When you hear the word delivery, what comes to mind? For many of us, our minds immediately turn to Amazon–to an item we ordered earlier today, perhaps, on Prime; a book, a shower curtain, a set of speakers. We might think about the price of the item, the quality, whether it will arrive on time, and whether or not we’ll receive the thing we actually ordered. What most of us are probably not thinking about is the process that is set in motion when we place the order– the technology, the factories, the trucks, and the people all working together to get the item from wherever it may be to our doorsteps, all in one piece.

As the Head of Delivery at Cake & Arrow, these behind-the-scenes inner workings, the how of something getting from point A to point B, is where I come in. But rather than ensuring the delivery of books, electronics or household goods, I’m overseeing the delivery of websites, apps, experiences, strategies, ideas, and sometimes things even less tangible than these. A big part of my job involves not only planning how we will get a project from point A to point B, but mitigating the risks it might face to getting there in a timely manner and at a reasonable price, without sacrificing the quality–all while keeping the people involved excited, happy, and motivated. It’s this last part that really defines what I do; the human side of what we call Agile delivery.

What we talk about when we talk about agile

Technically speaking, Agile is a set of management practices for software development that came to prominence in the early aughts in response to the more rigid “waterfall” processes that had dominated the field. Modeled after assembly-line manufacturing, this waterfall approach to software development often led to unnecessary project bottlenecks and, more significantly, a privileging of the process itself over the product and the value it would deliver to customers.

More than simply another process or methodology, Agile is a philosophy. As a philosophy, Agile promotes “individuals and interactions over processes and tools, working software over comprehensive documentation, customer collaboration over contract negotiation and responding to change over following a plan.” In short, an Agile philosophy embraces people – the people working to create something together and the people who will eventually derive value from whatever that creation may be. It’s a philosophy that has, in recent years, been embraced far and wide by businesses and organizations, across all disciplines, including my own.

As someone who is, by nature, extremely process-driven and who has been, as long as I can remember, physically addicted to productivity, feeding off the dopamine release associated with even the smallest accomplishments, adapting to an agile approach to work hasn’t always come naturally. But as much as I thrive off of process and productivity, the satisfaction I get from building and growing relationships, from seeing people happy, thriving, and loving what they do, runs far deeper than any dopamine release I get from checking off an item on my to-do list. An Agile, human-centered approach to delivery lends to building these kind of relationships. And while balancing budgets, meeting project deadlines, and driving efficiencies –all things my job requires of me– may be more challenging when trying to account for different personalities and working styles, unexpected circumstances and events, and the varying constraints and limitations different clients bring to the table, the ability to do so lays the groundwork for killer work, successful client relationships, and thriving teams–ultimately making me not only more successful at what I do, but making my work far more rewarding in the end.

Here are some of the ways I have learned to put people at the heart of everything I do, while still remaining productive and focused on the goal at hand:

Client-side reconnaissance

When working on a project, there are typically three groups of people involved: those on the client side, our internal team, and the customer or end user. When leading delivery, all should be considered stakeholders in the success of a project.

When kicking off a new project, one of the first things I like to do is get to know everything I can about our client. I don’t just want to know the basics; I want to get the inside scoop. I try to learn everything I can about the company culture, about the office politics, and about the internal structure of the organization. All of this will help me with planning the project effectively.

Here are a few of the questions I try to answer:

  • What does the hierarchy structure look like? By knowing this, I can get a grasp on how many layers of approvals will be necessary, which will in turn help me get a sense of expected turnaround time for feedback and approvals. This information can have a huge impact on project timelines.

  • What is our main point of contact’s biggest concern and why? We typically have one key contact that we are working with to plan and execute the project. This person is foundational to the client relationship, and ensuring that they are happy and their needs are met is critical to having a long-term relationship with a client.

  • When and how should we plan on pulling in the executive stakeholders? While keeping our main point of contact happy and engaged is key, this person is typically reporting to someone else. We want to be thoughtful about how and when we pull these people into the process. For example, do we need to plan for an executive summary read out at the end of the project to present our work? Alternatively, should we be doing this at regular intervals along the way?

  • What cultural differences do I need to understand to make this relationship successful? For example, certain things that might seem perfectly okay with our U.S. clients may come off as rude or unprofessional to our clients in Japan. Asking the right questions early on can help avoid a misstep in this regard.

Checking in with my team

When processes fail, it often means that working styles and personality types were not considered. Over the years, I’ve run into challenges I didn’t anticipate when introducing new people into the mix. What I’ve learned is that it’s important to realize that different people have different needs and different working styles. Creation, support, collaboration, and oversight for one person may look completely different for another–different dynamics are at play when a new team comes together. At Cake & Arrow, we make it part of our jobs to get to know one another on a personal level before and throughout a project–learning what makes each other tick and what brings each other joy. To overcome and preemptively plan for these challenges, I do the following:

  • Bring individual needs, preferences, and working styles to the forefront. At the beginning of a project, we’ll often have team members fill out a “How I work” survey to learn about their working styles and what they feel they need to succeed. We then share our responses and discuss how we can plan around our learnings.

  • Help new team members integrate. We try our best to give new team members an opportunity to formally and informally talk one-to-one with veteran employees to get a deeper sense of what it is like to work with individual team members. Veteran employees can answer questions and share the “ins and outs” of how others work and their quirks, making for a smooth transition so new team members can better navigate their role.

Reality check

While it’s important to understand clients and teammates on an interpersonal level, it’s equally important to fully grasp the realities and constraints of people's lives, in and outside of work. I used to think we could uphold the same expectations of everybody. I expected all coworkers to work five days a week, in the office, between the hours of 9am and 6pm, and I expected all clients to provide consolidated feedback within 48 hours of handing something off. By living in a false reality, I was setting my team up for failure. I soon began to grasp that I could only control so much, and that in order to be successful, I should plan for the reality of each situation based on the varying needs of the people I was working with and adapting our plan accordingly. Here are a few of my key considerations upfront:

  • Where are people physically working? This applies to clients and internal team members. Is everyone in the office together? Are there remote teammates or remote clients? What time zone is everyone in? Understanding these details will help to strategically plan for face-to-face interactions when necessary and determine what kinds of tools will be needed for success (e.g., Slack, Zoom, etc.). Working remotely myself has helped me to be a more thoughtful and effective planner.

  • Who works when? This may seem obvious, but as project management has become more agile, so has the workplace in general. Not only do many people work remotely, but alternative work schedules and hours are increasingly common, so it’s important to plan accordingly. For example, one of our employees only works Mondays, Wednesdays, and Fridays, has two kids at home, a hard-stop at 6pm, and a husband who travels frequently for work.

  • What are the client constraints? While we may have an agile work structure and a team fully resourced to a project, the same is not necessarily true for our client. What other commitments do they have during our engagement? What is the work structure within their organization? Knowing this can help us anticipate bottlenecks and delays and adapt our own process to accommodate theirs.

  • Is the budget reasonable? We work hard to scope out a budget that accommodates our clients, but we also need to make sure the budget makes sense for our own internal team. We want to avoid allocating hours to a project that don’t align with the amount of work that needs to be accomplished. Pulling team members into project planning early can help us ensure a reasonable budget and identify any red flags.

Plan for the unexpected

Even the best-laid plans go awry. Being flexible and adaptable is a key component of the Agile philosophy. Valuing the people and the relationships over project deadlines and plans helps me stay flexible and react calmly and empathetically when things change. Here’s some advice:

  • Expect things to change. This way you won’t be surprised when they do, and you will be the hero of the situation - the one who remains calm and finds a solution. Remember that you can only control so much.

  • Watch the weather. Literally. Weather is definitely NOT something in your control, and it can throw a major wrench in plans. Flights get cancelled, power goes out, people get snowed in. It may seem silly, but when working with a client or vendor in another location, keep an eye on their weather, as well as the weather where you and your team are. This can help you avoid a major catastrophe.

  • Shift gears when real life happens. While it may be possible to leave work at work, you can’t always leave home at home. Being honest about things that are going on in your life– a health issue, a death in the family, a divorce, anything that may distract you professionally–and creating a culture where people feel they can be honest with you makes it easier for others to step up when you need them.

  • Rally the troops. A major part of my job is recognizing when a situation is turning south and working with my team to course correct. Intervene and get your team members on board as early as you can when something goes wrong.

Reflect often and together

In the agency world, it can be easy to move from one project to another without taking the time to reflect. But talking, reflecting, sharing, and confiding helps you identify problems, work through issues, call out successes, and, most importantly, build trust and foster relationships. Here are a few ways I try to embed feedback and reflection into our work culture:

  • Remove ego. If you take nothing else from this article, remember this–when trying to foster a successful, impactful team there are few occasions when an ego will serve you well. If you want people to talk, share, and reflect honestly, adapt to the mentality that rank means nothing. Learn to motivate your team members without being “the boss.”

  • Create communities. When stressed or frustrated, it’s important to have a group of people, sometimes outside of the project team, that you can rely on. Create communities that share the same working styles or interests–management teams, working groups, people who like dogs or go to spin class together. Having these communities can help alleviate stress and remind people of what they love about their job– the friends, relationships, and the community. Even the most introverted people crave this.

  • Schedule reflection time. Whether at regular intervals throughout a project, and/or at the end, schedule time with a project team to talk about what made a project successful or fun. How can you bottle that up and sprinkle it onto the next project? How can you share that with others in your company so they can learn too? Always look out for what’s bigger than you–what did you learn from a project that can be applied at the company level vs. project specific level?

  • Reflect with clients. Talk with your partners on the client-side about what went well and why, and what needs improvement.

And now for the special sauce

Throughout the years, I have realized that a lot of what makes me good at what I do has little to do with planning, process, strategy, or anything I could have learned in school. Rather, the interpersonal skills I have learned through the meaningful and loving relationships I have been honored to have with the people in my life–my friends, my family, my husband–have meant far more to my career than I ever would have imagined. For most of us, these are things we already know how to do, we just don’t think of applying them to work. What makes me a good friend, sister, daughter, and wife is what also makes me a good manager, teammate, client partner, and overall good person to confide in; things like:

  • Showing curiosity. Ask people, colleagues, and clients personal and professional questions about themselves. What did they do before starting their current position? Where did they go to college? What’s their favorite part about their job? How old are their kids? How was the event they went to over the weekend?

  • Writing things down. When someone mentions something meaningful to them–baby due dates, vacation plans, etc. make a note to follow up. This can help build a trusting relationship and takes little effort.

  • Doing something unexpected. People (clients especially) will expect a gift around the holidays, but they won’t expect that you remembered their birthday, their son’s graduation, or their spouse’s promotion.

  • Engaging in small acts of kindness. Do things just because, even when there’s no occasion. “Thinking of you” notes, leaving a sunflower or cookie on someone’s desk, compliments, or favors can go a long way, especially when trying to build relationships with colleagues.

  • Being authentic. Don’t create relationships solely to network and “get ahead.” People see right through this. You won’t find me wining and dining my clients or bribing my coworkers to work an extra few hours. I’m naturally introverted. But when I genuinely care about someone and want to get to know them, it’s easy to show interest in their lives and spend time with them.

  • Encouraging people to be themselves. When someone makes a mistake, be there to support them. When they’re nervous, nudge them to take a risk. When they feel like they’re failing, remind them why they’re not. Grant people the freedom to be whoever they want to be and push them to be a better version of themselves. Stand by their side so they know that no matter where they end up you’ll be right there with them.

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When traveling as a student-athlete throughout grade school and college, I always stayed awake on the plane or bus ride to our next game studying or doing homework while the rest of the team drifted off to music on their headphones. As long as I can remember, I’ve been obsessed with being productive and trying to squeeze every last ounce out of every hour of the day to get as much done as humanly possible. This obsession continued as I transitioned from college to my first job as a project manager at Cake & Arrow.

My obsession with being productive and accomplishing my goals have made me who I am today. But when I look back at why I love my job and what’s really made me successful, it’s not how productive I have been–it’s the meaningful relationships I’ve created with both my colleagues and our clients–and the pure joy of seeing others excel. It just so happens that the killer work that delivers value to customers is a direct byproduct of building these kinds of relationships.

Do I still geek out over creating a fresh project plan, a new spreadsheet template or process, or at checking things off my to-do list? Can I sometimes be too rigid and solutions-focused? Of course. These things are deeply ingrained in who I am. But it wasn’t until I started to put people first that I really became a leader. In my 13+ years of doing what I do, I have learned that giving people autonomy and freedom while educating, guiding, listening to them, and taking the time to learn how they work and how to get the best out of them builds trust–and trust is at the core of every successful team and all great work.