Jason Westland- CEO and Founder of ProjectManager.com

When I arrive at work, the first thing I do is take 10 minutes to set a daily goal.

Jason Westland is the CEO and founder of ProjectManager.com. He has over 20 years experience managing large projects including a $1b project for British Rail in the UK. Jason has been the founder of several companies; Method123 and MPMM.com became the leading toolsets in the PM templates and methodology industry. Jason founded ProjectManager.com in 2008, innovating in the online Gantt and online project management software industry. He is the author of the best-selling book The Project Management Life Cycle and writes for ComputerWorld and CIO Magazine.

Where did the idea for ProjectManager.com come from?

I’ve managed projects all my life. And the biggest frustration is always knowing whether your projects are on track. In most cases then you need to use complex spreadsheets and formulas to work it out for yourself, so I was inspired to solve that problem for other project managers. The crux of our product is the online Gantt, which rivals Microsoft Project, but it goes further because as teams are updating the status of their tasks in real time, and all of that real-time data is populated in the Gantt chart and the dashboard and reports. This allows managers of projects to see in real-time if their projects are on track.

What does your typical day look like and how do you make it productive?

Like any CEO, I’m constantly having to balance meetings workshops, calls, emails… but underneath all of that is a desire to move the needle, if only a fraction, by actions that I undertake that day. When I arrive at work, the first thing I do is take 10 minutes to set a daily goal. A goal, for instance, might be to increase signups from a particular web page or to be able to improve the customer retention rate by improving our value to customers. So throughout the day I do try to balance the meetings and workshops, etc with that goal. A typical day for me is setting the priorities for the day in the first 10 minutes, and then I try to clear all email within the first ¾ of an hour, and then I carry on with the workshops and strategy meetings with key players in the organization and see where I can to try to influence the needle in the particular areas I outlined that day.

How do you bring ideas to life?

So we’re a relatively small company, with a 35-person staff, so it’s extremely easy for us to take an idea through to execution, simply because we can make it happen within a day or two. It’s what enables us to be more agile and ahead of the competition, especially since we’re competing with the likes of Microsoft. We’ve got a pretty solid process internally for ideas. Firstly, ideas that are discussed or come about as a part of workshops or meetings get tabled. We then run a specific session on that topic with key players to uncover the benefits or merits of that idea. And it’s then prioritized. If the idea has a high priority in terms of adding value to the business, typically, that day we’ll bring about all the relevant parties to make it happen. And if it requires execution on the website, then usually we roll that idea out within 24 hours. If it’s within the product, it might usually be a week.

What’s one trend that really excites you?

I’m still excited by the movement to mobile both the increasing processing power of mobile phones, as well as the number of people globally that have larger phones because all of that means we can now give that much more information to our customers. In the old-fashioned days, we might have text alerts, to be able to distribute data to customers. For example, a data item might be that “Bob has updated his timesheets.” Or “Bob is unavailable on Tuesday.” But in the new world, that allows us to send out information related to that data throughout mobile apps and mobile website in the form of more visual methods. Like demonstrating progress… Instead of an alert telling you a project is 23% complete, now we can actually visually show them a progress indicator and within the project apps show them visually which project is ahead or behind.

What is one habit of yours that makes you more productive as an entrepreneur?

I would argue it’s my habit of getting up on the whiteboard with a marker. Sometimes it makes meetings slightly longer! But what it does generate is a lot of ideas that allows us to think outside the scope of whatever problem or solution we’re discussing before.

What was the worst job you ever had and what did you learn from it?

When I was 10 years old, I went to work for my father at his construction business. One day he had me move a pallet of bricks from one side of the site to the other. The next day, while apologizing up and down, he had me move them back. Another time he had me build a trench for drainage alongside the building foundation. The next day, same story. He is nice as pie apologizing that he had me dig it on the wrong side of the building. Little did I realize he was just giving me paid work, at a time when there was little to be found. But I did learn how to work hard without complaining.

Years later, when I was a young man and worked for New Zealand Police, I managed a big business process for engineering. As part of that, we had to document the entire police operation for distributing information across the organization. It was a big laborious process that took several months to just be able to document the current process not even to look at the process improvements. After 3 months, I learned the documentation process wasn’t even needed. The problems with the process were actually immediately visible right at the highest level. And with a series of workshops, we could have actually identified where those processes were broken, and identified what needed fixing. We could have probably achieved in 3 weeks what took us 3 months to do. But I still didn’t complain.

If you were to start again, what would you do differently?

When we started ProjectManager.com, we definitely tried to build too much too quickly. We built out an entire feature set that we thought was needed by customers in one big-bang project and went live with it. This time, if I was starting the business over again, I’d use the Lean Startup model and release one feature to customers, and get their feedback on it, before building out the next. And that’s the process that #Slack have operated, and it’s made them successful.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Mine is to think outside the square. It’s why I pick up the whiteboard marker every time a business problem presents itself because I’m always convinced there are ways to solve problems without having to take a sledgehammer to a nail, and without having to make a lot of change in the business. We often come up with really smart solutions, as a result.

What is one strategy that has helped you grow your business? Please explain how.

In the early days, I was the only person responsible for marketing in the organization. The one strategy I focused on was our content marketing. I built out our YouTube channel, our content channel on our website, our LinkedIn group, and I think that’s the one strategy that helped us to springboard to the next level. It enabled us to reach hundreds of thousands of people without having to have dozens of staff and enabled us to get early visibility for an early-stage product.

What is one failure you had as an entrepreneur, and how did you overcome it?

When I came to the US, I hired marketing people, and I thought I was better than them. I had a lot of knowledge, and I think that my marketing experience combined with a good knowledge of the target market made me think I knew the business better than anyone. As a result, I didn’t listen to staff in the early days as well as I should have. But I soon realized that certain staff members were exceeding my expectations, that, in fact in the most successful businesses, the entrepreneur doesn’t act or think that they know it all. They rely heavily on people with talents and skills and expertise, and they empower them instead of trying to direct their work daily. And that is a change that I made.

What is one business idea that you’re willing to give away to our readers?

I’ve got tons of ideas for business, but I’m not willing to give any of them away. Okay, that said, here’s one: To build a marketplace that connects business people that have ideas for new businesses and young entrepreneurs that want to take ideas and run with them. Some kind of accelerator with VC backing that supports those connections. There’s a lot of young entrepreneurs that want to manage a business, but they don’t have the benefit of experience to have truly viable ideas. Conversely, there are tons of entrepreneurs with great ideas that don’t have the time to execute them.

What is the best $100 you recently spent? What and why?

My fitness watch. Cost exactly $100. I bought it recently. I spend a lot of time in my chair for 4 or 6 hours straight without taking a break. And it does actually force me to get up and get out and take a 3-minute walk around the building. I find when I come back to my desk, I’ve actually thought of ideas that save time. And it’s healthier. It’s almost like getting a restart to the day, every hour of the day.

What software and web services do you use? What do you love about them?

Obviously, I used ProjectManager.com, which allows me to see the work performed across the organization, and the progress that’s being made. I also use GoToMeeting. I love the simplicity of being able to connect through Android or smartphone device or the web. And I record meetings, which I find really valuable. And another tool I love it called FastStone Capture. It’s an image capture tool, a little screen snippet tool, that allows you to capture high-quality screen grabs and edit them.

What is the one book that you recommend our community should read and why?

The one book I’d recommend is Blue Ocean Strategy. It’s the best book I’ve ever read that has an actual methodology to make you step back from the business and widen the scope of what is possible to achieve and to create a unique product or service offering to a marketplace. It talks about red oceans, where there are lots of sharks, companies competing for the same customers, versus a blue ocean, which is a whole new customer segment that you may not be tackling at the moment. I think every CEO should read that book.

What people have influenced your thinking and might be of interest to others?

Rand Fishkin, CEO of MOZ. I watch his Whiteboard Fridays weekly.