WordSouth Q&A — Project Management Software With Stephen Smith And Jared Dovers

October 3, 2018

This issue we begin an occasional feature where a pair of WordSouth experts dig deep into a subject they are passionate about. We’ve chosen topics we hope will give you some ideas that you can apply to your department or company.

To get us started, we asked WordSouth President and CEO Stephen V. Smith and COO Jared Dovers about the heart of any operation — the software and systems that manage the day-to-day workflow.

1) As WordSouth has expanded to serve multiple clients across several states, what project management software have you used? How has this evolved during the company’s rapid growth?

Jared: When I started, we mostly managed projects by email. We had an overall project tracker that had ways to visualize projects, but collaboration was done in Gmail. I think that’s where some people find themselves — managing their inbox, not necessarily their projects. There are huge advantages to getting out of email and into a good project management software.

So, we moved the company to Basecamp. It was in its original implementation, and we’ve followed it along to Basecamp 2 and 3. It’s become the core of how we communicate, and we say that “our culture lives in Basecamp.”

But, every app has its strengths and weaknesses. Basecamp isn’t built to manage hundreds of small tasks as much as it is designed for small-team collaboration. As we’ve grown, we’ve needed something with more ways to easily visualize what’s happening across the entire company. Over the last six months, we’ve switched much of our day-to-day work to Monday.com. It’s amazing! We still do a lot of our communication in Basecamp, and we use it for our calendar as well.

Stephen: What Jared fails to mention is the pain and sorrow with which I left that first project management system. It was called Daylite, and I absolutely loved it. We were not putting all its features to full use, but it was still doing a good job for us on the surface. So how did Jared convince me that we needed to move to Basecamp? The way Basecamp enabled collaboration across the company helped us make significant progress in the way we managed our work. Plus, Basecamp was browser-based, whereas Daylite required a network app installed on our local server that everyone had to link to. Funny, we don’t even have a centralized server anymore!

The one thing I missed (and still do) was the way Daylite integrated contact management into the overall project management workflow, something Basecamp has never seen as important to the project management task. To me, it seems you would want all the information about the companies you are working with (the people who work there, how to reach them, what projects might be in the proposal phase) readily available in the same environment where you are doing the rest of your work. That said, I’ve come to accept that customer relationship management is different enough from project management that it functions best as its own separate app. We’ve tried a few solutions for CRM but have come back to Highrise (which, incidentally, was developed by Basecamp).

I tell that story to say this: When choosing software to run your projects, know going in that there will be some give and take. If there were one program that did everything you needed to do, it would be so bloated and clunky that you couldn’t use it. With enough thought and trial/error, you can find three or four apps that will provide a solid foundation for managing the processes that run your department or company. Your goal is to arrive at a solution where you can say “this system helps me get work done.”

2) What does the ideal management system allow you to do?

Stephen: One thing that sets the human race apart from other creatures, besides our opposable thumbs and fear of public speaking, is our skill at creating tools to do complex tasks. For centuries, these tools were literal extensions of ourselves — sticks for fighting off predators, hoes for tilling the soil, levers for moving heavy objects. These were the gadgets that extended the functionality of our natural attributes.

While not as apparent as shovels and wrenches and hammers, today’s software is nonetheless a tool for getting a job done that we couldn’t do using only our limbs, hands and feet. And as such, a good piece of software should feel like an extension of ourselves. After the learning curve that comes with adapting any tool, management software should be as natural to use as a screwdriver. It should be intuitive. Muscle memory should take over whenever you use it. Software should be designed in such a way that the user experience is seamless, that it “disappears into the fabric,” as it were, and helps us get our jobs done without thinking about the actual tool we are using. That’s what we look for in software to run our business.

Jared: A lot of my day-to-day job is making sure WordSouth’s employees are able to work better and go further. Management tools are a huge part of that. Working better can mean completing tasks more efficiently, but it also has to mean working with excellence. You can be incredibly efficient and not produce outstanding work.

We select tools that allow collaboration but also periods of focus. We have a lot of creative professionals laying out pages, coding websites or writing stories. Creative work requires long stretches of time focusing on a single task. We’re also a remote company. To that end, we choose tools that can get out of people’s way, that don’t require a lot of time spent in giving updates or cutting into other people’s time in order to get the work done. Some of our tools communicate the status of a project to team leaders by simply clicking a button. A writer can choose a status such as “I’m working on it” or “I’m stuck” or “I’ve seen this, but I can’t get to it right now” without having to type in a lot of details or even open another window. For a staff member who doesn’t want to spend their day giving status updates, that’s a win. As a manager, when you’re looking at over 300 project items — that’s a necessity.

So the ideal management system, for me, lets people collaborate deeply when they need to, but also communicate statuses and other simple updates very quickly and with little time invested. I think we’ve come a long way with that in our software usage here at WordSouth.

3) What has been the key to changing systems and implementing a new program?

Jared: This is tough! You have to be empathetic before asking people to change the way they work. That’s the first, most important step after you’ve decided you have to change and what the solution is. Your team members are busy, and they probably feel like they’re doing just fine with the old tools and that they’ve learned to be productive with them. You need to clearly articulate the reasons for a change before asking them to invest.

Then, realize your team has people who are super comfortable with new software and will “just get it” no matter what you throw at them. You also have people who struggle with new technology and view getting a root canal as preferable to learning a new web app. You need to be ready to meet each of these personalities where they are and get them to where you need them to go. If you take the Tech Wiz and try to very slowly explain how to do basic tasks, they’re going to be frustrated with you. This is their work time, and they also probably want to be recognized as being competent.

At the same time, if you come across as in a rush with the team member who is struggling, they’re not going to ask you the questions they need answered. This is true also if you’re not patient enough. Be kind. Be considerate. Take your time with your team member and let them know they can ask questions both now and later.

Stephen: Beyond dealing with individuals, you have to look at how those people’s jobs intersect with others throughout the organization. Workflow process is not an “all things equal” proposition across all disciplines. For us, we had to understand how a new management system was going to impact every step in our creative cycle and plan the rollout with that in mind.

Perhaps the most important point is to take your time and get it as close to right as possible the first time. People will eagerly give feedback and suggest tweaks. But roll out the wrong system altogether and it will be harder to convince people to follow you down a different path the next time.

4) What do you think is the software’s impact on office culture?

Stephen: For software to be effective, it needs to fit the culture of the company. A firm full of engineers will take to a very different type of software than, say, a creative services company like ours. If you try to force your workflow into software that is not a good fit, your people will be slow to adapt. Worse yet, it will feel to employees like an unnecessary requirement that stands in the way of getting their jobs done instead of supporting their efforts. When you find the right workflow or management software, your team will appreciate it and thrive. When you try to make a bad fit work, your culture will absolutely suffer — and so will your service to clients and customers.

Jared: I think software and culture is a two-way relationship. As Stephen says above, the software has to fit your culture, but the software will also help make your culture.

We’re remote. Most of us don’t see each other face to face very often, but we still have this really strong work culture that encourages us to know our co-workers as friends. We celebrate what’s going on in each other’s lives, we know about each other’s families, and we have a lot of super witty creative people on staff, so our daily team chats are pretty hilarious!

The software we use helps that happen. It makes team and 1:1 communication easy, but not overwhelming. If it were harder to be able to talk about your son’s birthday party or share a photo of your dog, we probably wouldn’t do it as much.

Your software needs to provide opportunities for deep collaboration and sharing of ideas. At the same time, the software needs to get out of the way when it’s time to work. You don’t want to be answering personal messages all day when you have tasks to complete. So, ideally your culture fosters communication and uninterrupted blocks of time for productivity. And the software enables that to happen.

5) How do you think project management software could benefit the marketing or communications department for a telco or utility?

Jared: Communication is all about intentionality. Having a clear message that’s repeated over well-developed channels to a defined audience is the goal. Even if that’s a single channel and just a few messages, you still need to have a way to manage that work. That’s what a good project management software will do.

Now, if you have multiple channels — print, web, social media, e-newsletter — and multiple programs or products you’re selling, you can absolutely benefit from treating your communications work as trackable projects. Where are you recording steps that you’ve taken? What is the status of this or that message? Do you have all your posts scheduled for your new promotion? Are you sure to get your promotion information over to the folks at WordSouth for your magazine?

Taking it to the next level — how are you tracking results? How are you comparing what promotions led to sales and which ones were less successful? Your software should help you do all this. Then, when it’s time to plan your next quarter, or year, you have data to help guide your decisions.

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