Project management is critical in the increasingly complex IT industry—especially as the technological needs of enterprises and risk associated with valuable assets grow. For the sake of software and technology products, there are two approaches to IT project management: waterfall and agile. As the saying goes, there is a time and place for everything; but there is also a time and place for choosing each method.

However, today’s business world requires enterprise technology solutions that are built and deployed with empathy in mind—a trait that doesn’t come easy to many left-brain CIOs.

Although waterfall isn’t dead, agile is the better choice when dealing with riskier projects or upon entering a strategic partnership. Agile ensures stakeholders are continuously collaborating toward the common goal. With waterfall, all information is shared upfront and a complete roadmap is determined ahead of time.

Sometimes it can be difficult to decide which method is right for a particular project. However, no matter which method you choose, these do’s and don’ts will help you execute a smoother project.

The 5 Do's of it Project Management

1. Do plan—Nothing fancy, just necessity

Think of hurricane forecasting—once you get into a certain time frame, having an idea of what will happen becomes less useful. That is, everything you plan is something else you have to continuously change based on external factors. This is the idea behind Mike Cohn’s Cone of Uncertainty in Agile Estimating and Planning.

So with that mindset, when it comes to agile, planning is important—but not to the point where alterations will throw off the project. With agile, you decouple time and scope. Usually if you pre-plan these constraints and pull the correct levers, you believe you’re on track to a successful project, right? Wrong. There's no magic formula for project management success.


Project management is about planning for risk and quality, proactively looking for potential problems and tightening loops. If you decide to make a big fancy plan, continuously update it as product ideation manipulates project requirements.

2. Do be transparent and engaging

There are a few good rules of thumb for staying honest and positive with internal and external stakeholders. First off, keeping stakeholders in clear view of your deliverables is essential for good project management. It’s about being a conduit of communication between the customer, the technical team, and management. It’s your job to constantly engage with these parties throughout the project lifecycle. Without it, project failure is inevitable.

Being able to accept and give feedback gracefully speaks highly for a strong project manager. You can’t be afraid to deliver difficult messages. They only get worse over time. This also applies to raising concerns immediately instead of waiting until they become an actual problem.

If you have bad news, be sure to inform stakeholders immediately. Go beyond that and deliver bad news with options/solutions. Lastly, you should be able to communicate the current project status, at the user story level, at any time.

3. Do know your role

It’s tempting to try and take control and manage the day to day activities of the project, but don’t forget you are there to manage the big picture. It’s your job to schedule and attend daily standups, sprint planning, and sprint retrospective meetings.

Considering more complex projects with larger teams—project management has value in making sure there is some shared language or understanding. Back end or front end, all of your team members are approaching the same problem in different ways and at different times. Having a way to bridge that communication is more than valuable. And frankly, it’s our job to do that.

It isn’t wrong to be myopic, it’s just more necessary to guide that big picture goal and take charge of the project as a whole.

4. Do manage expectations

IT people get what it takes to complete a project, but non-IT people are usually the ones drawing up the budget. Therefore, it takes everyone being involved and having their defined role in digital transformation for it to become successful.

On both the internal and external stakeholder sides, managing expectations is crucial. Be sure to forecast the outcomes and ask yourself—“what could go right?” and “what could go wrong?”— then plan ahead for both. It’s about risk management. You can’t plan for everything, but you can prepare for some. Managing your stakeholders expectation, both good and bad, will make sure no one is blindsided before execution.

5. Do define the terms of the project's success

It’s important to define project success because this line can blur as the project nears its end. Is the project successful if the scope, cost, and time constraints were met, but customers are not happy with the product? Is the project then a failure? These are things that need to be discussed before a project starts.

In reality, projects can be successful even if the product fails. A recent example of project versus product management is Apple’s iPhone 7. The project was successful, but will the lack of a headphone jack result in a product failure?

These two separate phases are independent from one another. What if consumers don’t buy the product? What if scope and time constraints are met, but costs aren’t? These fears aren’t just for the paranoid. No success is guaranteed.

With a skilled project manager, a successful project is more likely than not. It’s up to your product manager and marketing to carry out a successful product. Project management failures occur somewhere between the concept of what is going to be built, and the execution. Don’t allow stakeholders to rewrite that definition and put the blame on you if the product’s success didn’t quite reach what they had hoped.



The 5 Don'ts of IT Project Management

1. Don’t underestimate the importance of the kick-off meeting

A kick-off meeting is a great start for defining both the “what” of the project and the “why.”

Reestablish the scope, time, cost, and quality constraints to make sure all stakeholders are on the same page. The average project manager can lock down these specifics for a project, but understanding why you’re carrying the project out in the first place is what makes exceptional project management—and a kick-off meeting is the key to understanding the why.

2. Don’t reinvent the wheel

Organization is crucial for mapping out the project’s best means for success. Be smart and use everything you can at your disposal to cut down on those time and cost constraints.

Any pre-existing software will be better in the long run as opposed to wasting time and resources on an in-house management system. Think of what business needs you need to address, then choose the right application based on those needs.

Whether you work with notes in Google Drive, or post messages in basecamp, it truly doesn’t matter. It just matters that you know ahead of time what you are going to do, and then pick the system that is going to make it easiest to execute.

Stick to the system wholeheartedly with daily updates to make sure no careless inconsistencies arise.

3. Don’t confuse monitoring with control

Take corrective action when necessary. There is a time to monitor and a time to control, but no matter the situation they call for one or the other. Assuming that the scope stays the same, where’s the fallout going to be—time or money? On the agile side, these factors are more directly related because you are paying a team for their time. Therefore, it begs the question: what’s more important—the budget or the number of features in the MVP?

Responsible Accountable Consult and Inform—you have to keep the RACI mentality in mind. However granular or large scale you want, only one person can be accountable. If you have two people accountable then effectively no one is accountable.

It’s good to have multiple people responsible, but only one should be accountable. This is where the HR part of project management kicks in, by assigning that matrix for the whole project, you know ahead of time what people are supposed to be doing. Theoretically, if you have a well-functioning team that abides by those rules, you can simply monitor what is happening and not have to step in and control.

4. Don’t lose sight of the goals throughout the project

This applies to all stakeholders. Don’t forget why you started the project in the first place. If you ever feel the motive start to slip, skip the phone call and hold an interactive meeting addressing the issue.

It’s better to lose sight of the purpose and mutually agree to terminate the project than to carry it out half-heartedly. If you can fix it, do it. If you can’t, it’s better to call it quits before wasting more time and resources on a black-hole project.

5. Don’t avoid failed projects

If the project is failing there’s no need to drag it out. With failed projects, there is always something of value to take away.

From a practical side, there is architecture, database schema, and design artifacts that can help aid the next project. On the business side, take away those failures to formulate a lessons learned report. These reports prove more useful than you might imagine. This will be the start of your own do’s and don’ts list for future projects.

The bottom line is that all businesses have projects. These projects need to be driven by strategy and best practices. Therefore, in order to aid both tactical and strategic goals these projects need experienced project managers.

Dialexa’s project managers have seen it all. If you can’t quite do it alone, our skilled project managers would love to help guide your project to not only completion but to success. If you want to know how we do it, download our free ebook, How to Set Up Your Own Innovation Practice.

If you liked this article, listen to guests Scott Harper, Dialexa’s co-founder and CEO, and Chris Garrick, Sr Partner here at Dialexa, on Custom Made, where we discuss how to drive innovation within an enterprise organization:

Listen to all episodes of Custom Made for insights and perspectives from industry disruptors and technology leaders.

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