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How to Fail Successfully: knowing when to right the ship and when to jump ship

By: Natalee Webb

I grew up with this quote from Charles Kettering: ”It doesn't matter if you try and try and try again, and fail. It does matter if you try and fail, and fail to try again.” While excellent advice, I have also learned, through trying and failing, that there are times to call it quits.

Projects can be a lot like relationships; at a certain point they’re no longer tenable.Some things just don’t work out, and no matter how hard you work to save them, the ship is going down. At that point, being able to fail successfully becomes an essential skill! It’s the difference between getting on the lifeboat and going down with the ship.

Evaluating progress

Remember progress reports from high school? They were supposed to gauge performance in the middle of the semester so that if you were underperforming, your parents, teachers, and you could work together to steady the course before you flunked the entire class. Well, project management and high school have a lot in common. If you have a project in the pipeline or are actively in the middle of one, it might be a good idea to stop and ask yourself if you have a project reporting system in place. Without regular progress reports, a failing project could nosedive indefinitely.

Sometimes project managers may not even realize their project has become unhinged. Unless you have key indicators (e.g. budget, timeline, deliverables, etc.) to chart the progress of a project, it can be difficult to get an accurate reading on project health. Accountability is created not only through transparency, but also by mutually agreed upon bellwethers (completing deliverables on time and within budget) through which success and failure are measured.  

How to say stop

So your project’s failing. Your budget is maxed out. Deadlines have become elastic. Nobody remembers what the deliverables even were. In the real world, this can mean people’s jobs are at stake, and for large projects at small companies, it can be the difference between solvency and bankruptcy. It takes a lot of courage to stand up and admit there’s a problem.

I recently led an effort to vet and select a new tool for tracking projects for our consulting team. I spent months demo-ing and trying out different products that met our ‘must have’s’ list and even had some of our ‘nice-to-have’s’. I purchased licenses for the new tool, we built a custom integration for it and we ran a live project through it. Running the project was meant to act as a final check, but instead raised many red flags.

It had become clear that as it was, the new tool didn’t meet one of our core needs for client interaction. We were months into it and thousands of dollars invested in time and resources but the ROI for staying the course would have cost us even more. I went to our leadership and laid out the reasons we would need to abandon the ship. I got approval to cancel our contract and look for a new solution. It was very disappointing and we lost money, but in the long run, it was the right decision for us, our team and our clients.

Building in checkpoints

While you measure the temperature of your project with progress reports, it’s also ideal to reflect on the successes and failures of the project to date. Don’t wait till the end of the project to do some soul searching. Every time you reach a benchmark or wrap up a deliverable, conduct a lessons learned workshop with your team. Discuss what you’ve done well so far and what’s been lacking, and try to outline best practices moving forward.

Turning failure into success

There’s a great quote from an old Abbot and Costello movie that goes something like, “But if you don’t chase mirages, how do you know they’re mirages?” In other words, sometimes you have to fail in order to realize you’re trying to achieve the impossible. To fail successfully means to know when your goals are unattainable and to abandon ship before you go under. There can be many successes within a failed project. Just make sure you don’t fail the same way twice.

There is a big difference between failing and being a failure; people frequently confuse the two. If anything, the act of failing should be a reminder of your fortitude. Likely, it means you’ve risked something and left your comfort zone, and if you failed successfully, you learned from the experience.

If you’re preparing for a big technology project and could use a little help, check out our whitepaper on setting up benchmarks to ensure success.

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