As a founder of multiple startups and current COO of Hightail, I’ve led many projects - from launching new websites to rebranding a multi-billion dollar global company. While I’ve had some great wins, I don’t mind admitting that there have also been a few disasters.
Here are five mistakes that have caused projects to fail and how entrepreneurs can avoid them.
We'd all love to run a Super Bowl ad, but you can’t do it on a shoestring budget. And while businesses need goals and dreams, leaders need to temper them with a healthy dose of reality and expectation setting. This helps make it clear what you can actually achieve given your available time, resources and budget.
Recognizing your constraints can lead to unexpected benefits. When the founders of 37 Signals began work on their signature product Basecamp, they made an honest assessment of how much time each person could invest. As most of the founders still had full-time jobs, their time constraints forced them to develop a feature-lite project management tool. This simplicity turned out to be one of the major factors behind the success of the app.
To avoid misaligning dreams with reality, your business needs a culture of honest communication that encourages clear-sighted discussion across all levels, instead of just having unquestioned orders flow downstream.
Whatever the project, a company’s first instinct is to put an in-house team on it. After all, that’s what they’re there for, right? But just because someone is part of your company doesn’t mean they’re the right person for a specific project.
The key is to be honest with yourself and your employees and, if necessary, look outside your core team to find the best people for a project. Start building relationships now with agencies, contractors and consultants so you have a network ready to fulfill specialized tasks when the time comes.
In Hollywood, they say it’s easy to make a bad film from a good script but impossible to make a good film from a bad script. Though you won’t always recognize a bad idea straight away, once you do, never assume that you’ll make it work or believe that you’ve put in too much effort to change course.
The minute you recognize that an idea won’t work, you have to pull the plug.
I once worked with an external agency on a series of digital ads but after a number of designs, tweaks and iterations, I still couldn’t convince myself that we’d hit gold. Eventually I realized that the visual approach we had agreed upon at the beginning of the project was wrong. After we decided to start over and work with a brand new set of stylistic references, the project came together very quickly.
The minute you recognize that an idea won’t work, you have to pull the plug. It’s usually impossible to retrieve a bad idea, and you’ll only waste time, money and energy trying to put lipstick on a pig.
A project often has multiple parties interested in its outcome and groups may even have divergent goals and expectations. I once spent weeks working with a designer and copywriter on a website homepage redesign, only to have our carefully-crafted work dismantled by the company’s various heads of department demanding changes to meet their individual needs. Our problem was that we failed to establish who owned the project and therefore didn’t deal with potential conflicts and disappointments in advance.
Renowned animation studio Pixar has a large group of people it calls the “brain trust” that meets to review films at different stages of production. Though the committee’s job is to provide notes on potential problems and offer solutions, none of the advice is mandatory. The film’s director retains complete control over the final product.
Feedback is an essential stage of any project. But decision-by-committee rarely leads to the best outcome. Every project should start by establishing clear, workable goals and give one person the ultimate ownership and accountability for meeting them.
Typically the bulk of work on a project happens below the level of the final approver. You often get a situation where, for example, a freelancer works closely with their contact at a company to complete a piece of work, only to hear the dreaded words: “now I just have to run this past my boss.” I call this “the contractor’s nightmare”.
As someone who is often the boss, I find it remarkable that I am expected to just give a thumb up on a final version that I saw at the end of the project. In reality, my first experience of a project is likely to produce lots of questions, comments and suggestions. While I don’t believe in micromanaging talented people, being able to review a project at certain set stages makes for a better overall process.
When beginning a project, establish clear checkpoints for the ultimate approver to provide feedback. This will help ensure a smoother path to the finish line.
Applying these suggested preemptive strikes and remedies should help you avoid catastrophe on your next big project.