What to do after an unsuccessful contractor engagement

Working with a contractor is a great way to get work done. You get all the benefits, speciality, flexibility, without having to commit to a full time team member. Like all projects, sometimes the project does not go as planned. You start out a project, things are great. At some point things get rocky. The project devolves, timelines are missed, deliverables are missed. Sometimes a project fails regardless of your level of management. You end up breaking off the engagement and are back at square one. What do you do next?

Take some time off

Do not dive right into a new engagement. You will likely repeat the same mistakes again. This is difficult to follow because you probably have deadlines to hit and are now set back even further because of this failed engagement. Resist the urge to dive back in and keep pushing forward. Step back and get clarity on the situation. Take one day off. You can come back to review the project less charged with emotion and analyze what happened with a more logical mind.

Be honest with yourself

When reviewing a failed engagement, be honest to both sides. Sure the contractor might have not executed. They failed on deliverables, were slow to respond to communication and eventually ghosted. However, ask yourself - how was your execution? Did your actions contribute to this project failing? Some questions to consider here are:

  • Did you do your due diligence in vetting the contractor before jumping into a project?
  • Did you run a PLANNING SESSION prior to kickoff?
  • Were there warning flags you ignored before or during a project?
  • Did you give the contractor enough details?
  • Was everyone clear on expectations?
  • Were deadlines, milestones and deliverables clearly set and communicated?
  • Were communication expectations set?

It is difficult to examine the role you played in a project when things go wrong, but I encourage you to do it.

Review what went wrong

Go over the timeline of the project. How did introductions go? How did project kickoff go? How did the milestone achievements progress? When did you start seeing the warning flags? How did the project go downhill from there? When did the project go off the cliff?

Address each of those points. Think about how you can avoid them in the future. Can you improve systems and processes associated with each point? Can you better communicate across the board? Take these improvement and apply them to your contractor engagement process before you work on any more projects.

Move on

Sometimes we just make a bad call in business or contracting. Acknowledge that it was a bad call, learn from it, and move on. Take time off, be honest with yourself, review what went wrong, apply changes and move on. It is the nature of business to have risk and reward.