3 Tools for Investigating (and Fixing) Struggling Projects

It’s always challenging when an essential or strategic project hits a series of roadblocks or stumbles. Here are some tools for investigating and starting to correct your struggling projects.
July 4, 2022
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For many tech leaders, projects are one of the greatest joys and most significant challenges of their roles. Projects bring our tech vision to life and are often where technology connects to the broader businesses’ strategic priorities. Projects are also a chance to collaborate with outside experts and perhaps experience new technologies firsthand. Done well, projects can also serve as a proving ground for your future leaders and a way to cement strategic partner relationships.

However, when these types of projects struggle, they become one of the most significant challenges for tech leaders. A failing project can call into question a leader’s competence, judgment, and fiscal prudence and may even derail other positive elements of the leader’s agenda. 

While unpleasant, not every project will proceed according to plan. Here are 3 techniques that can help you get to the bottom of why a project might be struggling and start the process of taking corrective action.

Find an Unbiased “Investigator”

An obvious first step in investigating a project that appears to be struggling is understanding the root causes and magnitude of the problem. While this sounds simple, it can be quite challenging.

As the leader that likely had some hand in approving, selling, or launching the project, an early challenge is having the humility to acknowledge that something is going wrong to the point that you require corrective actions. No one wants to admit that an effort they sponsored might be hitting some challenges. Still, concerns about reputational risk must be balanced with the fact that fixing a wayward project grows increasingly difficult as time wears on.

Members of the project team are likely too immersed in the operational details of the project to make an unbiased assessment, and the project’s leaders and sponsors, yourself included, have too much personal stake in the success of the project to make a dispassionate assessment. Find someone from outside the project that can make an initial assessment of what’s going wrong and even offer some initial avenues to explore for corrective action.

There are several good sources of unbiased investigators. The key is to find someone interested in the organization’s overall success without having a personal interest in that individual project. New hires to the organization can be effective investigators since they’re approaching the project and organization with “fresh eyes” and minimal biases. Doing a project assessment can also be an excellent first major task in their new job. It will allow them to meet colleagues, see how the business works, and perform a highly impactful role that doesn’t require deep operational knowledge.

External partners can also be good sources of project investigators. They’ve likely seen dozens of similar projects and know what pitfalls and challenges might have befallen yours and potential corrective actions. Be aware that external partners will probably assume that they can “do it better” and arrive with an unstated objective of taking over your project.

Provide “Pressure Relief”

If you’ve ever cooked with a pressure cooker, or the modern “instant pot”-style cookers, you’ve had to release the pressure inside the pot at some point. You rotate a small valve, and a torrent of steam violently hisses from the pot, eventually turning into a small wafting trail of vapor. 

That sort of happens when working on a complicated project. There’s likely intense pressure, frayed nerves, and frustrated staff. As a leader, you can open the metaphorical valve on your struggling project to release some of this tension. Aside from providing a temporary reprieve from whatever challenges the team is facing, this activity can also provide a forum for airing whatever challenges the project is facing while resolving some of the interpersonal tensions.

Call a “pause” to the project for a day or two, and facilitate separate sessions with the project’s leadership, line managers, and staff, as well as a group session. Solicit and capture what’s going well, what could be improved, and 2-5 actions that the team and leadership will take immediately to improve the state of the project.

The effect of this pressure relief can seem cathartic at the moment, but it will be short-lived if you don’t ensure the corrective actions that the team agreed upon are immediately put into practice.

Change the Project Leadership

It can be a risky proposition, but sometimes new leadership can reinvigorate a project and get it back on track.

This intervention should usually be held in reserve until an unbiased investigator finishes their work and concludes that project leadership is responsible for many of the project’s struggles. Unless warranted, try to avoid the project “blaming and shaming” the outgoing project leader for every battle the project faces. 

Projects are a great proving ground for developing future leaders, so carefully avoid creating a situation where these people actively avoid leading a project for fear of being punished for taking on a challenging role.

Use the installation of a new project leader as a “reset” for the project, and allow that leader to institute other changes to team leadership or staff as one of their early actions.

Changing leaders can be costly in terms of the project timeline, so balance the benefits of new leadership with the “startup penalty” you’ll incur when swapping leaders. You may also consider external leadership and hiring a trusted partner to take over the project’s leadership. You’ll likely get a competent leader with the additional support of their organization behind them but risk creating an “us versus them” mentality if you don’t carefully manage the relationship.

As a tech leader, developing, proposing, and launching projects is a critical aspect of the job. It’s often one of the more exciting elements as it’s a chance to see your strategy come to life. However, carefully monitoring your portfolio of projects and intervening effectively and appropriately before they go awry is also a critical task. Using the above tools can help get your struggling projects back on track and are worth deploying as soon as you suspect a project is facing headwinds.

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