An Interview with NearForm Technical Director, Dee O’Callaghan

At NearForm we take an Outcome-Based Approach to software development.

The Outcome-Based Approach is a non-traditional consulting approach focused on identifying, measuring and achieving project outcomes.

It changes the way we think, talk and act in the workplace, by challenging business as usual through the use of critical thinking, questioning assumptions and making progress.

We sat down with NearForm Technical Director, Dee O’Callaghan, to talk about the Technical Director role and her outcome-based approach to building great software that delivers real results to our clients.

NearForm:

What does your role entail?

Dee O’Callaghan:

The Technical Director role at NearForm has traditionally been more focused on the technical side.

My role at my previous company was as an engineering manager with a team of 15 talented software engineers, but I also was a delivery lead for a variety of customers ranging from the US Federal Government to major insurance companies. These two roles play an important part in being a Technical Director here at NearForm.

It is a hands-on, cross-disciplinary role that brings a unified vision of the customer engagement, ensuring a timely and successful delivery.

The Technical Director is the main point of contact for the customer, the account team, and the delivery team.

Being a Technical Director is like being a conductor of an orchestra. The delivery team, the account team, the stakeholders, etc all need to be in concert. I bring everybody together to make good music. And if you think about it, that is what conductors do, they serve as a messenger for the composer.

So, in the same way, a Technical Director is like the messenger for the customer, the account team and the delivery team.

NearForm:

That’s a great analogy for the role. Now that we have a very good picture of your role can you give us a high-level overview of some of the responsibilities Technical Directors have? We will get into more detail later.

Dee O’Callaghan:

It is a Technical Director’s responsibility to understand both the business and the technical side of things to make sure that we’re delivering great outcomes.

We are tasked with leading our teams.

Some of our biggest responsibilities are making sure that communication is clear and transparent and managing relationships. I think that’s the magic key here in being successful. I think actually the magic in life is communication in order to be successful at anything, be it family, relationships or work. Good communication is vital to make sure that everybody’s aligned.

We take an Outcome-Based Approach to consulting here at NearForm. If we’re not aligned on what the outcomes are, then we’re starting off on the wrong foot. So from the get-go, I start driving out alignment and I continually drive out that alignment.

We work very closely with our stakeholders on the customer side.

As we do demos, we make sure that stakeholders are happy, that we’re still on track and that we’re helping them get to where they want to go. We make sure that we’re moving the needle in the right direction and keeping a steady course when we’re on that pathway.

And again we have to be very good communicators with our clients to ensure that we are all on the same page.

So from the customer standpoint, my main focus is success for the customer and making sure that they’re successful in the work that they brought us on to do.

I tell customers, “I’m not here to just talk fluff, I’m here to take action and get things done.”

We work very closely with our delivery team.

We are motivators, leaders and confidants for our team members. It’s our responsibility to get a pulse on how our teams are doing and a temperature gauge on their understanding of their purpose in regards to the customer and what they’re working towards.

From there we can start to drive out where the pain points are for the delivery team. It’s my job then to make sure that I remove those pain points or remove those blockers and basically help them to do what they do best. They’re the boots on the ground. They’re the real heroes of the work. I just want to make sure that they’re being set up for success.

NearForm:

You spoke about leadership as one of your main responsibilities. Did you have any leadership training or experience before you took on this role?

Dee O’Callaghan:

I did a specialization in organizational leadership at Harvard Business School online recently which consisted of three different certificates over a space of about a year and a half.

Also, my first job was with Microsoft. At the time they recognized that I would make a good leader and they pushed me in that direction. Throughout my career, I have consistently been drawn into either sales or management.

For a long time, I had imposter syndrome that was kind of blocking me. I used to think, “that’s not for me.” It wasn’t until later on in my career that I thought, “looking back, I actually wasn’t half bad at that particular role.” So it took time for me to recognize where my strengths were and believe that I was a good leader.

NearForm:

Every leader has their own style of leadership. Were there any changes you made when you first started to kind of establish your style and improve team spirit?

Dee O’Callaghan:

When I started, my team members were attending meetings on top of meetings. I recently read a book, The Art of Gathering: How We Meet and Why it Matters. There was a line in that book that I quote all the time, “if everybody’s invited then nobody’s invited.” In other words, you have to be careful of your invite list because if you’re inviting everybody, then you’re kind of missing the whole point.

I started working with the team to make sure that there’s a purpose for us attending a meeting and that we come away with an action from that meeting or some piece of knowledge. Otherwise, why are we there? It’s just wasting time. And again, part of my role is to help everybody stay focused on that north star or the outcomes. Because it’s the outcomes that we’re here to deliver on.

NearForm:

That’s a great segway because I wanted to ask you more about the role of a Technical Director in defining the outcomes for your projects.

Dee O’Callaghan:

Typically, when I start with a customer I have a high-level idea of what they are working towards thanks to the work done in the presale phase. It’s my job to go in and really drive out what that is and drive out the alignments.

Not only do I identify what the objectives are and get alignment across the entire business, but I also start to identify the risks that are going to prevent us or slow us down from delivering on those outcomes. And, if we do identify risks, we identify who to go to in order to mitigate those.

So I like to get all my ducks in a row in the first couple of weeks. And from that point on I keep repeating the outcomes to make sure our team and the stakeholders are aligned.

I always say, “repetition won’t spoil the prayer”.

It’s crucial to keep repeating the outcomes. Because everything in life evolves and changes. Technology evolves and changes daily. And so, too, may the customer’s objectives that they’re working towards, be that because of a financial decision, or be it because of a technical decision, things are changing quickly.

This is what makes communication so important in this role.  I must continually talk about direction and alignment on the outcomes the customer wants NearForm to help deliver.

NearForm:

It definitely sounds like communication is a large part of the role. That makes sense because as a TD, you’re overseeing multiple projects at any one time, correct?

Dee O’Callaghan:

That is correct. I currently oversee a team of 15 people. And we’re working on about five different projects at the moment.

One of the things that you have to try and balance is how each of those projects is progressing. I work with a project tracker that tracks not only how we’re progressing week on week, but how the team health is doing and identifying any risks.

If we’re going into a red zone and the team happiness is not good and we’re not on track, then there may be something that we need to pull together as a wider organization and figure out a more strategic plan to shift that needle from red to green.

NearForm:

One of the characteristics of a good communicator is being a good listener. How does that play into your role as a Technical Director?

Dee O’Callaghan:

Yes, listening is just as important as speaking, if not more so. A lot of what I do is listening. Part of that communication is listening to the feedback that I’m hearing and looking at opportunities where we can help our clients even further.

Also listening to the account team and identifying other opportunities to help them overcome some of the hurdles that I can identify. That’s where the communication of the account team comes into play.

NearForm:

What do you like the most about being a Technical Director?

Dee O’Callaghan:

I love people. Even though I’ve got a technical background, I’ve been in managing roles and I work very closely with sales. I have a real appetite for working with people and I have a good knack for helping people get out of their own way.

A lot of times customers know where their north star is, but they’re actually blocking themselves from getting there. I have a good way of helping them get out of their own way so that they can get to the place they want to go.

Also, overall, just keeping people motivated and driven and feeding into their appetite. I’m always looking for red flags and acting on them, for example, if people are getting bored or they’re not happy or they’re not learning. I’m always looking for ways to motivate them or shake things up to get them back in the fold.

I also enjoy talking about NearForm’s services (digital product development, application modernization, DevOps, data engineering and Web3) and how we operate and evangelizing those with the customer and helping the customer learn how we do things and why we do things the way we do.

If you go back to our overall mission, it’s to empower customers and to empower them, you have to lead by example and help them along the way.

NearForm:

NearFormers know you as a fun-loving and enthusiastic person. That can be hard to get across in a blog article. I know you have your own style of leadership. What are some fun or quirky things that you do with your team to keep them motivated?

Dee O’Callaghan:

You have to have fun even at work, and I’ve just got a good knack for people. I’m all about creating a safe place. And I think especially with NearForm, when we have our team syncs every week (and I make sure that we have a team sync every week) to remind them that we’re NearForm. My team knows that team syncs are a safe place where we can bubble up any concerns.

One thing I do every week is kudos. I’ve got a kudos board and I have everybody on the team give kudos to somebody on the team. And every week I’m hearing really good feedback that I probably wouldn’t have heard otherwise.

Another thing I do on Slack every week is asking everyone how their weekend was and I share photos of my weekend. Now they’re sharing photos of their weekend and it makes it more human and brings us together, especially since we’re remote.

I think reminding people that we’re human and that it’s okay to have a bad day or it’s okay to have a good day is crucial. It’s important just to talk about it and keep that communication going, but also make fun of it.

NearForm:

That is awesome and so important for team building to have that camaraderie and openness. What advice would you give to someone who is interested in becoming a Technical Director?

Dee O’Callaghan:

One thing I would like to know is what is their driving factor for it? Because I’m someone that is not driven by titles. I am more concerned with what a role’s responsibilities are.

What is it that that individual is looking to get out of their career? They should make sure that their career goals align with the role. Oftentimes, once it’s too late, people suddenly realize, “Oh okay, there’s a lot of strategic thinking and there’s a lot of communication with the customer and you have to deal with all of those meetings.”

It’s important to understand that these things are a big part of the job. Once you are in the role it’s too late to say, “no, that’s not what I want. I want to be designing their architecture.”

So it’s really important to know why you want to go into this role from the start.

NearForm:

That’s great advice! Do you have any learning resources or any go-to places where you get inspiration for your job?

Dee O’Callaghan:

I mentioned earlier that I received a specialization in organizational leadership at Harvard Business School online. That consisted of three different courses covering Leadership Principles, Organizational Leadership and Strategic Execution and it took about a year and a half to complete.

There are several books that I feel have helped me along the way as well:

NearForm:

Thanks a lot, Dee, for this comprehensive look into the life of a Technical Director here at NearForm. Just one more question, what attracted you to NearForm?

Dee O’Callaghan:

The culture first and foremost, the fact that it’s Irish. I’m Irish and I live in Boston, Massachusetts, and it’s empowering to work for an Irish company. And the challenge, taking on the new challenge, I think they’re the top ones.

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