool around your career timeline [that shows] peaks and troughs, and homes in on some of those troughs. It's about reflecting on it and seeing when you made this mistake in your career, or as a leader, didn't take into account the challenges that other people were facing and that had negative impacts. What could I do differently, and how could I move forward?

It's good for the leader to have that self-reflection and develop self-awareness, but it also sends a very strong signal to the rest of the organization that you can be successful but still have had a lot of failures along the way. It gives people permission and ties into the idea of embracing failure as something to learn from rather than being something to blame people for.

Is there resistance to that, as people are usually reluctant to talk about their failures and might see that as a checkmark against them?

O'Donohue: The traditional leadership mindset values or traits would have been reluctant to do that. But certainly around the pandemic and the leadership changes that came from that -- and now with AI -- you want to make your people feel like it's OK to fail, to create a psychologically safe environment. More leaders are embracing human-centric leadership approaches. But it is a culture and mind shift, so you have to demonstrate what that looks like.

Traditionally, failure or success is looked at as binary -- you either succeed or you fail. Whereas, you can think of failure on a spectrum. You can have a really bad failure, but you can also have a really good failure. You're then able to put criteria around what a good failure looks like -- but also a great failure and a bad failure -- and then as a leader recognize people for their great failures.

This taps into recognition and motivation. If you're a leader and talking about the great failures that you've had that were the big turning points in your career, and then actively recognizing people who are willing to take risks and have some of these failures, you send the message that it's absolutely OK. It's not that you want everybody to try things and fail and then get reprimanded for it, that needs to change. But the only way you can do that is by behaving that way yourself and recognizing that when others make a mistake, it's not career-limiting.

Are there any specific examples that you can point to?

O'Donohue: [Gartner] did a case study on a company called Tata, which had an innovation competition that had a "Dare to Try" award. They gave an award to the team or individual that effectively had a great failure, that they tried hard to follow the right criteria but they didn't achieve what they were planning to do. It's one thing to talk about it, but then to recognize and carry through and have your behavior meet what you're valuing is a key way to operationalize it.

So, if you don't take a risk that has a chance of some failure, then you might not be suited to lead a large IT organization?

O'Donohue: There are slogans like "let's fail fast," "fail forward," "learn from our mistakes" and "we have a blame-free culture" -- they're words on an email or a memo or on a poster in the office. But unless you are actually highlighting the failures and giving recognition for doing that, it doesn't become that virtuous circle.

If you see that someone has failed but they're still being talked about in an all-hands meeting for doing things the right way, that inspires others to think they're not going to get blamed for a failure. Leaders can demonstrate it, talk about it, humanize it, normalize the failure, but then it's important that when that failure happens and somebody takes the risk that doesn't pay off, they're recognized for it in a positive way.

So having the failure resume essentially formalizes that process?

O'Donohue: Exactly. Every leader should have their failure resume and publish it on their intranet. Make it visible to others, share it with their teams, encourage their managers to do the same thing so that it takes the stigma out of it. It can be challenging for some people in those positions to do that because it's maybe not their normal way of behaving. They hide their failures and only highlight what they were successful at. But there's not authenticity to that. There's something genuine and very relatable to the failure resume and the idea that we all have had failures along the way, and there's no getting away from it. It's about normalizing it, making it OK and encouraging others to do the same. 

Jim O'Donnell is a news director for TechTarget, where he covers IT strategy and enterprise ESG.