As we come off of the high of the U.S. Women’s National Soccer Team Championship win earlier this summer and enter into the NFL pre-season, it’s fitting to reflect on what makes a team successful–inspiring leadership, effective communication, managed conflict, trust, respect, diversity, support, a combination of specialized talent, and a clear vision with a focus on outcomes. A blend of all of these things, no matter the circumstance, culminates in a “W” for all.

At Cake & Arrow, we pride ourselves on the ability to create successful teams. There’s a lot that goes into this. We meet weekly to assess the forecast of project and resource needs for the upcoming 3-9 months based on active projects, organic growth opportunities that have a high probability of closing, and net-new client engagements that are in a certain stage of the new business development lifecycle. And while we have a base foundation of full-time employees and contractors across various disciplines with different personalities, skill sets, and levels of experience to call upon, the stars don’t often align so that the exact people with the exact criteria a project needs are all available at the same time. Pulling together a winning team for every project requires planning, flexibility, intuition, a deep understanding of our clients and their needs, and sometimes a little luck.

So how do we do it? There are three important considerations that guide this process of building a winning team.

1. The Client Relationship and Project Outcomes

Understanding client business needs, the types of stakeholders we’ll be working with and the outcomes each one is seeking at the end of each project is at the core of determining who works on what and when. Questions we ask include:

  • Is this an already existing relationship where current employees have previously worked with this client and built a good rapport with stakeholders and a knowledge-base that would help them serve as an internal subject-matter-expert (SME) within the specific industry this client sits? If yes and all went well, we try to keep at least one of these employees working on the next engagement. If not, we try to staff someone who has experience working in the client’s industry. This helps ensure that someone on our team is speaking the client’s language and builds trust with the client early on.

  • Is this a brand new client that has the potential for a long-term commitment and many projects beyond the initial engagement? If yes, we do our best to staff the project with full-time employees before we turn to contractors. This way we are sure to retain institutional knowledge and relationships that we can carry through to other projects with the client, beyond the initial engagement.

  • What are the success criteria that the project will be measured against when it’s finished? Possessing a shared vision with the client of the outcome we are working toward is critical in helping us assemble the right team, plot out the appropriate activities, and determine what the deliverables will be. These success criteria become the basis for every decision we make in planning out a project, and can be an indispensable asset when justifying and advocating for the decisions we make, particularly when it comes to staffing a project.

The answers to these questions will impact the types of people we choose to staff on each project. There are many things to consider. But, when it comes to assembling teams, it’s not only about delivering value to the client based on their needs, but also about how the internal team comes together, and how they will feel about their experience. A happy client is the result of a happy internal well-oiled internal team.

2. The Team Dynamic and Morale

When examining the many components that go into assembling teams, one of our goals is that a team can look back on their experience positively and replicate what worked well on future projects. When designing the team dynamic, we consider the following:

  • Who will be the team leader? Teams need a captain, someone to follow that has a strong presence and leads with empathy. Identifying this person from the get-go is key, and it can be played by many roles depending on the project.

  • Do the team members care about the subject matter, have prior experience in the industry, or some other kind of personal connection to the client or the work? Team members with a vested interest in or even a personal connection to the subject matter, the client, or the industry are going to bring a different kind of energy and enthusiasm to their team that can be contagious to everyone involved. To whatever extent possible, we look for these connections when staffing a project.

  • Where are internal team members located? We have both in-office employees and remote employees. If we already know we are going to be assigning someone to the team who works remotely, it may make sense to staff the project with other remote workers. If the project lead works in our office, then maybe we want an entire team of on-site employees.

  • What have we learned from previous pairings of team members? Everyone has their own style of working, collaborating, and receiving feedback. How can we assess individual needs and preferences upfront to surface any foreseen risks and issues early and ensure the team can thrive?

  • Should we hire someone new? Sometimes a project may require a resource we don’t have available. Adding a new person to the team, let alone the company, comes with its own set of challenges, including onboarding time and a learning curve for everyone on how to work together and build trust. This can take a toll on existing employees, but it can also be refreshing and the right thing for the project and the team. We frequently ask ourselves if this is the right project to experiment with the unknown. If hiring someone new doesn’t feel right, we may shift other projects around to allow for trusted resources to work together.

Creating a winning team isn’t just about staffing a project with the right skill sets and subject matter expertise, but about designing a team dynamic that has as much to do with skill sets as it does with personalities. Creating the right dynamic is hard, and while it’s up to the company to create the right conditions for success, it’s ultimately up to the team itself to come together and succeed. A hard and fast rule is to never staff a project with all new team members; it’s proven to be a recipe for failure.

3. The Bottom Line - Ours and the Clients’

When assembling a project team, it’s critical that we consider both the impact to our company’s revenue and how to deliver the most value to our clients within a specified budget. With the bottom line in mind, these are some of the questions we ask:

  • What is the client’s budget, and what is our target profit margin? Having a clear picture of this allows us to understand the total costs we can incur with staffing and informs decisions around how we go about staffing a project. Keeping the project goals and success criteria always in the forefront of our minds, we’ll want to determine what the estimated cost rates are for the individual types of roles required for the project and determine whether we’ll be able to stay within the budget and hit our target profit margin, all while maximizing value to the client. Depending on the answer, we might have to pivot. For instance, we might determine that on a given project, if we invest in a more senior Experience Designer to act as the project lead, we may be able to staff the project with fewer resources or a more junior Visual Designer. A clear picture of the budget, the bottom line, and how these relate to the stated goals and desired outcomes of the project will help us make smart staffing decisions.

  • Are there any out-of-pocket costs or third party costs to factor in that may take away from the amount apportioned for staff? It’s not only important to know what the project budget is, but to understand what part of the budget may already be allocated. For example, the client might already be assuming they are giving part of the budget to a third party vendor (like a dev shop, for instance). This information will also inform how we go about staffing a project, and may create more or less flexibility in the budget when it comes to staffing.

  • What is the estimated project start date and duration? Is there anything driving this date? Knowing the hard and fast deadlines and where we may have some flexibility is critical when it comes to building a project team. For example, can we move up the project start date if we have the resources available to contribute to our revenue targets earlier? Can we afford to push the project to start later if we want specific resources to work on it that aren’t available yet without leaving others twiddling their thumbs? These considerations can make a world of difference in staffing the right resources for a project, and when it comes to the bottom line, can help us more efficiently put our resources to use.

  • Are there other projects on the horizon that we should be considering before committing a resource to a specific project? Looking ahead and across the entire pipeline and multiple accounts is key. This not only helps us with our bottom line by ensuring we are fully utilizing our resources on the right projects, but can also be beneficial to the client, especially if we foresee the project turning into a longer-term engagement, as it may not make sense to staff someone on a project we know will not be available for future projects with the client.

Gathering the answers to the above inputs and balancing our bottom line with that of our clients requires working internally with Management, Delivery, New Business Development, the Client Success team, People Operations, and also requires a certain level of transparency with our clients as we work to make a project team a win-win for both parties. At Cake & Arrow, we combine insights and data from all of these groups to ensure the best possible outcome for not only the client, but Cake & Arrow itself.


The decisions made when assembling teams have the capacity to impact our relationships with our clients, project outcomes, the morale of the humans behind the work, and both companies' bottom line. According to Harvest, the company that makes the tools we use to track both actual time spent and planned forecasted time for our projects, a forecast-enabled company understands how to deliver great service and how to be profitable. It has the data to anticipate change and talk to a client before a project goes off the rails. It knows when to hire and when to say no. It knows who works on what and when. It learns from its past and is informed for the future. It controls its destiny, and at Cake & Arrow we definitely do.

Assembling a project team can sometimes feel like a game of Tetris. Each employee’s allocation, a different shape that falls faster and faster as the weeks go on. In this game of Tetris, it’s important to proactively position each shape early on, as the gaping holes where the pieces don’t fit together can be costly for both us and our clients.


As Head of Delivery at Cake & Arrow, I combine all of the above considerations with the tools that make the assessment possible and ensure the right people are consulted along the way. The needs of our business and clients will forever change; priorities will constantly shift, and what was the right answer for one project may not be the right answer for another. Creating teams is definitely an art, and while there is no one-size-fits-all approach, having a system in place to evaluate the proper inputs and the levers we have to pull empowers us to create winning teams time and time again.