7 Strategies for Managing Tricky Technical Work

I was sitting in a room with our director of customer relationship management (CRM) and the manager of our data entry team, asking them to explain what exact steps needed to happen when we set up a donation webpage, to make sure a donor’s information flows correctly through our 3rd-party donation software and into our CRM software.

They had made multiple attempts to explain this to me by email, and I was already feeling bad that I’d asked them to spend time explaining this process to me in person. Now, sitting in the same room, they’d just finished their second attempt to offer verbal clarification, and I still wasn’t getting it. I still couldn’t wrap my head around how all the steps fit together. 

I put my head down and cried a little.

Beyond Your Grasp

As project managers, we rarely understand everything our project team members do—their expertise is a major reason we need them. At the same time, we need to understand enough about their work to do our jobs—plan the project work, facilitate clear communication among team members and stakeholders, make sure our project teams have enough people and the right people, etc.

For years, most of my projects developed physical and digital products that I could see, interact with, or easily imagine. Even before I’d supported a video project, for example, it wasn’t hard to understand that creating a video typically involves writing a script, planning the visuals, filming, and editing.

More recently, I’ve been invited to support more IT projects. Even though using software comes easily to me, understanding what is going on ‘under the hood’ of software does not. I can’t really see and interact with those intermediary deliverables (like I can with a script or raw footage for a video).

Perhaps it is not IT vs. creative projects for you like it is for me. But you probably have or will bump into project work that is outside your grasp as a project manager, and yet you’ll still need to oversee it to achieve project outcomes.

Here are the strategies I’ve discovered so far to help me in situations like this. I hope they help you activate your PM superpowers! 

1. Set expectations about your needs from the beginning.

If you already know that some of the work on your project is going to be hard for you to understand, you’re in a much stronger position than if you don’t. During the kickoff call or your first interaction with your technical professionals, let them know:

• How much you appreciate the value they bring to the project.
• Your goal is to support them and get their needs met so they can do their best work.
• Unfortunately understanding [their type of work] doesn’t come easily to you.
• You’re going to need a little extra time and patience from them in order to support them in an optimal way.

Projects have needs like this all the time, and honesty goes a long way. Getting your reality out in the open before people have the opportunity to form a different expectation can reduce frustration in the future.

2. Be willing to be a little vulnerable.

As the project manager, I am often the one who understands what one stakeholder is trying to say, and I communicate it on their behalf to another stakeholder. Ensuring clear communication is a major way I provide value to a project. So, when I can’t understand someone’s meaning, not only do I feel like I’ve wasted someone’s time, but I have a mini project-manager-identity-crisis. I can’t do one of the central things I’m here to do.

Which is why I’m working to admit this is okay. It’s okay to let your team come around you and support you. It’s okay to sometimes just tell them what’s not working and not have a solution. It’s okay to let them be creative and figure out how to close the communication gap.

That’s what I had to do with my director of CRM and manager of data entry in the situation above. I had to fall just a little bit and let them catch me. You can become closer as a team—and more productive in the long run —when you show your weaknesses and let someone help you.

3. Can you table it for another day?

Are you ever surprised by the new solutions to a problem you come up with after a good night’s sleep? We’ve all had this experience, but I don’t think it’s a tool we often choose on purpose.

In terms of understanding technical work on a project, it’s important to make an initial attempt to understand. This is how you at least know what you do know, and have some sense of where you’re getting stuck. On another day, you might have a fresh idea about how to have a conversation about those remaining pieces.

Seriously, it never hurts to let your confusion breathe for a minute before you move forward with your team.

4. When words don’t work, ask them to show you.

There’s a reason we love illustrated stories from the time we’re kids. Visuals can work when words fail.

Instead of telling you about the work need to do, is there something a team member can show you? Maybe they can show you partially working software. Maybe they can show you some steps they perform in order. Maybe they can show you a database, or even walk you through the code and explain what specific pieces do.

Lean into screen-sharing and whiteboards in your video-conferencing software. Struggles in understanding often happen when one person doesn’t know what you need to know, and you don’t understand what you need to ask. Visuals can help close this gap by adding more context to the conversation.

5. Give them context.

Speaking of context, another way you can increase your opportunity for understanding is to give people more context on why you need the information.

What is the situation causing you to ask the question? What action are you hoping to take based on their answer? Not everyone is good at tailoring their answer based on more information, but many people are.

6. Paraphrase back to them.

Paraphrasing is a great tool in active listening, and in our situation, it serves two purposes: 

• It checks your understanding
• It gives your team member hints as to why you may not understand, to help them try again. 

Whatever phrasing you use for their work is probably how you’re going to go on to explain it to other stakeholders. So it’s useful to get the expert’s informal sign-off on your preferred terminology!

7. Leave room for the unknowns.

For some projects, it may be more worthwhile to simply add some margin (in the form of time, money, etc.) into your estimates than for you and your team members to spend extra time hashing through details. Or it may be a good solution for the last few mystery pieces if you all have put in a good deal of time trying to build understanding already. Obviously it will vary a lot by project if this makes sense, but it’s an option worth considering.

I don’t have everything figured out about managing technical work, but I can tell you this is the next set of strategies that is going to move me forward. I hope one or more of these tips cracks open a door to understanding and progress on your projects as well!