The art of managing digital projects

Yomi Ajilore, Project Manager at simply-communicate

We ask simply’s resident PM, Yomi Ajilore, when did project management become an art?

I believe it was the moment project management became an integral part of any business. Project management is not like being a manager of a specific department; it’s about being a manager of various departments, people, activities, and goals, and somehow bringing these all together to deliver a shared outcome. How successful you are is based on how you go about managing this mixture of things, and your perception.

Every time a project manager starts a project, they are given a list of requirements, a number of resources / departments to manage and a budget. Their job is to go away and essentially make it happen, to be thrown right in the deep end and expected to swim to the other side without an instructor.

Project managers are also translators, between the technical and business teams, they make what may otherwise sound like a foreign language, become understandable to all teams.

Seek First to understand, (not to react), then to be understood.

Have you ever been in a meeting where everyone is talking, but no one is listening?

Where there is so much passion and anxiety to be understood, that colleagues were just talking over each other? That’s something that as a project manager, you can’t afford to have, because If everyone is talking, then who’s listening?

You must actively seek to understand something from another viewpoint – not only hearing, but processing this information. Ask open questions, then repeat the idea back to the person in your own words, letting them know that you have heard them. This is key for the early stages of any project as you’ll need this to clarify requirements and build relationships that will serve you well in the long run.

Once someone realizes that you are honestly engaged in trying to understand them, they will usually show you the same respect and you’ll find that you acquire much more useful information. It’s in the best interest of the team and project to give everyone an equal understanding, so if something is not clear, ask questions to ensure you and the team understand completely.

You should be willing to communicate with your team members frequently to ensure everyone takes part in the successful completion of a project, this helps to foster team collaboration and avoid mistakes, which could go unnoticed, it is also important to communicate your expectations of all involved in a project including yourself.  

See the bigger picture.

There are more factors that come into play when managing a project, both internal and external, which could negatively affect projects of all types. This could be technology, legal and legislative restrictions or international and cultural factors, among others, which could create additional complexities that need to be managed. if you don’t have a strong understanding of how your project fits within the overall strategic vision, you put yourself in danger of having a blind spot that can hinder your ability of delivering a successful project.

Imagine you have an ecommerce website project that is being built to bring in new customers, this project is part of a marketing campaign around a new product being launched in 6 months. Without the knowledge of that, you might get overly creative with the design (which takes 2 months to sign off) that it will actually take 6 months to build, and therefore won’t be ready in time for the launch of the new product.

“As a project manager you should always keep the overall vision in mind …”

As a project manager you should always keep the overall vision in mind and understand how the small activities in the project contribute towards that. It’s your job to steer your team towards this vision. By making this connection, you’ll see your team working together with more synergy and towards a shared goal, instead of their individual roles. You must also believe in this vision, be fully vested in seeing your project strengthen that vision so every time I start a project, I always ask where it sits within the overall strategic objectives of the company.

Being Proactive, Not Reactive

Plan for uncertainty; no matter how much you try to plan, there will always be things you can’t prepare for. However, there are many things you can do to prepare for the eventuality that you get thrown lemons instead of lemonade, here are a few:

  • Secure a contingency budget (that we hope we never have to use)
  • Be adequately resourced for your project (I can’t stress this enough, the worst thing is for you to have a set of activities, but no resource to carry them out)
  • Have a shared repository for all documentation (SharePoint, G-drive, digital workplace)
  • Get senior management involved form an early stage. They’ll most likely spot things you can’t see because they’re looking through a different lens, this also ensures they are aware of the activities in the project.

Sharpen the Sword | Know enough to be dangerous

“Give me six hours to chop down a tree and I will spend the first four sharpening the axe.” – Abraham Lincoln

This quote has always stuck with me; you must always be eager to learn more, it’s not enough to just have passed your PRINCE2, it’s not enough to rely on your experience, because there will be tools you haven’t used and industries you haven’t worked in. If your project includes a new PM tool, you can’t say “I don’t know it”.

“it’s not enough to just have passed your PRINCE2..”

It’s up to you to go the extra mile and keep up with industry trends and best practices, take courses that may not be paid for by your organisation, watch YouTube tutorials on new systems, download a free trial and actually get hands on with a tool you haven’t used before.

I don’t remember the last day I didn’t check out what’s happening in the industry, whether its reading articles about start-ups on TechCrunch or downloading a report from E-consultancy or BI intelligence, I recently signed up for a free trial of so I could design an app I’m currently building, I’m even learning to code through Codecademy. Join Slack, LinkedIn and Facebook communities, be active in these forums as they allow you to gain knowledge and insights that you can’t pay for, these are real people, with real experiences that most of the time relate to what you’re doing. Attend relevant events, join a MeetUp so you can grow your network and finally, google things, (there’s a load of information there that 20+ years ago, people had to go to the library or have studied at school to learn).

Often I’m managing projects that involve people from all levels of a business, who are more experienced and expert than I am, especially in their specific field. You need to be comfortable with this and welcome the opportunity to work with new people. Rather than trying to be a jack of all trades, leverage the knowledge and skills of your team members.

Once this concept is integrated into your daily habits, they will serve you throughout your entire career.


In my time as a project manager, I’ve had to use a variety of tools to manage projects, here are a few I would recommend:

Trello/Jira  – Every digital project manager uses one of the two daily, to manage issues and tasks, if you want a way to organise and visualise your tasks for the day, weeks or month then you can’t go wrong with either. Trello is free for 1 user and Jira is free for 7 days, Jira also has a slick app that allows you to manage your tickets and teams on the go.

Synergist / Harvest – I’ve used both of these systems for Customer management and accounting, they both allow you to manage your client accounts, raise invoices, track the burn of your project so you can make timely decisions, create estimates that you can share with your client, submit expenses, manage timesheets and utilisation plus more. I recommend Synergist for big corporate organisations and Harvest for everyone else as it has a cooler UI. Harvest has a 30 days’ free trial if you want to see how it works, its also totally free for 1 user managing 2 projects.

Resource Guru – I used resource Guru to manage design and development resource for a year and up to date I haven’t found a better resource management platform, I thoroughly love the UI and ease of use it provides. It’s cost effective and you can subscribe for a 30-day free trial to test it out. – One of my favourite tools, mostly because it’s on the cloud and allows multiple team members to collaborate on multiple projects. You can manage your tasks, report on time and budget, share files and communicate with your team via the mobile/tablet app. It also has the ability to integrate with over 400 apps including 0365, Slack, QuickBooks and Salesforce to name a few. There’s a 30-day free trial if you want check out the cool features it offers.

Slack – This is my favourite messaging app, even over WhatsApp, this is due to the fact that slack understands the people it’s built for, I’ve used slack for 3 years now and I continue to use it even in my personal life to communicate with family and friends. It’s packed with a multitude of integrations with third party apps including but not limited to Google drive, Trello, Dropbox, Github, Jira Cloud, One Drive and Zoom. Other features I enjoy are voice and video calls, the deep search of conversations, channels for different teams and topics, the most important feature for me is being able to sign into different teams using one interface.

Subject matter expertise

There’s always something new to learn, especially with the pace of Digital. You must aim to understand the technology and platforms your team works with, the opportunities and the limitations, this allows you to have effective conversations with your team, clients, stakeholders, and vendors.

Being expert means:

  • giving accurate estimates on timings and cost.
  • challenging developers when they over or under estimate development.
  • managing developers effectively, suggesting workarounds to issues and deciding what tools/platforms are right for you
  • communicating accurately and effectively to a client

You should aim to understand how all aspects of a project work, from strategy to design, user experience, front and back end development, QA, SEO, analytics, CMS, social media and more. If you can be the designated expert on everything from 0365 implementations to banner ads to algorithms and more, not only will your team and company appreciate you, but your clients will too. While I learn lessons from my past projects, I am often leading and guiding something new and unique every day.

That is the challenge and fun of the job. I enjoy project management because it keeps me on my toes, a field where I can be involved in just about any type of project. There are days where it feels easy and I know exactly what I’m doing, then there are days where I spend the day asking questions because I need to get my head around something, no matter what the story is, I find myself appreciating what this industry allows me to learn, who it allows me to meet, where it allows me to go and what it allows me to achieve. I take great pride in my achievements through successfully delivering projects, I have a network that if not for Project Management, I really can’t say I would have. The variety of experience this field provides you with, is what I believe the jobs of the future will require.